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From the moment you enter, the effect is unforgettable. Dramatic floor-to-ceiling windows create an immediate WOW factor, drawing your eye out to the tranquil canal, your own 55’ dock and expansive view of mangroves. An abundance of natural light and a sense of openness defines this special residence. Completely reimagined and extensively rebuilt inside and out between 2022 and 2026, this is far more than a traditional renovation. Every space reflects a thoughtful approach to contemporary design, with attention to details. From the stunning custom kitchen featuring sleek European-inspired cabinetry, Bosch appliances, quartz waterfall island to the sophisticated lighting, impact resistant windows and doors, wide-plank wood-look porcelain tile flooring throughout and beautifully updated bathrooms to the resort-style 34’ pool plus expansive covered outdoor entertaining area, a new metal roof, this distinctive property offers the appeal of contemporary luxury in one of Longboat Key’s most desirable island settings.

3 Beds ⋅ 2 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code

From the moment you enter, the effect is unforgettable. Dramatic floor-to-ceiling windows create an immediate WOW factor, drawing your eye out to the tranquil canal, your own 55’ dock and expansive view of mangroves. An abundance of natural light and a sense of openness defines this special residence. Completely reimagined and extensively rebuilt inside and out between 2022 and 2026, this is far more than a traditional renovation. Every space reflects a thoughtful approach to contemporary design, with attention to details. From the stunning custom kitchen featuring sleek European-inspired cabinetry, Bosch appliances, quartz waterfall island to the sophisticated lighting, impact resistant windows and doors, wide-plank wood-look porcelain tile flooring throughout and beautifully updated bathrooms to the resort-style 34’ pool plus expansive covered outdoor entertaining area, a new metal roof, this distinctive property offers the appeal of contemporary luxury in one of Longboat Key’s most desirable island settings.

660 Penfield Street, Longboat Key

738 Spanish Drive S Unit 98, Longboat Key

$495,000

Discover the best of Longboat Key living in this freestanding, well-maintained 2-bedroom, 1.5-bath freestanding villa in the sought-after Spanish Main Yacht Club. With about 1,200 sq ft of living space plus an enclosed Florida room, this light-filled home features plantation shutters, terrazzo flooring and an updated kitchen with wood cabinetry and granite counters. Outside, enjoy a covered carport, private entrance and a private back yard with added privacy, plus block construction and a tile roof. Spanish Main Yacht Club offers deeded private beach access, a heated community pool, clubhouse, shuffleboard, kayak storage and a 40-slip private marina — just a short stroll from Gulf sunsets and minutes from St. Armand's Circle and Sarasota dining and shopping. Buyer association approval required; leasing permitted with a one-month minimum, up to twice annually. Check out the videos of the home and the community now, then call for a tour!

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

Discover the best of Longboat Key living in this freestanding, well-maintained 2-bedroom, 1.5-bath freestanding villa in the sought-after Spanish Main Yacht Club. With about 1,200 sq ft of living space plus an enclosed Florida room, this light-filled home features plantation shutters, terrazzo flooring and an updated kitchen with wood cabinetry and granite counters. Outside, enjoy a covered carport, private entrance and a private back yard with added privacy, plus block construction and a tile roof. Spanish Main Yacht Club offers deeded private beach access, a heated community pool, clubhouse, shuffleboard, kayak storage and a 40-slip private marina — just a short stroll from Gulf sunsets and minutes from St. Armand's Circle and Sarasota dining and shopping. Buyer association approval required; leasing permitted with a one-month minimum, up to twice annually. Check out the videos of the home and the community now, then call for a tour!

738 Spanish Drive S Unit 98, Longboat Key

2600 Harbourside Drive Unit Q8, Longboat Key

$189,000

**NO LONGBOAT KEY CLUB MEMBERSHIP REQUIRED!** A rare and highly desirable opportunity to own a 48' x 21' deep-water slip at the prestigious Longboat Key Club Moorings without the expense or obligation of club membership! This valuable distinction offers owners the flexibility to enjoy a world-class marina while avoiding mandatory club membership fees. Accommodating vessels up to 43' long and 19' wide, this ideally located slip boasts stunning Sarasota skyline views and direct access to Sarasota Bay and the Intracoastal Waterway. Longboat Key Club Moorings offers a resort-style marina experience within an elegant Mediterranean-inspired waterfront village, complete with on-site dining, shopping, social activities, professional maintenance, and concierge services. Conveniently located near Publix, CVS, and specialty shops, the marina combines luxury with everyday convenience. Slip amenities include electric, water, and wireless internet access. For those interested, Longboat Key Club membership remains entirely optional, with the opportunity to join at any time. All vessels require Association Board approval prior to entering the marina, and allowable beam depends on vessel specifications. Enjoy the prestige and convenience of Longboat Key Club Moorings with the freedom of ownership without mandatory club membership!

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

**NO LONGBOAT KEY CLUB MEMBERSHIP REQUIRED!** A rare and highly desirable opportunity to own a 48' x 21' deep-water slip at the prestigious Longboat Key Club Moorings without the expense or obligation of club membership! This valuable distinction offers owners the flexibility to enjoy a world-class marina while avoiding mandatory club membership fees. Accommodating vessels up to 43' long and 19' wide, this ideally located slip boasts stunning Sarasota skyline views and direct access to Sarasota Bay and the Intracoastal Waterway. Longboat Key Club Moorings offers a resort-style marina experience within an elegant Mediterranean-inspired waterfront village, complete with on-site dining, shopping, social activities, professional maintenance, and concierge services. Conveniently located near Publix, CVS, and specialty shops, the marina combines luxury with everyday convenience. Slip amenities include electric, water, and wireless internet access. For those interested, Longboat Key Club membership remains entirely optional, with the opportunity to join at any time. All vessels require Association Board approval prior to entering the marina, and allowable beam depends on vessel specifications. Enjoy the prestige and convenience of Longboat Key Club Moorings with the freedom of ownership without mandatory club membership!

2600 Harbourside Drive Unit Q8, Longboat Key

$15,000,000

Be renewed and inspired by this striking Gulf-front residence in an exclusive island community, featuring an impressive 100 feet of direct beachfront. Renovated and redesigned in 2025 to offer seamless indoor-outdoor integration and wide, unobstructed Gulf views, the setting is simply spectacular. This sophisticated contemporary masterpiece captures the relaxed spirit of beachfront living through clean lines, organic textures, and a crisp, minimalist aesthetic, creating a space that feels airy, bright, and deeply connected to nature. Interior layouts embrace high ceilings and expansive open-plan living zones that share light across the entire footprint through vast expanses of glass. The distinctive 6,660-square-foot beach house blends rigorous structural engineering with minimalist design to celebrate the coastal environment. Luxury finishes and fixtures include Louis XIV champagne White Oak floors, Dennis & Leen custom chandeliers and sconces, and a custom Murano glass chandelier. The living room, dining room, and kitchen span nearly 1,200 square feet of open living, enhanced by a dramatic two-story ceiling and seamless access to the oversized lanai. Multiple sets of triple-glazed sliders open wide, dissolving the boundaries between indoors and out and creating a dramatic setting for effortless entertaining, relaxed gatherings, and unforgettable open-air living. In addition to mesmerizing tropical views and a light-drenched workspace, the extraordinary kitchen and butler’s pantry feature marble counters and high-end appliances, including a Wolf double-range oven, a Wolf steam oven, an integrated Sub-Zero refrigerator and freezer, and two Sub-Zero beverage refrigerators. Elevated to showcase the 180-degree unobstructed horizon views, a glamorous primary suite offers an exquisite bath surrounded by plush comfort amenities, with gorgeous vistas dominating the space. Two additional en-suite bedrooms, a third bedroom currently used as an office with a bath, and a loft library with a long wall of built-in bookcases offer plenty of room for everyone to unwind and rejuvenate at day’s end. The ground-floor space has 2 garage doors for vehicle and water-toy access, an elevator to the second and third levels, a huge lounge with abundant seating, a large-screen TV, an adjoining exercise room, and 2 mini-split air conditioners dedicated to this enormous ground-level space. Notable features throughout the house include 5 full bathrooms, a laundry room with marble counters and flooring, a water filtration system and softener, a Generac generator, a security system with ten cameras, and a Sonos audio system. Outdoor living is integral to this exceptional beachside residence, with multiple levels designed to capture breathtaking water panoramas and embrace the surrounding beauty. Spanning the entire Gulf-facing façade, a covered ground-level patio, a second-level lanai, and a third-level balcony create an effortless progression of spaces for relaxing, entertaining, and enjoying spectacular sunsets. A truly exceptional beachside retreat, 6529 Gulfside Road delivers a refined coastal experience that embraces everything that makes Florida living so extraordinary. From its spectacular setting to its thoughtfully designed spaces, every element celebrates the beauty, ease, and allure of Gulfside living. *Variance in place and plans drawn for 1,000 sq. ft. guest house and pool, making the square footage over 7,500 under air.

5 Beds ⋅ 5 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code

Be renewed and inspired by this striking Gulf-front residence in an exclusive island community, featuring an impressive 100 feet of direct beachfront. Renovated and redesigned in 2025 to offer seamless indoor-outdoor integration and wide, unobstructed Gulf views, the setting is simply spectacular. This sophisticated contemporary masterpiece captures the relaxed spirit of beachfront living through clean lines, organic textures, and a crisp, minimalist aesthetic, creating a space that feels airy, bright, and deeply connected to nature. Interior layouts embrace high ceilings and expansive open-plan living zones that share light across the entire footprint through vast expanses of glass. The distinctive 6,660-square-foot beach house blends rigorous structural engineering with minimalist design to celebrate the coastal environment. Luxury finishes and fixtures include Louis XIV champagne White Oak floors, Dennis & Leen custom chandeliers and sconces, and a custom Murano glass chandelier. The living room, dining room, and kitchen span nearly 1,200 square feet of open living, enhanced by a dramatic two-story ceiling and seamless access to the oversized lanai. Multiple sets of triple-glazed sliders open wide, dissolving the boundaries between indoors and out and creating a dramatic setting for effortless entertaining, relaxed gatherings, and unforgettable open-air living. In addition to mesmerizing tropical views and a light-drenched workspace, the extraordinary kitchen and butler’s pantry feature marble counters and high-end appliances, including a Wolf double-range oven, a Wolf steam oven, an integrated Sub-Zero refrigerator and freezer, and two Sub-Zero beverage refrigerators. Elevated to showcase the 180-degree unobstructed horizon views, a glamorous primary suite offers an exquisite bath surrounded by plush comfort amenities, with gorgeous vistas dominating the space. Two additional en-suite bedrooms, a third bedroom currently used as an office with a bath, and a loft library with a long wall of built-in bookcases offer plenty of room for everyone to unwind and rejuvenate at day’s end. The ground-floor space has 2 garage doors for vehicle and water-toy access, an elevator to the second and third levels, a huge lounge with abundant seating, a large-screen TV, an adjoining exercise room, and 2 mini-split air conditioners dedicated to this enormous ground-level space. Notable features throughout the house include 5 full bathrooms, a laundry room with marble counters and flooring, a water filtration system and softener, a Generac generator, a security system with ten cameras, and a Sonos audio system. Outdoor living is integral to this exceptional beachside residence, with multiple levels designed to capture breathtaking water panoramas and embrace the surrounding beauty. Spanning the entire Gulf-facing façade, a covered ground-level patio, a second-level lanai, and a third-level balcony create an effortless progression of spaces for relaxing, entertaining, and enjoying spectacular sunsets. A truly exceptional beachside retreat, 6529 Gulfside Road delivers a refined coastal experience that embraces everything that makes Florida living so extraordinary. From its spectacular setting to its thoughtfully designed spaces, every element celebrates the beauty, ease, and allure of Gulfside living. *Variance in place and plans drawn for 1,000 sq. ft. guest house and pool, making the square footage over 7,500 under air.

6529 Gulfside Road, Longboat Key

1955 Gulf Of Mexico Drive Unit G6-407, Longboat Key

$769,000

Gulf-front view in Seaplace with reserved covered parking! This is a special opportunity to own a rarely available floor plan on the penthouse level in an atrium-style building. This residence has extra-high ceilings and spectacular Gulf water views, a large screened-in lanai overlooking the Gulf, and an extra-spacious open floor plan. It's being sold turnkey furnished and is ready to enjoy from day one. The open living and dining areas flow seamlessly to the expansive screened-in lanai, creating the perfect setting to relax, entertain, and take in the stunning Gulf sunsets. The generous primary bedroom offers an abundance of closet storage, while an in-unit washer and dryer provide everyday convenience. Additional features include a new impact-rated front door with a digital lock system, impact window and door shutters, and a private locking storage unit conveniently located on the same floor. The reserved covered parking space is very convenient to the elevator. HVAC, 2025. Set on 42 acres of Gulf-front, meticulously landscaped grounds, Seaplace offers resort-style amenities that make this community especially inviting. There are 2 large swimming pools with spas and a separate kiddie pool that provide plenty of options for relaxing and enjoying the Florida sunshine. At the beach, lounges and umbrellas are set up for residents to enjoy, making a day by the Gulf effortless. There are 3 har-tru tennis courts, and a mile of walking trails on the property. The modern clubhouse offers a state-of-the-art gym and an inviting gathering room where residents come together for parties, card games, social activities, or simply to get to know their neighbors. A special lending library adds another thoughtful touch. As the sun begins to set, residents gather around the clubhouse firepit to socialize, grill dinner, and watch the spectacular sunsets together over the Gulf. Seaplace is just a short 5 minute drive to St. Armand's Circle, where you'll find fantastic shopping and incredible restaurants and cafes. Also, at Seaplace you'll have the convenience of being close to Publix and CVS on Longboat Key which are within walking or biking riding distance or minutes away by car. Visit this residence in Seaplace to see how wonderful Longboat Key life can truly be. Book your appointment today.

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

Gulf-front view in Seaplace with reserved covered parking! This is a special opportunity to own a rarely available floor plan on the penthouse level in an atrium-style building. This residence has extra-high ceilings and spectacular Gulf water views, a large screened-in lanai overlooking the Gulf, and an extra-spacious open floor plan. It's being sold turnkey furnished and is ready to enjoy from day one. The open living and dining areas flow seamlessly to the expansive screened-in lanai, creating the perfect setting to relax, entertain, and take in the stunning Gulf sunsets. The generous primary bedroom offers an abundance of closet storage, while an in-unit washer and dryer provide everyday convenience. Additional features include a new impact-rated front door with a digital lock system, impact window and door shutters, and a private locking storage unit conveniently located on the same floor. The reserved covered parking space is very convenient to the elevator. HVAC, 2025. Set on 42 acres of Gulf-front, meticulously landscaped grounds, Seaplace offers resort-style amenities that make this community especially inviting. There are 2 large swimming pools with spas and a separate kiddie pool that provide plenty of options for relaxing and enjoying the Florida sunshine. At the beach, lounges and umbrellas are set up for residents to enjoy, making a day by the Gulf effortless. There are 3 har-tru tennis courts, and a mile of walking trails on the property. The modern clubhouse offers a state-of-the-art gym and an inviting gathering room where residents come together for parties, card games, social activities, or simply to get to know their neighbors. A special lending library adds another thoughtful touch. As the sun begins to set, residents gather around the clubhouse firepit to socialize, grill dinner, and watch the spectacular sunsets together over the Gulf. Seaplace is just a short 5 minute drive to St. Armand's Circle, where you'll find fantastic shopping and incredible restaurants and cafes. Also, at Seaplace you'll have the convenience of being close to Publix and CVS on Longboat Key which are within walking or biking riding distance or minutes away by car. Visit this residence in Seaplace to see how wonderful Longboat Key life can truly be. Book your appointment today.

1955 Gulf Of Mexico Drive Unit G6-407, Longboat Key

408 Gulf Of Mexico Drive Unit 2207, Longboat Key

$49,000

Welcome to Slip #2207 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 28 feet in length, with a maximum height of 7'8" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

Boathouse On Longboat SubDv. ⋅ 34228 Zip Code

Welcome to Slip #2207 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 28 feet in length, with a maximum height of 7'8" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

408 Gulf Of Mexico Drive Unit 2207, Longboat Key

408 Gulf Of Mexico Drive Unit 1206, Longboat Key

$65,000

Welcome to Slip #1206 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 31.5 feet in length, with a maximum height of 8'4" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

Boathouse On Longboat SubDv. ⋅ 34228 Zip Code

Welcome to Slip #1206 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 31.5 feet in length, with a maximum height of 8'4" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

408 Gulf Of Mexico Drive Unit 1206, Longboat Key

408 Gulf Of Mexico Drive Unit 2114, Longboat Key

$39,000

Welcome to Slip #2114 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 23.5 feet in length, with a maximum height of 7'2" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

Boathouse On Longboat SubDv. ⋅ 34228 Zip Code

Welcome to Slip #2114 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This premium slip accommodates boats up to 23.5 feet in length, with a maximum height of 7'2" and an 8'6" beam (no T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!

408 Gulf Of Mexico Drive Unit 2114, Longboat Key

$840,000

Nestled in the heart of Longboat Key's historic North-End "Village", this beautifully restored 1920s beach bungalow seamlessly blends historic coastal charm with modern, high-end updates. Located just steps from the island's finest beaches, bay access points, and local dining, this coastal sanctuary sits on a private, oversized 9,400 sq. ft. lot surrounded by lush tropical landscaping. Inside, classic details like white tongue-and-groove ceilings, a cozy masonry wood-burning fireplace, and warm Saltillo tile floors complement a fully updated gourmet kitchen equipped with solid-surface countertops, custom shaker cabinetry, gas cooking, and striking tile flooring and backsplash. The main living space features a bright open layout, with vintage charm mixed with today's luxuries. Charming enclosed Florida Room sets the vibes with its panoramic views of the lush, tropical gardens. Oversized primary bedroom radiates the beach cottage vibes you're looking for. Spa-inspired bathrooms with frame-less glass showers, and stylish finishes throughout.The guest bedroom, currently used as a den, features walls of glass and continued vintage charm. Adding incredible versatility, an adjoining mother-in-law suite complete with its own kitchenette offers private accommodations for extended family, guests, or flexible living space. This area was designed to be both an extension of the primary living space with its continuous flow or, with its separate entrance, it's ideal for guests seeking privacy. Step outside into your private backyard oasis featuring a paver patio, lush gardens, an outdoor lounge area, and a private hot tub (2025) - perfect for relaxing after a day on the water. The oversized backyard is completely fenced and secured ready for the dream pool ($10K pool builder credit and permit convey). This residence features extensive, high-quality updates designed for modern comfort and efficiency. Recent improvements include, Energy & Climate: A 10kW solar panel system (2021), a new central air conditioning system (2025), and a mini-split system (2024). Interior & Structural: Comprehensive kitchen and bathroom renovations, new weather-grade subflooring in the cottage, and upgraded electrical service featuring an EV car charger and Cat-6W wiring throughout. Technology & Entertainment: A whole-home Bose integrated audio system. Utilities & Appliances: Completely updated cottage plumbing, instant hot water heater and a full suite of new appliances, including a washer and dryer. Windows: Replacement cottage windows installed in 2020 and new impact windows in the Mother-in-Law Suite. New interior paint and lighting (2026). Exterior Improvements: New landscaping, irrigation, electrical, and fencing just installed. Discover contemporary elegance blended with classic Florida island charm in one of Longboat Key's most sought-after historic areas. Set within a vibrant, golf-cart-accessible neighborhood, this exceptional property puts you close to local cafés, waterfront dining, unique boutiques, fitness facilities, and fishing piers. Enjoy convenient access to Sarasota Bay with a nearby boat launch and kayak areas, while pristine Gulf beaches are only minutes away - all with the freedom of no mandatory HOA. Schedule a visit to experience the unique lifestyle and character of this remarkable home firsthand.

3 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Nestled in the heart of Longboat Key's historic North-End "Village", this beautifully restored 1920s beach bungalow seamlessly blends historic coastal charm with modern, high-end updates. Located just steps from the island's finest beaches, bay access points, and local dining, this coastal sanctuary sits on a private, oversized 9,400 sq. ft. lot surrounded by lush tropical landscaping. Inside, classic details like white tongue-and-groove ceilings, a cozy masonry wood-burning fireplace, and warm Saltillo tile floors complement a fully updated gourmet kitchen equipped with solid-surface countertops, custom shaker cabinetry, gas cooking, and striking tile flooring and backsplash. The main living space features a bright open layout, with vintage charm mixed with today's luxuries. Charming enclosed Florida Room sets the vibes with its panoramic views of the lush, tropical gardens. Oversized primary bedroom radiates the beach cottage vibes you're looking for. Spa-inspired bathrooms with frame-less glass showers, and stylish finishes throughout.The guest bedroom, currently used as a den, features walls of glass and continued vintage charm. Adding incredible versatility, an adjoining mother-in-law suite complete with its own kitchenette offers private accommodations for extended family, guests, or flexible living space. This area was designed to be both an extension of the primary living space with its continuous flow or, with its separate entrance, it's ideal for guests seeking privacy. Step outside into your private backyard oasis featuring a paver patio, lush gardens, an outdoor lounge area, and a private hot tub (2025) - perfect for relaxing after a day on the water. The oversized backyard is completely fenced and secured ready for the dream pool ($10K pool builder credit and permit convey). This residence features extensive, high-quality updates designed for modern comfort and efficiency. Recent improvements include, Energy & Climate: A 10kW solar panel system (2021), a new central air conditioning system (2025), and a mini-split system (2024). Interior & Structural: Comprehensive kitchen and bathroom renovations, new weather-grade subflooring in the cottage, and upgraded electrical service featuring an EV car charger and Cat-6W wiring throughout. Technology & Entertainment: A whole-home Bose integrated audio system. Utilities & Appliances: Completely updated cottage plumbing, instant hot water heater and a full suite of new appliances, including a washer and dryer. Windows: Replacement cottage windows installed in 2020 and new impact windows in the Mother-in-Law Suite. New interior paint and lighting (2026). Exterior Improvements: New landscaping, irrigation, electrical, and fencing just installed. Discover contemporary elegance blended with classic Florida island charm in one of Longboat Key's most sought-after historic areas. Set within a vibrant, golf-cart-accessible neighborhood, this exceptional property puts you close to local cafés, waterfront dining, unique boutiques, fitness facilities, and fishing piers. Enjoy convenient access to Sarasota Bay with a nearby boat launch and kayak areas, while pristine Gulf beaches are only minutes away - all with the freedom of no mandatory HOA. Schedule a visit to experience the unique lifestyle and character of this remarkable home firsthand.

760 Longboat Court, Longboat Key

2800 Harbourside Drive Unit E-21, Longboat Key

$385,000

JUST INSIDE THE T-DOCK! An easy access premium 63 x 23.5 ft. slip, with a unique configuration; it has a pier extension, a 9 ft wide finger pier, and the extended portion is a concrete floating dock providing alternate boarding options. The slip is located on the north side of the pier. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. 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, a Mediterranean-style village that includes restaurants, 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. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside & Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association before entering the marina. A current photo must be submitted. Max length of vessel allowed is 58 LOA, usable beam is 19 ft at the head of the slip.

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

JUST INSIDE THE T-DOCK! An easy access premium 63 x 23.5 ft. slip, with a unique configuration; it has a pier extension, a 9 ft wide finger pier, and the extended portion is a concrete floating dock providing alternate boarding options. The slip is located on the north side of the pier. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. 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, a Mediterranean-style village that includes restaurants, 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. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside & Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association before entering the marina. A current photo must be submitted. Max length of vessel allowed is 58 LOA, usable beam is 19 ft at the head of the slip.

2800 Harbourside Drive Unit E-21, Longboat Key

$815,000

Situated on an extra large 11,250 sf waterfront lot, with a 2020 seawall, and deeded beach access, this fabulous single family home represents one of the best investments on all of Longboat Key! Completely renovated and ready for you to move right in and start enjoying island life or a dreamy location for you to earn monthly rental income while you envision building your own island getaway. Charmingly decorated, with a new kitchen and all new appliances, in an open floor plan with beautiful wood look tile that flows seamlessly from room to room. 2022 storm windows provide a full wall of light while taking in the views overlooking the canal; A day out on the boat can be a routine adventure with easy access to the intracoastal waterway and no fixed bridges to the Gulf of Mexico. When you return, the 2nd bath has a door to the back so you can come right off the boat to the showers or it also could provide a perfect location as a pool bath if you choose to put in a pool. A covered carport provides a perfect place for outdoor dining. In only a short walk or bike ride down the street, you have your deeded beach access point, and you have access to multiple restaurants, shopping, 11 miles of bike paths and the beautiful nature trails of Joan Durante Park. With this mid-key location it's just a short drive to the new St.Regis Resort, world famous St. Armands Circle and just beyond that, the culture rich city of downtown Sarasota. This is truly what laid back island life on Longboat Key is all about. Make an appointment to see this island home today. At this price point, it will not last long!

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

Situated on an extra large 11,250 sf waterfront lot, with a 2020 seawall, and deeded beach access, this fabulous single family home represents one of the best investments on all of Longboat Key! Completely renovated and ready for you to move right in and start enjoying island life or a dreamy location for you to earn monthly rental income while you envision building your own island getaway. Charmingly decorated, with a new kitchen and all new appliances, in an open floor plan with beautiful wood look tile that flows seamlessly from room to room. 2022 storm windows provide a full wall of light while taking in the views overlooking the canal; A day out on the boat can be a routine adventure with easy access to the intracoastal waterway and no fixed bridges to the Gulf of Mexico. When you return, the 2nd bath has a door to the back so you can come right off the boat to the showers or it also could provide a perfect location as a pool bath if you choose to put in a pool. A covered carport provides a perfect place for outdoor dining. In only a short walk or bike ride down the street, you have your deeded beach access point, and you have access to multiple restaurants, shopping, 11 miles of bike paths and the beautiful nature trails of Joan Durante Park. With this mid-key location it's just a short drive to the new St.Regis Resort, world famous St. Armands Circle and just beyond that, the culture rich city of downtown Sarasota. This is truly what laid back island life on Longboat Key is all about. Make an appointment to see this island home today. At this price point, it will not last long!

691 Tarawitt Drive, Longboat Key

3453 Gulf Of Mexico Drive Unit 242, Longboat Key

$489,900

Sea Horse is a resort community on the Gulf of Longboat Key and this unit offers a large balcony with sweeping views of the Gulf, beach, pool and epic Longboat Key sunsets. Unit 242 is a deluxe 1 bedroom with an open kitchen, dining room and living for guests to gather and a private bedroom with ensuite. The living room and bedroom share the balcony. As a resort, the on-site management office handles your rentals, maintenance, and guest needs. Parking is limited to one car for this unit. This is a quality investment property and rental projections are available upon request, but also consider this your little oasis to visit, enjoy and when you leave it's taken care of.

1 Beds ⋅ 1 Baths ⋅ Sea Horse Beach Resort SubDv. ⋅ 34228 Zip Code

Sea Horse is a resort community on the Gulf of Longboat Key and this unit offers a large balcony with sweeping views of the Gulf, beach, pool and epic Longboat Key sunsets. Unit 242 is a deluxe 1 bedroom with an open kitchen, dining room and living for guests to gather and a private bedroom with ensuite. The living room and bedroom share the balcony. As a resort, the on-site management office handles your rentals, maintenance, and guest needs. Parking is limited to one car for this unit. This is a quality investment property and rental projections are available upon request, but also consider this your little oasis to visit, enjoy and when you leave it's taken care of.

3453 Gulf Of Mexico Drive Unit 242, Longboat Key

$3,249,000

A rare opportunity to craft a bespoke waterfront estate on the coveted north end of Longboat Key. Situated on over 11,000 square feet, this exceptional vacant homesite offers sweeping water views overlooking picturesque Jewfish Island, creating a serene and ever-changing coastal backdrop for your future residence. Cleared and ready for your builder, the property invites endless architectural possibilities—from a contemporary coastal retreat to a timeless island classic—designed to capture breathtaking sunsets, early morning sunrises and gentle bay breezes.Tucked away on a quiet street, this prime location offers the perfect balance of privacy and convenience. Enjoy a short stroll to the pristine Gulf beaches, where powdery white sands and turquoise waters define the Longboat Key lifestyle. Equally close are the coastal restaurants of the north end, allowing you to savor waterfront dining, casual cafés, and evening strolls without ever getting in the car. Whether you envision expansive indoor-outdoor living, a resort-style pool and lanai, or a private dock to explore Sarasota Bay and beyond, this homesite provides the canvas to bring your vision to life. Surrounded by natural beauty and neighboring luxury residences, 7049 Longboat Drive N represents an increasingly rare chance to build new on Longboat Key—one of Florida’s most desirable barrier islands. Create your legacy property in a setting defined by tranquility, walkability, and stunning waterfront vistas, all just moments from the Gulf of Mexico. Opportunities like this on Longboat Key’s north end are limited—secure your place and begin designing the extraordinary.

Longboat Key SubDv. ⋅ 34228 Zip Code

A rare opportunity to craft a bespoke waterfront estate on the coveted north end of Longboat Key. Situated on over 11,000 square feet, this exceptional vacant homesite offers sweeping water views overlooking picturesque Jewfish Island, creating a serene and ever-changing coastal backdrop for your future residence. Cleared and ready for your builder, the property invites endless architectural possibilities—from a contemporary coastal retreat to a timeless island classic—designed to capture breathtaking sunsets, early morning sunrises and gentle bay breezes.Tucked away on a quiet street, this prime location offers the perfect balance of privacy and convenience. Enjoy a short stroll to the pristine Gulf beaches, where powdery white sands and turquoise waters define the Longboat Key lifestyle. Equally close are the coastal restaurants of the north end, allowing you to savor waterfront dining, casual cafés, and evening strolls without ever getting in the car. Whether you envision expansive indoor-outdoor living, a resort-style pool and lanai, or a private dock to explore Sarasota Bay and beyond, this homesite provides the canvas to bring your vision to life. Surrounded by natural beauty and neighboring luxury residences, 7049 Longboat Drive N represents an increasingly rare chance to build new on Longboat Key—one of Florida’s most desirable barrier islands. Create your legacy property in a setting defined by tranquility, walkability, and stunning waterfront vistas, all just moments from the Gulf of Mexico. Opportunities like this on Longboat Key’s north end are limited—secure your place and begin designing the extraordinary.

7094 Longboat Drive E, Longboat Key

$1,350,000

Virtually Staged. VIRTUALLY EVERYTHING NEW — BOAT IN YOUR BACKYARD, PRIVATE BEACH DOWN THE STREET. This is the Longboat Key lifestyle buyers dream about: boating from home, sunset walks on the Gulf, and a beautifully reimagined coastal residence that is truly move-in ready. Previously appraised at $1.65 million late last year and most recently at $1.5 million, with no material changes to the home, it is now offered at $1.35 million—an opportunity to purchase below its most recent appraised value. Set along 120 feet of canal frontage, this 4-bedroom, 2-bath waterfront home offers DIRECT BOATING ACCESS TO SARASOTA BAY AND THE INTRACOASTAL plus PRIVATE DEEDED GULF BEACH ACCESS JUST EIGHT HOMES AWAY. It is a rare Longboat Key combination: keep your boat at home and enjoy your private Gulf beach access just down the street. Joan M. Durante Park, Cedars Tennis Resort & Club, and favorite Longboat Key restaurants, boutiques and shops are all nearby. Optional Cedars membership offers tennis and pickleball courts, a Jr. Olympic pool, 24/7 fitness center and additional amenities. This is far more than a cosmetic update. With the exception of the foundation, VIRTUALLY EVERYTHING HAS BEEN RENOVATED OR REPLACED, INSIDE AND OUT. Improvements include a new roof, new AC systems, new interior walls and flooring, newer electrical and plumbing, new decking, cabinetry, landscaping and finishes, plus impact windows, high-impact sliding glass doors and impact-rated exterior doors. Inside, vaulted ceilings, expansive water views and an open, light-filled layout create effortless coastal living. The kitchen features solid-wood cabinetry, soft-close hardware, quartz countertops, a gas range, stainless-steel appliances, a copper hood and copper farmhouse sink. Updated baths continue the elevated finishes throughout. The living space opens to an approximately 1,000-square-foot screened lanai overlooking the canal and backyard—an incredible extension of the home for dining, entertaining or relaxing by the water. Launch a kayak from your own property, step aboard your boat for a cruise toward Sarasota Bay, then end the day with a sunset at your private Gulf beach access. The spacious, fenced, side yard adds another exciting possibility: a pool. A local pool contractor has prepared a conceptual design and proposal for an approximately 12' x 24' custom pool with an oversized sun shelf, resort-style entry steps, swim-out bench and approximately 600 square feet of paver decking. The contractor’s proposal dated 9/22/26 reflects a $59,950 base project price, including permits, taxes and fees as specified in the proposal. Conceptual plan and full proposal available upon request. Pool is not installed or included in the sale; design, dimensions, pricing, permitting, site conditions and feasibility are subject to change and buyer verification. The property’s higher elevation relative to many ground-level Longboat Key homes is another notable feature. Offered FULLY FURNISHED / TURNKEY WITH NO HOA, the home is ready for immediate enjoyment as a primary residence, second home or coastal retreat. Few properties at this price combine 120 feet of waterfront, direct boating access, deeded private beach access, extensive renovation, impact features, turnkey furnishings and no HOA. $1.65M EARLIER APPRAISAL. $1.5M MOST RECENT APPRAISAL. NOW OFFERED AT $1.35M. YOUR BOAT IN THE BACKYARD. YOUR BEACH DOWN THE STREET. WELCOME TO LONGBOAT KEY.

4 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Virtually Staged. VIRTUALLY EVERYTHING NEW — BOAT IN YOUR BACKYARD, PRIVATE BEACH DOWN THE STREET. This is the Longboat Key lifestyle buyers dream about: boating from home, sunset walks on the Gulf, and a beautifully reimagined coastal residence that is truly move-in ready. Previously appraised at $1.65 million late last year and most recently at $1.5 million, with no material changes to the home, it is now offered at $1.35 million—an opportunity to purchase below its most recent appraised value. Set along 120 feet of canal frontage, this 4-bedroom, 2-bath waterfront home offers DIRECT BOATING ACCESS TO SARASOTA BAY AND THE INTRACOASTAL plus PRIVATE DEEDED GULF BEACH ACCESS JUST EIGHT HOMES AWAY. It is a rare Longboat Key combination: keep your boat at home and enjoy your private Gulf beach access just down the street. Joan M. Durante Park, Cedars Tennis Resort & Club, and favorite Longboat Key restaurants, boutiques and shops are all nearby. Optional Cedars membership offers tennis and pickleball courts, a Jr. Olympic pool, 24/7 fitness center and additional amenities. This is far more than a cosmetic update. With the exception of the foundation, VIRTUALLY EVERYTHING HAS BEEN RENOVATED OR REPLACED, INSIDE AND OUT. Improvements include a new roof, new AC systems, new interior walls and flooring, newer electrical and plumbing, new decking, cabinetry, landscaping and finishes, plus impact windows, high-impact sliding glass doors and impact-rated exterior doors. Inside, vaulted ceilings, expansive water views and an open, light-filled layout create effortless coastal living. The kitchen features solid-wood cabinetry, soft-close hardware, quartz countertops, a gas range, stainless-steel appliances, a copper hood and copper farmhouse sink. Updated baths continue the elevated finishes throughout. The living space opens to an approximately 1,000-square-foot screened lanai overlooking the canal and backyard—an incredible extension of the home for dining, entertaining or relaxing by the water. Launch a kayak from your own property, step aboard your boat for a cruise toward Sarasota Bay, then end the day with a sunset at your private Gulf beach access. The spacious, fenced, side yard adds another exciting possibility: a pool. A local pool contractor has prepared a conceptual design and proposal for an approximately 12' x 24' custom pool with an oversized sun shelf, resort-style entry steps, swim-out bench and approximately 600 square feet of paver decking. The contractor’s proposal dated 9/22/26 reflects a $59,950 base project price, including permits, taxes and fees as specified in the proposal. Conceptual plan and full proposal available upon request. Pool is not installed or included in the sale; design, dimensions, pricing, permitting, site conditions and feasibility are subject to change and buyer verification. The property’s higher elevation relative to many ground-level Longboat Key homes is another notable feature. Offered FULLY FURNISHED / TURNKEY WITH NO HOA, the home is ready for immediate enjoyment as a primary residence, second home or coastal retreat. Few properties at this price combine 120 feet of waterfront, direct boating access, deeded private beach access, extensive renovation, impact features, turnkey furnishings and no HOA. $1.65M EARLIER APPRAISAL. $1.5M MOST RECENT APPRAISAL. NOW OFFERED AT $1.35M. YOUR BOAT IN THE BACKYARD. YOUR BEACH DOWN THE STREET. WELCOME TO LONGBOAT KEY.

765 Saint Judes Drive N, Longboat Key

2800 Harbourside Drive Drive Unit M-10, Longboat Key

$289,000

A 58 ft. x 20 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. 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, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, 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. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. Max length of vessel allowed is 53 LOA, usable beam is 18 ft at the head of the slip. A current photo of the vessel must be provided, and the vessel approved by the Association before entering the marina.

Bay Isles SubDv. ⋅ 34228 Zip Code

A 58 ft. x 20 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. 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, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, 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. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. Max length of vessel allowed is 53 LOA, usable beam is 18 ft at the head of the slip. A current photo of the vessel must be provided, and the vessel approved by the Association before entering the marina.

2800 Harbourside Drive Drive Unit M-10, Longboat Key

729 Saint Judes Drive S Unit 2, Longboat Key

$525,000

Beautifully renovated waterfront unit at 729 St. Jude’s Way with gorgeous water views and a boat dock, plus easy access to the Intracoastal Waterway. Renovated from top to bottom, this move-in-ready home features all-new flooring, a beautifully updated kitchen and bathroom, and brand-new appliances. Ideally located near a variety of restaurants, beautiful beaches, downtown Sarasota, and Anna Maria Island. Enjoy the perfect blend of waterfront living, modern updates, and convenient access to everything the area has to offer!

2 Beds ⋅ 2 Baths ⋅ St Judes Apts SubDv. ⋅ 34228 Zip Code

Beautifully renovated waterfront unit at 729 St. Jude’s Way with gorgeous water views and a boat dock, plus easy access to the Intracoastal Waterway. Renovated from top to bottom, this move-in-ready home features all-new flooring, a beautifully updated kitchen and bathroom, and brand-new appliances. Ideally located near a variety of restaurants, beautiful beaches, downtown Sarasota, and Anna Maria Island. Enjoy the perfect blend of waterfront living, modern updates, and convenient access to everything the area has to offer!

729 Saint Judes Drive S Unit 2, Longboat Key

3802 Gulf Of Mexico Drive Unit A203, Longboat Key

$399,000

Gulf views! Just bring your flip flops and bathing suit to this move-in ready 2br/2ba condo on the 2nd floor in Beach Harbor Club. This beautifully maintained Gulf-to-bay community offers boat slips on the bay and private beach access on the Gulf side, as well as pool, clubhouse, gym and private beach access just across the street! This unit has been tastefully updated to include an all-new bright open kitchen with custom cabinetry, stone counters and high-end appliances, including a Fisher & Paykel fridge, a two-drawer Cafe dishwasher, and a Cafe two-oven, six-burner stove. Flooring throughout was replaced with a light blond luxury vinyl plank. Both baths had updates including cabinetry and same quartz countertops found in the kitchen. The AC was replaced in 2024. This home also has a sweet view of the Gulf from the outdoor seating area in the front. The monthly fee includes water, trash, internet, cable, and pest control, as well as the usual insurances, and exterior maintenances. Beach Harbor Club is an active and amenities-rich community with boat docks, a pool, a gym, private beach access, kayak storage, a ground-level storage closet for beach gear, a beautiful clubhouse and just upstairs from this unit is a wonderful rooftop deck for sunset viewing. No effort required to start living your beach life dream today!

2 Beds ⋅ 2 Baths ⋅ Beach Harbor Club SubDv. ⋅ 34228 Zip Code

Gulf views! Just bring your flip flops and bathing suit to this move-in ready 2br/2ba condo on the 2nd floor in Beach Harbor Club. This beautifully maintained Gulf-to-bay community offers boat slips on the bay and private beach access on the Gulf side, as well as pool, clubhouse, gym and private beach access just across the street! This unit has been tastefully updated to include an all-new bright open kitchen with custom cabinetry, stone counters and high-end appliances, including a Fisher & Paykel fridge, a two-drawer Cafe dishwasher, and a Cafe two-oven, six-burner stove. Flooring throughout was replaced with a light blond luxury vinyl plank. Both baths had updates including cabinetry and same quartz countertops found in the kitchen. The AC was replaced in 2024. This home also has a sweet view of the Gulf from the outdoor seating area in the front. The monthly fee includes water, trash, internet, cable, and pest control, as well as the usual insurances, and exterior maintenances. Beach Harbor Club is an active and amenities-rich community with boat docks, a pool, a gym, private beach access, kayak storage, a ground-level storage closet for beach gear, a beautiful clubhouse and just upstairs from this unit is a wonderful rooftop deck for sunset viewing. No effort required to start living your beach life dream today!

3802 Gulf Of Mexico Drive Unit A203, Longboat Key

$995,000

Build your dream waterfront home in the heart of Longboat Key's charming Historic Village. This offering consists of an approximately 7,730-square-foot newly created waterfront lot with approximately 177 feet of water frontage. Recently cleared and ready for your vision, the property provides an exceptional canvas for a custom coastal residence. Plans are available for a new seawall; please inquire for additional details. Recent feasibility study shows opportunity for a 3,400 square-foot home (available on request). Ideally located near some of the Historic Village's most beloved amenities, including a public boat launch, kayak launch, and waterfront dining at Mar Vista, Shore, and Whitney's, all just moments from the property. The sugar-sand beaches of the Gulf of Mexico are also just minutes away, offering convenient access to both Sarasota Bay and the Gulf. Whether you're envisioning a full-time residence or a private island retreat, this rare waterfront lot presents an exceptional opportunity to bring your custom dream home to life.

Long Beach SubDv. ⋅ 34228 Zip Code

Build your dream waterfront home in the heart of Longboat Key's charming Historic Village. This offering consists of an approximately 7,730-square-foot newly created waterfront lot with approximately 177 feet of water frontage. Recently cleared and ready for your vision, the property provides an exceptional canvas for a custom coastal residence. Plans are available for a new seawall; please inquire for additional details. Recent feasibility study shows opportunity for a 3,400 square-foot home (available on request). Ideally located near some of the Historic Village's most beloved amenities, including a public boat launch, kayak launch, and waterfront dining at Mar Vista, Shore, and Whitney's, all just moments from the property. The sugar-sand beaches of the Gulf of Mexico are also just minutes away, offering convenient access to both Sarasota Bay and the Gulf. Whether you're envisioning a full-time residence or a private island retreat, this rare waterfront lot presents an exceptional opportunity to bring your custom dream home to life.

6801 Longboat Drive S, Longboat Key

$2,250,000

Vacant waterfront homesite in one of Longboat Key’s most sought-after communities, offering approximately 50 feet of dockage on what is known as “Longboat’s Widest Canal.” Deeded beach access provides the best of both worlds—boating from your backyard and the Gulf of Mexico just moments away. GEOTECH STUDY SAYS - "structure can be supported on conventional shallow foundation". Bring your boat and build your vision. This oversized corner lot offers an exceptional opportunity to create a substantial custom waterfront residence. Enjoy dramatic eastern views down the canal toward Sarasota Bay, along with western views across the Longboat Key Club golf course and toward the Gulf of Mexico. A rare combination of waterfront, boating access, beach access, expansive views, and an oversized homesite in the heart of Longboat Key.

Country Club Shores SubDv. ⋅ 34228 Zip Code

Vacant waterfront homesite in one of Longboat Key’s most sought-after communities, offering approximately 50 feet of dockage on what is known as “Longboat’s Widest Canal.” Deeded beach access provides the best of both worlds—boating from your backyard and the Gulf of Mexico just moments away. GEOTECH STUDY SAYS - "structure can be supported on conventional shallow foundation". Bring your boat and build your vision. This oversized corner lot offers an exceptional opportunity to create a substantial custom waterfront residence. Enjoy dramatic eastern views down the canal toward Sarasota Bay, along with western views across the Longboat Key Club golf course and toward the Gulf of Mexico. A rare combination of waterfront, boating access, beach access, expansive views, and an oversized homesite in the heart of Longboat Key.

500 Outrigger Lane, Longboat Key

707 Saint Judes Drive S Unit 1, Longboat Key

$364,000

Have you ever dreamed of living on the water on Longboat Key, with your boat just steps from your back door? Imagine starting your morning with coffee outside in front of your dock and breakfast in the sun-filled breakfast nook overlooking the canal, spending the afternoon boating or kayaking on Sarasota Bay, and ending the day with your toes in the sand along the Gulf. Here, that can simply be your everyday life. Beautifully remodeled two years ago and offered furnished, this 1-bedroom, 1-bath canal-front end unit is ready to enjoy from day one. The bright coastal interior features a renovated kitchen that opens to the living room, an updated bathroom, newer appliances, impact-resistant windows and doors, and beautiful tile flooring throughout. A wall of windows surrounding the breakfast nook draws your eye toward the water and creates the perfect spot to linger over breakfast. At the end of the day, retreat to the spacious bedroom, where a long window brings in plenty of natural light and offers another glimpse toward the water. But the real magic begins outside. Step out to your own waterfront setting with a two-year-old dock just beyond your door, new pavers and a seawall replaced in 2021. Grab one of the included kayaks for a peaceful paddle, cast a line from the dock, or hop aboard your boat and head out to Sarasota Bay and the Intracoastal Waterway. There's even room along the side of the property to store your boat trailer. And on Longboat Key, life on the water is only half the story. When you're ready for the beach, Gulf access is just a short walk away. Joan M. Durante Park is practically next door, offering 32 acres of trails, gardens and gorgeous Sarasota Bay views, while island restaurants, shops, a deli, and bike and kayak rentals are all close to home. Perfectly positioned between Sarasota and Anna Maria Island, you can head south toward St. Armands Circle and downtown Sarasota or north toward the laid-back charm of Anna Maria Island. A newer metal roof and flood insurance included in the HOA fee offer additional peace of mind. Parking is easy with paver parking out front plus your own carport. Whether you're searching for your own island retreat, a waterfront investment, or simply a place where boating, beach days and sunsets become part of your routine, this is your opportunity to experience the Longboat Key lifestyle you've been dreaming about.

1 Beds ⋅ 1 Baths ⋅ St Judes Apts SubDv. ⋅ 34228 Zip Code

Have you ever dreamed of living on the water on Longboat Key, with your boat just steps from your back door? Imagine starting your morning with coffee outside in front of your dock and breakfast in the sun-filled breakfast nook overlooking the canal, spending the afternoon boating or kayaking on Sarasota Bay, and ending the day with your toes in the sand along the Gulf. Here, that can simply be your everyday life. Beautifully remodeled two years ago and offered furnished, this 1-bedroom, 1-bath canal-front end unit is ready to enjoy from day one. The bright coastal interior features a renovated kitchen that opens to the living room, an updated bathroom, newer appliances, impact-resistant windows and doors, and beautiful tile flooring throughout. A wall of windows surrounding the breakfast nook draws your eye toward the water and creates the perfect spot to linger over breakfast. At the end of the day, retreat to the spacious bedroom, where a long window brings in plenty of natural light and offers another glimpse toward the water. But the real magic begins outside. Step out to your own waterfront setting with a two-year-old dock just beyond your door, new pavers and a seawall replaced in 2021. Grab one of the included kayaks for a peaceful paddle, cast a line from the dock, or hop aboard your boat and head out to Sarasota Bay and the Intracoastal Waterway. There's even room along the side of the property to store your boat trailer. And on Longboat Key, life on the water is only half the story. When you're ready for the beach, Gulf access is just a short walk away. Joan M. Durante Park is practically next door, offering 32 acres of trails, gardens and gorgeous Sarasota Bay views, while island restaurants, shops, a deli, and bike and kayak rentals are all close to home. Perfectly positioned between Sarasota and Anna Maria Island, you can head south toward St. Armands Circle and downtown Sarasota or north toward the laid-back charm of Anna Maria Island. A newer metal roof and flood insurance included in the HOA fee offer additional peace of mind. Parking is easy with paver parking out front plus your own carport. Whether you're searching for your own island retreat, a waterfront investment, or simply a place where boating, beach days and sunsets become part of your routine, this is your opportunity to experience the Longboat Key lifestyle you've been dreaming about.

707 Saint Judes Drive S Unit 1, Longboat Key

2600 Harbourside Drive Unit I-12, Longboat Key

$200,000

The middle pier, right in front at Longboat Key Club! I-12, a 45 ft x 21 ft. slip in the marina. Purchase of this slip does require membership in the LBK Club. This is the only north-south pier in the marina; plenty of deep water and cool breezes. 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, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 40 LOA; beam depends on the vessel. Call to discuss.

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

The middle pier, right in front at Longboat Key Club! I-12, a 45 ft x 21 ft. slip in the marina. Purchase of this slip does require membership in the LBK Club. This is the only north-south pier in the marina; plenty of deep water and cool breezes. 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, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 40 LOA; beam depends on the vessel. Call to discuss.

2600 Harbourside Drive Unit I-12, Longboat Key

2600 Harbourside Drive Unit Q-10, Longboat Key

$225,000

A much sought after inside-the-T 48 x 23.5 foot slip at Longboat Key Club Moorings! Club membership is not required. 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, a Mediterranean style marina village that includes restaurants, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 43 LOA; beam depends on the vessel. Call to discuss!

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

A much sought after inside-the-T 48 x 23.5 foot slip at Longboat Key Club Moorings! Club membership is not required. 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, a Mediterranean style marina village that includes restaurants, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 43 LOA; beam depends on the vessel. Call to discuss!

2600 Harbourside Drive Unit Q-10, Longboat Key

713 Saint Judes Drive S Unit 2, Longboat Key

$560,000

WATERFRONT LONGBOAT KEY | PRIVATE DOCK | DIRECT INTRACOASTAL ACCESS | TURNKEY FURNISHED. Welcome to 713 Saint Judes Drive S #2, a beautifully renovated 2-bedroom, 2-bath waterfront residence in desirable Longboat Key. This turnkey furnished property offers private dockage with direct Intracoastal boating access—ideal for boaters, a vacation home, seasonal retreat or investment property. Extensively renovated in 2025 with a new kitchen featuring quartz countertops, updated cabinetry and appliances, renovated baths, new flooring, HVAC, water heater, windows and exterior doors, plus upgraded electrical and plumbing. Additional features include a one-car carport, interior laundry/storage and metal roof. Seasonal rentals began in November 2025, offering attractive income potential. The association fee includes master and flood insurance, water and sewer, trash and recycling, landscaping and tree trimming, pest control, and professional management. Conveniently located near Harry’s Continental Kitchens, Longboat Key beaches, Sarasota Bay, waterfront dining, St. Armands Circle and downtown Sarasota. A rare opportunity to enjoy renovated waterfront living, private dockage and boating access on Longboat Key.

2 Beds ⋅ 2 Baths ⋅ St Judes Apts SubDv. ⋅ 34228 Zip Code

WATERFRONT LONGBOAT KEY | PRIVATE DOCK | DIRECT INTRACOASTAL ACCESS | TURNKEY FURNISHED. Welcome to 713 Saint Judes Drive S #2, a beautifully renovated 2-bedroom, 2-bath waterfront residence in desirable Longboat Key. This turnkey furnished property offers private dockage with direct Intracoastal boating access—ideal for boaters, a vacation home, seasonal retreat or investment property. Extensively renovated in 2025 with a new kitchen featuring quartz countertops, updated cabinetry and appliances, renovated baths, new flooring, HVAC, water heater, windows and exterior doors, plus upgraded electrical and plumbing. Additional features include a one-car carport, interior laundry/storage and metal roof. Seasonal rentals began in November 2025, offering attractive income potential. The association fee includes master and flood insurance, water and sewer, trash and recycling, landscaping and tree trimming, pest control, and professional management. Conveniently located near Harry’s Continental Kitchens, Longboat Key beaches, Sarasota Bay, waterfront dining, St. Armands Circle and downtown Sarasota. A rare opportunity to enjoy renovated waterfront living, private dockage and boating access on Longboat Key.

713 Saint Judes Drive S Unit 2, Longboat Key

408 Gulf Of Mexico Drive Unit 2126, Longboat Key

$39,900

Experience the easiest, most carefree way to own a boat! This privately owned dry-stack boat slip offers exceptional convenience while protecting your investment in a fully enclosed, hurricane-resistant facility. Simply call ahead, and the professional dock staff will have your boat uncovered, launched, and ready when you arrive. After a day on the water, return to the dock and let the attendants handle the rest—they'll rinse your boat, flush the engines, replace the cover, and securely store it back in your assigned slip. Spend more time boating and less time cleaning and maintaining your vessel. The covered dry dock provides outstanding protection from sun, weather, tropical storms, and hurricanes, helping reduce maintenance, preserve your boat's condition, and extend its life. This slip accommodates vessels up to 23'6" L x 8'6" W x 7'2" H (collapsible T-tops only). The marina offers outstanding amenities, including: • Full-service fuel dock • Restrooms with showers • Covered service bays with water and electrical service • Leasing assistance for owners interested in generating rental income Perfectly located at the south end of Longboat Key, adjacent to the popular Dry Dock Grill, you'll enjoy quick access to Sarasota Bay, the Gulf of Mexico via New Pass, world-class fishing, waterfront dining, and countless boating destinations. Whether you're heading out for a sunset cruise, a day of fishing, or lunch by boat, this dry-stack slip makes every outing effortless. Don't miss this opportunity to own a premium boat slip in one of Longboat Key's most desirable boating locations—start enjoying truly hassle-free boating in paradise.

Boathouse On Longboat SubDv. ⋅ 34228 Zip Code

Experience the easiest, most carefree way to own a boat! This privately owned dry-stack boat slip offers exceptional convenience while protecting your investment in a fully enclosed, hurricane-resistant facility. Simply call ahead, and the professional dock staff will have your boat uncovered, launched, and ready when you arrive. After a day on the water, return to the dock and let the attendants handle the rest—they'll rinse your boat, flush the engines, replace the cover, and securely store it back in your assigned slip. Spend more time boating and less time cleaning and maintaining your vessel. The covered dry dock provides outstanding protection from sun, weather, tropical storms, and hurricanes, helping reduce maintenance, preserve your boat's condition, and extend its life. This slip accommodates vessels up to 23'6" L x 8'6" W x 7'2" H (collapsible T-tops only). The marina offers outstanding amenities, including: • Full-service fuel dock • Restrooms with showers • Covered service bays with water and electrical service • Leasing assistance for owners interested in generating rental income Perfectly located at the south end of Longboat Key, adjacent to the popular Dry Dock Grill, you'll enjoy quick access to Sarasota Bay, the Gulf of Mexico via New Pass, world-class fishing, waterfront dining, and countless boating destinations. Whether you're heading out for a sunset cruise, a day of fishing, or lunch by boat, this dry-stack slip makes every outing effortless. Don't miss this opportunity to own a premium boat slip in one of Longboat Key's most desirable boating locations—start enjoying truly hassle-free boating in paradise.

408 Gulf Of Mexico Drive Unit 2126, Longboat Key

2600 Harbourside Drive Unit O-07, Longboat Key

$216,000

Super city skyline views along with easy boat access! This 45 x 20 foot slip at Longboat Key Club Moorings is located on the north side of O-dock. Club membership is not required. 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, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and on-site concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 40 LOA; beam depends on the vessel. Call for more information.

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

Super city skyline views along with easy boat access! This 45 x 20 foot slip at Longboat Key Club Moorings is located on the north side of O-dock. Club membership is not required. 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, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and on-site concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 40 LOA; beam depends on the vessel. Call for more information.

2600 Harbourside Drive Unit O-07, Longboat Key

711 Spanish Drive S Unit 211, Longboat Key

$450,000

Discover the best of Longboat Key living in this beautifully renovated 2-bedroom, 2-bath first-floor villa in the sought-after Spanish Main Yacht Club. Offering 1,327 square feet of light-filled living space, this south-facing residence features a stunning vaulted open-beam ceiling, new kitchen with wood cabinetry, solid-surface counters, stainless steel appliances, oversized island and breakfast bar, plus luxury vinyl and tile flooring throughout. The spacious primary suite includes a walk-in closet and beautifully renovated en-suite bath with walk-in shower, while the guest bedroom and bath are equally well appointed. A bright Florida room adds flexible living space and includes a stacked washer and dryer. Enjoy a brick patio, storage area, hurricane-rated windows and doors, ceiling fans, block construction, tile roof and assigned carport. Spanish Main Yacht Club offers deeded private beach access, heated community pool, clubhouse, shuffleboard, kayak storage and a coveted 40-slip private marina. A boat slip is currently available for lease, making this an exceptional opportunity for boating enthusiasts. Enjoy easy access to boating and fishing, plus beautiful Gulf sunsets just a short stroll away. Ideally located minutes from St. Armands Circle, Sarasota dining, shopping, arts and entertainment, and an easy drive to Anna Maria Island. Association fees include water, sewer, trash, grounds and pool maintenance, management, common-area expenses and private road maintenance. Buyer association approval required; leasing permitted with a one-month minimum, up to twice annually.

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

Discover the best of Longboat Key living in this beautifully renovated 2-bedroom, 2-bath first-floor villa in the sought-after Spanish Main Yacht Club. Offering 1,327 square feet of light-filled living space, this south-facing residence features a stunning vaulted open-beam ceiling, new kitchen with wood cabinetry, solid-surface counters, stainless steel appliances, oversized island and breakfast bar, plus luxury vinyl and tile flooring throughout. The spacious primary suite includes a walk-in closet and beautifully renovated en-suite bath with walk-in shower, while the guest bedroom and bath are equally well appointed. A bright Florida room adds flexible living space and includes a stacked washer and dryer. Enjoy a brick patio, storage area, hurricane-rated windows and doors, ceiling fans, block construction, tile roof and assigned carport. Spanish Main Yacht Club offers deeded private beach access, heated community pool, clubhouse, shuffleboard, kayak storage and a coveted 40-slip private marina. A boat slip is currently available for lease, making this an exceptional opportunity for boating enthusiasts. Enjoy easy access to boating and fishing, plus beautiful Gulf sunsets just a short stroll away. Ideally located minutes from St. Armands Circle, Sarasota dining, shopping, arts and entertainment, and an easy drive to Anna Maria Island. Association fees include water, sewer, trash, grounds and pool maintenance, management, common-area expenses and private road maintenance. Buyer association approval required; leasing permitted with a one-month minimum, up to twice annually.

711 Spanish Drive S Unit 211, Longboat Key

$935,000

** FULLY FURNISHED TURN KEY AIR BNB!! WITH FURTURE BOOKINGS IN PLACE** You're purchasing fun and income with this truly rare homes, offering on one of Longboat Key’s most coveted streets, 608 St. Jude Drive embodies the essence of refined coastal living. Set on an extraordinary DOUBLE LOT and backing to a serene nature preserve, this impeccably reimagined residence offers an unparalleled combination of luxury, privacy, and investment potential in one of the island’s most desirable locations. Spanning more than 2,100 square feet, this stunning four-bedroom, three-bath home has been thoughtfully transformed with uncompromising attention to detail. Every major component has been replaced following the recent storms with fully permitted improvements, including a new roof, hurricane-impact windows, all-new electrical, new HVAC systems, and beautifully updated appliances. Immaculately maintained and completely move-in ready, the home offers the confidence and peace of mind that only a comprehensive renovation can provide. Inside, light-filled living spaces flow effortlessly with timeless tile flooring throughout, creating a sophisticated yet relaxed coastal aesthetic. Every room has been designed for both comfort and effortless entertaining, making the home equally suited for everyday living or unforgettable island getaways. Beyond the interiors lies one of the property’s most extraordinary features—its expansive DOUBLE LOT. A rarity on Longboat Key, this oversized homesite offers exceptional flexibility with room to expand, build upward, or create the custom outdoor oasis you’ve always envisioned, all while enjoying the privacy of having no rear neighbors thanks to the lush natural preserve. Perfectly positioned between the Gulf of Mexico and intercoastal water ways, you’re just a short stroll to the pristine beaches on the west side of the island and the Intracoastal Waterway to the east. Enjoy morning walks to the beach, afternoons on the water, and evenings dining at nearby neighborhood restaurants just moments from your front door. World-class destinations including St. Armands Circle, the iconic The St. Regis Longboat Key Resort, and The Shore Longboat Key are only minutes away, placing the very best of Longboat Key’s celebrated lifestyle within effortless reach. Equally appealing as a private coastal sanctuary or a high-performing investment, the property has an established vacation rental history with upcoming reservations already in place, allowing the next owner to begin generating income immediately. The seller is also open to negotiating the home fully furnished, creating an exceptional turnkey opportunity. Properties offering this level of quality, location, and future potential are increasingly rare. With its coveted address, remarkable DOUBLE LOT, comprehensive renovations, and timeless coastal appeal, 608 St. Jude Drive is more than a home—it’s an opportunity to own one of Longboat Key’s most exceptional island retreats.

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

** FULLY FURNISHED TURN KEY AIR BNB!! WITH FURTURE BOOKINGS IN PLACE** You're purchasing fun and income with this truly rare homes, offering on one of Longboat Key’s most coveted streets, 608 St. Jude Drive embodies the essence of refined coastal living. Set on an extraordinary DOUBLE LOT and backing to a serene nature preserve, this impeccably reimagined residence offers an unparalleled combination of luxury, privacy, and investment potential in one of the island’s most desirable locations. Spanning more than 2,100 square feet, this stunning four-bedroom, three-bath home has been thoughtfully transformed with uncompromising attention to detail. Every major component has been replaced following the recent storms with fully permitted improvements, including a new roof, hurricane-impact windows, all-new electrical, new HVAC systems, and beautifully updated appliances. Immaculately maintained and completely move-in ready, the home offers the confidence and peace of mind that only a comprehensive renovation can provide. Inside, light-filled living spaces flow effortlessly with timeless tile flooring throughout, creating a sophisticated yet relaxed coastal aesthetic. Every room has been designed for both comfort and effortless entertaining, making the home equally suited for everyday living or unforgettable island getaways. Beyond the interiors lies one of the property’s most extraordinary features—its expansive DOUBLE LOT. A rarity on Longboat Key, this oversized homesite offers exceptional flexibility with room to expand, build upward, or create the custom outdoor oasis you’ve always envisioned, all while enjoying the privacy of having no rear neighbors thanks to the lush natural preserve. Perfectly positioned between the Gulf of Mexico and intercoastal water ways, you’re just a short stroll to the pristine beaches on the west side of the island and the Intracoastal Waterway to the east. Enjoy morning walks to the beach, afternoons on the water, and evenings dining at nearby neighborhood restaurants just moments from your front door. World-class destinations including St. Armands Circle, the iconic The St. Regis Longboat Key Resort, and The Shore Longboat Key are only minutes away, placing the very best of Longboat Key’s celebrated lifestyle within effortless reach. Equally appealing as a private coastal sanctuary or a high-performing investment, the property has an established vacation rental history with upcoming reservations already in place, allowing the next owner to begin generating income immediately. The seller is also open to negotiating the home fully furnished, creating an exceptional turnkey opportunity. Properties offering this level of quality, location, and future potential are increasingly rare. With its coveted address, remarkable DOUBLE LOT, comprehensive renovations, and timeless coastal appeal, 608 St. Jude Drive is more than a home—it’s an opportunity to own one of Longboat Key’s most exceptional island retreats.

608 Saint Judes Drive, Longboat Key

2600 Harbourside Drive Unit P-05, Longboat Key

$200,000

**No Longboat Key Club Membership is Required** Nestled in a beautifully protected marina on the exclusive Longboat Key. This premium 48x20-foot wet slip accommodates vessels up to 43 feet and provides a true vacation lifestyle with full-time live-aboard privileges. Boating enthusiasts will enjoy seamless, unrestricted deep-water access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico with zero fixed bridges. The slip is fully equipped with robust dual 50-amp and dual 30-amp electrical hookups, while the marina provides comprehensive dockside services including both diesel and gasoline at the fuel dock and complimentary vessel pump-outs by professional dock hands. Owners also enjoy the flexibility to lease the slip to marina-approved vessels. Life at the marina combines everyday convenience with resort-style perks, featuring stunning, unobstructed sunrise and sunset views daily. The property includes water, sewer, cable TV, and Wi-Fi, alongside access to a well-maintained bathhouse, coin laundry facilities, a secure package delivery center, and free bicycle rentals. Parking is highly accessible with multiple spaces located directly next to the dock. Ownership integrates you into the Bay Isles HOA, which ensures peace of mind through 24-hour guarded gates, active security, and immaculate common area maintenance. For just $600 a year, owners can also join the walkable Bay Isles Beach Club to enjoy newly renovated beachfront facilities, volleyball nets, and picnic areas with grills. To complete the luxury experience, a complimentary community shuttle is available to transport you directly to the premier shopping and dining at St. Armand's Circle or the Longboat Key Club Resort properties.

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

**No Longboat Key Club Membership is Required** Nestled in a beautifully protected marina on the exclusive Longboat Key. This premium 48x20-foot wet slip accommodates vessels up to 43 feet and provides a true vacation lifestyle with full-time live-aboard privileges. Boating enthusiasts will enjoy seamless, unrestricted deep-water access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico with zero fixed bridges. The slip is fully equipped with robust dual 50-amp and dual 30-amp electrical hookups, while the marina provides comprehensive dockside services including both diesel and gasoline at the fuel dock and complimentary vessel pump-outs by professional dock hands. Owners also enjoy the flexibility to lease the slip to marina-approved vessels. Life at the marina combines everyday convenience with resort-style perks, featuring stunning, unobstructed sunrise and sunset views daily. The property includes water, sewer, cable TV, and Wi-Fi, alongside access to a well-maintained bathhouse, coin laundry facilities, a secure package delivery center, and free bicycle rentals. Parking is highly accessible with multiple spaces located directly next to the dock. Ownership integrates you into the Bay Isles HOA, which ensures peace of mind through 24-hour guarded gates, active security, and immaculate common area maintenance. For just $600 a year, owners can also join the walkable Bay Isles Beach Club to enjoy newly renovated beachfront facilities, volleyball nets, and picnic areas with grills. To complete the luxury experience, a complimentary community shuttle is available to transport you directly to the premier shopping and dining at St. Armand's Circle or the Longboat Key Club Resort properties.

2600 Harbourside Drive Unit P-05, Longboat Key

2800 Harbourside Drive Unit D-16, Longboat Key

$425,000

Easy access and docking at this 75 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina on D-dock. Located on the West side of the marina. Ample turning radius between piers, so lots of room to maneuver. Direct access to Sarasota Bay and the ICW; 15 minutes to the Gulf. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village and restaurants, shopping (close to Publix, CVS, and other shops), recreational and social activities, on-site maintenance and concierge services. Each slip includes wifi, water, pump out and metered electric, along with trash pick up and dockhands to assist. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 70 LOA, usable beam is 23 ft at the head of the slip. Each vessel must be approved by the Association's Board of Directors prior to entering the marina by submitting a current photo and boat specs.

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code

Easy access and docking at this 75 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina on D-dock. Located on the West side of the marina. Ample turning radius between piers, so lots of room to maneuver. Direct access to Sarasota Bay and the ICW; 15 minutes to the Gulf. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village and restaurants, shopping (close to Publix, CVS, and other shops), recreational and social activities, on-site maintenance and concierge services. Each slip includes wifi, water, pump out and metered electric, along with trash pick up and dockhands to assist. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 70 LOA, usable beam is 23 ft at the head of the slip. Each vessel must be approved by the Association's Board of Directors prior to entering the marina by submitting a current photo and boat specs.

2800 Harbourside Drive Unit D-16, Longboat Key

$695,000

Create your custom coastal retreat or bring the seller’s thoughtfully prepared plans to life at 561 Gulf Bay Road. This rare 9,990-square-foot vacant homesite is ideally located in the heart of Longboat Key, between the charm of Anna Maria Island and the sophistication of St. Armands Circle. Bordering the 32-acre Joan M. Durante Community Park, the property offers exceptional privacy, peaceful natural surroundings, and convenient access to scenic walking trails, a picnic pavilion, and picturesque views of Sarasota Bay and the Sarasota skyline. Imagine watching eagles, ospreys, and other native wildlife from your future home or backyard. With no HOA or deed restrictions, you have the flexibility to personalize the available plans or design a custom residence that reflects your vision and lifestyle. The property also includes deeded beach access to a quiet stretch of white sand along the Gulf of Mexico, allowing you to enjoy the best of both Gulf and bay living. Nearby destinations include Euphemia Haye, Harry’s Continental Kitchens, boutique shopping, and a neighborhood deli, with additional dining, recreation, shopping, and entertainment available throughout Longboat Key, Anna Maria Island, and Sarasota. Underground utility improvements throughout the area are complete. Previously prepared plans for a custom single-family residence and an elevation study are available upon request, providing an excellent starting point for your future island home. Buyers should independently verify current building requirements and property suitability. This is a special opportunity to build in one of Longboat Key’s most naturally beautiful and desirable locations. Schedule your private showing and begin planning your Florida coastal lifestyle. Representative Photos Added to listing showcase preliminary renderings showcasing Conditioned Square Footage of 4,936 and Unconditioned Square Footage of 4,053.

Bailey-Dobson SubDv. ⋅ 34228 Zip Code

Create your custom coastal retreat or bring the seller’s thoughtfully prepared plans to life at 561 Gulf Bay Road. This rare 9,990-square-foot vacant homesite is ideally located in the heart of Longboat Key, between the charm of Anna Maria Island and the sophistication of St. Armands Circle. Bordering the 32-acre Joan M. Durante Community Park, the property offers exceptional privacy, peaceful natural surroundings, and convenient access to scenic walking trails, a picnic pavilion, and picturesque views of Sarasota Bay and the Sarasota skyline. Imagine watching eagles, ospreys, and other native wildlife from your future home or backyard. With no HOA or deed restrictions, you have the flexibility to personalize the available plans or design a custom residence that reflects your vision and lifestyle. The property also includes deeded beach access to a quiet stretch of white sand along the Gulf of Mexico, allowing you to enjoy the best of both Gulf and bay living. Nearby destinations include Euphemia Haye, Harry’s Continental Kitchens, boutique shopping, and a neighborhood deli, with additional dining, recreation, shopping, and entertainment available throughout Longboat Key, Anna Maria Island, and Sarasota. Underground utility improvements throughout the area are complete. Previously prepared plans for a custom single-family residence and an elevation study are available upon request, providing an excellent starting point for your future island home. Buyers should independently verify current building requirements and property suitability. This is a special opportunity to build in one of Longboat Key’s most naturally beautiful and desirable locations. Schedule your private showing and begin planning your Florida coastal lifestyle. Representative Photos Added to listing showcase preliminary renderings showcasing Conditioned Square Footage of 4,936 and Unconditioned Square Footage of 4,053.

561 Gulf Bay Road, Longboat Key

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