Location: Longboat Key
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
1915 HARBOUR LINKS CIR #6, LONGBOAT KEY, FL 34228
$1,950,00073 Days on yellowkey MLS ID: A4688148
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2476 Built: 2002 Tax: $19,319 (2025)Community: Bay IslesSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$19,319
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Private Beach Access + Gated Bay Isles Living on Longboat Key! Welcome to Emerald Pointe South, where maintenance-free coastal living meets one of the island’s most desirable gated communities. This beautifully maintained villa offers the relaxed Florida lifestyle buyers are searching for — ideal as a full-time residence, seasonal retreat, or investment opportunity. Inside, a bright and open floor plan features spacious living and dining areas filled with natural light from expansive sliding glass doors. The private screened lanai overlooks lush tropical landscaping, creating the perfect setting for morning coffee or evening relaxation. The kitchen offers solid surface countertops, abundant cabinetry, a breakfast nook, and newer appliances including a microwave, dishwasher, and stove. The spacious primary suite features dual walk-in closets and a large en-suite bath with dual vanities, soaking tub, and separate shower. Upstairs, two additional bedrooms each include private en-suite baths, providing comfort and privacy for guests and family. Residents enjoy the security of gated Bay Isles along with coveted private beach access to the Gulf of Mexico. Located just minutes from St. Armands Circle and downtown Sarasota, this home offers easy access to waterfront dining, shopping, golf, marinas, and world-renowned beaches. Low-maintenance island living, private beach access, and an unbeatable Longboat Key location — this is the coastal lifestyle buyers dream about.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Cathy Palmer (678-524-1104)
3271 BAYOU RD, LONGBOAT KEY, FL 34228
$1,995,0009 Days on yellowkey MLS ID: TB8515918
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3059 Built: 2014Monthly Fee: $104 Tax: $27,748 (2025)Community: Bay IslesSingle Family
Taxes:$27,748
High School: Booker High
Remarks: Nestled behind the gates of prestigious Bay Isles on Longboat Key, this exceptional residence offers over 3,000 square feet of thoughtfully designed living space surrounded by lush tropical landscaping and just moments from the Gulf of Mexico. Combining timeless architecture, spacious interiors, and resort-style outdoor living, this home delivers the privacy and elegance that define the Longboat Key lifestyle. A grand entry welcomes you into an open and inviting floor plan featuring soaring ceilings, abundant natural light, and generous living and entertaining spaces. The expansive great room flows seamlessly into the dining area and well-appointed kitchen, complete with ample cabinetry, extensive counter space, and a convenient wet bar for effortless entertaining. The first-floor primary suite serves as a private retreat with a spacious bedroom, large walk-in closet, and luxurious en-suite bath. Additional guest bedrooms are thoughtfully positioned for privacy and comfort, while the second floor offers a private guest suite with balcony access—perfect for visitors seeking their own space and enjoying tropical views. Designed for year-round enjoyment, the screened outdoor living area is a true highlight. Relax poolside in the sparkling heated pool and spa, entertain under the covered lanai, or unwind amidst the lush tropical surroundings that create a secluded backyard oasis. Located within the highly sought-after Bay Isles community, residents enjoy 24-hour gated security, beautifully maintained grounds, and exclusive access to the private Bay Isles Beach Club on the Gulf of Mexico. Just minutes away are the Longboat Key Club's championship golf courses, tennis facilities, marina, waterfront dining, boutique shopping, and renowned St. Armands Circle. Offering the perfect blend of luxury, privacy, and coastal convenience, this exceptional Longboat Key residence presents a rare opportunity to enjoy one of Sarasota's most desirable island lifestyles.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Robert Johnson (813-364-2250)
1281 GULF OF MEXICO DR #708, LONGBOAT KEY, FL 34228
$3,275,000155 Days on yellowkey MLS ID: A4677632
1 Days Off yellowkey (back on 6/11/2026)
Bed: 3 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 3273 Built: 1999 Tax: $26,304 (2024)Community: Water Club At Longboat KeySpa: NoCondo
Taxes:$26,304
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Welcome to an extraordinary corner residence at The Water Club where timeless elegance meets effortless coastal living on Longboat Key. Offering 3,275 square feet of beautifully designed interior space, this 3-bedroom, 4.5-bath condominium captures sweeping unobstructed expansive views of the Gulf of Mexico, glowing sunsets, Sarasota Bay, and the city skyline from nearly every room. Floor-to-ceiling windows and expansive sightlines fill the home with natural light, creating a serene and sophisticated atmosphere throughout. Designed with refined craftsmanship, the residence showcases custom woodworking, hardwood floors, and soaring 10-foot ceilings that enhance the sense of scale and luxury. The thoughtfully designed layout provides generous living and entertaining spaces while maintaining privacy for guests. The home is in true move-in condition and has been thoughtfully updated with all-new appliances in 2025, blending modern convenience with classic finishes. Enjoy the exclusivity of private elevator access directly to the residence, along with full concierge services that elevate everyday living. The building offers an impressive collection of resort-style amenities, including a Gulf-front swimming pool overlooking pristine white sand beaches, a fully equipped fitness studio, an elegant library, a grand ballroom for entertaining, and a game room for relaxation and recreation, a premier parking space, and as well as climate controlled storage units. This exceptional property delivers the best of beachfront living with luxury, privacy, and breathtaking views all within one of Longboat Key’s most desirable addresses. A rare opportunity to own a refined coastal retreat where every detail has been carefully considered and every day feels like a getaway.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
617 ROUNTREE DR, LONGBOAT KEY, FL 34228
$2,350,00033 Days on yellowkey MLS ID: A4692822
REDUCED by $145,000 (5.8%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1972 Built: 1973Monthly Fee: $250 Tax: $7,892 (2025)Community: Longboat Key EstatesSpa: NoSingle Family
Taxes:$7,892
Remarks: Premier waterfront opportunity in Longboat Key Estates, offering direct canal frontage in one of the island’s most desirable residential enclaves. Positioned along a quiet interior street, this property offers the opportunity to own or build a custom coastal residence in an area undergoing continued redevelopment and investment potential. Surrounding properties reflect the neighborhood's transformation, with new-construction homes setting a high standard for modern, exclusive waterfront living. The canal setting provides protected waters for boating with access to Sarasota Bay, while deeded, private beach access offers the rare combination of boating and beachside lifestyle. This property offers views of Sarasota Bay and the Intracoastal Waterway directly from your Lanai and dock, featuring a 100 feet of seawall frontage (2022) and a 16,000-pound boat lift (2022). Generous lot dimensions and a tranquil waterfront setting create an exceptional opportunity for boating enthusiasts and the ideal canvas for a thoughtfully designed custom residence. As a resident of Longboat Key Estates, a deed-restricted single-family waterfront community, you have deeded access to the Gulf and a private resident-only Tiki within a five-minute walk. Enjoy close proximity to Bayfront Park offering pickleball and tennis, kayaking, along within close distance to fine dining, St. Armands Circle, downtown Sarasota, Sarasota International Airport, and Florida’s Gulf Coast, all at your doorstep!
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Judi Taulbee (941-544-6227)
2055 GULF OF MEXICO DR #G2-213, LONGBOAT KEY, FL 34228
$610,00094 Days on yellowkey MLS ID: TB8485915
REDUCED by $12,000 (1.9%) on 06/10/2026
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 1094 Built: 1974 Tax: $5,426 (2025)Community: Seaplace ICondo
Taxes:$5,426
Remarks: NO expense spared and everything replaced! Gulf and greenbelt views await from your top floor Seaplace condo! Completely remodeled. This gorgeous gulf-facing oversized one bedroom, 1.5 bath end unit with vaulted ceilings features 1,094 square feet of living space and spacious lanai adding an additional 112 square feet with custom 95% UV blocking solar shades. The convenient second floor location provides quick access to the beach, which is only 178 yards from your front door. Enjoy beautiful sunsets with a glass of wine, while taking in the peaceful greenbelt and gulf views from your screened-in lanai complete with high quality Polywood outdoor furniture and Modern Forms WIFI enabled ceiling fan. The spectacular remodel includes new hurricane impact sliding glass doors and bedroom window, new front door and casement window, HVAC unit replaced in 2022, LG Thin Q stacked washer and dryer, ceiling fans in bedroom and living room, Nest programable WIFI thermostat, all new plumbing and plumbing fixtures, all electrical replaced including electrical outlets, new switches and LED recessed lighting throughout. The new porcelain plank "driftwood look" floor tiles throughout the condo and into the Lanai compliment the coastal, beachy vibe of the Cypress Pecky Wood and shiplap accent walls. The gourmet kitchen was completely redesigned with an open concept and includes Kraftmaid soft close wood cabinetry and drawers, GE Cafe appliances suite with convection oven, warming drawer and conduction cooktop, floating shelves and Cambria Quartz counters. The popcorn ceilings were removed and re-plastered with smooth texture throughout. Both bathrooms have new vanities with Cararra marble counters, tile accent walls, including Calcatta Gold Marble Penny tile in half bath and redesigned primary bath. The bedroom features custom open concept built-in closets with soft close drawers and doors. Custom woven wood shades in living room and black out shades in bedroom. Other features include all new solid core interior doors, expansive storage closet under the stairs, owner's locker in common area, dedicated bike storage room adjacent to condo and one assigned parking space. Situated on 42 acres of manicured resort grounds and amenities, Seaplace is one of Longboat Key's most desirable communities. Enjoy two Olympic sized swimming pools, spas, one mile of trails along the shore and throughout the complex, 3 tennis courts, remodeled club house, fitness center, barbecue islands and parklike grounds. Whether you are looking for a vacation get-away, second home, investment property or permanent residence, this is the one! Seaplace is a gated community with a 24-hour guarded gate. Situated only one complex North of the famed St. Regis Luxury Hotel and Residences. This lovely condo is sold completed outfitted, fully-furnished with high quality furnishings from Pottery Barn, Restoration Hardware and comes complete with two fairly new Schwinn bicycles. Must see to appreciate. Owner has a real estate license in CA.
Listing is courtesy of: CONTINENTAL REAL ESTATE GROUP (877-996-5728)
Listing Agent: Derek Eisenberg
455 LONGBOAT CLUB RD #707, LONGBOAT KEY, FL 34228
$1,850,000135 Days on yellowkey MLS ID: A4680080
REDUCED by $149,950 (7.5%) on 06/10/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2410 Built: 1990 Tax: $9,861 (2025)Community: PierreCondo
Taxes:$9,861
Remarks: Welcome to The Pierre, a distinguished Gulf-front address behind the private gates of the Longboat Key Club, offering a rare blend of refined coastal living, privacy, and world-class resort lifestyle appeal for discerning buyers from around the globe. Located on the seventh floor, Residence 707 showcases spectacular sunset skies over the Gulf of Mexico, complemented by peaceful bay and city vistas, creating a dynamic panorama from sunrise through evening. Expansive windows fill the interiors with natural light while framing the natural beauty of Longboat Key’s shoreline and Sarasota Bay. Thoughtfully designed for both relaxed living and gracious entertaining, the residence offers generous living spaces and a seamless indoor-outdoor connection. The floor plan includes two ensuite bedrooms and a flexible third bedroom with sliding retractable wall, three full baths, and spacious living and dining areas—each with direct access to the residence’s gracious balconies. Residents of The Pierre enjoy an exceptional array of amenities, including direct private beach access, a beachfront pool, spa, fitness center,, tennis courts, a newly renovated lobby, club gathering room, meeting room and 24-hour guard security. Private guest suites are also available for visiting family and guests on a nominal rental basis. Ownership is further enhanced by secure garage parking, a private secured storage area, and onsite professional management, providing ease and confidence for both year-round and seasonal owners. Beyond the residence, membership opportunities at the renowned Longboat Key Club provide access to a celebrated resort lifestyle, featuring championship golf courses, world-class tennis, spa and wellness facilities, multiple dining venues, beach services, and an active social calendar (membership subject to application and availability). Perfectly situated near St. Armands Circle and downtown Sarasota’s cultural attractions, Residence 707 represents a rare opportunity to own within one of Longboat Key’s most prestigious waterfront communities—where international sophistication, panoramic views, and a coveted club lifestyle converge in one extraordinary coastal setting.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Judy Wright, Pa (941-232-8041)
1932 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228
$1,175,00067 Days on yellowkey MLS ID: A4689076
REDUCED by $25,000 (2.1%) on 06/09/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1192 Built: 1982 Tax: $9,436 (2024)Community: Fairway Bay 1Condo
Taxes:$9,436
Remarks: Welcome to this breathtaking, fully remodeled, turnkey furnished contemporary residence in Fairway Bay—nestled on picturesque Longboat Key. From the moment you enter, you're greeted by a thoughtfully redesigned open floor plan, elevated ceilings, solid core doors, and impeccable high-end finishes. IT IS TRULY ONE OF A KIND! This condominium is truly one-of-a-kind! Exceptional Kitchen features include: Bertazzoni induction range, refrigerator, and dishwasher, built-in Miele plumbed espresso machine, sleek, low-profile custom cabinetry with quartz countertops, glass tile backsplash and ambient lighting and an expansive quartz island perfect for formal dining or casual entertaining. The living room flows effortlessly from the kitchen, opening onto a covered, tiled lanai—blurring the line between indoor and outdoor living. Floor-to-ceiling impact windows frame panoramic views of Sarasota Bay, the Ringling Bridge, and the city skyline, offering million-dollar scenery from the comfort of your home. Enter the generously sized and luxurious Primary Suite with custom built-ins and ample closet space. The ensuite bath is a spa-inspired bath with dual vanities, Hansgrohe Axor faucets, Toto washlet, walk-in shower with multiple heads and elegant finishes. The guest suite features custom cabinetry and an ensuite bathroom with a Victoria & Albert volcanic limestone bathtub. Other recent upgrades include Hurricane-impact windows and doors, tankless water heater, additional upper cabinetry in kitchen and utility room, ceiling fans and more. For your convenience & comfort there is easy elevator access, coveted garage parking space and private onsite storage. Fairway Bay residents enjoy the resort-Style amenities including Deeded beach access & exclusive beach club, 24-hour gated security, pool, spa, tennis courts, and fitness center plus all the perks of Bay Isles living. Whether you're soaking in the sun, enjoying vibrant Sarasota culture and nightlife, or relaxing in your private retreat, this home is a perfect sanctuary.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Jan Jordan (941-737-4169)
2525 GULF OF MEXICO DR #3D, LONGBOAT KEY, FL 34228
$1,650,0006 Days on yellowkey MLS ID: A4696213
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1468 Built: 1972 Tax: $18,254 (2025)Community: Islands WestSpa: YesCondo
Taxes:$18,254
Elementary School: None
Remarks: Professional Photo's coming soon. Wake up to breathtaking, direct panoramic views of the Gulf of Mexico from this stunning third-floor beachfront residence on Longboat Key. Perfectly positioned to capture endless turquoise waters and spectacular sunsets, this coastal retreat offers unobstructed Gulf views, creating a serene backdrop for everyday living. The completely updated condo features two bedrooms, two baths, a spacious great room, dining area, and a kitchen with a charming breakfast nook. Walls of impact glass flood the interior with natural light, while floor-to-ceiling windows in both bedrooms showcase the ever-changing beauty of the shoreline. A wraparound balcony provides the perfect setting to enjoy morning coffee, coastal breezes, and mesmerizing sunsets over the Gulf. Ideally located mid-island, this residence offers the perfect balance of tranquility and convenience. Bay Isles Shoppes is just across the street, offering Publix, CVS, banking, dining, the Longboat Key Tennis Center, and Bayfront Park. World-renowned St. Armands Circle is only four miles away, while downtown Sarasota's acclaimed dining, shopping, arts, and entertainment are within a short seven-mile drive. Residents of Islands West enjoy an exceptional Gulf-front lifestyle with an impressive collection of resort-style amenities. The 15-story community features secure key-fob entry, a heated beachfront pool and spa, outdoor grilling and lounge areas, tennis and pickleball courts, and dedicated storage for bicycles, kayaks, and paddleboards. The clubhouse is currently being transformed to include a stylish social room with library, state-of-the-art fitness center, and catering kitchen. Pet lovers will appreciate the welcoming two-pet policy. Experience the ultimate beachfront lifestyle where spectacular views, resort-inspired amenities, and an unbeatable Longboat Key location come together in one extraordinary residence.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Midge Mccarthy (941-809-3800)
706 BAYPORT WAY #706, LONGBOAT KEY, FL 34228
$739,00067 Days on yellowkey MLS ID: A4688503
3 Days Off yellowkey (back on 6/8/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1601 Built: 1980Monthly Fee: $1,978 Tax: $6,727 (2025)Community: Bayport Bch & Ten Ph CCondo
Taxes:$6,727
Remarks: Under contract-accepting backup offers. This stylish turnkey furnished beach retreat at Bayport Beach & Tennis Club is the perfect blend of classy with a modern flair. Before entering the home take note of the huge 16’ x 13’ outdoor deck where you can enjoy a partial view of the Gulf. It's a great place to start your day with a cup of morning coffee, or enjoy a nice meal in the evening, and catch the spectacular colors of the sky as the sun sets! Step inside to this inviting, beautifully appointed 2-bedroom 2-bath condominium with luxury vinyl flooring and crown molding throughout. The entire living/ dining areas, lanai, both bedrooms and second bathroom have all been recently updated. Giving the condo a fresh polished appearance accentuated by recessed glass display shelving and an abundance of recessed lights. The depth of workmanship in the updates carries onto the stylized door moldings into the primary bedroom. All popcorn has been removed! The kitchen offers a coffee bar, stainless steel appliances, a pantry, a nice arrangement of cabinets, and granite countertops open to the dining room and living room, perfect for entertaining. Take in the view of the lush tropical landscape and gorgeous pond right below the lanai that is open to the living room. Perfect for a Murphy bed, extra living space, a reading nook or your second favorite spot for your morning coffee as the sun rises. The primary bedroom offers an additional 6’ by 6’ area that is perfect for an office desk looking out over nature. The primary also offers a walk-in closet and a generously sized ensuite bath with dual vanities. Bayport Beach & Tennis Club is a gem with 27 tropical landscaped acres and 1200 feet of private Gulf waterfront deeded access. Where you can grab a chair and umbrella and soak up the sun, or take in the breathtaking sunsets. Enjoy Sarasota Bay just outside your door and stroll to the private dock where you can fish, kayak, paddleboard, and watch for the manatees and dolphins as they cruise by. This community also offers a clubhouse, fitness center, 4 Har-Ter tennis courts, golf practice net, and a Junior-Olympic heated pool. Bayport Beach & Tennis Club consists of 17 buildings built between 1979 and 1983. Designed by architect Tim Seibert of the Sarasota School of Architecture. Located mid-key with a wealth of attractions moments away, including Bayfront Park, steps away, offering Pickle Ball, Basketball, Shuffleboard courts, playground, bike paths, kayak launch and Publix 2 miles away.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Kelly Erb (941-720-9586)
535 SANCTUARY DR #A603, LONGBOAT KEY, FL 34228
$2,899,00061 Days on yellowkey MLS ID: A4689260
REDUCED by $100,000 (3.3%) on 06/02/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2375 Built: 1990 Tax: $33,878 (2025)Community: SanctuarySpa: YesCondo
Taxes:$33,878
Remarks: Welcome to refined coastal living at The Sanctuary—an exclusive gulf-side enclave tucked behind the gates of the Longboat Key Club. This beautifully updated 6th-floor residence offers 2BR plus den, 2.5BA, and over 2,375± sq. ft. of sophisticated interiors paired with sweeping wrap-around terraces that capture panoramic views of the Gulf of Mexico, the Links golf course, and the Sarasota skyline. Thoughtfully renovated with a designer’s eye, the residence showcases rich wood flooring, high-impact glass throughout, and light-filled living spaces that seamlessly connect indoors and out. The gourmet kitchen is both stylish and functional, featuring crisp cabinetry, solid-surface countertops, stainless appliances, and a center island ideal for casual dining or entertaining. The primary suite is a private retreat with terrace access, stunning Gulf views, a spacious walk-in closet, and a spa-inspired bath. Guests are comfortably accommodated in a separate suite, while the den offers flexibility for a home office or additional sleeping space. Residents enjoy a true resort lifestyle with private deeded beach access just steps away, 24-hour gated security, under-building parking, on-site management, heated pool and spa, Har-Tru tennis courts, and a fitness center. Ownership also places you within the coveted Longboat Key Club, with world-class golf, tennis, and beachfront amenities. Perfectly positioned on the south end of Longboat Key, you’re just minutes from the renowned shopping, dining, and social scene of St. Armands Circle, along with the vibrant arts, culture, and waterfront restaurants of downtown Sarasota. For those seeking a luxury Gulf Coast lifestyle defined by elegance, privacy, and activity, this exceptional residence delivers. Schedule your private showing today and experience The Sanctuary at Longboat Key firsthand. Bonus space is currently set up as a den with sleeper sofa and sliding door for privacy but can easily be converted back to a third bedroom with closet”.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
1241 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228
$2,765,000229 Days on yellowkey MLS ID: A4669837
REDUCED by $10,000 (0.4%) on 06/08/2026
Bed: 3 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3045 Built: 1996 Tax: $25,341 (2024)Community: Water Club 01 At Longboat KeyCondo
Taxes:$25,341
Remarks: Welcome to The Water Club at Longboat Key, where privacy, spaciousness, and resort-style amenities complement the natural beauty of the setting at the edge of the sparkling waters of the Gulf of Mexico. Residents benefit from a semi-private elevator that opens directly into an impressive foyer, offering sweeping views of Sarasota Bay and the city skyline through floor-to-ceiling windows. This residence is on the north side of the south building, the sunset view side, overlooking the beautiful pool deck amenity of the community. This eighth-floor Brighton residence is highly coveted for its three-bedroom configuration with panoramic vistas of the Gulf, beach, and bay from two expansive terraces. Features include ten-foot ceilings, extensive glass walls, and storm protection shutters , enhancing both comfort and sophistication. The living room is designed to maximize openness and showcase sunsets over the Gulf. The primary suite offers a private terrace, den, walk-in closet, and dual bathrooms. With a split-bedroom plan, privacy is maintained for two generous guest suites, each featuring an en-suite bath. The kitchen is efficiently appointed with significant storage and a breakfast area overlooking the water. The Water Club stands as Longboat Key’s premier gated beachfront community, situated on 16 acres of meticulously landscaped grounds. Amenities include a 17,000-square-foot clubhouse, well-equipped fitness center and spa, heated lap pool and hot tub, four Har-Tru tennis courts, concierge services, and versatile gathering spaces such as a library, billiards room, ballroom, firepit, and grilling area. Additional conveniences include under-building parking, climate-controlled storage, on-site management, and 24-hour security. Ideally located on the south end of Longboat Key, residents enjoy proximity to Longboat Key Club golf facilities, Publix shopping center, exclusive St. Armands Circle, downtown Sarasota’s cultural offerings, and Sarasota International Airport, just 20 minutes away. The Water Club is pet-friendly and impeccably maintained, providing the pinnacle of coastal luxury living.
Listing Agent: Michael Moulton (941-928-3559)
3563 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,650,00015 Days on yellowkey MLS ID: A4695291
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3544 Built: 1996Monthly Fee: $833 Tax: $16,169 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$16,169
Remarks: Behind the private gates of Bay Isles, this exquisitely renovated four-bedroom, four-and-a-half-bath residence in Queens Harbour presents a refined interpretation of coastal living, where timeless elegance, thoughtful design, and relaxed Longboat Key luxury come together seamlessly. Beautifully appointed and move-in ready, the home welcomes you with an open, light-filled floor plan enhanced by hardwood flooring throughout, fresh interior paint, new baseboards, plantation shutters, new hurricane-impact windows throughout, and vaulted ceiling in the great room. Designer details elevate the interiors, including Philip Jeffries grasscloth in the foyer and Serena & Lily wallpaper in the powder bath, adding texture, warmth, and sophistication. At the heart of the home, the newly redesigned chef’s kitchen blends classic style with everyday functionality. Features include custom shaker-style cabinetry, an oversized island, honed marble countertops, a Viking Professional Series gas cooktop, new built-in refrigerator, all new appliances, extended upper and lower cabinetry, and a charming breakfast area. The kitchen opens gracefully to the main living spaces, creating an elegant yet comfortable setting for entertaining and daily living. The desirable floor plan offers a spacious first-floor primary suite, an additional first-level guest suite with en-suite bath, a private office, formal dining room, and expansive great room. Each space has been thoughtfully updated to feel polished, inviting, and effortlessly livable. Outdoors, a tranquil private retreat awaits with a covered patio, pool and spa, fenced yard, and lush tropical landscaping, offering the ideal backdrop for quiet relaxation or intimate gatherings. Queens Harbour residents enjoy the coveted Bay Isles lifestyle, including private access to the Bay Isles Beach Club on the Gulf of Mexico. Optional membership at the Longboat Key Club provides additional access to golf, tennis, boating, dining, and resort-style amenities. Elegant, beautifully updated, and perfectly positioned within one of Longboat Key’s most desirable gated communities, this Queens Harbour residence captures the essence of refined island living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Kelly Gettel (941-315-2525)
1425 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$1,000,000184 Days on yellowkey MLS ID: A4674194
REDUCED by $25,000 (2.4%) on 05/28/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1707 Built: 1983 Tax: $11,336 (2025)Community: Players Club IvCondo
Taxes:$11,336
Remarks: Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view backdrop. Continue into the spacious living room, where expansive windows draw in the coastal scenery and lead seamlessly to the covered balcony. It’s the perfect place to unwind, entertain, or simply take in the soothing sound of the waves. The primary suite offers private balcony access, a split bathroom layout, and an oversized walk-in closet. Visitors will appreciate the two spacious guest suites ideally located for optimal privacy and relaxing at the end of the day. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, and a heated saltwater pool and spa. The community is ideally located just a short drive from the dining and boutiques of St. Armands Circle and the vibrant cultural offerings of downtown Sarasota. Additional conveniences include on-site management, and a 24-hour staffed gate, ensuring comfort and peace of mind. This residence blends light-filled interiors, generous living spaces, and world-class amenities—offering an exceptional opportunity to enjoy the best of life on the desired southern end of Longboat Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Mairead Smialek (847-334-4848)
560 HARBOR COVE CIR, LONGBOAT KEY, FL 34228
$7,900,000213 Days on yellowkey MLS ID: A4672059
REDUCED by $800,000 (9.2%) on 05/06/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3485 Built: 1981Monthly Fee: $517 Tax: $28,036 (2024)Community: Bay IslesSingle Family
Taxes:$28,036
Remarks: An exceedingly rare offering within the exclusive Bay Harbour enclave of Bay Isles on Longboat Key, this extraordinary peninsula estate delivers exceptional privacy, dramatic Sarasota Bay views, and direct boating access to both the Intracoastal Waterway and the Gulf of Mexico. Positioned at the end of a quiet cul-de-sac on a three-sided waterfront peninsula, the property features two private docks with water and electric, including one with a 15,000-lb lift designed for easy access. The Gulf is reachable through the nearby jetty with drawbridge, with an additional route via the John Ringling Bridge. The seawall was newly capped in 2020, and the pier deck and boat lift controls were replaced in 2025, ensuring superior waterfront infrastructure. Extensively rebuilt and structurally engineered, the residence is warm, refined, and filled with natural light, capturing sweeping bay views from nearly every room. The chef-inspired kitchen showcases custom rare wood cabinetry, an extended breakfast bar, a three-sink layout, double dishwashers, Sub-Zero refrigerator, Wolf warming drawer, standalone ice maker, and beautifully finished wood ceilings. The living and dining areas feature a custom jazz club floor and open seamlessly to a wraparound screened lanai, fully reconstructed with multilayer waterproof construction, a rich teak ceiling, and an open-sky section ideal for coastal breezes and stargazing. Multiple seating and dining areas create effortless indoor-outdoor living with uninterrupted water views. Outdoors, the pool area offers a private retreat surrounded by tropical landscaping and expansive travertine decking designed for both relaxation and entertaining. A custom palm-terrace garden enhances the tranquil ambiance along the east side of the deck. All bathrooms have been fully remodeled with premium finishes, floor-to-ceiling tilework, and frosted glass shower doors. The primary suite features an elegant, spa-like bath designed with refined materials. Additional upgrades include hurricane-rated windows and doors, 5-ton A/C units installed in 2024 and 2025, all-new plumbing, electrical, and HVAC ductwork, a whole-house water purification system, a full security camera system, and extensive structural improvements completed under engineering oversight. Exterior enhancements include landscape lighting, a resurfaced epoxy garage floor with mini-split A/C, and cell-foam insulation for efficiency. Residents of Bay Isles enjoy private Gulf beach access at the Bay Isles Beach Club, offering tiki huts, restrooms, BBQ areas, and gathering spaces. The gated community provides 24/7 security, community pools, and miles of shaded sidewalks ideal for walking and cycling. With its unrivaled peninsula setting, exceptional boating amenities, unmatched privacy, and sweeping water views at every turn, this estate represents one of Longboat Key’s most remarkable waterfront opportunities—an extraordinary residence defined by craftsmanship, luxury, and coastal elegance.
Listing Agent: Rachel Tritschler (941-993-5892)
360 GULF OF MEXICO DR #333, LONGBOAT KEY, FL 34228
$1,795,000153 Days on yellowkey MLS ID: A4675387
REDUCED by $5,000 (0.3%) on 04/20/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2581 Built: 1992Monthly Fee: $50 Tax: $10,264 (2025)Community: Tangerine Bay ClubCondo
Taxes:$10,264
Remarks: Welcome to this rarely available corner penthouse with its stunning bayfront views artfully framed by the freshly landscaped tropical oasis surrounding the resort-style pool. Boasting nearly 2600 square feet of interior space on two levels, this serene sanctuary offers three terraces plus 3 bedrooms and 3.5 baths (3045 square feet in total). A private courtyard sets the stage for a gracious residence with a warm European feel that lives like a single family home. Relaxed open spaces beckon with soaring ceilings, extra windows in the kitchen and great room (available only in end units), and a gas fireplace. The kitchen features a morning room with built-in desk and an aquarium window over the sink. Sliding glass doors seamlessly connect indoor and outdoor spaces. Mahogany double doors open into the primary suite with its patio access overlooking the bay and lush landscaping, volume ceilings, acacia wood flooring, walk-in and built-in closets and recently renovated luxurious bath. An additional guest bedroom (currently used as a den) with ensuite bath, laundry room and powder room complete the first level. On the second level a spacious third bedroom, office with built-in desk, shelving and storage, and full bath provide additional accommodations for family and friends. The home offers impact windows, plus storm shutters on larger windows for added protection. Enjoy the resort style amenities of Tangerine Bay Club, including a lagoon pool with waterfalls, lap lane and spa, day dock, fishing, kayak launch, tennis and pickleball courts, fitness center, clubhouse, walking paths and tropical landscaping. An oversized garage provides ample space for sports equipment and storage. Owners may join the newly remodeled Bay Isles Beach Club providing access to the Gulf of Mexico for a modest annual fee. Located on Longboat's south end, this gated community is just minutes from the new St. Regis resort and St. Armand's Circle with its shops and fine dining. A short drive over the Ringling Bridge brings the vibrant culture and renowned arts of downtown Sarasota. Optional membership in the Longboat Key Club across the street from TBC offers 45 holes of award winning golf, fine dining and a marina. Come see why Tangerine Bay Club is one of Longboat's most sought after communities and why Forbes named Longboat Key one of the top 25 destinations in 2025.
Listing Agent: Sherry Dominick (203-605-9582)
1241 GULF OF MEXICO DR #803, LONGBOAT KEY, FL 34228
$3,350,000248 Days on yellowkey MLS ID: A4667938
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3045 Built: 1996 Tax: $31,926 (2025)Community: Water Club 01 At Longboat KeySpa: YesCondo
Taxes:$31,926
Remarks: The epitome of beachfront luxury awaits in this meticulously renovated 8th-floor residence at the prestigious Water Club on Longboat Key. This stunning 3-bedroom plus oversized study, 4-bath home is a rare offering in one of the Gulf Coast’s premier direct beachfront communities. From the moment you step off the private elevator into the foyer, you’re greeted by serene neutral tones, 10-foot ceilings, and wide-plank engineered hardwood floors that set the tone for elegant coastal living. Walls of glass frame spectacular, unobstructed views of the Gulf of Mexico, filling the expansive living spaces with natural light and breathtaking scenery. The open-concept floor plan seamlessly blends comfort and sophistication, enhanced by recessed lighting and a calming contemporary palette. The spacious living room flows onto a generous beachfront terrace—perfect for soaking in mesmerizing views and the soothing sounds of the surf. The designer kitchen is a showcase of modern design, featuring white glass subway tile backsplash, solid wood cabinetry, an induction cooktop with pot filler, Sub-Zero refrigerator, and premium stainless-steel appliances. A large center island and adjacent breakfast area provide the perfect setting for casual meals with sweeping water views. Each guest suite is a luxurious haven, including one with double queen beds and an en suite bath with soaking tub and separate shower. The third bedroom is currently configured as an office, yet spacious enough to accommodate a queen-size bed, and offers beautiful views of downtown Sarasota. The primary suite is a private retreat, featuring its own beachfront terrace, a separate sitting area, custom-fitted dual closets, and a spacious study with built-in office space. The spa-inspired primary bath is the essence of indulgence with white marble floors and walls, a freestanding soaking tub, and a glass-enclosed walk-in shower. Additional highlights include two under-building covered garage parking spaces, a private storage closet, and access to all the amenities of the Water Club—24-hour security, full concierge service, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and over 16 acres of pristine beachfront grounds. This is beachfront living redefined! Located just a short distance to St. Armands and downtown Sarasota's shopping, dining & cultural events.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3527 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,550,00023 Days on yellowkey MLS ID: A4694532
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4154 Built: 1994Monthly Fee: $833 Tax: $22,710 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$22,710
Remarks: Experience refined coastal luxury in this impeccably renovated 4,154-square-foot golf course estate, ideally positioned within the exclusive Queens Harbour enclave of gated Bay Isles on Longboat Key. This extraordinary two-story residence offers 4 bedrooms, 4.5 bathrooms, and an elegant open floor plan thoughtfully curated with exquisite finishes and designer details throughout. Extensive recent enhancements include a newer roof (2021), new panoramic pool cage with picture-frame screening (2025), new hurricane Armor Screen shutters protecting every opening (2025), and a custom two-person Pneumatic Vacuum elevator, along with numerous additional upgrades and improvements. Dramatic two-story windows fill the expansive great room and chef’s kitchen with natural light while showcasing breathtaking views of the sparkling pool, serene lake, lush landscaping, majestic oak trees, and the manicured fairway. Designed for both everyday living and entertaining, the gourmet kitchen is a culinary masterpiece, complete with a large gas range, dual ovens, solid wood cabinetry, abundant counter space, and a charming breakfast nook framed by bay windows overlooking the pool and golf course. The luxurious first-floor owner’s retreat offers Brazilian cherry wood flooring, vaulted ceilings, French doors opening to the lanai, dual walk-in closets, and a spa-inspired bathroom. Two additional guest bedrooms on the main level are connected by a beautifully appointed Jack-and-Jill bathroom. Outdoor living is equally exceptional, with an oversized pool and spa set within a spacious private lanai designed for relaxation and entertaining while enjoying tranquil sunsets over the lake and golf course. Residents of Queens Harbour enjoy maintenance-free living, a private community pool, and exclusive access to the Bay Isles Beach Club with deeded Gulf beach access. Ideally located near the Longboat Key Club Harbourside golf course, tennis facilities, and the Moorings Yacht Club, this residence embodies the finest in Longboat Key luxury living.
Listing Agent: Miriam Pearson (941-726-4687)
1211 GULF OF MEXICO DR #701, LONGBOAT KEY, FL 34228
$2,125,00012 Days on yellowkey MLS ID: A4694983
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2100 Built: 1985 Tax: $17,857 (2025)Community: PromenadeSpa: YesCondo
Taxes:$17,857
Remarks: Sweeping sunrise to sunset views define this beautifully reimagined 7th floor residence at the Promenade on Longboat Key. Fully renovated in 2026, this three-bedroom, three full bath home offers floor to ceiling windows, abundant natural light, and 180- degree views of both the Gulf of Mexico and Sarasota Bay. The double door entry opens to a freshly painted residence with new luxury plank flooring, nine-foot ceilings and modern lighting throughout. This residence is designed for entertaining with a large open living area and a full wet bar and wine refrigerator. The kitchen features quartz countertops and full quartz backsplash, Sub-Zero refrigerator, Cafe stove and double convection oven, and matching panel dishwasher. The custom modern white soft closed cabinetry with polished nickel hardware provides a stylish look as well as large amounts of storage and pantry space. A reimagined kitchen layout allows for a separate island that can be used for morning coffee, workspace or meal preparation all while enjoying gorgeous bay views. The primary suite features a spa-like oasis with new enlarged glass enclosed shower featuring waterfall and wall shower-heads, all quartz countertops, dual sinks, polished nickel faucets, fully backlit electric mirrors, separate water closet, linen storage and a custom designed walk-in closet. The two additional bedrooms each offer private bathrooms, one with a dazzling walk-in shower and the other with a new bathtub/shower. The renovations included removing all popcorn ceilings, updates to electrical and plumbing systems, all new fire sprinkler hardware and base boards. The full-sized laundry room includes new storage cabinetry, full sized washer/dryer and a wash-sink. All new interior doors fitted with Emtek polished nickel door hardware. The residence includes a private storage locker that is humidity and temperature controlled and a deeded underground parking space. The Promenade has undergone significant renovation over the past few years and features elegant marble foyer, 24-hour gate security, manned concierge desk, his and hers fitness rooms with shower and sauna, luxurious party rooms, EV charging station, a well-maintained pool deck and hot tub, verdant tropical landscaping and dual BBQ areas. The beach is located directly behind the building and features a secure entrance and beach chairs. There are also 4 Har-Tru tennis courts to complete the Longboat Key lifestyle. The Promenade is located near the south end of Longboat Key, minutes from St. Armand's Circle and the restaurants and arts offerings of downtown Sarasota. The Longboat Key Club and its golf, tennis and marina offerings is available for membership and just outside the property.
Listing Agent: Maggie Hicks (941-321-1759)
548 HORNBLOWER LN, LONGBOAT KEY, FL 34228
$4,950,000243 Days on yellowkey MLS ID: A4668463
1 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3976 Built: 2015Monthly Fee: $8 Tax: $47,046 (2024)Community: Country Club Shores Sec 02Spa: YesSingle Family
Taxes:$47,046
Remarks: Under contract-accepting backup offers. This exquisite home is sure to exceed expectations! This exceptional 4 bed/5 bath canal-front estate is located in coveted Country Club Shores, where chic architecture, thoughtful craftsmanship, and effortless coastal luxury converge. Designed by DSDG architects to maximize the contemporary sightlines and southern exposure, this Voight built custom residence offers a spectacular open floor plan and is positioned just three lots from the open waters of Sarasota Bay. This extraordinary residence is better-than-new with a recently installed metal roof, AC systems, and whole home generator and has been impeccably maintained. The home has been built to effortlessly withstand the Florida coastal environment while maintaining its magnificent beauty and clean lines. Boaters will appreciate the Trex dock equipped with a 20,000-lb boat lift, kayak and paddleboard racks, and convenient launch deck - providing quick, easy access to bay and Gulf waters. Inside, the home is both stunning and impressive with exquisite finishings and custom millwork. The first-floor owner’s suite is a luxurious retreat highlighted by soaring triple-coffered tray ceilings, tranquil views, and private pool access for a midnight swim. The spa-like bathroom is pure luxury. The chef’s kitchen is a true showpiece, featuring Viking appliances, a Sub-Zero Pro refrigerator, a walk-in pantry, expansive countertops, and a dramatic 14-foot quartz island perfect for large gatherings. The integrated dining area is framed by an aquarium window which emphasizes the tranquil water views. The family room is a natural extension of the kitchen and provides a generous area with direct access to the lanai, grille and dining areas and is perfect for enjoying movies, or just gathering with friends and family. The great room is spacious with large archways, gas fireplace, custom built-in shelving, and coffered shiplap ceilings which add to the drama of this cozy but elegant space. A wall of windows provides access to the covered lanai area and expands the feeling of openness highlighting the pool, sparkling spa, and water views. The second floor has been completely reimagined to elevate both style and function, offering three private guest suites, a versatile and spacious Florida room, wet bar, and a 300+ bottle state-of-the-art walk-in wine cellar. The enclosed upper lanai enhances ambiance and panoramic views. The Florida room provides a flexible space for enjoying sporting events or wine tastings, and includes a full bath for convenience. The 3 bedrooms on the second level are generous in size and 2 of the 3 include ensuite baths. Outdoor living is equally exceptional. The lanai with a Cypress-clad ceiling includes a new grill and dining area and pool bath, which steps down to the saltwater pool, spa, and sun deck - an ideal setting for entertaining or enjoying sunshine year-round. Additional features include a two-car garage with generous overhead storage, a rear enclosed storage compartment, and an electric vehicle charger. There is ample vertical height in the garage to add a car lift as an option. Residents of Country Club Shores enjoy private deeded beach access to the Gulf of Mexico, with optional golf and tennis memberships available at the nearby Resort at the Longboat Key Club. This is waterfront living at its finest - refined, relaxed, and designed to be enjoyed. A must-see property to fully appreciate the exceptional lifestyle, upgrades, and craftsmanship throughout.
Listing Agent: Kathy Callahan (941-900-8088)
2425 GULF OF MEXICO DR #14E, LONGBOAT KEY, FL 34228
$1,700,00089 Days on yellowkey MLS ID: A4686539
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $13,728 (2025)Community: Sea Gate ClubSpa: YesCondo
Taxes:$13,728
High School: Riverview High
Remarks: Back on the market, buyer's financing fell through. Home inspection already completed and all good, and appraisal from bank already completed with no issues. Amazing and Unobstructed 14th Floor Gulf and Beach Views! This is the perfectly remodeled unit you've been waiting for, with stunning sky views! Open floor plan, tile floors throughout, gorgeous open kitchen, and split bedroom floor plan. Just move right in and enjoy the views and amenities. The building has been completely remodeled. New roof, new windows, new railings, new pool, new storage lockers, updated elevators, new parking lot paving. NO PENDING SPECIAL ASSESSMENTS! Every owner has paid over $130K in the last 5 years to update the building and facilities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Robert Delaney (941-315-3185)
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