Location: Longboat Key
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
3271 BAYOU RD, LONGBOAT KEY, FL 34228
$1,995,00045 Days on yellowkey MLS ID: TB8515918
0 Days Off yellowkey (back on 7/7/2026)
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3059 Built: 2014Monthly Fee: $104 Tax: $27,748 (2025)Community: Bay IslesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$27,748
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. 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)
600 PUTTER LN, LONGBOAT KEY, FL 34228
$9,400,000563 Days on yellowkey MLS ID: A4633484
REDUCED by $1,100,000 (10.5%) on 05/19/2026
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 5982 Built: 2017Monthly Fee: $17 Tax: $69,287 (2025)Community: Country Club Shores, Unit 5, Sec 3Spa: YesSingle Family
Taxes:$69,287
Remarks: Welcome to Paradise on Longboat Key. This coastal modern home is located on the direct bayfront with a total of 270 feet of waterfront on an oversized lot consisting of 18,290 square feet. As you enter the home, your first view is a serene and expansive view of Sarasota Bay all the way from the Ringling Museum to Downtown Sarasota and the Ringling Bridge. Enjoy different types of boating as the dock includes 2 jet ski lifts and a 13,000 pound boat lift. With plenty of interior space, there are 5 bedrooms and 5 baths plus a dedicated office/den, family room and game room. Every bedroom is filled with bay views. As an added advantage, guests have their own space upstairs that includes a kitchenette. Outfitted with an elevator that stops at every floor, including the three car garage, convenience is just a step away. To enjoy the views outside, there is an outdoor surround lanai with disappearing screens, fireplace and summer kitchen. Large covered terraces on both levels provide views of beautiful sunrises over Sarasota Bay and Downtown Sarasota.
Listing is courtesy of: FLORIDA CAPITAL REALTY (786-953-5870)
Listing Agent: Kathleen Callender (941-321-3115)
3527 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,550,00059 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 is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Miriam Pearson (941-726-4687)
806 BAYPORT WAY #806, LONGBOAT KEY, FL 34228
$949,000113 Days on yellowkey MLS ID: TB8489326
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981 Tax: $5,917 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$5,917
Remarks: Welcome to this beautifully appointed ground floor residence that combines modern elegance with functional design. Newly remodeled in 2025, this residence features high-end finishes and modern amenities, making it an ideal retreat for those seeking luxury in a serene environment. Upon entering, you are greeted by a bright and spacious interior filled with natural light, thanks to strategically placed additional windows featured in corner/end units of this community. The subtle elegance of the interior is complemented by sleek flooring that enhances the flow from room to room. The kitchen is a true highlight, featuring quality cabinetry, elegant quartz counters, and modern stainless-steel appliances, which allow a harmonious flow, delivering both functionality and sophistication. The open-concept layout continues through the dining and living areas, combining a blend of textures and stylish finishes to cohesively create an environment of relaxed elegance. An abundance of natural light floods this space through large retractable sliding glass doors, which provide the option of extending the outdoors in. A private outdoor patio showcases a beautiful backdrop of lush tropical landscaping, adding to the property’s overall appeal. The bedrooms within the property are thoughtfully designed, each offering generous space and natural light. The primary suite offers a restful retreat, complete with an ensuite bathroom featuring modern fixtures and thoughtful design, ensuring comfort and privacy. This property will continue to amaze, as beauty extends beyond its walls into an amenity-rich community of 27 acres of picturesque tropical landscaping. This gulf-to-bay community offers an active island lifestyle with 4 Har-Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court, and amazing nature trails. A distinct advantage and unique selling point of this property is its proximity to a private, deeded beach. This property offers future owners not just exclusive beach access, but a revitalizing retreat amidst the hustle and bustle of life—truly a valuable benefit that amplifies the charm of this residence. Close to local amenities yet precisely positioned to offer privacy and quietude, this property represents an excellent opportunity for discerning buyers. Experience the best of coastal living in this beautiful home, where modern comfort meets natural beauty. Welcome home!
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Antonietta Car (813-684-9500)
1445 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$1,180,000143 Days on yellowkey MLS ID: A4684021
REDUCED by $15,000 (1.3%) on 06/25/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2092 Built: 1982 Tax: $11,749 (2025)Community: Players Club IiiSpa: YesCondo
Taxes:$11,749
Remarks: Step into this highly desirable corner residence featuring three bedrooms, three full baths, and an expansive 36’ x 11’ sunroom at The Players Club. You’ll immediately be drawn to the impressive 31-foot balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. Inside, the sun-filled kitchen is thoughtfully designed with custom cabinetry and a built-in breakfast table that expands both workspace and storage. It flows seamlessly into the main living and dining areas, creating a warm and open environment for entertaining or daily living. Just off the kitchen, elegant French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The owner’s suite provides a private sanctuary with a spa-inspired bathroom featuring a soaking tub, separate glass-enclosed shower, dual vanities, and a spacious walk-in closet. The second bedroom functions as a true secondary master, complete with dual sinks, a full vanity, and a fitted walk-in closet, offering comfort and privacy for family or visitors. A third bedroom adds flexibility for guests, workspace, or hobbies. A unique feature of this residence is the private garage, offering rare security and convenience for residents, plus an additional covered parking space underneath the building for extra guest or secondary vehicle use. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves. Just minutes from St. Armands Circle, downtown Longboat Key, and Longboat Key Club, with championship golf, premier tennis, and a deep-water marina, this corner residence blends privacy, convenience, and resort-style coastal living. Units with this versatile layout and resort-ready features are highly sought after. Offered partially furnished. Seller is willing to discuss a subsidy on the quarterly condominium fee for reserve increase over the next two years!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
595 BOWSPRIT LN, LONGBOAT KEY, FL 34228
$3,099,000276 Days on yellowkey MLS ID: A4668868
REDUCED by $41,000 (1.3%) on 07/05/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2550 Built: 1966Monthly Fee: $21 Tax: $26,814 (2025)Community: Country Club ShoresSingle Family
Taxes:$26,814
Remarks: Longboat Key Waterfront Luxury. Experience the ultimate in waterfront living in this 4-bedroom, 2.5-bath Country Club Shores residence, tucked just off Sarasota Bay on a nice canal with quick access to the Gulf, sandbars, and every boating adventure Sarasota has to offer. A private dock, two boat lifts (20,000 lb and 7,000 lb), new seawall, and a custom fish cleaning station create a true boater’s paradise, while canal and bay views enhance the coastal setting. After a day of boating, sandbar hopping, fishing, or cruising the bay, come home to your heated pool, travertine-decked outdoor retreat. Retractable glass sliders, and pool bar blur the line between indoors and out, making this the perfect place to gather, unwind, and relive the day’s best moments on the water. Thoughtfully remodeled twice in recent years, the home blends refined coastal style with exceptional updates including a 2016 effective build year, roof, plumbing, electrical, PGT hurricane-impact windows and sliders, and two new A/C systems in 2024. The chef’s kitchen is a standout, featuring custom Devittori cabinetry, leathered granite, a dramatic 11’x5’ island, and premium Sub-Zero and Wolf appliances. Deeded private beach access, nearby Longboat Key Club amenities, and close proximity to St. Armands Circle and Downtown Sarasota complete this exceptional island offering.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Melissa Gissinger (941-404-2722)
549 HALYARD LN, LONGBOAT KEY, FL 34228
$2,195,00028 Days on yellowkey MLS ID: A4696535
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1594 Built: 1965Monthly Fee: $23 Tax: $20,602 (2025)Community: Country Club ShoresSingle Family
Taxes:$20,602
Remarks: This is the one * PERFECTLY POSITIONED ON A QUIET CUL DE SAC STREET AT THE PREFERRED SOUTH END OF LONGBOAT KEY * Located on the QUIET END OF THE CANAL with OPEN WATER JUST BEYOND YOUR DOCK and the PRIVATE BEACH ACCESS ONLY MINUTES AWAY * A quick 3 minute cruise to Sarasota Bay & the ICW & The GULF * This coveted Country Club Shores IV home has been LOVINGLY RENOVATED with a NEW Kitchen & modern amenities while retaining its classic charm * NEW KITCHEN CABINETS * NATURAL GAS STOVE * GE CAFE APPLIANCES * NEW Solid Core Doors * FULL HURRICANE PROTECTION * NEW TILE Flooring throughout * 2 Car Garage has a NEW Mini Split A/C * Primary Suite with a Spa-style Bath featuring a LARGE Walk-in Shower * BEAUTIFUL VIEWS OF YOUR POOL & PRIVATE CANAL * This THOUGHTFULLY CURATED HOME is an open floor plan * The additional Bedrooms are well-appointed and located in a way that allows for guest privacy * Impact Sliding Glass Doors surround the Outdoor Area * ROOF IS 9 YEARS YOUNG * WATER HEATER IS 3 YEARS YOUNG * All of this wraps your Caged Pool with Paver Decking and a Paver Walkway to your 2021 NEW SEAWALL & COMPOSITE DOCK with a 10,000lb Boat Lift & 2 Additional NEW Jetski Lifts PLUS a 2-step down Kayak Dock Launch with Power & Water * THIS IS A BOATER'S DREAM * The PERFECT HOME & OUTDOOR OASIS to entertain family & friends or just simply relaxing in your slice of paradise * PRIDE OF OWNERSHIP SHOWS IN THIS IMMACULATE HOME * Furniture is available * Just bring your suitcase * Country Club Shores is a well established waterfront neighborhood offering DEEDED BEACH ACCESS with a convenient south end location close to ST ARMAND'S CIRCLE, The new ST REGIS, and even downtown Sarasota * Join the Longboat Key Club offering 45 holes of championship golf & world class tennis * Your family will love this home * One look & you'll fall in love! *
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Ryan Brown (941-330-7774)
1241 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228
$2,745,000265 Days on yellowkey MLS ID: A4669837
0 Days Off yellowkey (back on 6/26/2026)
REDUCED by $10,000 (0.4%) on 06/23/2026
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
Tax Year: 2024
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. You must live on the side of this building where this residence is located to see the sunset.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Michael Moulton (941-928-3559)
3710 GULF OF MEXICO DR #F2, LONGBOAT KEY, FL 34228
$475,000136 Days on yellowkey MLS ID: A4681154
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 740 Built: 2026Monthly Fee: $290 Tax: $2,070 (2025)Community: Gulfshore Of Longboat KeyManufactured Home
Taxes:$2,070
Remarks: Island Living at Its Finest – Brand New Home on Longboat Key. Welcome to Gulfshore of Longboat, a highly desirable waterfront co-op community offering private beach access, boat docks, and sweeping views of the Gulf of Mexico and Sarasota Bay. This beautifully built 2-bedroom home combines modern efficiency with relaxed coastal living. An outdoor bathroom with a shower is a wonderful convenience for those enjoying the pool or boating. Step inside to an open, sun-filled floor plan featuring soaring ceilings with tray accents in both the living room and the primary bedroom, creating a bright, spacious atmosphere throughout. The kitchen is designed for everyday comfort and entertaining, complete with a center island, hardwood shaker cabinetry with soft-close doors and drawers, and a full stainless appliance package including refrigerator with ice and water, range, dishwasher, microwave, and garbage disposal. Built to current HUD hurricane standards and Energy Star certified, the home offers peace of mind with 2x6 construction, upgraded insulation, and low-E vinyl windows for year-round comfort and efficiency. Enjoy mornings at the private beach, afternoons at the heated pool, and evenings watching sunsets over the water. The community clubhouse hosts regular activities, making it easy to relax and connect with neighbors in a friendly coastal setting. Whether you’re looking for a winter retreat or full-time residence, this move-in-ready island home delivers comfort, security, and the lifestyle Longboat Key is known for. No pets (except for service animals or emotional support animals with appropriate paperwork) or Rentals permitted. Schedule your private showing today and start living the Gulf Coast dream.
Listing is courtesy of: WAGNER REALTY (941-751-0670)
Listing Agent: Marsha Winegarden (248-563-2820)
2425 GULF OF MEXICO DR #14E, LONGBOAT KEY, FL 34228
$1,675,000125 Days on yellowkey MLS ID: A4686539
0 Days Off yellowkey (back on 6/30/2026)
REDUCED by $25,000 (1.5%) on 06/25/2026
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: Under contract-accepting backup offers. 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)
2301 GULF OF MEXICO DR #43N, LONGBOAT KEY, FL 34228
$1,000,000129 Days on yellowkey MLS ID: A4686190
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $10,915 (2025)Community: Islander Club Of LongboatCondo
Taxes:$10,915
Remarks: Virtually Staged. Perfectly positioned in the sought-after Islander Club Condominium, this 2-bedroom, 2-bath residence offers commanding Gulf and beach views from the living room, dining room, and both bedrooms. Expansive windows frame the sparkling waters of the Gulf of Mexico, creating a breathtaking backdrop for everyday living while showcasing spectacular sunset skies each evening. Situated front and center on the 4th floor, the residence enjoys one of the most desirable vantage points in the building, elevated enough for panoramic shoreline views yet close enough to feel immersed in the beauty and rhythm of the beach below. Competitively priced, the condominium presents a rare opportunity for the next owner to create their own vision of coastal living. Whether designing a sophisticated modern retreat or a relaxed island escape, the residence offers a blank canvas ready to be transformed to your personal taste and style—truly a chance to make it your own. Residents of the Islander Club enjoy a collection of resort-style amenities including direct access to the pristine Gulf Beach, a beachfront Olympic size swimming pool, tennis courts, fitness center, clubhouse, library, and beautifully landscaped tropical grounds. Located on the coveted south end of Longboat Key, the community offers convenient access to Publix, the world-class shopping and dining of St. Armands Circle as well as the vibrant arts, cultural venues, and waterfront restaurants of downtown Sarasota. Go ahead – Make it your own and have it your way!
Listing Agent: Steve Nursey (941-356-7010)
775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228
$2,195,000150 Days on yellowkey MLS ID: A4683021
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2122 Built: 1984 Tax: $17,930 (2025)Community: Beaches Of Longboat KeyCondo
Taxes:$17,930
Remarks: Behind the gates of the Longboat Key Club, this exceptional residence at The Beaches captures sweeping, unobstructed views of the Gulf of Mexico and its pristine shoreline, where vivid sunsets paint the horizon each evening. Perched on the eighth floor, this coveted Star floor plan is ideally positioned as a spacious end residence, offering 2,122 square feet of thoughtfully designed living space with 3 bedrooms and 3 full baths. Walls of glass frame panoramic water vistas and invite natural light to pour into the main living areas. Newly installed impact-rated sliders enhance both storm protection and seamless indoor-outdoor living, while oak engineered hardwood flooring flows beautifully through the living room, dining area, and kitchen, creating a warm yet sophisticated coastal aesthetic. The generous layout provides an effortless blend of comfort and refinement, with well-proportioned bedrooms and baths designed to accommodate both everyday living and gracious entertaining. The Beaches is recognized as one of the premier beachfront addresses within the Longboat Key Club, offering direct access to the sugar-white sands and turquoise waters of the Gulf. Residents enjoy an elevated level of service and amenities, including a 24-hour concierge, resort-style pool, fitness center, tennis courts, and impeccably maintained grounds. Ideally located on the southern end of Longboat Key, this gated community affords convenient access to the fine dining and boutiques of St. Armands Circle, the vibrant arts and culture of downtown Sarasota, and the exclusive offerings of the Longboat Key Club. This is a rare opportunity to secure a front-row seat to the Gulf and embrace the effortless elegance of Florida’s most sought-after coastal lifestyle.
Listing Agent: Lenore Treiman (941-356-9642)
1241 GULF OF MEXICO DR #803, LONGBOAT KEY, FL 34228
$3,249,000284 Days on yellowkey MLS ID: A4667938
REDUCED by $101,000 (3.0%) on 06/29/2026
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.
2600 HARBOURSIDE DRIVE #R-13, LONGBOAT KEY, FL 34228
$400,00025 Days on yellowkey MLS ID: A4697978
Bed: Bath: 0.0 Built: 1985Monthly Fee: $540 Tax: $3,753 (2025)Community: 7981 Longboat Key Moorings MarinaDock-Rackominium
Taxes:$3,753
Remarks: Stunning Sarasota Bay Views! An easy access slip with the views to go along with the superb amenity package, Slip R-13 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 80 x 23.5, and a usable beam of 19 feet and extra wide finger pier. This is a desired 'inside the T-head' slip location. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis, pickleball and golf facilities, fitness center, with spa and beach access. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 75 feet. Beam depends on the vessel type and measure. Membership in the Longboat Key Club is required.
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
500 HARBOR COVE CIR, LONGBOAT KEY, FL 34228
$12,250,00028 Days on yellowkey MLS ID: A4697649
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5120 Built: 2026 Tax: $20,619 (2025)Community: Bay IslesSpa: YesSingle Family
Taxes:$20,619
Remarks: Under Construction. Now nearing completion and expected to be delivered in approximately 60 days. Positioned within the exclusive Harbor Section of Bay Isles on Longboat Key, 500 Harbor Cove Circle is a newly constructed waterfront estate offering a rare combination of exceptional boating access, modern architecture, resort-inspired living, and one of the Gulf Coast’s most coveted addresses. Located behind the double gates of Bay Isles and directly across from The St. Regis Longboat Key Resort, residents enjoy immediate proximity to world-class hospitality, fine dining, marina services, championship golf, and tennis, while ownership includes access to the Bay Isles Beach Club. Encompassing 5,120 square feet under air and 8,564 square feet total, the residence features 5 bedrooms, 5 full baths, 1 half bath, a private office, elevator access to all levels, and a 4-car garage. A fully integrated smart home automation system provides seamless control of lighting, climate, security, audio, window treatments, pool and spa functions, and key home systems throughout the property. The arrival experience unfolds through a lagoon-inspired reflecting pool, floating stairway, and lush tropical landscaping, creating a dramatic resort-style arrival. Architectural lighting, natural stone, warm wood accents, and expansive walls of glass establish a sophisticated coastal aesthetic throughout the residence. Inside, expansive living spaces are enhanced by Venetian plaster, custom millwork, large-format stone surfaces, and carefully curated architectural details. One of the home’s defining architectural statements is a dramatic 20+ foot monolithic travertine feature wall wrapping an entire corner of the residence, creating a striking design element rarely found in residential construction. The chef’s kitchen is anchored by an oversized Calacatta marble waterfall island, premium custom cabinetry, integrated appliances, and generous entertaining space. Designed for seamless indoor-outdoor living, the residence opens to expansive covered terraces, a resort-style pool and spa, and a fully equipped outdoor kitchen featuring a grill, pizza oven, refrigeration, and multiple gathering spaces. Wellness-focused amenities include a private fitness area, sauna, cold plunge, and dedicated spaces for relaxation and recovery, creating a private wellness retreat. For boating enthusiasts, the property offers approximately 100 feet of protected waterfront frontage with direct access to Sarasota Bay and the Gulf of Mexico in less than two minutes. The dock is designed to accommodate a substantial yacht while still providing room for multiple additional lifts for a tender, fishing boat, personal watercraft, and other recreational vessels—an increasingly rare offering among Florida’s premier waterfront estates. One of the Gulf Coast’s rare opportunities to enjoy new construction, large-yacht capability, and resort-inspired living within the exclusive Harbor Section of Bay Isles.
Listing Agent: Rinat Sikdar (941-993-9292)
1965 GULF OF MEXICO DR #G5-103, LONGBOAT KEY, FL 34228
$649,00058 Days on yellowkey MLS ID: A4694695
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 933 Built: 1977Monthly Fee: $1,500 Tax: $3,123 (2025)Community: Seaplace IiiSpa: YesCondo
Taxes:$3,123
Remarks: Experience coastal living at its finest in this beautifully updated ground-floor residence at Seaplace on Longboat Key. This 2-bedroom, 2.5-bath condominium in the desirable G5 building offers northwest Gulf views and stunning sunset skies from the screened lanai, just steps from the beach. The bright, open-concept floor plan features a sleek modern kitchen with glossy cabinetry, quartz countertops, stainless steel appliances, and a spacious breakfast bar perfect for entertaining. Floor-to-ceiling mirrors enhance the natural light and create a spacious, contemporary feel throughout the living and dining areas. The primary suite offers a peaceful retreat with an updated en-suite bath, while the guest bedroom provides comfort and privacy for family and visitors. Hurricane-impact sliding glass doors and windows provide peace of mind and energy efficiency. Whether you are seeking a vacation getaway, seasonal retreat, investment property, or full-time residence, this move-in-ready condo checks every box. Seaplace is a gated Gulf-front community situated on 42 beautifully landscaped acres spanning from the Gulf to the Bay. Residents enjoy resort-style amenities including 24-hour guard-gated security, a newly remodeled clubhouse, two heated swimming pools, kiddie pool, two hot tubs, three Har-Tru tennis courts, walking trails, fitness center, and private beach access with beach chairs and umbrellas provided. Conveniently located near the Longboat Key Club, St. Armands Circle, and Sarasota’s dining and cultural attractions. Schedule your private showing today and start enjoying the Longboat Key lifestyle!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
1925 GULF OF MEXICO DR #G8-302, LONGBOAT KEY, FL 34228
$629,000123 Days on yellowkey MLS ID: A4686871
REDUCED by $20,000 (3.1%) on 05/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1978Monthly Fee: $1,467 Tax: $6,897 (2025)Community: Seaplace ViSpa: YesCondo
Taxes:$6,897
Remarks: Experience the Best of Gulfside Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2-bath residence offering the perfect blend of comfort, style, and coastal charm. This light-filled unit features an updated kitchen with rich wood cabinetry, granite countertops, and ample storage—ideal for both everyday living and entertaining. The spacious primary suite offers a relaxing retreat with generous closet space and an en-suite bath, while the guest bedroom provides comfort and privacy for visitors. Both bathrooms are tastefully updated, and the open-concept living and dining areas flow seamlessly to the screened lanai. Step outside to your private lanai with hurricane impact screening, where you can enjoy tranquil views and refreshing Gulf breezes. The home is further enhanced with hurricane-impact windows, providing peace of mind and energy efficiency. Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an exceptional array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center, and a clubhouse with kitchen, library, and sauna. Additional features include a playground, grilling areas, on-site management, and a 24-hour staffed gatehouse. Whether you're seeking a full-time residence, seasonal retreat, or investment opportunity, this property offers a low-maintenance island lifestyle in one of Longboat Key’s most desirable communities. Enjoy breathtaking sunsets, beachside strolls, and resort-style living—schedule your private showing today!
1425 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$975,000220 Days on yellowkey MLS ID: A4674194
REDUCED by $25,000 (2.5%) on 06/25/2026
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 Agent: Mairead Smialek (847-334-4848)
775 LONGBOAT CLUB RD #401, LONGBOAT KEY, FL 34228
$1,595,000141 Days on yellowkey MLS ID: A4681439
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1510 Built: 1984 Tax: $13,823 (2025)Community: Beaches Of Longboat Key Ph-1Spa: YesCondo
Taxes:$13,823
Remarks: Discover Coastal Elegance at The Beaches of Longboat Key! Nestled behind the renowned gated entrance of the Longboat Key Club, The Beaches offers an unparalleled Gulf-front retreat on one of Florida's most exclusive barrier islands. This stunning 4th-floor, 2-bedroom/2-bath residence boasts direct western exposure, delivering breathtaking, forever Gulf of Mexico views and spectacular sunsets that paint the sky in vibrant hues every evening. Step inside to find stylish, move-in-ready finishes, including brand-new porcelain tile flooring throughout the living areas and elegant marble in both bathrooms. The updated kitchen shines with fresh cabinetry, a new GE Profile refrigerator, and dishwasher—perfect for effortless entertaining or quiet evenings at home. The spacious living room and both bedrooms feature impact-resistant sliders that open to a private balcony, seamlessly blending indoor comfort with the soothing sights and sounds of the beach and surf just steps away. Residents enjoy an exceptional array of resort-style amenities: 24-hour concierge service for added security and convenience, Gulfside heated pool and spa, Modern fitness center, Two Har-Tru tennis courts, Social room with a full catering kitchen, Direct beach walkway with complimentary beach chairs (and often umbrellas) provided. Additional perks include two assigned parking spaces in the secure garage and a dedicated storage unit. Priced to impress in this highly sought-after community, this turnkey condo combines modern luxury, prime beachfront access, and the prestige of Longboat Key Club living—without requiring club membership. Opportunities like this rarely last long on Longboat Key. Don't miss your chance to own a slice of paradise—schedule your private showing today!
Listing Agent: Larry Brzostek (941-993-3125)
100 SANDS POINT RD #324, LONGBOAT KEY, FL 34228
$980,000801 Days on yellowkey MLS ID: A4609759
INCREASED by $90,000 (10.1%) on 06/23/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1941 Built: 1966Monthly Fee: $1,614 Tax: $11,167 (2023)Community: Sands PointSpa: YesCondo
Taxes:$11,167
High School: Sarasota High
Tax Year: 2023
Remarks: BACK on the market after beautiful renovations!! Unit is impeccably maintained. It has a new air conditioner, roof and upgraded insulation. It is being offered below appraised value! Sands Point is the most remarkable and unique complex on Longboat Key. Built in 1966, the building is a magnificent example of mid-century modern architecture. The complex faces directly onto New Pass, and the outdoor pool and patio have both privacy and spectacular views. The center of the unit is a large great room that features a wall of windows and a view of lush Florida greenery, the boat dock and the navigable inlet which leads to the Gulf of Mexico. Kitchen and bathrooms are renovated. Furniture and furnishings are included in the sale. Windows have been upgraded to the highest level available. Each unit comes with a small storage locker near the boat docks and covered parking. There are boat docks on the premises, approximately 30 ft., that can be rented depending on availability. Management has updated status and detailed information. Sands Point is located adjacent to The Resort at Longboat Key Club with its amenities of golf, health spa, lodging and a restaurant. Nearby is the famous St. Armand's Circle that offers elegant or casual dining and entertainment. Seasonal rental is a huge draw for this property. It may be rented once a year for a minimum of one month.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Carolyn Clark, Pa (941-685-6131)
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