Longboat Key Real Estate

Longboat Key Real Estate

Welcome to Longboat Key, Florida—a hidden gem nestled along the sparkling shores of the Gulf of Mexico. This enchanting barrier island is renowned for its pristine beaches, luxurious living, and a laid-back atmosphere that beckons both residents and visitors alike. Spanning just over 10 miles, Longboat Key offers a unique blend of natural beauty and upscale amenities, making it the perfect destination for beach lovers, golf enthusiasts, and those seeking a tranquil escape.

With its soft white sands and crystal-clear waters, Longboat Key boasts some of the most picturesque beaches in Florida. Whether you’re lounging under the sun, taking a leisurely stroll along the shoreline, or indulging in water sports, the beach is the heart of this vibrant community. The island is also home to a variety of parks and nature preserves, inviting you to explore the lush landscapes and diverse wildlife.

Longboat Key is not just about stunning scenery; it’s also a hub for fine dining, boutique shopping, and cultural experiences. The island features an array of gourmet restaurants, many of which offer breathtaking views of the sunset over the Gulf. For those who enjoy the arts, the nearby city of Sarasota presents a rich tapestry of galleries, theaters, and museums.

With a strong sense of community and an array of events throughout the year, Longboat Key fosters a welcoming environment for families, retirees, and everyone in between. Whether you’re looking to invest in a luxurious waterfront property or searching for a serene vacation retreat, Longboat Key is a captivating choice that promises a lifestyle of elegance and relaxation. Come discover the magic of Longboat Key—your paradise awaits!

Newest Listings in Longboat Key

$599,900
2 Beds 3 Baths Cedars East SubDv. 34228 Zip Code
Discover your ultimate island escape in this beautifully updated, fully furnished, and pet-friendly 2-bedroom, 2.5-bathroom townhome located within the desirable Cedars Tennis Resort & Club on Longboat Key. Set across a lush, village-like community enveloped by nature on the island's scenic north end, this property offers a rare combination of relaxed coastal living and an excellent short-term rental opportunity featuring a flexible two-week policy. Step inside to find a turnkey, coastal-chic interior highlighted by crisp shiplap accents, warm wood-style flooring, and elegant metallic hardware throughout. The updated kitchen features white shaker cabinetry, premium stone countertops, custom tile backsplash, and a breakfast bar with seating, all while offering a subtle peekaboo views of the glistening Gulf of Mexico. It flows seamlessly into a bright dining space framed by a shell-pendant chandelier and an inviting living room that opens through sliding glass doors to a private, screened lanai framed by tropical palms and water views. Upstairs, the layout is designed for comfort and convenience. The primary suite serves as a serene retreat with water views, large closet space, and barn-door entry into an upgraded bathroom featuring dual vanities, white shiplap walls, and a walk-in shower with floor-to-ceiling marble tile and gold hardware accents. Just down the hall, the secondary bedroom, which also catches a peekaboo Gullf view, is accompanied by a second full bathroom and ther is also a dedicated upstairs laundry closet with front-loading washer and dryer units. Outside, the property enjoys tranquil views of lush tropical foliage and a quiet island setting, complete with recent structural and mechanical improvements like updated windows, a brand new roof, 2021 air conditioning units, and a private garage with recently install hurricane rated garage door. Cedars Tennis Club provides an unmatched resort-style atmosphere. Meander along lit boardwalks winding through mangroves to access an exceptional array of community amenities, including a heated Junior Olympic-sized swimming pool, a vibrant tiki bar, nine Har-Tru tennis courts, three Har-Tru pickleball courts, a clubhouse with a pro shop, a 24-hour fitness center, an on-site Google 5-star restaurant Hugo's II, a fishing pier, and a kayak launch (please note that some amenities require an additional club membership). When you are ready to venture out, you are within easy walking distance of Longboat Key's world-renowned sugary white sand beaches, the tranquil trails of Joan Durante Park, and local culinary staples like Harry's Deli & Continental Kitchen, Lo-Key Bar and Grill and Euphemia Haye Restaurant & The Haye Loft. For broader entertainment, shopping, and cultural experiences, St. Armands Circle, downtown Sarasota, the Ringling Museum complex, Mote Marine and Anna Maria Island are just a short drive away. Whether you are searching for the dream beach house, a lucrative investment property, or your own private full-time retreat complete with stunning evening sunsets, this Longboat Key gem delivers on every front.

521 Forest Way, Longboat Key

$1,050,000
2 Beds 2 Baths Bayport Bch & Ten SubDv. 34228 Zip Code
Welcome to 732 Bayport Way, a completely remodeled and beautifully furnished coastal retreat offering a rare Gulf view within Bayport Beach & Tennis Club, one of Longboat Key’s distinctive Gulf to Bay communities. Thoughtfully redesigned and renovated in 2023, this 2 bedroom, 2 bath residence offers approximately 1,456 square feet of sophisticated, move in ready living with virtually every detail updated. The renovation includes new flooring, countertops and windows, along with a dedicated home office that creates the perfect space for working remotely or enjoying a quiet study. The sleek, redesigned kitchen features premium JennAir appliances, crisp contemporary cabinetry, beautiful countertops, a water purification system and thoughtful finishes throughout. Designed with entertaining in mind, the residence also features a custom bar complete with a wine cooler, dedicated whisky display and built in cigar humidor, creating a distinctive space for cocktails, wine and evenings with friends. New furnishings throughout, including select pieces from Restoration Hardware, complete the refined yet relaxed coastal feel. Bayport offers an exceptional Longboat Key lifestyle, stretching from the Gulf of Mexico to Sarasota Bay and giving residents the opportunity to enjoy both beach and bay. Community amenities include private Gulf beach access, a heated swimming pool, tennis courts, fitness facilities, clubhouse, walking and nature paths, kayak facilities and access to Sarasota Bay. Start the morning with a walk along the Gulf, work from your private home office, spend the afternoon by the pool or on the water, and finish the evening entertaining at home or taking in a Longboat Key sunset. Completely remodeled, beautifully furnished and ready to enjoy from day one, 732 Bayport Way offers the opportunity to step directly into the Longboat Key lifestyle without the time, expense or inconvenience of undertaking a major renovation.

732 Bayport Way, Longboat Key

$815,000
2 Beds 2 Baths Longboat Key SubDv. 34228 Zip Code
Situated on an extra large 11,250 sf waterfront lot, with a 2020 dock and 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

$1,495,000
3 Beds 3 Baths Harbor Oaks SubDv. 34228 Zip Code
3BR/2.5BA, 2,219 sf end-unit villa in gated Harbour Oaks at Bay Isles. Fairway views across hole #3 (White) of the Longboat Key Club golf course, plus a full-sized private heated pool on a large screened lanai. Three sliders open the living spaces to that outdoor room—ideal for gatherings, quiet evenings, and southwest-oriented sunsets over the greens. Renovated in a clean modern-farmhouse style: shiplap fireplace, new lighting and ceiling fans, paneled interior doors with dark hardware, and a wood-and-glass front door. The open, refreshed kitchen flows into the dining area overlooking the pool and golf course. The primary suite is a true retreat with multiple closets including a walk-in, double sinks, a newly tiled glass-enclosed shower, and a bathroom skylight. Two additional bedrooms and a bonus office with golf-course and garden-atrium views give the household room to work, guest, and spread out. Practical updates include a new roof with the assessment paid and a large two-car garage with epoxy floor and organized storage for beach and sports gear. Harbour Oaks residents have use of the private Bay Isles Beach Club on the Gulf (parking available). Longboat Key Club golf, tennis, pickleball, and dining are nearby by optional separate membership; the marina is a short walk, with slips available separately. Move-in ready Longboat Key living: golf-course backdrop, private pool, beach-club access, and lock-and-leave convenience behind the Bay Isles gates. Schedule your private showing and start living the island lifestyle.

2101 Harbourside Drive Unit 1103, Longboat Key

$699,000
2 Beds 2 Baths Fairway Bay SubDv. 34228 Zip Code
Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.

2020 Harbourside Drive Unit 442, Longboat Key

$1,595,000
2 Beds 2 Baths Promenade SubDv. 34228 Zip Code
Gulf views take center stage in this beautifully updated sixth-floor residence at The Promenade, where an elevated vantage point captures the turquoise waters of the Gulf of Mexico, the tropical grounds below and glimpses toward Sarasota Bay. Offering nearly 1,600 square feet of thoughtfully designed living space, this two-bedroom retreat pairs a light, sophisticated coastal aesthetic with the ease of resort-style living directly on the beach. Inside, walls of glass draw the Gulf backdrop into the main living areas while filling the residence with natural light. The open great room is designed for both everyday comfort and entertaining, with neutral finishes, tile flooring and an effortless connection to the private terrace. Step outside to enjoy Gulf breezes, views over the pool and landscaped grounds, and a front-row seat to Longboat Key’s spectacular sunsets. The living and dining spaces flow together beautifully, complemented by a stylish wet bar with beverage storage that creates a natural entertaining hub. Architectural wall detailing adds dimension to the dining area, while the soft coastal palette and contemporary furnishings reinforce the home’s relaxed sense of sophistication. The open kitchen is equally inviting, featuring naturally stained wood cabinetry, quartz countertops, stainless-steel appliances and a newer quartz backsplash. An expansive breakfast bar provides generous seating, while the adjacent dining nook offers another comfortable setting for morning coffee or casual meals. Privately positioned, the primary suite is a serene retreat with its own Gulf outlook and direct terrace access. Wake to blue water just beyond the glass, then step outside to begin the day in the Gulf breeze. Generous closet space accompanies the suite, while the renovated primary bath offers a spa-inspired setting with a dual-sink vanity, soaking tub, glass-enclosed shower and refined contemporary finishes. The guest suite provides comfortable accommodations for family and friends, with an updated bath featuring a glass-enclosed shower and coastal-inspired tile. Covered under-building parking and a separate storage unit add everyday convenience. Set directly along the Gulf of Mexico, The Promenade is one of Longboat Key’s established full-service beachfront communities, offering on-site management, concierge services, a 24-hour manned guard gate and an impressive collection of resort-style amenities. Residents enjoy a Gulfside heated swimming pool and spa surrounded by expansive sundecks and tropical landscaping, four Har-Tru tennis courts, fitness and health club facilities, social rooms, and direct beach access by private boardwalk. Tiki huts and beachfront lounging areas create an inviting setting for days spent along the shoreline. Beyond the gates, the location puts the best of Longboat Key and Sarasota within easy reach. Enjoy nearby dining and shopping along Longboat Key, explore the boutiques and restaurants of St. Armands Circle, or continue across the Ringling Bridge to downtown Sarasota for its acclaimed restaurants, galleries, performing arts, farmers market and vibrant waterfront. From mornings on the beach to evenings overlooking a Gulf sunset, Promenade #603 offers an exceptional opportunity to experience the Longboat Key lifestyle from a beautifully updated home by the sea.

1211 Gulf Of Mexico Drive Unit 603, Longboat Key

$3,249,000
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

$2,200,000
2 Beds 4 Baths Longboat Key Club SubDv. 34228 Zip Code
Welcome to an extraordinary opportunity at The Water Club on Longboat Key, where spectacular Gulf and Sarasota Bay views create a breathtaking backdrop from nearly every room. Residence 608 offers approximately 2,965 square feet of coastal living space with 2 bedrooms plus a versatile den, 4 full baths, 10-foot ceilings and an expansive open floor plan designed for both everyday living and effortless entertaining. Walls of glass sliders fill the residence with natural light while showcasing incredible water views at every turn. The spacious living and dining areas flow together, complemented by a dedicated entertaining bar that makes this home ideal for hosting family and friends. Multiple covered terraces extend the living space outdoors, providing wonderful places to enjoy morning coffee, Gulf breezes, colorful skies and unforgettable Florida sunsets. The generously sized primary suite is a peaceful retreat, while the additional bedroom and flexible den provide plenty of space for overnight guests, a home office or additional sleeping accommodations. Abundant storage throughout the residence adds exceptional functionality, along with two parking spaces in the secure covered garage, additional private storage and a wine/beverage storage area. Life at The Water Club feels more like a five-star resort than a condominium. Set along the white sands of Longboat Key, this premier gated Gulf-front community offers exceptional service, privacy and security with a 24-hour staffed gated entrance and dedicated concierge staff available seven days a week. Residents enjoy an impressive collection of amenities including a junior Olympic-size heated pool, children's pool, three hot tubs, four lighted Har-Tru tennis courts and a beautifully appointed clubhouse designed for recreation, wellness and entertaining. The clubhouse features a fully equipped fitness center, steam and sauna facilities, locker rooms and private massage areas, an elegant ballroom overlooking the grounds and Gulf, catering kitchen, wood-paneled bar and lounge, library with fireplace and recreation room with billiards and table tennis. From days spent on the beach and afternoons by the pool to sunset cocktails overlooking the Gulf, Residence 608 offers the opportunity to experience Longboat Key living at its finest. All of this is ideally positioned on the south end of Longboat Key, just minutes from the shopping and dining of St. Armands Circle and the arts, culture and waterfront attractions of downtown Sarasota. This is more than a residence—it is the effortless, resort-style Gulf Coast lifestyle that makes The Water Club one of Longboat Key's most coveted addresses. All information provided by the sellers is deemed reliable but is not guaranteed. Buyers are encouraged to verify all information independently.

1241 Gulf Of Mexico Drive Unit 608, Longboat Key

$12,750,000
3 Beds 4 Baths St Regis SubDv. 34228 Zip Code
Presented in the most coveted beachfront enclave at The St. Regis Longboat Key Resort, this is a rare opportunity to own a spectacular residence in the prestigious Armand building — the closest to the Gulf, with breathtaking, unobstructed views of the Gulf of Mexico. Encompassing nearly 5,000 square feet and offered fully furnished, this extraordinary home was masterfully designed by the award-winning Rowland and Broughton of Aspen, Colorado. Thoughtfully curated throughout, it lives like a private single-family home while enjoying the legendary St. Regis services and amenities, including butler service and in-residence dining. The gracious great room is designed for effortless entertaining, featuring porcelain wood plank flooring and dramatic accordion doors that fully retract to a sprawling terrace with a private gas grill and panoramic views of the Gulf, resort, and saltwater lagoon — creating seamless indoor-outdoor living. The chef’s kitchen is a true showpiece, anchored by a large statement island clad in exquisite Pininfarina Crystal quartzite with a dramatic waterfall edge — blending sculptural beauty with everyday functionality. The space is impeccably appointed with dual Cove dishwashers, a Wolf six-burner cooktop, Wolf double ovens and microwave, and a Sub-Zero refrigerator. A charming breakfast area offers built-in storage and shelving, along with an ice maker and beverage refrigerator for ultimate convenience. A private club room provides the perfect setting for lounging or game day gatherings, highlighted by custom built-ins and striking in-wall wine storage. The luxurious owner’s suite captures sweeping Gulf views and opens directly onto the expansive terrace. A stunning feature wall wrapped in Bijou Knits wallpaper by Phillip Jeffries adds refined texture and sophistication, complementing the custom built-ins that define this serene retreat. The spa-inspired bath features dual oversized vanities (including a dedicated makeup area), illuminated mirrors, a soaking tub, seamless glass shower, two private water closets with Toto electric toilets, and custom closets. Two additional guest suites offer comfort and privacy. The second features custom built-ins with a king Murphy bed, integrated desk, generous closets, and a bath with double vanities and glass shower, opening to terrace views of Sarasota Bay. The third is equally spacious, also opening to the terrace with bay views and offering double vanities and custom closets. An elegant laundry room continues the home’s elevated aesthetic with custom cabinetry, a utility sink, and SM Quartz by Santa Margherita countertops. Throughout, porcelain wood plank floors, electronic shades, and a state-of-the-art Crestron smart home system enhance everyday living. The integrated technology package — valued at approximately $400,000 — controls lighting, blinds, televisions, and music throughout the home. This is an exceptional opportunity to own one of the most refined residences on Longboat Key — where five-star resort living meets the privacy and comfort of a grand coastal home. Residents enjoy a private clubhouse with fitness center, resident-only pool and spa, St. Regis Butler and Concierge services, an oceanfront spa, dining venues, beachfront cabanas, lazy river, and saltwater lagoon. Set on 17 acres of pristine beachfront just 3.5 miles from St. Armands Circle, this home invites you to embrace the legendary St. Regis lifestyle.

1561 Gulf Of Mexico Drive Unit 404, Longboat Key

$795,000
3 Beds 2 Baths Club Longboat Beach & Tennis SubDv. 34228 Zip Code
Welcome to effortless Gulf-front living at Club Longboat Beach & Tennis Resort, one of Longboat Key’s established and sought-after beachfront communities. This beautifully updated three-bedroom, two-bath residence is offered turnkey furnished, making it an exceptional opportunity for a full-time residence, coastal retreat or potential income-producing investment. In desirable Building 1, this spacious first-floor residence offers approximately 1,484 square feet of comfortable, thoughtfully designed living space with the rare convenience of no elevators or long walks. The open, split-bedroom floor plan features wide-plank flooring, a light and inviting coastal palette, and an easy flow for everyday living and entertaining. The updated kitchen is the heart of the home, featuring crisp white cabinetry, stainless steel appliances, under-cabinet lighting, a glass tile backsplash and a large center island with seating. Floor-to-ceiling sliders in the great room open to a private, lushly landscaped patio, extending the living space outdoors and creating a peaceful place to enjoy the Longboat Key lifestyle. The spacious primary suite offers direct patio access, a beautifully updated bath with walk-in glass shower and generous closet space. Two additional bedrooms provide flexibility for family and guests, including a den/third bedroom with Murphy bed. A second full bath, full-size washer and dryer, additional laundry cabinetry and abundant storage complete the interior. Just outside your front door is a private storage room and covered parking space, with ample additional guest and resident parking throughout the community. Club Longboat offers approximately 750 feet of direct Gulf-front beach and an exceptional resort-style lifestyle. Amenities include eight Har-Tru tennis courts, several lighted for evening play, an on-site tennis professional, pickleball, two heated swimming pools including separate adult and family pool areas, spa/whirlpool, sauna, beach chairs and umbrellas, grilling areas, bocce, fishing, on-site management and an active social calendar. A new clubhouse with fitness and social spaces is also planned as part of the community’s hurricane restoration, with exciting improvements ahead. Owners enjoy a welcoming community with regular social events, including Friday happy hours and seasonal celebrations. Club Longboat is also pet-friendly for owners and offers exceptional rental flexibility, with a 30-day minimum and up to 12 leases per year. For buyers looking to offset ownership costs, this residence offers a particularly compelling advantage, such as a proven rental history with substantial demand and future bookings potential. The combination of a three-bedroom floor plan, turnkey furnishings, direct Gulf access and flexible leasing has made this an exceptionally desirable rental. Ideally on the Gulf side of Longboat Key, you are minutes from outstanding dining, boating, golf and recreation, with the shops and restaurants of St. Armands Circle and the arts and culture of downtown Sarasota just a short drive away. Whether you are searching for a turnkey beach home, seasonal escape or investment property, this beautifully furnished Club Longboat residence offers the combination buyers want most, direct gulf access, resort-style amenities, three bedrooms, rental flexibility and unmistakable lifestyle of Longboat Key. Simply arrive, unpack and head to the beach.

5055 Gulf Of Mexico Drive Unit 115, Longboat Key

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