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Welcome home to Bayport Beach & Tennis Club conveniently located directly across from the best stretch of beach Longboat Key has to offer. This 2nd floor condo offers a bright and airy living space with an abundance of natural light. Once inside, it is immediately evident that this residence has been well maintained and updated. The beautifully renovated kitchen features granite countertops, newer windows, a pantry, stainless steel appliances, a breakfast bar, ample counter space for creating culinary delights while easily conversing with guests and family in the combined living/dining area. The primary suite pampers owners with a nook currently being used as an office space, a large renovated primary bathroom featuring a walk-in closet, granite countertops, dual vanities and a modern glass enclosed shower. Guests will be comfortable in the ensuite guest bedroom with their own large walk-in closet. A screened rear patio surrounded by lush landscaping is the perfect spot for reading, bird watching and enjoying the outdoor air and feels like being in a luxury treehouse. The spacious front patio is ideal for alfresco dining and grilling. There is a carport with additional storage provided on the ground level and guest parking directly in front of the carport. In addition to the fantastic interior features, this condo also offers excellent amenities that enhance the overall living experience. These include a bocci ball court, kayak storage, a fishing pier, a clubhouse with fitness center, heated Olympic size swimming pool, 4 Har Tru tennis courts, onsite management and picturesque tree lined walking trails. For beach lovers, Bayport Beach & Tennis Club offers deeded beach access to easily enjoy the sun, sand and surf, with beach chairs and umbrellas on 1200 feet of white sand beach. Conveniently located mid-Longboat Key close to Publix, Bayfront Park, shopping, fine & casual dining, St. Armands Circle and the cultural hub of southwest Florida, downtown Sarasota.

2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code

Welcome home to Bayport Beach & Tennis Club conveniently located directly across from the best stretch of beach Longboat Key has to offer. This 2nd floor condo offers a bright and airy living space with an abundance of natural light. Once inside, it is immediately evident that this residence has been well maintained and updated. The beautifully renovated kitchen features granite countertops, newer windows, a pantry, stainless steel appliances, a breakfast bar, ample counter space for creating culinary delights while easily conversing with guests and family in the combined living/dining area. The primary suite pampers owners with a nook currently being used as an office space, a large renovated primary bathroom featuring a walk-in closet, granite countertops, dual vanities and a modern glass enclosed shower. Guests will be comfortable in the ensuite guest bedroom with their own large walk-in closet. A screened rear patio surrounded by lush landscaping is the perfect spot for reading, bird watching and enjoying the outdoor air and feels like being in a luxury treehouse. The spacious front patio is ideal for alfresco dining and grilling. There is a carport with additional storage provided on the ground level and guest parking directly in front of the carport. In addition to the fantastic interior features, this condo also offers excellent amenities that enhance the overall living experience. These include a bocci ball court, kayak storage, a fishing pier, a clubhouse with fitness center, heated Olympic size swimming pool, 4 Har Tru tennis courts, onsite management and picturesque tree lined walking trails. For beach lovers, Bayport Beach & Tennis Club offers deeded beach access to easily enjoy the sun, sand and surf, with beach chairs and umbrellas on 1200 feet of white sand beach. Conveniently located mid-Longboat Key close to Publix, Bayfront Park, shopping, fine & casual dining, St. Armands Circle and the cultural hub of southwest Florida, downtown Sarasota.

831 Bayport Way Unit 831, Longboat Key

2110 Harbourside Drive Unit 548, Longboat Key

$999,000

Virtually Staged. Sweeping Sarasota Bay views, expansive outdoor living, and an exceptional opportunity to create your own coastal retreat await at The Atrium at Fairway Bay. Located on the fourth floor within the gated Bay Isles community, this spacious corner residence offers the sought-after Banyan floor plan with 2,616 square feet of living space, three bedrooms, two-and-a-half baths, and 3,301 total square feet. Ready for a new owner's vision and updates, the residence offers generous proportions, an open layout, and multiple private balconies overlooking Sarasota Bay and the surrounding tropical landscape. A welcoming entry foyer leads to spacious living and dining areas with wood flooring, crown molding, and walls of glass that bring in natural light and showcase the views. The living room features built-in shelving and opens to a large wraparound waterfront balcony. The adjoining dining room also enjoys bay views, while a separate breakfast area provides additional casual dining space. The eat-in kitchen features granite countertops, wood cabinetry, stainless steel appliances, breakfast bar seating, and pantry storage, offering an opportunity to reimagine the space to suit your personal style. The primary suite features floor-to-ceiling glass, balcony access, and sweeping views of Sarasota Bay. Its bathroom, updated in 2016, includes dual sinks, a freestanding soaking tub, and a separate glass-enclosed shower. Two additional bedrooms offer flexibility for guests, a home office, or den, each with access to an outdoor balcony. A guest bathroom, separate powder room, and dedicated interior laundry room with additional storage complete the floor plan. With more than 600 square feet of balcony space, the residence offers exceptional opportunities for outdoor living, from morning coffee overlooking the bay to relaxing in the afternoon breeze. Under-building garage parking and additional storage add everyday convenience. While comfortable in its current condition, this residence presents an exciting opportunity for a comprehensive renovation, allowing the next owner to transform its spacious interiors into a personalized waterfront home. Residents of The Atrium at Fairway Bay enjoy 24-hour gated security, a heated swimming pool and spa, fitness facilities, tennis and pickleball courts, a clubhouse, and beautifully maintained tropical grounds. Ownership also provides access to the private Bay Isles Beach Club, offering a Gulf-front retreat along Longboat Key's white-sand shoreline. Ideally situated near Longboat Key Club's golf and marina amenities, the community is convenient to St. Armands Circle's boutiques and restaurants, the beaches of Longboat and Lido Key, and downtown Sarasota's celebrated dining, theaters, galleries, and cultural attractions. With its desirable fourth-floor setting, expansive balconies, captivating bay views, and exceptional renovation potential, Fairway Bay Atrium #548 offers a compelling opportunity to create a distinctive Longboat Key residence.

3 Beds ⋅ 3 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code

Virtually Staged. Sweeping Sarasota Bay views, expansive outdoor living, and an exceptional opportunity to create your own coastal retreat await at The Atrium at Fairway Bay. Located on the fourth floor within the gated Bay Isles community, this spacious corner residence offers the sought-after Banyan floor plan with 2,616 square feet of living space, three bedrooms, two-and-a-half baths, and 3,301 total square feet. Ready for a new owner's vision and updates, the residence offers generous proportions, an open layout, and multiple private balconies overlooking Sarasota Bay and the surrounding tropical landscape. A welcoming entry foyer leads to spacious living and dining areas with wood flooring, crown molding, and walls of glass that bring in natural light and showcase the views. The living room features built-in shelving and opens to a large wraparound waterfront balcony. The adjoining dining room also enjoys bay views, while a separate breakfast area provides additional casual dining space. The eat-in kitchen features granite countertops, wood cabinetry, stainless steel appliances, breakfast bar seating, and pantry storage, offering an opportunity to reimagine the space to suit your personal style. The primary suite features floor-to-ceiling glass, balcony access, and sweeping views of Sarasota Bay. Its bathroom, updated in 2016, includes dual sinks, a freestanding soaking tub, and a separate glass-enclosed shower. Two additional bedrooms offer flexibility for guests, a home office, or den, each with access to an outdoor balcony. A guest bathroom, separate powder room, and dedicated interior laundry room with additional storage complete the floor plan. With more than 600 square feet of balcony space, the residence offers exceptional opportunities for outdoor living, from morning coffee overlooking the bay to relaxing in the afternoon breeze. Under-building garage parking and additional storage add everyday convenience. While comfortable in its current condition, this residence presents an exciting opportunity for a comprehensive renovation, allowing the next owner to transform its spacious interiors into a personalized waterfront home. Residents of The Atrium at Fairway Bay enjoy 24-hour gated security, a heated swimming pool and spa, fitness facilities, tennis and pickleball courts, a clubhouse, and beautifully maintained tropical grounds. Ownership also provides access to the private Bay Isles Beach Club, offering a Gulf-front retreat along Longboat Key's white-sand shoreline. Ideally situated near Longboat Key Club's golf and marina amenities, the community is convenient to St. Armands Circle's boutiques and restaurants, the beaches of Longboat and Lido Key, and downtown Sarasota's celebrated dining, theaters, galleries, and cultural attractions. With its desirable fourth-floor setting, expansive balconies, captivating bay views, and exceptional renovation potential, Fairway Bay Atrium #548 offers a compelling opportunity to create a distinctive Longboat Key residence.

2110 Harbourside Drive Unit 548, Longboat Key

$3,750,000

Under Construction. **NEW CONSTRUCTION WATERFRONT LUXURY IN HISTORIC LONGBOAT KEY VILLAGE!** Discover an exceptional opportunity to enjoy modern coastal living in one of Longboat Key's most charming and sought-after neighborhoods. Situated on a canal-front homesite, this beautifully designed contemporary residence offers approximately **3,472 square feet of living space and 5,955 square feet under roof**, blending premium architecture, thoughtfully designed interiors, and the relaxed elegance of Florida's island lifestyle. Designed for both entertaining and everyday comfort, the residence features four spacious bedrooms, an expansive great room, an elegant dining area, and a beautifully appointed kitchen with a generous center island, premium appliance provisions, and seamless access to the covered outdoor entertaining area. Expansive windows invite abundant natural light while creating an open, airy atmosphere throughout the home. The primary suite offers a private retreat with a spacious bedroom, luxurious bath, walk-in closet, and thoughtfully designed amenities. Additional guest accommodations provide comfort and privacy for family and visitors. Outdoor living is central to the home's design, featuring a covered main-level lanai with outdoor kitchen provisions, an upper-level sun deck, and a ground-level covered lanai overlooking the planned pool area and canal. Multiple outdoor gathering spaces create opportunities to enjoy the island's tropical surroundings, coastal breezes, and beautiful Florida weather. The elevated architectural design incorporates generous garage and storage space, contemporary exterior finishes, and an impressive combination of clean lines and coastal-inspired details. **LOCATION, LOCATION, LOCATION!** Nestled in the heart of historic Longboat Key Village, this residence offers convenient access to the beautiful Gulf beaches, nearby waterfront dining, boating, fishing, and the authentic Old Florida charm that makes this neighborhood so special. Enjoy the atmosphere of a close-knit island community while remaining within easy reach of St. Armands Circle, downtown Sarasota, world-class shopping, cultural attractions, and entertainment. Whether envisioned as a full-time residence or an exceptional island retreat, **531 Broadway Street offers a rare combination of new construction, waterfront living, modern luxury, and the timeless appeal of Longboat Key Village.** **Experience the very best of Florida's Gulf Coast lifestyle!**

4 Beds ⋅ 4 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code

Under Construction. **NEW CONSTRUCTION WATERFRONT LUXURY IN HISTORIC LONGBOAT KEY VILLAGE!** Discover an exceptional opportunity to enjoy modern coastal living in one of Longboat Key's most charming and sought-after neighborhoods. Situated on a canal-front homesite, this beautifully designed contemporary residence offers approximately **3,472 square feet of living space and 5,955 square feet under roof**, blending premium architecture, thoughtfully designed interiors, and the relaxed elegance of Florida's island lifestyle. Designed for both entertaining and everyday comfort, the residence features four spacious bedrooms, an expansive great room, an elegant dining area, and a beautifully appointed kitchen with a generous center island, premium appliance provisions, and seamless access to the covered outdoor entertaining area. Expansive windows invite abundant natural light while creating an open, airy atmosphere throughout the home. The primary suite offers a private retreat with a spacious bedroom, luxurious bath, walk-in closet, and thoughtfully designed amenities. Additional guest accommodations provide comfort and privacy for family and visitors. Outdoor living is central to the home's design, featuring a covered main-level lanai with outdoor kitchen provisions, an upper-level sun deck, and a ground-level covered lanai overlooking the planned pool area and canal. Multiple outdoor gathering spaces create opportunities to enjoy the island's tropical surroundings, coastal breezes, and beautiful Florida weather. The elevated architectural design incorporates generous garage and storage space, contemporary exterior finishes, and an impressive combination of clean lines and coastal-inspired details. **LOCATION, LOCATION, LOCATION!** Nestled in the heart of historic Longboat Key Village, this residence offers convenient access to the beautiful Gulf beaches, nearby waterfront dining, boating, fishing, and the authentic Old Florida charm that makes this neighborhood so special. Enjoy the atmosphere of a close-knit island community while remaining within easy reach of St. Armands Circle, downtown Sarasota, world-class shopping, cultural attractions, and entertainment. Whether envisioned as a full-time residence or an exceptional island retreat, **531 Broadway Street offers a rare combination of new construction, waterfront living, modern luxury, and the timeless appeal of Longboat Key Village.** **Experience the very best of Florida's Gulf Coast lifestyle!**

531 Broadway Street, Longboat Key

3330 Gulf Of Mexico Drive Unit 301D, Longboat Key

$795,000

Longboat Arms - real coastal living at it best, a tranquil, low-density waterfront enclave. This waterfront unit has it all, both bedrooms with water views, as well as the living and dining area, just the best location within the community. Unrivaled amenities with a renovated Clubhouse, boat ramp, private boat slips, kayak storage and launch and assigned covered parking. A heated community pool, tennis courts and all just steps from a deeded Beach Access. This waterfront enclave is ideally located mid-key and only one mile north of the Publix shopping center. Schedule your private tour today!

2 Beds ⋅ 2 Baths ⋅ Longboat Arms SubDv. ⋅ 34228 Zip Code

Longboat Arms - real coastal living at it best, a tranquil, low-density waterfront enclave. This waterfront unit has it all, both bedrooms with water views, as well as the living and dining area, just the best location within the community. Unrivaled amenities with a renovated Clubhouse, boat ramp, private boat slips, kayak storage and launch and assigned covered parking. A heated community pool, tennis courts and all just steps from a deeded Beach Access. This waterfront enclave is ideally located mid-key and only one mile north of the Publix shopping center. Schedule your private tour today!

3330 Gulf Of Mexico Drive Unit 301D, Longboat Key

$3,500,000

Under Construction. NEW CONSTRUCTION - ISLAND LIVING IN HISTORIC LONGBOAT KEY VILLAGE! Discover a rare opportunity to own a newly constructed coastal residence in one of Longboat Key's most charming and distinctive neighborhoods. Situated across the street from the Whitney Beach Access. This exceptional property combines the appeal of modern luxury with the relaxed character of Old Florida waterfront living. Thoughtfully designed for today's coastal lifestyle, this home will provide the benefits of brand-new construction in a setting that is increasingly difficult to replicate. Enjoy tranquil canal views, a waterfront atmosphere, and the opportunity to experience the very best of island living. Located in the heart of historic Longboat Key Village, this property offers convenient access to neighborhood restaurants, waterfront dining, local shops, and the beautiful beaches of Longboat Key. Take a morning stroll for coffee, enjoy an afternoon on the water, or spend the evening discovering the exceptional dining and laid-back lifestyle that make this northern end of the island so desirable. Currently under construction, this is an opportunity to secure a brand-new waterfront home in one of Longboat Key's most sought-after historic neighborhoods.

4 Beds ⋅ 4 Baths ⋅ Long Beach SubDv. ⋅ 34228 Zip Code

Under Construction. NEW CONSTRUCTION - ISLAND LIVING IN HISTORIC LONGBOAT KEY VILLAGE! Discover a rare opportunity to own a newly constructed coastal residence in one of Longboat Key's most charming and distinctive neighborhoods. Situated across the street from the Whitney Beach Access. This exceptional property combines the appeal of modern luxury with the relaxed character of Old Florida waterfront living. Thoughtfully designed for today's coastal lifestyle, this home will provide the benefits of brand-new construction in a setting that is increasingly difficult to replicate. Enjoy tranquil canal views, a waterfront atmosphere, and the opportunity to experience the very best of island living. Located in the heart of historic Longboat Key Village, this property offers convenient access to neighborhood restaurants, waterfront dining, local shops, and the beautiful beaches of Longboat Key. Take a morning stroll for coffee, enjoy an afternoon on the water, or spend the evening discovering the exceptional dining and laid-back lifestyle that make this northern end of the island so desirable. Currently under construction, this is an opportunity to secure a brand-new waterfront home in one of Longboat Key's most sought-after historic neighborhoods.

521 Broadway Street, Longboat Key

360 Gulf Of Mexico Drive Unit 333, Longboat Key

$1,575,000

Virtually Staged. Complete Interior Photos Coming Soon! One of Tangerine Bay Club's coveted few corner penthouses, this exceptional residence showcases stunning bayfront views and nearly 2,600 sq. ft. of interior space on two levels that live like a single-family home. Freshly painted interiors, partially furnished and attractively priced, this serene sanctuary offers two terraces (3045 square feet in total), 3 bedrooms, 3 1/2 baths, a private courtyard and oversized garage with storage. Soaring ceilings, a gas fireplace and extra windows available only in end units create an inviting ambiance. The kitchen features a morning room with built-in desk, and an aquarium window over the sink. The adjoining dining and great rooms flow effortlessly, while sliding glass doors extend the living experience outdoors. Mahogany double doors lead to the primary suite, a peaceful retreat with its terrace access, bay views, volume ceilings, custom walk-in and built-in closets, and beautifully renovated bath. An additional guest bedroom (used as a den) with ensuite bath, a laundry room, and powder room, complete the first level. On the second level a spacious guest suite, office with built-in desk, shelving and storage, and a full bath provide comfortable accommodations and privacy for family and friends. Impact windows, plus storm shutters on larger windows, provide peace of mind. Tangerine Bay offers an enviable resort-like lifestyle amid lush tropical landscaping. Enjoy the lagoon pool with waterfalls, lap lane and spa, along with a day dock, fishing, kayak launch, tennis and pickleball courts, fitness center, clubhouse, and scenic walking paths. Owners may join the Bay Isles Beach Club directly on the Gulf of Mexico for a modest annual fee. Ideally situated on Longboat Key's south end, this gated community is just minutes from the St. Regis resort and St. Armand's Circle, with its shops and fine dining. Downtown Sarasota, with its celebrated arts, dining and culture, is a short drive across the Ringling Bridge. Optional membership at the Longboat Key Club, just across the street, offers 45 holes of championship golf, fine dining and a marina. A rare corner-penthouse opportunity, exceptional bayfront views and lifestyle--discover why Tangerine Bay Club remains one of Longboat Key's most desirable waterfront communities.

3 Beds ⋅ 4 Baths ⋅ Tangerine Bay Club SubDv. ⋅ 34228 Zip Code

Virtually Staged. Complete Interior Photos Coming Soon! One of Tangerine Bay Club's coveted few corner penthouses, this exceptional residence showcases stunning bayfront views and nearly 2,600 sq. ft. of interior space on two levels that live like a single-family home. Freshly painted interiors, partially furnished and attractively priced, this serene sanctuary offers two terraces (3045 square feet in total), 3 bedrooms, 3 1/2 baths, a private courtyard and oversized garage with storage. Soaring ceilings, a gas fireplace and extra windows available only in end units create an inviting ambiance. The kitchen features a morning room with built-in desk, and an aquarium window over the sink. The adjoining dining and great rooms flow effortlessly, while sliding glass doors extend the living experience outdoors. Mahogany double doors lead to the primary suite, a peaceful retreat with its terrace access, bay views, volume ceilings, custom walk-in and built-in closets, and beautifully renovated bath. An additional guest bedroom (used as a den) with ensuite bath, a laundry room, and powder room, complete the first level. On the second level a spacious guest suite, office with built-in desk, shelving and storage, and a full bath provide comfortable accommodations and privacy for family and friends. Impact windows, plus storm shutters on larger windows, provide peace of mind. Tangerine Bay offers an enviable resort-like lifestyle amid lush tropical landscaping. Enjoy the lagoon pool with waterfalls, lap lane and spa, along with a day dock, fishing, kayak launch, tennis and pickleball courts, fitness center, clubhouse, and scenic walking paths. Owners may join the Bay Isles Beach Club directly on the Gulf of Mexico for a modest annual fee. Ideally situated on Longboat Key's south end, this gated community is just minutes from the St. Regis resort and St. Armand's Circle, with its shops and fine dining. Downtown Sarasota, with its celebrated arts, dining and culture, is a short drive across the Ringling Bridge. Optional membership at the Longboat Key Club, just across the street, offers 45 holes of championship golf, fine dining and a marina. A rare corner-penthouse opportunity, exceptional bayfront views and lifestyle--discover why Tangerine Bay Club remains one of Longboat Key's most desirable waterfront communities.

360 Gulf Of Mexico Drive Unit 333, Longboat Key

3235 Gulf Of Mexico Drive Unit A201, Longboat Key

$1,195,000

**BREATHTAKING BEACHFRONT CORNER CONDO WITH PANORAMIC GULF VIEWS!** Experience the beauty of beachfront living in this spacious, beautifully appointed two-bedroom, two-bath residence overlooking the Gulf of Mexico. Located on the second floor of the desirable Portobello community on Longboat Key, this exceptional corner unit offers approximately 1,500 square feet of living space, a thoughtfully designed split-bedroom floor plan, and two balconies offering spectacular coastal views. Offered turnkey furnished, this residence is ready to enjoy! Wake up to the soothing sounds of the waves in the spacious primary suite, complete with a generous walk-in closet, updated en-suite bathroom with stone countertops, dual sinks and a walk-in shower, and sliding glass doors opening directly onto the expansive waterfront balcony shared with the living room. The generously sized kitchen features beautiful wood cabinetry, stone countertops, a breakfast bar, and abundant storage, while the separate dining area offers additional space for gathering with family and friends. The guest bedroom provides its own private Gulf-view balcony and walk-in closet, creating a comfortable retreat for visitors. **HOME FEATURES:** - DESIRABLE SECOND-FLOOR CORNER UNIT - TWO PRIVATE BALCONIES - SPACIOUS SPLIT-BEDROOM FLOOR PLAN - TURNKEY FURNISHED - UPDATED KITCHEN AND BATHROOMS - CROWN MOLDING AND GENEROUS WALK-IN CLOSETS - IN-UNIT WASHER AND DRYER - WATER HEATER (2022) - NEWER ROOF (2025) Additional conveniences include elevator access and assigned parking. **COMMUNITY INFORMATION:** Nestled within the sought-after Portobello community, residents enjoy an exceptional coastal lifestyle with amenities on both the beach and bay sides of Longboat Key. Enjoy private, gated beach access, a heated swimming pool, tennis courts, kayak storage, an outdoor grilling area, and a bayside day dock and fishing pier. Whether spending the afternoon on the sand, enjoying a sunset, or exploring the waters of Sarasota Bay, Portobello offers opportunities to embrace island living. Conveniently located mid-key, just minutes from shopping, dining, golf courses, Publix, the world-renowned St. Armands Circle, and downtown Sarasota, this residence provides the perfect combination of island tranquility and nearby conveniences. **Discover the beauty of beachfront living in this spacious Longboat Key retreat, where spectacular views and coastal comfort come together.**

2 Beds ⋅ 2 Baths ⋅ Portobello SubDv. ⋅ 34228 Zip Code

**BREATHTAKING BEACHFRONT CORNER CONDO WITH PANORAMIC GULF VIEWS!** Experience the beauty of beachfront living in this spacious, beautifully appointed two-bedroom, two-bath residence overlooking the Gulf of Mexico. Located on the second floor of the desirable Portobello community on Longboat Key, this exceptional corner unit offers approximately 1,500 square feet of living space, a thoughtfully designed split-bedroom floor plan, and two balconies offering spectacular coastal views. Offered turnkey furnished, this residence is ready to enjoy! Wake up to the soothing sounds of the waves in the spacious primary suite, complete with a generous walk-in closet, updated en-suite bathroom with stone countertops, dual sinks and a walk-in shower, and sliding glass doors opening directly onto the expansive waterfront balcony shared with the living room. The generously sized kitchen features beautiful wood cabinetry, stone countertops, a breakfast bar, and abundant storage, while the separate dining area offers additional space for gathering with family and friends. The guest bedroom provides its own private Gulf-view balcony and walk-in closet, creating a comfortable retreat for visitors. **HOME FEATURES:** - DESIRABLE SECOND-FLOOR CORNER UNIT - TWO PRIVATE BALCONIES - SPACIOUS SPLIT-BEDROOM FLOOR PLAN - TURNKEY FURNISHED - UPDATED KITCHEN AND BATHROOMS - CROWN MOLDING AND GENEROUS WALK-IN CLOSETS - IN-UNIT WASHER AND DRYER - WATER HEATER (2022) - NEWER ROOF (2025) Additional conveniences include elevator access and assigned parking. **COMMUNITY INFORMATION:** Nestled within the sought-after Portobello community, residents enjoy an exceptional coastal lifestyle with amenities on both the beach and bay sides of Longboat Key. Enjoy private, gated beach access, a heated swimming pool, tennis courts, kayak storage, an outdoor grilling area, and a bayside day dock and fishing pier. Whether spending the afternoon on the sand, enjoying a sunset, or exploring the waters of Sarasota Bay, Portobello offers opportunities to embrace island living. Conveniently located mid-key, just minutes from shopping, dining, golf courses, Publix, the world-renowned St. Armands Circle, and downtown Sarasota, this residence provides the perfect combination of island tranquility and nearby conveniences. **Discover the beauty of beachfront living in this spacious Longboat Key retreat, where spectacular views and coastal comfort come together.**

3235 Gulf Of Mexico Drive Unit A201, Longboat Key

$20,000,000

A modern architectural masterpiece on the southern end of Longboat Key, this extraordinary waterfront estate designed by renowned Sarasota architect Guy Peterson occupies nearly ¾-acres in exclusive Lighthouse Point, overlooking New Pass where Sarasota Bay meets the Gulf of Mexico. Built in 2013, the elevated family compound offers 6,800 square feet of interior living, seven en-suite bedrooms, and 123 feet of waterfrontage. Walls of impact glass, striking contemporary lines, and spectacular water views define this exceptional coastal retreat. A dramatic courtyard entrance features a reflecting pool and towering glass curtain wall with exterior louvered sunscreens. Inside, soaring ceilings, beautiful hardwood accents, and expansive glass create an impressive sense of light and space. Tile flooring flows throughout the main living areas, while plush carpeting adds comfort to the bedrooms. The two-story great room opens to the pool terrace and waterfront beyond. The gourmet kitchen features leathered quartz countertops, an oversized island, custom cabinetry, and a seamless connection to the dining and entertaining spaces. Three en-suite guest bedrooms on the main level are thoughtfully arranged for privacy. An open upper-level promenade and connecting bridge overlook the great room below, leading to a spacious loft with custom built-ins, sitting areas, and a family room with morning kitchen. The private north wing houses the primary suite and an oversized guest suite suitable as a second primary retreat. Additional bedroom accommodations and multiple covered outdoor areas provide exceptional flexibility for family and guests. A detached one-bedroom casita with private entrance, bathroom, kitchenette, and bonus room offers a secluded retreat for extended stays. Outside, the heated swimming pool and spa anchor a private waterfront oasis with expansive terraces, covered dining, and a built-in grilling station. An elevated rooftop deck captures refreshing Gulf breezes, spectacular sunsets, and sweeping views of the surrounding waterways. Additional conveniences include laundry rooms on both living levels and an oversized three-car garage. A private 45-foot dock at the nearby community waterfront provides boating access to New Pass, Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico. Within the gated Lighthouse Point enclave, residents enjoy community tennis facilities and nearby Gulf beach access. This coveted southern Longboat Key location is moments from Longboat Key Club golf and marina amenities, St. Armands Circle's boutiques and restaurants, and the beautiful beaches of Longboat and Lido Key. Downtown Sarasota's celebrated dining, theaters, galleries, and cultural attractions are also within easy reach. Combining architectural distinction, expansive living spaces, exceptional privacy, and a premier waterfront setting, 40 Lighthouse Point Drive represents a remarkable expression of contemporary coastal luxury.

7 Beds ⋅ 8 Baths ⋅ Lighthouse Point SubDv. ⋅ 34228 Zip Code

A modern architectural masterpiece on the southern end of Longboat Key, this extraordinary waterfront estate designed by renowned Sarasota architect Guy Peterson occupies nearly ¾-acres in exclusive Lighthouse Point, overlooking New Pass where Sarasota Bay meets the Gulf of Mexico. Built in 2013, the elevated family compound offers 6,800 square feet of interior living, seven en-suite bedrooms, and 123 feet of waterfrontage. Walls of impact glass, striking contemporary lines, and spectacular water views define this exceptional coastal retreat. A dramatic courtyard entrance features a reflecting pool and towering glass curtain wall with exterior louvered sunscreens. Inside, soaring ceilings, beautiful hardwood accents, and expansive glass create an impressive sense of light and space. Tile flooring flows throughout the main living areas, while plush carpeting adds comfort to the bedrooms. The two-story great room opens to the pool terrace and waterfront beyond. The gourmet kitchen features leathered quartz countertops, an oversized island, custom cabinetry, and a seamless connection to the dining and entertaining spaces. Three en-suite guest bedrooms on the main level are thoughtfully arranged for privacy. An open upper-level promenade and connecting bridge overlook the great room below, leading to a spacious loft with custom built-ins, sitting areas, and a family room with morning kitchen. The private north wing houses the primary suite and an oversized guest suite suitable as a second primary retreat. Additional bedroom accommodations and multiple covered outdoor areas provide exceptional flexibility for family and guests. A detached one-bedroom casita with private entrance, bathroom, kitchenette, and bonus room offers a secluded retreat for extended stays. Outside, the heated swimming pool and spa anchor a private waterfront oasis with expansive terraces, covered dining, and a built-in grilling station. An elevated rooftop deck captures refreshing Gulf breezes, spectacular sunsets, and sweeping views of the surrounding waterways. Additional conveniences include laundry rooms on both living levels and an oversized three-car garage. A private 45-foot dock at the nearby community waterfront provides boating access to New Pass, Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico. Within the gated Lighthouse Point enclave, residents enjoy community tennis facilities and nearby Gulf beach access. This coveted southern Longboat Key location is moments from Longboat Key Club golf and marina amenities, St. Armands Circle's boutiques and restaurants, and the beautiful beaches of Longboat and Lido Key. Downtown Sarasota's celebrated dining, theaters, galleries, and cultural attractions are also within easy reach. Combining architectural distinction, expansive living spaces, exceptional privacy, and a premier waterfront setting, 40 Lighthouse Point Drive represents a remarkable expression of contemporary coastal luxury.

40 Lighthouse Point Drive, Longboat Key

726 Spanish Drive N Unit 164, Longboat Key

$389,000

Your Longboat Key coastal retreat awaits! Beautifully renovated and move-in ready, this 2-bedroom, 2-bath villa in the desirable Spanish Main Yacht Club combines modern upgrades with the best of Florida coastal living. Major improvements include hurricane-impact windows and doors, a new electrical panel, new water heater, and all new interior doors. The bright, open living area features polished terrazzo flooring, recessed lighting, and coastal-inspired finishes. The updated kitchen offers quartz-style countertops, shaker-style cabinetry, stainless steel appliances, subway tile backsplash, and a spacious breakfast bar. Both bathrooms have been tastefully renovated with modern vanities and stylish tilework. Additional highlights include sliding barn doors and an inviting enclosed sunroom with a new mini-split A/C, exposed beam ceilings, and wood accents. Outside, enjoy a new paver driveway, sidewalk, and back patio, covered carport, and tropical landscaping. Spanish Main Yacht Club offers a heated community pool, clubhouse, shuffleboard courts, and deep-water marina with boat slips and access to Sarasota Bay and the Intracoastal Waterway. Best of all, deeded beach access puts Longboat Key's beautiful Gulf beaches within easy reach! Conveniently located near St. Armands Circle, waterfront dining, shopping, and downtown Sarasota. Whether you're seeking a seasonal escape or full-time residence, this beautifully updated villa is ready for you to enjoy the Longboat Key lifestyle!

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Your Longboat Key coastal retreat awaits! Beautifully renovated and move-in ready, this 2-bedroom, 2-bath villa in the desirable Spanish Main Yacht Club combines modern upgrades with the best of Florida coastal living. Major improvements include hurricane-impact windows and doors, a new electrical panel, new water heater, and all new interior doors. The bright, open living area features polished terrazzo flooring, recessed lighting, and coastal-inspired finishes. The updated kitchen offers quartz-style countertops, shaker-style cabinetry, stainless steel appliances, subway tile backsplash, and a spacious breakfast bar. Both bathrooms have been tastefully renovated with modern vanities and stylish tilework. Additional highlights include sliding barn doors and an inviting enclosed sunroom with a new mini-split A/C, exposed beam ceilings, and wood accents. Outside, enjoy a new paver driveway, sidewalk, and back patio, covered carport, and tropical landscaping. Spanish Main Yacht Club offers a heated community pool, clubhouse, shuffleboard courts, and deep-water marina with boat slips and access to Sarasota Bay and the Intracoastal Waterway. Best of all, deeded beach access puts Longboat Key's beautiful Gulf beaches within easy reach! Conveniently located near St. Armands Circle, waterfront dining, shopping, and downtown Sarasota. Whether you're seeking a seasonal escape or full-time residence, this beautifully updated villa is ready for you to enjoy the Longboat Key lifestyle!

726 Spanish Drive N Unit 164, Longboat Key

1932 Harbourside Drive Unit 242, Longboat Key

$539,000

Value opportunity behind the gates of Bay Isles in the highly sought after Fairway Bay community. This partially furnished move-in ready two-bedroom, two-bath residence includes a valuable under-building garage parking space. Enjoy peaceful views of Sarasota Bay from an open floor plan designed to maximize natural light and comfortable indoor and outdoor living. White tile flooring runs throughout the main living areas, while a wall of sliding glass doors opens to the terrace, ideal for relaxing outdoor eating. The kitchen features light cabinetry, custom lighting and captures water views. The primary suite offers direct terrace access and an ensuite bath with dual vanities, upgraded shower, and a fitted walk-in closet. A welcoming guest bedroom has an ensuite bath with upgraded spa tub. Ownership includes membership to the private Bay Isles Beach Club with deeded beach access and facilities for social activities. Residents of Fairway Bay enjoy walking trails, heated pools, a fitness center, tennis and pickleball courts, clubhouse amenities, and kayak launches. Optional membership to the Longboat Key Club provides access to championship golf, Har Tru tennis, spa services, waterfront dining, and a deep-water marina. Ideally located just minutes from St. Armands Circle and downtown Sarasota’s renowned arts and dining scene, this residence offers comfort, convenience, and an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle within one of the island’s most desirable gated communities.

2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code

Value opportunity behind the gates of Bay Isles in the highly sought after Fairway Bay community. This partially furnished move-in ready two-bedroom, two-bath residence includes a valuable under-building garage parking space. Enjoy peaceful views of Sarasota Bay from an open floor plan designed to maximize natural light and comfortable indoor and outdoor living. White tile flooring runs throughout the main living areas, while a wall of sliding glass doors opens to the terrace, ideal for relaxing outdoor eating. The kitchen features light cabinetry, custom lighting and captures water views. The primary suite offers direct terrace access and an ensuite bath with dual vanities, upgraded shower, and a fitted walk-in closet. A welcoming guest bedroom has an ensuite bath with upgraded spa tub. Ownership includes membership to the private Bay Isles Beach Club with deeded beach access and facilities for social activities. Residents of Fairway Bay enjoy walking trails, heated pools, a fitness center, tennis and pickleball courts, clubhouse amenities, and kayak launches. Optional membership to the Longboat Key Club provides access to championship golf, Har Tru tennis, spa services, waterfront dining, and a deep-water marina. Ideally located just minutes from St. Armands Circle and downtown Sarasota’s renowned arts and dining scene, this residence offers comfort, convenience, and an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle within one of the island’s most desirable gated communities.

1932 Harbourside Drive Unit 242, Longboat Key

3070 Grand Bay Boulevard Unit 632, Longboat Key

$675,000

Experience ultimate maintenance-free coastal living in this move-in ready 2BR/2BA Bimini model, perfectly positioned behind the secure gates of Bay Isles in Grand Bay. Located on the third living level of Building 6, this exceptional residence features an expansive, nearly 400 sq. ft. wraparound terrace showcasing panoramic Sarasota Bay views and unforgettable sunrises and sunsets. No detail has been overlooked in this thoughtfully modernized home: • Kitchen & Systems: Significantly updated kitchen and new water heater (2026); high-efficiency variable-speed HVAC with humidity control, Wi-Fi thermostat, and 12-year compressor warranty (2024). • Appliances & Finishes: New refrigerator, washer, dryer, updated plumbing/lighting fixtures, and fresh paint (2023). • Luxury Conveniences: Hunter Douglas battery-operated, remote-controlled window treatments (2023) and a renewed, transferable Home-Tech service contract. Grand Bay offers a world-class resort lifestyle with two heated pools and spas, tennis courts, a fitness center, an active clubhouse, and scenic trails along the bay front, marina, and golf courses. Best of all, enjoy private beach access at the gated Bay Isles Beach Club on the Gulf of Mexico. Fine dining along Gulf of Mexico Drive, St. Armands Circle, and downtown Sarasota are all just minutes away.

2 Beds ⋅ 2 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code

Experience ultimate maintenance-free coastal living in this move-in ready 2BR/2BA Bimini model, perfectly positioned behind the secure gates of Bay Isles in Grand Bay. Located on the third living level of Building 6, this exceptional residence features an expansive, nearly 400 sq. ft. wraparound terrace showcasing panoramic Sarasota Bay views and unforgettable sunrises and sunsets. No detail has been overlooked in this thoughtfully modernized home: • Kitchen & Systems: Significantly updated kitchen and new water heater (2026); high-efficiency variable-speed HVAC with humidity control, Wi-Fi thermostat, and 12-year compressor warranty (2024). • Appliances & Finishes: New refrigerator, washer, dryer, updated plumbing/lighting fixtures, and fresh paint (2023). • Luxury Conveniences: Hunter Douglas battery-operated, remote-controlled window treatments (2023) and a renewed, transferable Home-Tech service contract. Grand Bay offers a world-class resort lifestyle with two heated pools and spas, tennis courts, a fitness center, an active clubhouse, and scenic trails along the bay front, marina, and golf courses. Best of all, enjoy private beach access at the gated Bay Isles Beach Club on the Gulf of Mexico. Fine dining along Gulf of Mexico Drive, St. Armands Circle, and downtown Sarasota are all just minutes away.

3070 Grand Bay Boulevard Unit 632, Longboat Key

$3,400,000

Enter the gates of Sandhamn Place and let your senses delight in all that this small enclave has to offer. Often referred to as the "hidden gem" of Longboat Key, a canopied private drive leads to sweeping views of Sarasota Bay where dolphins, manatees and paddleboarders drift by and where through traffic & unattractive seawalls are non existent. The exclusive amenities of this secluded community of just nine custom designed bayfront residences include a tennis court, marina with deeded boat slip and community maintenance and all only minutes from the island's finest dining , shopping and the natural beauty of Durante Park with 32 acres of walking trails and bayfront boardwalks. This Key West inspired home sits at the end of a quiet cul de sac, offering a relaxed coastal lifestyle, heated pool and observation dock with a serene primary suite & balcony overlooking the expansive blue waters of Sarasota Bay; truly waterfront living at its finest on Longboat Key.

3 Beds ⋅ 3 Baths ⋅ Sandhamn Sub SubDv. ⋅ 34228 Zip Code

Enter the gates of Sandhamn Place and let your senses delight in all that this small enclave has to offer. Often referred to as the "hidden gem" of Longboat Key, a canopied private drive leads to sweeping views of Sarasota Bay where dolphins, manatees and paddleboarders drift by and where through traffic & unattractive seawalls are non existent. The exclusive amenities of this secluded community of just nine custom designed bayfront residences include a tennis court, marina with deeded boat slip and community maintenance and all only minutes from the island's finest dining , shopping and the natural beauty of Durante Park with 32 acres of walking trails and bayfront boardwalks. This Key West inspired home sits at the end of a quiet cul de sac, offering a relaxed coastal lifestyle, heated pool and observation dock with a serene primary suite & balcony overlooking the expansive blue waters of Sarasota Bay; truly waterfront living at its finest on Longboat Key.

5422 Sandhamn Place, Longboat Key

435 L Ambiance Drive Unit L707, Longboat Key

$2,850,000

Enjoy some of the most spectacular views on Longboat Key from this desirable seventh-floor corner residence at L’Ambiance. With sweeping views of the Gulf of Mexico, Sarasota Bay, downtown Sarasota, and the lush fairways of the Longboat Key Club golf course, there is something beautiful to enjoy from every direction. Expansive walls of glass and a wraparound terrace make the most of this exceptional setting. A private elevator opens to your own foyer, welcoming you into a spacious residence filled with natural light. Pecky cypress ceiling accents, custom built-ins, soft cove lighting, and a convenient dry bar complement the generous living and dining areas. The kitchen features a center island with the added convenience of refrigerator and freezer drawers, while the breakfast nook opens directly to the terrace.The thoughtfully designed split-bedroom floor plan offers two bedrooms and two-and-a-half baths, providing privacy for owners and guests. The primary suite enjoys beautiful Gulf views and includes a recently customized, oversized closet. An added convenience is the availability of reservable guest suites, providing comfortable accommodations for visiting family and friends without the need to maintain an additional bedroom. Other features include motorized window treatments, a full-sized laundry room, separate service entrance, private parking, a storage unit, and an assigned wine locker. L’Ambiance is highly regarded on the island and is known for its beautifully maintained grounds, privacy, and exceptional service. A fountain-lined entrance leads to a 24-hour staffed gatehouse and secure building with a full-time concierge. Residents enjoy a beachfront swimming pool, direct beach access, two Har-Tru tennis courts, a fitness center, social rooms, and guest parking. Located just minutes from St. Armands Circle and downtown Sarasota, you'll enjoy convenient access to outstanding restaurants, shopping, and cultural attractions. Optional membership at the Longboat Key Club offers golf, tennis, boating, dining, and an active social calendar. with its outstanding views, spacious terrace, and the convenience of luxury condominium living, this residence offers a wonderful opportunity to enjoy the Longboat Key lifestyle.

2 Beds ⋅ 3 Baths ⋅ L'Ambiance SubDv. ⋅ 34228 Zip Code

Enjoy some of the most spectacular views on Longboat Key from this desirable seventh-floor corner residence at L’Ambiance. With sweeping views of the Gulf of Mexico, Sarasota Bay, downtown Sarasota, and the lush fairways of the Longboat Key Club golf course, there is something beautiful to enjoy from every direction. Expansive walls of glass and a wraparound terrace make the most of this exceptional setting. A private elevator opens to your own foyer, welcoming you into a spacious residence filled with natural light. Pecky cypress ceiling accents, custom built-ins, soft cove lighting, and a convenient dry bar complement the generous living and dining areas. The kitchen features a center island with the added convenience of refrigerator and freezer drawers, while the breakfast nook opens directly to the terrace.The thoughtfully designed split-bedroom floor plan offers two bedrooms and two-and-a-half baths, providing privacy for owners and guests. The primary suite enjoys beautiful Gulf views and includes a recently customized, oversized closet. An added convenience is the availability of reservable guest suites, providing comfortable accommodations for visiting family and friends without the need to maintain an additional bedroom. Other features include motorized window treatments, a full-sized laundry room, separate service entrance, private parking, a storage unit, and an assigned wine locker. L’Ambiance is highly regarded on the island and is known for its beautifully maintained grounds, privacy, and exceptional service. A fountain-lined entrance leads to a 24-hour staffed gatehouse and secure building with a full-time concierge. Residents enjoy a beachfront swimming pool, direct beach access, two Har-Tru tennis courts, a fitness center, social rooms, and guest parking. Located just minutes from St. Armands Circle and downtown Sarasota, you'll enjoy convenient access to outstanding restaurants, shopping, and cultural attractions. Optional membership at the Longboat Key Club offers golf, tennis, boating, dining, and an active social calendar. with its outstanding views, spacious terrace, and the convenience of luxury condominium living, this residence offers a wonderful opportunity to enjoy the Longboat Key lifestyle.

435 L Ambiance Drive Unit L707, Longboat Key

3030 Grand Bay Boulevard Unit 315, Longboat Key

$1,395,000

Welcome to the sophisticated elegance of this stunning 3 bedroom, 3.5 bath end unit, with its open floor plan and mesmerizing views of Sarasota Bay, downtown skyline, LBK Club marina and golf course. The foyer, with its artfully executed console, ushers you into a light, airy great room with elevated ceilings, discreet art deco bar, floor-to-ceiling sliders, marble flooring, and expansive wraparound terrace. Automated shades grace the space and ensure year round comfort. The updated open kitchen, with its ample cabinetry and new white quartz countertops and backsplash, flows seamlessly into the dining area and great room, making entertaining a pleasure. Retreat to the luxurious owner's suite with its serene bay views, sliders to the bayfront terrace, and a spacious marble bath. Guests will relish the ensuite guest bedroom located on the west side of the residence, which offers relaxing privacy and its own terrace access. A conveniently located office/den can be closed off from the great room and, with its own ensuite bath, can easily be used as a 3rd bedroom. Enjoy a dip in the softly lighted resort style pool located below, a coveted retreat for you and your guests. The condominium is being sold partially furnished so new owners can start enjoying their new home immediately. Grand Bay residents enjoy exceptional resort like amenities, with a state of the art fitness center, sauna, two heated pools, a spa, two Har-Tru tennis courts, 24-hour security gate, and on site management. Relax in the natural beauty that abounds along the miles of sidewalks and trails winding throughout Bay Isles. Membership in the coveted Bay Isles beach club directly on the Gulf is included for a modest fee, with its private beach access, outdoor grills, covered gathering areas, full kitchen, key card gated parking, changing rooms, restrooms and showers. Schedule your private tour now and start living the Florida dream!

3 Beds ⋅ 4 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code

Welcome to the sophisticated elegance of this stunning 3 bedroom, 3.5 bath end unit, with its open floor plan and mesmerizing views of Sarasota Bay, downtown skyline, LBK Club marina and golf course. The foyer, with its artfully executed console, ushers you into a light, airy great room with elevated ceilings, discreet art deco bar, floor-to-ceiling sliders, marble flooring, and expansive wraparound terrace. Automated shades grace the space and ensure year round comfort. The updated open kitchen, with its ample cabinetry and new white quartz countertops and backsplash, flows seamlessly into the dining area and great room, making entertaining a pleasure. Retreat to the luxurious owner's suite with its serene bay views, sliders to the bayfront terrace, and a spacious marble bath. Guests will relish the ensuite guest bedroom located on the west side of the residence, which offers relaxing privacy and its own terrace access. A conveniently located office/den can be closed off from the great room and, with its own ensuite bath, can easily be used as a 3rd bedroom. Enjoy a dip in the softly lighted resort style pool located below, a coveted retreat for you and your guests. The condominium is being sold partially furnished so new owners can start enjoying their new home immediately. Grand Bay residents enjoy exceptional resort like amenities, with a state of the art fitness center, sauna, two heated pools, a spa, two Har-Tru tennis courts, 24-hour security gate, and on site management. Relax in the natural beauty that abounds along the miles of sidewalks and trails winding throughout Bay Isles. Membership in the coveted Bay Isles beach club directly on the Gulf is included for a modest fee, with its private beach access, outdoor grills, covered gathering areas, full kitchen, key card gated parking, changing rooms, restrooms and showers. Schedule your private tour now and start living the Florida dream!

3030 Grand Bay Boulevard Unit 315, Longboat Key

2800 Harbourside Drive Unit E06, Longboat Key

$275,000

Embrace effortless coastal living with this prime 55-foot boat slip in an elite deep-water harbor on scenic Longboat Key, perfectly positioned just off Sarasota Bay. Sized to fit vessels up to 50 feet with a 19-foot beam total length, the slip comes fully equipped with water, high-speed Wi-Fi, and a private metered power pedestal. Marina residents enjoy exceptional conveniences including a full-service fuel station, flexible pump-out service, a complimentary shuttle to St. Armands, and a 24-hour bathhouse with laundry and a ship store. Tailor your coastal lifestyle further with optional upgrades: join the Bay Isle Beach Club for exclusive beachfront sunset access, or secure a membership at the prestigious Longboat Key Club for resort pools and fine dining. Situated only half a mile from Publix, CVS, and local conveniences, this is your ultimate island headquarters.

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

Embrace effortless coastal living with this prime 55-foot boat slip in an elite deep-water harbor on scenic Longboat Key, perfectly positioned just off Sarasota Bay. Sized to fit vessels up to 50 feet with a 19-foot beam total length, the slip comes fully equipped with water, high-speed Wi-Fi, and a private metered power pedestal. Marina residents enjoy exceptional conveniences including a full-service fuel station, flexible pump-out service, a complimentary shuttle to St. Armands, and a 24-hour bathhouse with laundry and a ship store. Tailor your coastal lifestyle further with optional upgrades: join the Bay Isle Beach Club for exclusive beachfront sunset access, or secure a membership at the prestigious Longboat Key Club for resort pools and fine dining. Situated only half a mile from Publix, CVS, and local conveniences, this is your ultimate island headquarters.

2800 Harbourside Drive Unit E06, Longboat Key

$589,000

Experience refined coastal living at Sutton Place on Longboat Key, where an effortless Gulf-to-Bay lifestyle awaits. Ideally situated mid-key, this premier address offers rare peace of mind alongside private beach access just to the north at 4415 Gulf of Mexico Drive. Beyond the sand, you are minutes from St. Armands Circle, downtown Sarasota, and Anna Maria Island, and only a half-mile from Bayfront Park’s pickleball courts, dog park, playground, and walking trails. Sutton Place provides an exceptional suite of resort-style amenities. On the Gulf side, enjoy a covered beachfront pavilion with gated ample parking, restrooms, tables, outdoor showers, chair storage, and beach lockers ($30/yr). Bayside, take advantage of two heated pools, an active clubhouse, BBQ areas, a fishing pier, and a marina with boat slips for vessels up to 23’ ($300/yr), plus a kayak launch with storage ($150/yr; two kayaks included in the sale). A new 38’x33’ fitness center and sauna facility is also underway. The community is pet-friendly (two pets up to 25 lbs) and permits flexible 1-month minimum leasing twice per year. Inside this spacious 3-bedroom, 2.5-bathroom, 1,450-sq-ft townhouse, large diagonal porcelain tile flooring flows seamlessly throughout the entire property. The living and dining spaces feature classic plantation shutters, a ceiling fan, and a deep 7’x3’ under-stair storage closet. The well-appointed kitchen is outfitted with a sleek Samsung stainless steel appliance package—complete with a convection oven and built-in microwave—and casual breakfast bar seating for two. Just off the kitchen, a dedicated spacious laundry room with a closing privacy door houses GE laundry units, the water heater, an exterior fire exit door, and generous cabinetry and shelving for additional storage. The attached 20’ x 18' 1-car garage features durable tile flooring, dual side bump-outs for extra gear, a secondary refrigerator, and extensive storage capacity. Out back, step through sliders to your private screened lanai, positioned directly west-facing with sunshades to capture breathtaking evening sunsets over serene greenbelt views. Ascend the carpeted staircase to the tranquil primary suite, highlighted by plantation shutters, custom closet built-ins, and an en-suite bath finished with designer tilework and a sleek, glass-enclosed walk-in shower. Down the hall, the second bedroom offers a generous walk-in closet, while the updated full guest bath features a quartz-topped vanity and a glass-enclosed walk-in shower. Full hurricane impact windows throughout ensure pin-drop quiet and restful nights in every room. Exceptional resilience comes standard at an 11’ baseline elevation, with zero water or wind damage from recent storms. Notable mechanicals and structural updates include full impact windows and sliders, a 2023 water heater, a 2018 HVAC maintained on an active service contract, and a clean 10-year milestone certification passed in January 2024.

3 Beds ⋅ 3 Baths ⋅ Sutton Place Condo SubDv. ⋅ 34228 Zip Code

Experience refined coastal living at Sutton Place on Longboat Key, where an effortless Gulf-to-Bay lifestyle awaits. Ideally situated mid-key, this premier address offers rare peace of mind alongside private beach access just to the north at 4415 Gulf of Mexico Drive. Beyond the sand, you are minutes from St. Armands Circle, downtown Sarasota, and Anna Maria Island, and only a half-mile from Bayfront Park’s pickleball courts, dog park, playground, and walking trails. Sutton Place provides an exceptional suite of resort-style amenities. On the Gulf side, enjoy a covered beachfront pavilion with gated ample parking, restrooms, tables, outdoor showers, chair storage, and beach lockers ($30/yr). Bayside, take advantage of two heated pools, an active clubhouse, BBQ areas, a fishing pier, and a marina with boat slips for vessels up to 23’ ($300/yr), plus a kayak launch with storage ($150/yr; two kayaks included in the sale). A new 38’x33’ fitness center and sauna facility is also underway. The community is pet-friendly (two pets up to 25 lbs) and permits flexible 1-month minimum leasing twice per year. Inside this spacious 3-bedroom, 2.5-bathroom, 1,450-sq-ft townhouse, large diagonal porcelain tile flooring flows seamlessly throughout the entire property. The living and dining spaces feature classic plantation shutters, a ceiling fan, and a deep 7’x3’ under-stair storage closet. The well-appointed kitchen is outfitted with a sleek Samsung stainless steel appliance package—complete with a convection oven and built-in microwave—and casual breakfast bar seating for two. Just off the kitchen, a dedicated spacious laundry room with a closing privacy door houses GE laundry units, the water heater, an exterior fire exit door, and generous cabinetry and shelving for additional storage. The attached 20’ x 18' 1-car garage features durable tile flooring, dual side bump-outs for extra gear, a secondary refrigerator, and extensive storage capacity. Out back, step through sliders to your private screened lanai, positioned directly west-facing with sunshades to capture breathtaking evening sunsets over serene greenbelt views. Ascend the carpeted staircase to the tranquil primary suite, highlighted by plantation shutters, custom closet built-ins, and an en-suite bath finished with designer tilework and a sleek, glass-enclosed walk-in shower. Down the hall, the second bedroom offers a generous walk-in closet, while the updated full guest bath features a quartz-topped vanity and a glass-enclosed walk-in shower. Full hurricane impact windows throughout ensure pin-drop quiet and restful nights in every room. Exceptional resilience comes standard at an 11’ baseline elevation, with zero water or wind damage from recent storms. Notable mechanicals and structural updates include full impact windows and sliders, a 2023 water heater, a 2018 HVAC maintained on an active service contract, and a clean 10-year milestone certification passed in January 2024.

575 Sutton Place, Longboat Key

2600 Harbourside Dr Unit N-09, Longboat Key

$225,000

Only slip available on N-dock! Slip N-09 is a 45 x 20 Boat Slip at Longboat Key Moorings Marina for sale. The slip is located on the north side of the pier. Exceptional views of Sarasota Bay and the city skyline, mid-pier for easy access. LBK Club membership is optional. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes restaurant, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 40 LOA.

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

Only slip available on N-dock! Slip N-09 is a 45 x 20 Boat Slip at Longboat Key Moorings Marina for sale. The slip is located on the north side of the pier. Exceptional views of Sarasota Bay and the city skyline, mid-pier for easy access. LBK Club membership is optional. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes restaurant, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 40 LOA.

2600 Harbourside Dr Unit N-09, Longboat Key

3070 Grand Bay Boulevard Unit 645, Longboat Key

$925,000

Fully renovated 2BR/2BA Grand Bay condo with 2 parking spaces and Sarasota Bay and downtown views. Bright interiors feature easy-care tile floors and a kitchen with quartz counters, breakfast bar, and high-end appliances. Partially furnished with Robb & Stuckey pieces. A large wraparound balcony overlooks the Longboat Key Club golf course, Sarasota Bay, and downtown Sarasota. This gated community offers 24/7 guards, on-site management, and a clubhouse with fitness center and party room with bar and chef’s kitchen. Outside, enjoy the pool, spa, wading pool, grill area, and tennis courts. Bay Isles’ private beach club offers a pavilion, grills, and beach volleyball. Sidewalks throughout. Walk to Publix, CVS Pharmacy, a nail salon, and other shops. Optional Longboat Key Club membership (separate fee): 45 holes of golf, marina, beach club, spa, Har-Tru tennis courts, pickleball courts, and 5 restaurants. Resort-style living, ready to enjoy.

2 Beds ⋅ 2 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code

Fully renovated 2BR/2BA Grand Bay condo with 2 parking spaces and Sarasota Bay and downtown views. Bright interiors feature easy-care tile floors and a kitchen with quartz counters, breakfast bar, and high-end appliances. Partially furnished with Robb & Stuckey pieces. A large wraparound balcony overlooks the Longboat Key Club golf course, Sarasota Bay, and downtown Sarasota. This gated community offers 24/7 guards, on-site management, and a clubhouse with fitness center and party room with bar and chef’s kitchen. Outside, enjoy the pool, spa, wading pool, grill area, and tennis courts. Bay Isles’ private beach club offers a pavilion, grills, and beach volleyball. Sidewalks throughout. Walk to Publix, CVS Pharmacy, a nail salon, and other shops. Optional Longboat Key Club membership (separate fee): 45 holes of golf, marina, beach club, spa, Har-Tru tennis courts, pickleball courts, and 5 restaurants. Resort-style living, ready to enjoy.

3070 Grand Bay Boulevard Unit 645, Longboat Key

1241 Gulf Of Mexico Drive Unit 803, Longboat Key

$3,195,000

The epitome of beachfront luxury awaits in this meticulously renovated 8th-floor residence at the prestigious Water Club on Longboat Key. This stunning 3-bedroom, 4-bath home is a rare offering in one of the Gulf Coast’s premier direct beachfront communities. From the moment you step off the private elevator into the foyer, you’re greeted by serene neutral tones, 10-foot ceilings, and wide-plank engineered hardwood floors that set the tone for elegant coastal living. Walls of glass frame spectacular, unobstructed views of the Gulf of Mexico, filling the expansive living spaces with natural light and breathtaking scenery. The open-concept floor plan seamlessly blends comfort and sophistication, enhanced by recessed lighting and a calming contemporary palette. The spacious living room flows onto a generous beachfront terrace—perfect for soaking in mesmerizing views and the soothing sounds of the surf. The designer kitchen is a showcase of modern design, featuring white glass subway tile backsplash, solid wood cabinetry, an induction cooktop with pot filler, Sub-Zero refrigerator, and premium stainless-steel appliances. A large center island and adjacent breakfast area provide the perfect setting for casual meals with sweeping water views. Each guest suite is a luxurious haven, including one with double queen beds and an en suite bath with soaking tub and separate shower. The third bedroom is currently configured as an office, yet spacious enough to accommodate a queen-size bed, and offers beautiful views of downtown Sarasota. The primary suite is a private retreat, featuring its own beachfront terrace, a separate sitting area, custom-fitted dual closets, and a spacious study with built-in office space. The spa-inspired primary bath is the essence of indulgence with white marble floors and walls, a freestanding soaking tub, and a glass-enclosed walk-in shower. Additional highlights include TWO under-building covered garage parking spaces, a private storage closet, and access to all the amenities of the Water Club—24-hour security, full concierge service, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and over 16 acres of pristine beachfront grounds. This is beachfront living redefined! Located just a short distance to St. Armands and downtown Sarasota's shopping, dining & cultural events.

3 Beds ⋅ 4 Baths ⋅ Water Club At Longboat Key SubDv. ⋅ 34228 Zip Code

The epitome of beachfront luxury awaits in this meticulously renovated 8th-floor residence at the prestigious Water Club on Longboat Key. This stunning 3-bedroom, 4-bath home is a rare offering in one of the Gulf Coast’s premier direct beachfront communities. From the moment you step off the private elevator into the foyer, you’re greeted by serene neutral tones, 10-foot ceilings, and wide-plank engineered hardwood floors that set the tone for elegant coastal living. Walls of glass frame spectacular, unobstructed views of the Gulf of Mexico, filling the expansive living spaces with natural light and breathtaking scenery. The open-concept floor plan seamlessly blends comfort and sophistication, enhanced by recessed lighting and a calming contemporary palette. The spacious living room flows onto a generous beachfront terrace—perfect for soaking in mesmerizing views and the soothing sounds of the surf. The designer kitchen is a showcase of modern design, featuring white glass subway tile backsplash, solid wood cabinetry, an induction cooktop with pot filler, Sub-Zero refrigerator, and premium stainless-steel appliances. A large center island and adjacent breakfast area provide the perfect setting for casual meals with sweeping water views. Each guest suite is a luxurious haven, including one with double queen beds and an en suite bath with soaking tub and separate shower. The third bedroom is currently configured as an office, yet spacious enough to accommodate a queen-size bed, and offers beautiful views of downtown Sarasota. The primary suite is a private retreat, featuring its own beachfront terrace, a separate sitting area, custom-fitted dual closets, and a spacious study with built-in office space. The spa-inspired primary bath is the essence of indulgence with white marble floors and walls, a freestanding soaking tub, and a glass-enclosed walk-in shower. Additional highlights include TWO under-building covered garage parking spaces, a private storage closet, and access to all the amenities of the Water Club—24-hour security, full concierge service, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and over 16 acres of pristine beachfront grounds. This is beachfront living redefined! Located just a short distance to St. Armands and downtown Sarasota's shopping, dining & cultural events.

1241 Gulf Of Mexico Drive Unit 803, Longboat Key

4370 Chatham Drive Unit 102, Longboat Key

$400,000

Exceptional Value on Longboat Key! Seller has found her new home and is offering this beautifully updated, move-in-ready, turnkey-furnished condo priced below market value! Enjoy a desirable open floor plan with the enclosed lanai incorporated into the living area, creating extra living space and showcasing lovely boat basin views. Updates include luxury waterproof flooring, fresh paint, popcorn ceiling removal, an updated kitchen with granite countertops, beautifully updated bathrooms, newer A/C, new water heater and range. New hurricane-impact windows and sliders are in process, and the community features a new roof. Longboat Harbour is a well-managed, non-age-restricted, boater-friendly community with full-time staff and resort-style amenities: four heated pools, fitness center, sauna, tennis and pickleball, plus private gated and deeded beach access with private parking, indoor showers, restrooms, picnic areas and beach chair storage. Boat dock space is available for an additional fee, subject to availability. Includes deeded covered parking. Enjoy the best of Gulf-to-Bay living—boating, beaches and resort-style amenities at an outstanding value! Ideal for year-round living, a vacation retreat or investment opportunity.

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour SubDv. ⋅ 34228 Zip Code

Exceptional Value on Longboat Key! Seller has found her new home and is offering this beautifully updated, move-in-ready, turnkey-furnished condo priced below market value! Enjoy a desirable open floor plan with the enclosed lanai incorporated into the living area, creating extra living space and showcasing lovely boat basin views. Updates include luxury waterproof flooring, fresh paint, popcorn ceiling removal, an updated kitchen with granite countertops, beautifully updated bathrooms, newer A/C, new water heater and range. New hurricane-impact windows and sliders are in process, and the community features a new roof. Longboat Harbour is a well-managed, non-age-restricted, boater-friendly community with full-time staff and resort-style amenities: four heated pools, fitness center, sauna, tennis and pickleball, plus private gated and deeded beach access with private parking, indoor showers, restrooms, picnic areas and beach chair storage. Boat dock space is available for an additional fee, subject to availability. Includes deeded covered parking. Enjoy the best of Gulf-to-Bay living—boating, beaches and resort-style amenities at an outstanding value! Ideal for year-round living, a vacation retreat or investment opportunity.

4370 Chatham Drive Unit 102, Longboat Key

$499,999

Your Longboat Key lifestyle starts here! Imagine spending your mornings at the beach, afternoons by the pool, and evenings enjoying the island breeze. Located in the desirable Sutton Place community, this 2-bedroom, 1.5-bath townhome offers an incredible opportunity to create your own coastal retreat in one of Florida's most sought-after island destinations. Featuring a private garage, screened porch, and Italian tile flooring, this home is ready for your personal touch and updates. Whether you envision a stylish seasonal getaway or a comfortable year-round residence, the possibilities are yours to explore. The real highlight? The lifestyle! Sutton Place offers deeded private beach access to the Gulf, two community pools, a clubhouse, kayak storage, BBQ areas, and marina amenities with private boat slips potentially available, subject to availability and community regulations. Enjoy the best of Longboat Key living, from beautiful Gulf beaches and boating to nearby restaurants, shopping, and everything this special island has to offer. Bring your vision, make it your own, and start living the island lifestyle you've been dreaming of!

2 Beds ⋅ 2 Baths ⋅ Sutton Place Condo SubDv. ⋅ 34228 Zip Code

Your Longboat Key lifestyle starts here! Imagine spending your mornings at the beach, afternoons by the pool, and evenings enjoying the island breeze. Located in the desirable Sutton Place community, this 2-bedroom, 1.5-bath townhome offers an incredible opportunity to create your own coastal retreat in one of Florida's most sought-after island destinations. Featuring a private garage, screened porch, and Italian tile flooring, this home is ready for your personal touch and updates. Whether you envision a stylish seasonal getaway or a comfortable year-round residence, the possibilities are yours to explore. The real highlight? The lifestyle! Sutton Place offers deeded private beach access to the Gulf, two community pools, a clubhouse, kayak storage, BBQ areas, and marina amenities with private boat slips potentially available, subject to availability and community regulations. Enjoy the best of Longboat Key living, from beautiful Gulf beaches and boating to nearby restaurants, shopping, and everything this special island has to offer. Bring your vision, make it your own, and start living the island lifestyle you've been dreaming of!

597 Sutton Place, Longboat Key

1241 Gulf Of Mexico Drive Unit PH1102, Longboat Key

$5,995,000

Experience an exceptional expression of Gulf-front living in this impeccably maintained penthouse at The Water Club on Longboat Key. Occupying the coveted northwest penthouse position on the 11th floor of Building One, this pristine residence encompasses approximately 3,400 square feet with three bedrooms and four-and-a-half baths. Three separate balconies capture sweeping views of the Gulf of America, providing inviting settings for morning coffee, alfresco relaxation, and spectacular sunsets. An under-building parking space and an additional semi-private garage complement this distinguished waterfront offering. Set within 16 acres of magnificent beachfront grounds, The Water Club offers an extraordinary collection of amenities that extends the comforts of home well beyond your residence. The beautifully renovated, 18,000-square-foot clubhouse provides elegant spaces for relaxation, recreation, and entertaining, including a club room with billiards, a library with fireplace, and a ballroom with catering kitchen. Four lighted Har-Tru tennis courts, a heated junior Olympic pool, hot tub, spa, and fitness center create a resort experience, while a firepit, grills, and direct access to a beautiful stretch of beach invite you to embrace the coastal lifestyle. Gated security, concierge services, on-site management, and climate-controlled storage add everyday comfort and convenience. Ideally situated at the southern end of Longboat Key, this residence places you minutes from the boutiques and dining of St. Armands Circle, downtown Sarasota’s vibrant waterfront and cultural attractions, and an array of exceptional restaurants. Nearby conveniences include Publix and CVS, with the Longboat Key Club’s golf, tennis, and dining offerings close at hand. The neighboring St. Regis further enhances this desirable coastal setting, and Sarasota Bradenton International Airport is approximately 20 minutes away. Welcoming up to two pets, The Water Club is equally appealing as a full-time residence or a refined seasonal retreat. Discover the rare combination of penthouse privacy, generous living spaces, captivating Gulf views, and an exceptional beachfront lifestyle. Schedule your private showing today.

3 Beds ⋅ 5 Baths ⋅ Water Club At Longboat Key SubDv. ⋅ 34228 Zip Code

Experience an exceptional expression of Gulf-front living in this impeccably maintained penthouse at The Water Club on Longboat Key. Occupying the coveted northwest penthouse position on the 11th floor of Building One, this pristine residence encompasses approximately 3,400 square feet with three bedrooms and four-and-a-half baths. Three separate balconies capture sweeping views of the Gulf of America, providing inviting settings for morning coffee, alfresco relaxation, and spectacular sunsets. An under-building parking space and an additional semi-private garage complement this distinguished waterfront offering. Set within 16 acres of magnificent beachfront grounds, The Water Club offers an extraordinary collection of amenities that extends the comforts of home well beyond your residence. The beautifully renovated, 18,000-square-foot clubhouse provides elegant spaces for relaxation, recreation, and entertaining, including a club room with billiards, a library with fireplace, and a ballroom with catering kitchen. Four lighted Har-Tru tennis courts, a heated junior Olympic pool, hot tub, spa, and fitness center create a resort experience, while a firepit, grills, and direct access to a beautiful stretch of beach invite you to embrace the coastal lifestyle. Gated security, concierge services, on-site management, and climate-controlled storage add everyday comfort and convenience. Ideally situated at the southern end of Longboat Key, this residence places you minutes from the boutiques and dining of St. Armands Circle, downtown Sarasota’s vibrant waterfront and cultural attractions, and an array of exceptional restaurants. Nearby conveniences include Publix and CVS, with the Longboat Key Club’s golf, tennis, and dining offerings close at hand. The neighboring St. Regis further enhances this desirable coastal setting, and Sarasota Bradenton International Airport is approximately 20 minutes away. Welcoming up to two pets, The Water Club is equally appealing as a full-time residence or a refined seasonal retreat. Discover the rare combination of penthouse privacy, generous living spaces, captivating Gulf views, and an exceptional beachfront lifestyle. Schedule your private showing today.

1241 Gulf Of Mexico Drive Unit PH1102, Longboat Key

1591 Gulf Of Mexico Drive Unit 512, Longboat Key

$1,999,999

Fractional Ownership. FRACTIONAL OWNERSHIP AT THE ST. REGIS LONGBOAT KEY. Experience an extraordinary waterfront lifestyle with the opportunity to own a portion of a beautifully appointed private residence at one of Florida’s most prestigious luxury resorts. Located on the fifth floor of the Champagne building, Residence 512 offers 2,154 square feet of refined interior living space, two spacious bedrooms, two-and-a-half bathrooms, and an expansive private terrace overlooking the resort surroundings and Sarasota Bay. Thoughtfully designed for comfort and entertaining, the residence features an open living and dining area, floor-to-ceiling glass, and a beautifully equipped kitchen with Wolf and Sub-Zero appliances. The generous primary suite includes a luxurious bathroom with dual vanities, a soaking tub, and a separate walk-in shower. Offered fully furnished with Restoration Hardware interiors, the residence also features a private two-car garage and convenient elevator access. Ownership provides access to the exceptional amenities and personalized services of The St. Regis Longboat Key, including pristine Gulf beaches, resort-style pools, private residential amenities, fine dining, the St. Regis Spa, fitness facilities, and signature concierge and butler services. This distinctive fractional ownership opportunity allows buyers to enjoy the benefits of a luxury waterfront residence without the commitment of purchasing and maintaining an entire condominium. Ownership interests are offered in 30-day increments, with the opportunity to acquire multiple periods. An additional benefit is the inclusion of a St. Regis Resort Membership, providing year-round access to resort amenities without the customary membership initiation fee or annual dues, subject to the applicable membership terms. Discover a more flexible way to experience the elegance, service, and exceptional coastal lifestyle of The St. Regis Longboat Key.

2 Beds ⋅ 3 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code

Fractional Ownership. FRACTIONAL OWNERSHIP AT THE ST. REGIS LONGBOAT KEY. Experience an extraordinary waterfront lifestyle with the opportunity to own a portion of a beautifully appointed private residence at one of Florida’s most prestigious luxury resorts. Located on the fifth floor of the Champagne building, Residence 512 offers 2,154 square feet of refined interior living space, two spacious bedrooms, two-and-a-half bathrooms, and an expansive private terrace overlooking the resort surroundings and Sarasota Bay. Thoughtfully designed for comfort and entertaining, the residence features an open living and dining area, floor-to-ceiling glass, and a beautifully equipped kitchen with Wolf and Sub-Zero appliances. The generous primary suite includes a luxurious bathroom with dual vanities, a soaking tub, and a separate walk-in shower. Offered fully furnished with Restoration Hardware interiors, the residence also features a private two-car garage and convenient elevator access. Ownership provides access to the exceptional amenities and personalized services of The St. Regis Longboat Key, including pristine Gulf beaches, resort-style pools, private residential amenities, fine dining, the St. Regis Spa, fitness facilities, and signature concierge and butler services. This distinctive fractional ownership opportunity allows buyers to enjoy the benefits of a luxury waterfront residence without the commitment of purchasing and maintaining an entire condominium. Ownership interests are offered in 30-day increments, with the opportunity to acquire multiple periods. An additional benefit is the inclusion of a St. Regis Resort Membership, providing year-round access to resort amenities without the customary membership initiation fee or annual dues, subject to the applicable membership terms. Discover a more flexible way to experience the elegance, service, and exceptional coastal lifestyle of The St. Regis Longboat Key.

1591 Gulf Of Mexico Drive Unit 512, Longboat Key

4401 Gulf Of Mexico Drive Unit 601, Longboat Key

$995,000

Separate property Boat slip at the Boathouse can be included with the purchase of this 2 bedroom, 2 bath residence offering sweeping sixth-floor views of the Gulf of Mexico from Longboat Harbor Towers. This rare southwest corner condominium has completely unobstructed views west and south providing one of the most interesting and protected waterfront visages available anywhere on the key. In largely original condition, this spacious property presents an exceptional opportunity for renovation and customization in one of Longboat Key’s most coveted waterfront locations. Few properties combine this level of potential with such a remarkable setting. Positioned directly on the Gulf with more than 400 feet of pristine beach frontage, this fully amenitied community also enjoys eastern views of Sarasota Bay and the downtown Sarasota skyline—delivering breathtaking sunrises and sunsets from the same home. The southwest exposure also provides much more to view and enjoy with site lines extending down the entire length of the key. Common areas have been recently renovated and include a beachfront, heated, saltwater pool, a complete exercise room and spacious lounge with pool baths. Longboat Key is a sought-after barrier island community known for its relaxed coastal lifestyle, pristine beaches, and upscale residential atmosphere. Ideally located just minutes from the cultural and social energy of Sarasota, residents enjoy convenient access to world-class arts, dining, and entertainment while maintaining a sense of privacy and tranquility. A short drive south leads to iconic St. Armands Circle, renowned for its eclectic mix of boutiques, fine dining, cafés, and year-round events. Beyond St. Armands, downtown Sarasota offers theaters, galleries, live music, waterfront parks, and a thriving culinary scene, making Longboat Key an exceptional blend of island serenity and vibrant city living. This seller is also including a BOAT SLIP at The Boathouse, adjacent to the Dry Dock Restaurant just minutes away. Buy the condo and get the slip for a complete Florida lifestyle!

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour Towers SubDv. ⋅ 34228 Zip Code

Separate property Boat slip at the Boathouse can be included with the purchase of this 2 bedroom, 2 bath residence offering sweeping sixth-floor views of the Gulf of Mexico from Longboat Harbor Towers. This rare southwest corner condominium has completely unobstructed views west and south providing one of the most interesting and protected waterfront visages available anywhere on the key. In largely original condition, this spacious property presents an exceptional opportunity for renovation and customization in one of Longboat Key’s most coveted waterfront locations. Few properties combine this level of potential with such a remarkable setting. Positioned directly on the Gulf with more than 400 feet of pristine beach frontage, this fully amenitied community also enjoys eastern views of Sarasota Bay and the downtown Sarasota skyline—delivering breathtaking sunrises and sunsets from the same home. The southwest exposure also provides much more to view and enjoy with site lines extending down the entire length of the key. Common areas have been recently renovated and include a beachfront, heated, saltwater pool, a complete exercise room and spacious lounge with pool baths. Longboat Key is a sought-after barrier island community known for its relaxed coastal lifestyle, pristine beaches, and upscale residential atmosphere. Ideally located just minutes from the cultural and social energy of Sarasota, residents enjoy convenient access to world-class arts, dining, and entertainment while maintaining a sense of privacy and tranquility. A short drive south leads to iconic St. Armands Circle, renowned for its eclectic mix of boutiques, fine dining, cafés, and year-round events. Beyond St. Armands, downtown Sarasota offers theaters, galleries, live music, waterfront parks, and a thriving culinary scene, making Longboat Key an exceptional blend of island serenity and vibrant city living. This seller is also including a BOAT SLIP at The Boathouse, adjacent to the Dry Dock Restaurant just minutes away. Buy the condo and get the slip for a complete Florida lifestyle!

4401 Gulf Of Mexico Drive Unit 601, Longboat Key

$4,980,000

Some of the World’s Most Desirable Addresses Aren’t Reached by Road. There is an unmistakable distinction between owning a beautiful waterfront home and owning a private island retreat. At 7147 La Lenaire Drive, on the intimate shores of Jewfish Key, that distinction becomes extraordinary. Reached exclusively by boat, this remarkable estate offers a level of escape, natural beauty, and understated luxury in that is becoming increasingly difficult to find along Florida’s Gulf Coast. Set on approximately 1.35 acres amid a limited enclave of island residences, this five-bedroom, five-and-a-half-bath waterfront estate is as captivating in its architecture as it is in its setting. An inspired collection of elevated pavilions, interconnected by covered timber walkways, creates the atmosphere of a secluded luxury resort, where open-air living, beautifully appointed accommodations, and the surrounding tropical landscape come together in perfect harmony. From the moment you enter, the architecture makes an impression. Dramatic vaulted ceilings, magnificent exposed timber beams, rich natural wood, and expansive walls of glass lend the interiors an effortless sophistication. Sunlight moves through the living spaces, while the surrounding palms and shimmering water provide an ever-changing backdrop. Every architectural element contributes to a sense of warmth, grandeur, and individuality. Designed to accommodate both memorable entertaining and leisurely island living, the impressive great room flows into a beautifully updated kitchen with an expansive gathering island, sleek white cabinetry, stone countertops, and stainless steel appliances. Generous dining and lounging spaces invite everything from intimate evenings to extended visits with family and friends, all surrounded by the beauty of the island. The residence’s thoughtfully separated bedroom accommodations provide a wonderful balance of togetherness and privacy. The primary retreat is a sanctuary of its own, featuring soaring ceilings, captivating water views, and a beautifully appointed bath with a freestanding soaking tub overlooking the bay. Additional guest accommodations, including a separate suite with its own kitchen and bath, offer an elevated experience for extended visitors. Outdoors, the property becomes a private destination unto itself. An expansive sun-drenched deck surrounds the spectacular pool and spa, framed by graceful palms and the brilliant colors of the surrounding water. A beautifully crafted covered entertaining pavilion, complete with an outdoor kitchen, creates the perfect setting for evenings with friends. Screened gathering areas, inviting terraces, and a sandy waterfront shoreline offer a variety of intimate places to unwind. At the water’s edge, a private dock extends your lifestyle beyond the island. Spend the morning cruising the Intracoastal, discover the nearby beaches and waterfront restaurants, or simply enjoy the pleasures of being surrounded by water. With Longboat Key and Anna Maria Island within boating distance, the best of the Gulf Coast remains wonderfully accessible, yet the feeling of retreat is complete. Jewfish Key offers something even the most extraordinary mainland properties cannot replicate: the experience of arriving home by water, leaving the ordinary behind, and entering a world defined entirely by your own pace. For those who have experienced exceptional homes, this is an opportunity to experience an exceptional way of living.

5 Beds ⋅ 6 Baths ⋅ La Lenaire Isle SubDv. ⋅ 34228 Zip Code

Some of the World’s Most Desirable Addresses Aren’t Reached by Road. There is an unmistakable distinction between owning a beautiful waterfront home and owning a private island retreat. At 7147 La Lenaire Drive, on the intimate shores of Jewfish Key, that distinction becomes extraordinary. Reached exclusively by boat, this remarkable estate offers a level of escape, natural beauty, and understated luxury in that is becoming increasingly difficult to find along Florida’s Gulf Coast. Set on approximately 1.35 acres amid a limited enclave of island residences, this five-bedroom, five-and-a-half-bath waterfront estate is as captivating in its architecture as it is in its setting. An inspired collection of elevated pavilions, interconnected by covered timber walkways, creates the atmosphere of a secluded luxury resort, where open-air living, beautifully appointed accommodations, and the surrounding tropical landscape come together in perfect harmony. From the moment you enter, the architecture makes an impression. Dramatic vaulted ceilings, magnificent exposed timber beams, rich natural wood, and expansive walls of glass lend the interiors an effortless sophistication. Sunlight moves through the living spaces, while the surrounding palms and shimmering water provide an ever-changing backdrop. Every architectural element contributes to a sense of warmth, grandeur, and individuality. Designed to accommodate both memorable entertaining and leisurely island living, the impressive great room flows into a beautifully updated kitchen with an expansive gathering island, sleek white cabinetry, stone countertops, and stainless steel appliances. Generous dining and lounging spaces invite everything from intimate evenings to extended visits with family and friends, all surrounded by the beauty of the island. The residence’s thoughtfully separated bedroom accommodations provide a wonderful balance of togetherness and privacy. The primary retreat is a sanctuary of its own, featuring soaring ceilings, captivating water views, and a beautifully appointed bath with a freestanding soaking tub overlooking the bay. Additional guest accommodations, including a separate suite with its own kitchen and bath, offer an elevated experience for extended visitors. Outdoors, the property becomes a private destination unto itself. An expansive sun-drenched deck surrounds the spectacular pool and spa, framed by graceful palms and the brilliant colors of the surrounding water. A beautifully crafted covered entertaining pavilion, complete with an outdoor kitchen, creates the perfect setting for evenings with friends. Screened gathering areas, inviting terraces, and a sandy waterfront shoreline offer a variety of intimate places to unwind. At the water’s edge, a private dock extends your lifestyle beyond the island. Spend the morning cruising the Intracoastal, discover the nearby beaches and waterfront restaurants, or simply enjoy the pleasures of being surrounded by water. With Longboat Key and Anna Maria Island within boating distance, the best of the Gulf Coast remains wonderfully accessible, yet the feeling of retreat is complete. Jewfish Key offers something even the most extraordinary mainland properties cannot replicate: the experience of arriving home by water, leaving the ordinary behind, and entering a world defined entirely by your own pace. For those who have experienced exceptional homes, this is an opportunity to experience an exceptional way of living.

7147 La Lenaire Drive, Longboat Key

455 Longboat Club Road Unit 402, Longboat Key

$2,000,000

Beachfront mornings begin with dazzling Gulf views on your oversized terrace, above the palms and close enough to see and hear the surf. Spacious, bright and airy, this renovated waterfront three-bedroom condominium lives much larger than its 2,400-plus square feet. Behind the guarded gates of the Longboat Key Club on the island’s southern tip, this peaceful enclave offers an enchanting beach with a rare feeling of privacy. Only minutes from St. Armands Circle, Bay Isles Publix shopping center, the St. Regis and downtown Sarasota’s celebrated arts and culture scene, yet it feels worlds away. The Pierre strikes a rare balance, intimate yet spacious, just 66 residences on nearly seven lush acres. The heated pool, spa, Har-Tru tennis courts, fitness center and beach feel surprisingly uncrowded, even at the height of season. Gulf views fill nearly every room. Evenings bring unforgettable sunsets, then twinkling views of the golf course, Sarasota Bay and city lights to the east. Two expansive balconies make indoor/outdoor living and entertaining easy. The guest room has beach views and its terrace access. A kitchen designed by a serious cook flows beautifully into the living areas, and the dual-aspect dining area offers Gulf and city views with direct access to both balconies, ideal for dinner parties. The flexible layout lets the 3rd bedroom serve as an office or formal dining room, and some owners have added a fourth bedroom! The Pierre’s spacious floor plans stand apart on Longboat Key, where most condominiums are smaller two-bedroom units as few offer this much space at this price. Three guest suites (two one-bedroom, one two-bedroom with large living room and kitchen) welcome overflow guests. Concierge, garage parking, deeded beach access and pet-friendly. Optional Longboat Key Club membership adds 45 holes of golf, tennis, pickleball, spa, fitness, dining, marina and private beach service. Year-round or lock-and-leave, this is so much more than a beach house. It feels like home.

3 Beds ⋅ 4 Baths ⋅ Pierre SubDv. ⋅ 34228 Zip Code

Beachfront mornings begin with dazzling Gulf views on your oversized terrace, above the palms and close enough to see and hear the surf. Spacious, bright and airy, this renovated waterfront three-bedroom condominium lives much larger than its 2,400-plus square feet. Behind the guarded gates of the Longboat Key Club on the island’s southern tip, this peaceful enclave offers an enchanting beach with a rare feeling of privacy. Only minutes from St. Armands Circle, Bay Isles Publix shopping center, the St. Regis and downtown Sarasota’s celebrated arts and culture scene, yet it feels worlds away. The Pierre strikes a rare balance, intimate yet spacious, just 66 residences on nearly seven lush acres. The heated pool, spa, Har-Tru tennis courts, fitness center and beach feel surprisingly uncrowded, even at the height of season. Gulf views fill nearly every room. Evenings bring unforgettable sunsets, then twinkling views of the golf course, Sarasota Bay and city lights to the east. Two expansive balconies make indoor/outdoor living and entertaining easy. The guest room has beach views and its terrace access. A kitchen designed by a serious cook flows beautifully into the living areas, and the dual-aspect dining area offers Gulf and city views with direct access to both balconies, ideal for dinner parties. The flexible layout lets the 3rd bedroom serve as an office or formal dining room, and some owners have added a fourth bedroom! The Pierre’s spacious floor plans stand apart on Longboat Key, where most condominiums are smaller two-bedroom units as few offer this much space at this price. Three guest suites (two one-bedroom, one two-bedroom with large living room and kitchen) welcome overflow guests. Concierge, garage parking, deeded beach access and pet-friendly. Optional Longboat Key Club membership adds 45 holes of golf, tennis, pickleball, spa, fitness, dining, marina and private beach service. Year-round or lock-and-leave, this is so much more than a beach house. It feels like home.

455 Longboat Club Road Unit 402, Longboat Key

4330 Falmouth Drive Unit 107, Longboat Key

$399,000

First time on the market in 25 years with OWNER FINANCING AVAILABLE, 40% down, 5.5% interest on balloon note or amortization, all negotiable. This turnkey, first-floor, two-bedroom, two-full-bath condominium in gated Longboat Harbour has hosted a lifetime of memories and is ready for its next chapter. Freshly painted and move-in ready, it opens through a glass-enclosed lanai straight onto the lawn and harbor, with boats docked a short distance away and Sarasota Bay beyond. Tile floors, plantation shutters and a bright kitchen with a pass-through to the dining area keep life easy. Being on the ground floor, you skip the elevator and stairs and enter right out to the pool, your covered parking and the path to the beach. Owners report no flood damage in their 25 years of ownership. Amenities include heated pools, a fitness center, a sauna, billiards and game rooms, a clubhouse, a putting green, shuffleboard, a fishing pier, grills, kayak storage and a private Gulf-side beach house across Gulf of Mexico Drive with parking, restrooms, showers and gear storage. Bayside sunrises, Gulf sunsets, Publix and dining nearby and SRQ about 13 miles. Owner financing is available; ask for the terms. Quick close is possible. Approximately $15,000 in 2027 rental bookings are already in place, according to the current owner.

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code

First time on the market in 25 years with OWNER FINANCING AVAILABLE, 40% down, 5.5% interest on balloon note or amortization, all negotiable. This turnkey, first-floor, two-bedroom, two-full-bath condominium in gated Longboat Harbour has hosted a lifetime of memories and is ready for its next chapter. Freshly painted and move-in ready, it opens through a glass-enclosed lanai straight onto the lawn and harbor, with boats docked a short distance away and Sarasota Bay beyond. Tile floors, plantation shutters and a bright kitchen with a pass-through to the dining area keep life easy. Being on the ground floor, you skip the elevator and stairs and enter right out to the pool, your covered parking and the path to the beach. Owners report no flood damage in their 25 years of ownership. Amenities include heated pools, a fitness center, a sauna, billiards and game rooms, a clubhouse, a putting green, shuffleboard, a fishing pier, grills, kayak storage and a private Gulf-side beach house across Gulf of Mexico Drive with parking, restrooms, showers and gear storage. Bayside sunrises, Gulf sunsets, Publix and dining nearby and SRQ about 13 miles. Owner financing is available; ask for the terms. Quick close is possible. Approximately $15,000 in 2027 rental bookings are already in place, according to the current owner.

4330 Falmouth Drive Unit 107, Longboat Key

2110 Harbourside Drive Unit 523, Longboat Key

$628,000

Best value with SRQ Bay Views- great location. 3 bedrooms. Discover a relaxed island lifestyle at The Atrium in Bay Isles, where expansive water views and a generous, comfortable floor plan meet in this three-bedroom, two-bath residence. With 2,031 square feet of living space, this home offers room to gather and enjoy Longboat Key's natural beauty. A broad wraparound, covered balcony extends the living space outdoors and frames sweeping views across Sarasota Bay and the surrounding waterways. Start the day with coffee as the light moves across the water, or settle in at day’s end to watch the colors shift over the bay. The balcony’s generous proportions create multiple places to dine, read, or simply take in the coastal setting. Inside, the open living and dining area is designed for easy everyday living and entertaining. High ceilings, an open floor plan, and a wall of windows bring in natural light and keep the water view in focus. The spacious kitchen offers abundant cabinetry, stainless steel appliances, and a double oven, with plenty of room to prepare a casual breakfast or host a dinner with friends. A separate laundry room adds convenience. The primary suite provides a peaceful retreat, with a walk-in closet and a private bath. Two additional bedrooms offer flexibility for guests, a home office, or hobbies, while the second full bath serves both visitors and residents. Offered with furnishings negotiable, the residence gives its next owner the opportunity to make the space their own. The Atrium’s amenities support an active, easygoing island routine. Residents enjoy a gated setting with elevator access, a fitness center, a community pool, and tennis courts. Deeded beach access makes it easy to spend time on the Gulf of Mexico, while the community’s bayfront setting offers a different perspective on the island’s waters. A one-car garage and guest parking provide practical convenience. Located within Bay Isles on Longboat Key, the property is close to the island’s beaches, golf, boating, dining, and shopping. St. Armands Circle and downtown Sarasota are close, with restaurants, boutiques, cultural attractions, and waterfront events within reach. Whether you are looking for a full-time island home, a seasonal escape, or a place to enjoy between travels, this residence offers generous space, memorable bay views, and access to the best of the Longboat Key lifestyle.

3 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code

Best value with SRQ Bay Views- great location. 3 bedrooms. Discover a relaxed island lifestyle at The Atrium in Bay Isles, where expansive water views and a generous, comfortable floor plan meet in this three-bedroom, two-bath residence. With 2,031 square feet of living space, this home offers room to gather and enjoy Longboat Key's natural beauty. A broad wraparound, covered balcony extends the living space outdoors and frames sweeping views across Sarasota Bay and the surrounding waterways. Start the day with coffee as the light moves across the water, or settle in at day’s end to watch the colors shift over the bay. The balcony’s generous proportions create multiple places to dine, read, or simply take in the coastal setting. Inside, the open living and dining area is designed for easy everyday living and entertaining. High ceilings, an open floor plan, and a wall of windows bring in natural light and keep the water view in focus. The spacious kitchen offers abundant cabinetry, stainless steel appliances, and a double oven, with plenty of room to prepare a casual breakfast or host a dinner with friends. A separate laundry room adds convenience. The primary suite provides a peaceful retreat, with a walk-in closet and a private bath. Two additional bedrooms offer flexibility for guests, a home office, or hobbies, while the second full bath serves both visitors and residents. Offered with furnishings negotiable, the residence gives its next owner the opportunity to make the space their own. The Atrium’s amenities support an active, easygoing island routine. Residents enjoy a gated setting with elevator access, a fitness center, a community pool, and tennis courts. Deeded beach access makes it easy to spend time on the Gulf of Mexico, while the community’s bayfront setting offers a different perspective on the island’s waters. A one-car garage and guest parking provide practical convenience. Located within Bay Isles on Longboat Key, the property is close to the island’s beaches, golf, boating, dining, and shopping. St. Armands Circle and downtown Sarasota are close, with restaurants, boutiques, cultural attractions, and waterfront events within reach. Whether you are looking for a full-time island home, a seasonal escape, or a place to enjoy between travels, this residence offers generous space, memorable bay views, and access to the best of the Longboat Key lifestyle.

2110 Harbourside Drive Unit 523, Longboat Key

5320 Gulf Of Mexico Drive Unit 101, Longboat Key

$999,000

Rarely available within the intimate nine-residence bayfront community of Longboat Landing, this beautifully updated three-bedroom residence captures panoramic Sarasota Bay views and effortless waterfront living from its prized location on the north end of Longboat Key. Offered turnkey furnished and completely move-in ready, the getaway combines a refined coastal aesthetic with the rare convenience of on-site boat slips and docks (on a first-come basis) capable of accommodating up to a 26-foot vessel—creating an ideal opportunity for boating enthusiasts seeking immediate enjoyment. Spanning more than 1,300 square feet, the open-concept layout is filled with natural light and designed to maximize the calming bayfront setting. Contemporary wood-grain tile flooring flows throughout the residence, while crown molding, high ceilings, and chic modern finishes enhance the interiors. An extended foyer hallway leads to the sunlit great room, where walls of impact-rated floor-to-ceiling pocketing sliders open completely to the screened bayfront terrace, creating a seamless indoor-outdoor connection framed by sparkling blue water views. The granite kitchen overlooks the main living spaces and was thoughtfully designed for both entertaining and everyday living. Features include a wraparound breakfast bar, informal dining area, solid-wood cabinetry, granite countertops and backsplash, stainless steel appliances, and generous prep space. Recent upgrades provide added peace of mind, including a 2024 A/C replacement, 2023 Hardi Plank siding installation, impact-rated windows and sliding doors throughout, kitchen and bath renovations, updated finishes, ductwork modifications, and a newer roof. The primary suite is positioned directly along the bayfront, offering tranquil water views and private terrace access. Two additional guest bedrooms are arranged in a split plan for privacy, including one en-suite guest suite and a third bedroom currently utilized as a home office. Completing the residence are a private laundry room, two under-building parking spaces, and additional exterior storage. Outside, residents enjoy the relaxed waterfront lifestyle Longboat Landing is known for, with amenities including dock slips, fishing pier, heated community pool, and tennis court—all surrounded by lush tropical landscaping and Sarasota Bay vistas. Perfectly positioned along Gulf of Mexico Drive, this charming bayfront getaway is moments from Longboat Key’s renowned beaches, waterfront dining, boutique shopping, marinas, and scenic biking paths. St. Armands Circle and downtown Sarasota are just a short drive away, offering fine dining, galleries, theaters, Selby Gardens, and Sarasota’s vibrant cultural attractions. Rarely available, beautifully updated, and directly on Sarasota Bay, this residence offers an exceptional opportunity to embrace the best of Longboat Key waterfront living.

3 Beds ⋅ 2 Baths ⋅ Longboat Landing Condominium SubDv. ⋅ 34228 Zip Code

Rarely available within the intimate nine-residence bayfront community of Longboat Landing, this beautifully updated three-bedroom residence captures panoramic Sarasota Bay views and effortless waterfront living from its prized location on the north end of Longboat Key. Offered turnkey furnished and completely move-in ready, the getaway combines a refined coastal aesthetic with the rare convenience of on-site boat slips and docks (on a first-come basis) capable of accommodating up to a 26-foot vessel—creating an ideal opportunity for boating enthusiasts seeking immediate enjoyment. Spanning more than 1,300 square feet, the open-concept layout is filled with natural light and designed to maximize the calming bayfront setting. Contemporary wood-grain tile flooring flows throughout the residence, while crown molding, high ceilings, and chic modern finishes enhance the interiors. An extended foyer hallway leads to the sunlit great room, where walls of impact-rated floor-to-ceiling pocketing sliders open completely to the screened bayfront terrace, creating a seamless indoor-outdoor connection framed by sparkling blue water views. The granite kitchen overlooks the main living spaces and was thoughtfully designed for both entertaining and everyday living. Features include a wraparound breakfast bar, informal dining area, solid-wood cabinetry, granite countertops and backsplash, stainless steel appliances, and generous prep space. Recent upgrades provide added peace of mind, including a 2024 A/C replacement, 2023 Hardi Plank siding installation, impact-rated windows and sliding doors throughout, kitchen and bath renovations, updated finishes, ductwork modifications, and a newer roof. The primary suite is positioned directly along the bayfront, offering tranquil water views and private terrace access. Two additional guest bedrooms are arranged in a split plan for privacy, including one en-suite guest suite and a third bedroom currently utilized as a home office. Completing the residence are a private laundry room, two under-building parking spaces, and additional exterior storage. Outside, residents enjoy the relaxed waterfront lifestyle Longboat Landing is known for, with amenities including dock slips, fishing pier, heated community pool, and tennis court—all surrounded by lush tropical landscaping and Sarasota Bay vistas. Perfectly positioned along Gulf of Mexico Drive, this charming bayfront getaway is moments from Longboat Key’s renowned beaches, waterfront dining, boutique shopping, marinas, and scenic biking paths. St. Armands Circle and downtown Sarasota are just a short drive away, offering fine dining, galleries, theaters, Selby Gardens, and Sarasota’s vibrant cultural attractions. Rarely available, beautifully updated, and directly on Sarasota Bay, this residence offers an exceptional opportunity to embrace the best of Longboat Key waterfront living.

5320 Gulf Of Mexico Drive Unit 101, Longboat Key

3060 Grand Bay Boulevard Unit 124, Longboat Key

$1,699,000

Discover an exceptional opportunity to embrace the refined waterfront lifestyle at Grand Bay, one of Longboat Key’s most prestigious gated communities within Bay Isles. This beautifully updated 2-bedroom, 2.5-bath residence offers approximately 2,550 square feet of elegant living space, framed by sweeping views of Sarasota Bay, the manicured golf course, and the Sarasota skyline. From the moment you enter, warm wood floors, expansive living areas, and floor-to-ceiling windows create a sense of effortless sophistication. The living room opens through a wall of sliders to a private terrace, inviting morning coffee, sunset entertaining, and quiet moments above the water. A formal dining room with wet bar and wine refrigerator, along with a striking gourmet kitchen featuring stone countertops, an extended island, glass-panel cabinetry, pendant lighting, and premium stainless appliances, makes entertaining as seamless as it is memorable. The primary suite is a true sanctuary, opening to the terrace with panoramic bay views and featuring a spa-inspired bath with soaking tub, walk-in glass shower, dual vanities, and separate water closet. The guest suite offers its own terrace access and private en-suite bath, providing comfort and privacy for family and visitors. Life at Grand Bay extends well beyond the residence. Residents enjoy resort-caliber amenities including a clubhouse, two heated pools and spas, a fitness center with saunas, and Har-Tru tennis courts. Membership to the Bay Isles Beach Club provides private Gulf-front access, complete with gated entry, pavilion, restrooms, showers, picnic areas, BBQ grills, and beach chair storage. The pet-friendly community also welcomes large dogs, making it easy to bring the whole family into this exceptional coastal setting. Ideally positioned behind the gates of the Longboat Key Club in Bay Isles, this residence places you minutes from celebrated dining, boutique shopping, golf, boating, and the cultural attractions of Sarasota. It is more than a home; it is a rare opportunity to live the quintessential Longboat Key lifestyle, where luxury, privacy, and waterfront beauty come together every day.

2 Beds ⋅ 3 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code

Discover an exceptional opportunity to embrace the refined waterfront lifestyle at Grand Bay, one of Longboat Key’s most prestigious gated communities within Bay Isles. This beautifully updated 2-bedroom, 2.5-bath residence offers approximately 2,550 square feet of elegant living space, framed by sweeping views of Sarasota Bay, the manicured golf course, and the Sarasota skyline. From the moment you enter, warm wood floors, expansive living areas, and floor-to-ceiling windows create a sense of effortless sophistication. The living room opens through a wall of sliders to a private terrace, inviting morning coffee, sunset entertaining, and quiet moments above the water. A formal dining room with wet bar and wine refrigerator, along with a striking gourmet kitchen featuring stone countertops, an extended island, glass-panel cabinetry, pendant lighting, and premium stainless appliances, makes entertaining as seamless as it is memorable. The primary suite is a true sanctuary, opening to the terrace with panoramic bay views and featuring a spa-inspired bath with soaking tub, walk-in glass shower, dual vanities, and separate water closet. The guest suite offers its own terrace access and private en-suite bath, providing comfort and privacy for family and visitors. Life at Grand Bay extends well beyond the residence. Residents enjoy resort-caliber amenities including a clubhouse, two heated pools and spas, a fitness center with saunas, and Har-Tru tennis courts. Membership to the Bay Isles Beach Club provides private Gulf-front access, complete with gated entry, pavilion, restrooms, showers, picnic areas, BBQ grills, and beach chair storage. The pet-friendly community also welcomes large dogs, making it easy to bring the whole family into this exceptional coastal setting. Ideally positioned behind the gates of the Longboat Key Club in Bay Isles, this residence places you minutes from celebrated dining, boutique shopping, golf, boating, and the cultural attractions of Sarasota. It is more than a home; it is a rare opportunity to live the quintessential Longboat Key lifestyle, where luxury, privacy, and waterfront beauty come together every day.

3060 Grand Bay Boulevard Unit 124, Longboat Key

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