Location: Longboat Key
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
3527 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,550,00019 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$22,710
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
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)
2055 GULF OF MEXICO DR #G2-109, LONGBOAT KEY, FL 34228
$899,000108 Days on yellowkey MLS ID: A4681602
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1974 Tax: $7,398 (2025)Community: Seaplace ICondo
Taxes:$7,398
Remarks: Rarely available and a wonderful opportunity to own a three bedroom/two bath condominium located in a garden building with partial gulf views from all rooms. walk out to your lanai and enjoy the beautiful flowering trees & foliage. Bright and spacious with travertine tile and wooden flooring throughout, stainless steel appliances and cambria quartz countertops in the kitchen and both bathrooms. Plantation shutters on all windows and ceiling fans in the bedrooms & lanai. Beautiful crown molding in the living area & stunning light fixtures throughout. Newly installed Hurricane windows in all rooms and the sliding glass door in the living area. Coming with two parking spaces, one covered and one uncovered. Located in the beautiful community of Seaplace on 42 acres of land right on the Gulf of America. There are many amenities to enjoy, a half mile of gorgeous beach, two swimming pools with spas, kiddie swimming pool and playground area, fitness room, sauna, clubhouse for entertaining and enjoying many social events. Being on the south end of Longboat Key you are less than a mile to Publix, CVS & three different banks and only a few miles to famous Saint Armand's Circle where you will enjoy boutique shopping and fabulous restaurants and downtown Sarasota has a litany of options to enjoy as well, which includes Live Theatre, Opera, Ballet, Sarasota Orchestra, Art Galleries and not to leave out the variety of choices for dining and shopping.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Sandra Endres (941-735-2527)
3271 BAYOU RD, LONGBOAT KEY, FL 34228
$1,995,0005 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
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)
1211 GULF OF MEXICO DR #701, LONGBOAT KEY, FL 34228
$2,125,0008 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
$4,950,000239 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
Tax Year: 2024
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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Kathy Callahan (941-900-8088)
2425 GULF OF MEXICO DR #14E, LONGBOAT KEY, FL 34228
$1,700,00085 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)
250 SANDS POINT RD #5203, LONGBOAT KEY, FL 34228
$899,900131 Days on yellowkey MLS ID: A4680085
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 640 Built: 1982 Tax: $8,720 (2025)Community: Inn On The Beach Ph IiSpa: NoCondo
Taxes:$8,720
Remarks: Four Diamond Resort with five restaurants, 45 holes of Golf, Spa, Marina, 21 Tennis courts on Longboat Key!!!. This income producing property on the beachside with a golf course view is calling you!!!. It's a one-bedroom studio at the Resort on Longboat Key, a gated community. Presently the unit is in the Resort rental program and the owner may use the unit 28 days per year.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Tom Cinquegrano (941-284-5049)
1045 GULF OF MEXICO DR #301, LONGBOAT KEY, FL 34228
$950,00018 Days on yellowkey MLS ID: A4694202
0 Days Off yellowkey (back on 6/3/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1172 Built: 1981 Tax: $12,005 (2025)Community: Beachplace IiiSpa: YesCondo
Taxes:$12,005
Remarks: Coastal living at its finest and the perfect beach front retreat. This third floor corner residence is ready for your creative spirit. It offers views of the beach, the sparkling Gulf of Mexico, and breath taking sunsets year round. The new impact windows and sliding glass doors where installed in 2020 and the new HVAC system was replaced in March of 2026. This property is in very good condition and has been well maintained. Beachplace offers a Jr. Olympic sized swimming pool with swim lanes, a splash pool, hot tub, fitness center, grilling area, tennis, pickle ball, EV charger and a 24 hour guard gated entrance. All furnishings are included and this would make a great rental. New Roof in 2025
2185 GULF OF MEXICO DR #212, LONGBOAT KEY, FL 34228
$1,995,00012 Days on yellowkey MLS ID: A4694656
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2448 Built: 1996 Tax: $15,129 (2025)Community: Villa Di Lancia Ph 1Spa: NoCondo
Taxes:$15,129
Remarks: Discover elevated Gulf-front living in this rarely available 3BR/3BA residence spanning 2,448 square feet in the prestigious Villa Di Lancia on Longboat Key. Perfectly positioned to capture panoramic Gulf views, this spacious condominium offers the ideal blend of privacy, security, and effortless coastal luxury. Expansive glass sliders, transom windows, and high ceilings fill the interiors with natural light, enhancing open living spaces designed for both relaxed living and entertaining. The great room flows seamlessly to a generous covered terrace, creating a year-round indoor-outdoor lifestyle. A unique private walk-out with spiral staircase provides direct access to the lush grounds, resort-style pool, and the pristine Gulf beach just steps away—an exceptional feature rarely found in condominium living. The well-appointed kitchen features a center island, solid surface countertops, and a casual dining area, perfectly suited for hosting family and guests. The primary suite serves as a tranquil retreat with terrace access, a sitting area, and a spacious bath with dual vanities, soaking tub, and glass-enclosed shower. Two additional guest bedrooms offer comfort and privacy. Villa Di Lancia is one of Longboat Key’s most sought-after beachfront communities, offering 440 feet of private beach, gated security, a beachfront lap pool and spa, fitness center, clubhouse, Har-Tru tennis courts, and pet-friendly living. The residence includes two climate-controlled garage parking spaces. Turnkey furnishings are available. Enjoy a lifestyle defined by convenience and sophistication—just minutes to the Longboat Key Club’s golf, tennis, and marina, the world-class shopping and dining of St. Armands Circle, and the vibrant cultural scene of downtown Sarasota, including fine dining, theaters, opera, ballet, and art galleries. Schedule your private showing today and experience the best of Longboat Key Gulf-front living.
Listing Agent: Steve Walter (941-809-0907)
2251 GULF OF MEXICO DR #301, LONGBOAT KEY, FL 34228
$5,999,000334 Days on yellowkey MLS ID: A4658325
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3921 Built: 2016Monthly Fee: $7,501 Tax: $69,970 (2024)Community: Aria Longboat KeySpa: YesCondo
Taxes:$69,970
Remarks: Welcome to an exceptional Gulf-front residence within the prestigious Aria community on the coveted south end of Longboat Key where refined coastal living meets timeless elegance. Set along 300 feet of pristine private shoreline, this extraordinary property offers a rare opportunity to experience true beachfront luxury in one of Sarasota’s most exclusive enclaves. Beyond the gated entrance, Aria unveils a serene, resort-inspired setting with lush native landscaping, tranquil walking paths, and the historic Villa am Meer, a beautifully restored 1935 seaside mansion that serves as the community’s elegant social centerpiece. This impeccably designed, residence spans nearly 4,000 square feet and is accessed via a private elevator, opening to a grand foyer and expansive, light-filled interiors. Recent enhancements include freshly painted cabinetry throughout the home. The thoughtfully curated open-concept floor plan seamlessly integrates sophisticated living and dining spaces with a chef’s kitchen, creating an ideal environment for both everyday living and elevated entertaining. Walls of floor-to-ceiling glass and soaring ceilings invite natural light while framing sweeping, unobstructed views of the Gulf. Expansive wraparound terraces provide the perfect setting to enjoy breathtaking sunsets and coastal breezes from nearly every room. The gourmet kitchen is a statement of both form and function, featuring premium quartz surfaces, freshly painted custom wood cabinetry, and top-tier appliances by Wolf and Miele. The primary suite serves as a private sanctuary, offering a spa-inspired retreat with dual baths connected by an oversized walk-in shower an exceptional design element rarely found. Two additional ensuite bedrooms provide luxurious accommodations for guests, while a dedicated office or optional fourth bedroom adds versatility. A bonus room offers additional flexibility for hobbies, media, or storage. Residents of Aria enjoy an unparalleled suite of amenities, including a beachfront pool and spa, state-of-the-art fitness and yoga studios, massage room, and a private wine cellar. A full-time onsite caretaker ensures a seamless, service-oriented lifestyle. The residence also includes a private, oversized two-car dehumidified garage. Don't miss the NEW video tour.
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Rachel Woodruff, Pa (941-705-8686)
3511 FAIR OAKS CT, LONGBOAT KEY, FL 34228
$1,399,99996 Days on yellowkey MLS ID: A4684840
2 Days Off yellowkey (back on 6/2/2026)
REDUCED by $159,001 (10.2%) on 05/04/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2579 Built: 1998Monthly Fee: $833 Tax: $17,916 (2025)Community: Bay IslesSpa: YesSingle Family
Taxes:$17,916
Remarks: Under contract-accepting backup offers. Nestled behind the gates of Queens Harbour in Bay Isles, this exceptional single-story home offers a rare blend of privacy, space, and effortless Longboat Key living—perfectly positioned on a quiet cul-de-sac with sweeping views along the 4th hole of the Longboat Key Club’s Blue Heron golf course. Spanning approximately 2,579 sq. ft., the thoughtfully designed floor plan features three bedrooms, two full baths, and a half bath, with flexible spaces that adapt beautifully to your lifestyle. A large, dedicated office/den with beautiful glass French doors and custom cabinetry offers outstanding flexibility and can serve as an additional sleeping space if desired. Inside, soaring 14-foot ceilings, rich wood flooring, and an open living-and-dining layout create an airy, welcoming atmosphere. A generous great room is framed by walls of sliding glass doors, opening to the pool and patio for seamless indoor-outdoor living—ideal for entertaining or simply unwinding with tranquil golf course views. The kitchen is perfectly placed for everyday living and gathering, featuring solid wood cabinetry, stone countertops, a center island with a veggie sink, pantry storage, a gas cooktop, and stainless-steel appliances. Two generous guest suites are ideally situated in this split plan, sharing a full bath with the ability to be closed off from the main living area. The private primary suite is a true retreat with golf course views across your private pool and spa. The spa fountain’s soft, flowing water creates a soothing backdrop that drifts into the bedroom through the sliding door access to the patio. The spacious bedroom features a walk-in closet, additional wall closet and a well-appointed en-suite bath with dual sinks, a soaking tub, separate shower, and private water closet. Outdoors, enjoy the screened private pool and spa with multiple seating areas and ample room to lounge and entertain in total comfort. The home has been immaculately maintained and includes new pool equipment and pool heater, a resurfaced pool, tile roof (2020), tankless gas water heater, as well as several additional upgrades – perfect move-in condition. Queens Harbour residents enjoy a maintenance-free lifestyle with 24-hour guard-gated security, with a community heated pool and spa just across the street. Ownership also includes deeded access to the private Bay Isles Beach Club, offering Gulf-front pavilions, grilling areas, multiple beach volleyball courts and a pristine beach only minutes away. Perfectly located within the gates of the Resort at Longboat Key Club’s Harborside Golf course and 290 slip deep-water Moorings marina, and close to island dining—plus easy access to St. Armands Circle, Lido Beach, and downtown Sarasota—this golf course home delivers the space, privacy, and location that define Longboat Key at its best.
1281 GULF OF MEXICO DR #111, LONGBOAT KEY, FL 34228
$1,050,00072 Days on yellowkey MLS ID: A4688079
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 1999 Tax: $9,956 (2025)Community: Water Club 01 At Longboat KeySpa: YesCondo
Taxes:$9,956
Remarks: Welcome to a little piece of paradise on Longboat Key at the stunning gated Gulf-front condominium community of Water Club, which offers a coastal lifestyle complete with direct access to sandy beaches, high-end amenities and exceptional security and concierge services. This designer-inspired, two-bedroom, 2.5-bath condominium is on the newer north building's plaza level and features nearly 1,400 square feet, 10-foot ceilings, double crown molding, plank wood flooring in the living areas, natural colors and floor to ceiling storm impact windows and doors. An open floor plan offers garden views from the spacious living room and the kitchen, which has both a breakfast bar and a seating area. A beautiful kitchen renovation was completed in December 2025 with handsome wood cabinets, stone countertops and GE Profile appliances. The split plan allows privacy for owners and guests in the two separate primary en-suite bedrooms, each with large windows, custom drapes and carpet, wall closets with built-ins and baths with combination tub/showers. ?An expansive balcony with glass railing barriers can be accessed through the living area and one of the primary suites. This lovely condo conveniently has a stack washer and dryer, linen closet, underbuilding storage unit and assigned parking and its own front desk concierge. Behind the 24-hour guarded-gate is true luxury living with a modern clubhouse, state-of-the-art fitness room, locker room and spa, sauna, bar and lounge, library, game room, ballroom and catering kitchen and outside terrace for gatherings and watching sunsets over the Gulf waters. Besides the magnificent beach and Florida-friendly landscaped grounds, the outdoor amenities include a peaceful courtyard, fire pit, resort-style pool and hot tub and new Har-tru tennis courts. Water Club is conveniently near island golf courses and Publix, and a short distance from St. Armands Circle and downtown Sarasota for dining, shopping, entertainment and cultural venues.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kathleen Ucci (941-302-2344)
1912 HARBOURSIDE DR #604, LONGBOAT KEY, FL 34228
$835,000103 Days on yellowkey MLS ID: A4683819
REDUCED by $15,000 (1.8%) on 06/01/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2207 Built: 1982 Tax: $7,734 (2025)Community: Fairway Bay 1Townhouse
Taxes:$7,734
Remarks: Embrace the island life style within the gates of Longboat Key's premier resort community of Bay Isles. You'll love this spacious townhome-style condo in Fairway Bay. Designed with soaring ceilings and large windows to allow maximum light and expansive views of the neighborhood’s tropical foliage, this beautifully and thoughtfully renovated home offers lots of space for gatherings with friends or family. The main living area opens effortlessly to a screened porch through sliding doors, creating a bright and airy space perfect for entertaining. The open floorplan, cozy fireplace, freshly painted interiors, fully updated kitchen and bathrooms, two bedrooms, and abundant storage make this home as functional as it is inviting. Downstairs, a flexible bonus space off the oversized 2-car garage offers endless possibilities. This non-conforming, bonus area includes a spacious living room, a flex space (currently set up as a 3rd bedroom), a full bath, and laundry room – perfect for guests, hobbies, or working from home. Just a few steps away, enjoy one of the community’s pools and hot tubs, or explore all the amenities this vibrant neighborhood offers – another heated pool and hot tub, miles of manicured paths, a clubhouse, fitness center, tennis/pickleball courts, and 24-hour gated security. Plus, gain deeded access to the Bay Isles Beach Club, a private, gated Gulf-side retreat with a covered pavilion, parking, restrooms, grills, a beach volleyball court, and sunsets that will take your breath away. This home truly lives like a retreat. Just 10 miles from Anna Maria Island to the North, South 4 miles to St. Armands Circle, and another 4 to Downtown Sarasota, with plenty of shopping, dining, and entertainment options. Your tropical beach getaway is ready and waiting – come make it yours!
Listing is courtesy of: S&N REAL ESTATE, INC. (941-320-5482)
Listing Agent: Darlena Nelms (941-320-5482)
3070 GRAND BAY BLVD #632, LONGBOAT KEY, FL 34228
$699,000583 Days on yellowkey MLS ID: A4627468
REDUCED by $25,900 (3.6%) on 04/28/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1276 Built: 1995 Tax: $7,802 (2024)Community: Grand Bay 6Spa: YesCondo
Taxes:$7,802
Remarks: Move in ready and beautifully updated two bedroom two bath Bimini model in Grand Bay nestled within the secure gated enclave of Bay Isles. Located on the third living level of the four level over parking building 6, you will enjoy panoramic views of Sarasota Bay as you gaze out from your almost 400 foot wrap around terrace offering sunrise and sunset views. This particular condo has been tastefully updated with new variable speed HVAC with humidity control, Wi-Fi Thermostat & 12 year warranty on compressor in 2024; new water heater & significantly updated kitchen in 2026; new refrigerator, washer & dryer, Hunter Douglas battery operated remote-controlled window treatments, lighting & plumbing fixtures & freshly painted all in 2023. Nothing more to do but to move in and enjoy everything Grand Bay, Longboat Key and Sarasota have to offer especially with the recently renewed transferable Home-Tech service contract! Your amenities include two large resort style heated swimming pools and spas, tennis courts, state of the art fitness center and expansive clubhouse with social activities as well as access to the private white sandy well maintained beach at the Bay Isles Beach Club on the Gulf of Mexico. You will also have access to beautiful peaceful walking trails winding along the bay front, marina and golf courses. A short drive will lead you to choice eateries along Gulf of Mexico Drive or over the bridge to St Armands Circle and downtown Sarasota.
Listing Agent: Richard Perlman (941-228-8580)
3435 WINDING OAKS DR #18, LONGBOAT KEY, FL 34228
$949,000127 Days on yellowkey MLS ID: A4680403
REDUCED by $101,000 (9.6%) on 05/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2555 Built: 1988 Tax: $8,565 (2025)Community: Winding OaksSpa: NoCondo
Taxes:$8,565
Remarks: Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.
Listing Agent: Sean Clark (941-312-1146)
1581 GULF OF MEXICO DR #406, LONGBOAT KEY, FL 34228
$6,600,00092 Days on yellowkey MLS ID: A4685503
1 Days Off yellowkey (back on 6/2/2026)
REDUCED by $150,000 (2.2%) on 04/30/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2347 Built: 2024 Tax: $50,055 (2025)Community: St. RegisSpa: NoCondo
Taxes:$50,055
High School: Sarasota High
Remarks: Perched above the shimmering shoreline, this exquisite two-bedroom, two-and-a-half-bath residence at The St. Regis Longboat Key Resort offers breathtaking panoramic views of the turquoise waters of the Gulf of Mexico and the resort’s serene saltwater lagoon. Designed for both refined comfort and effortless coastal living, the residence showcases exceptional craftsmanship and sophisticated design throughout. A defining feature of this residence is the expansive private terrace, where all principal rooms open seamlessly to the outdoors. Complete with a gas grill, this exceptional outdoor living space provides sweeping views of the Gulf of Mexico and the tranquil lagoon—creating the perfect setting for al fresco dining, entertaining, or simply enjoying spectacular sunsets over the water. The gourmet kitchen is a true showpiece, appointed with sleek Poggenpohl cabinetry and premium appliances including Wolf double ovens, a gas cooktop, microwave, icemaker, and wine refrigerator. A generously sized island provides abundant built-in storage, making the space as functional as it is beautiful. This thoughtfully designed floor plan features two luxurious owner’s suites. The primary suite enjoys stunning views of the Gulf of Mexico and opens directly onto the large terrace. The spa-inspired bathroom features a large double vanity with elegant lighted mirrors plus a separate makeup vanity, two private water closets, a seamless glass shower, and a freestanding soaking tub. Electronic sheers and blackout shades provide effortless ambiance and privacy, while a custom-built closet offers exceptional storage. The second owner’s suite also captures captivating Gulf views and opens onto the terrace. Its spacious bath includes dual vanities with lighted mirrors, a water closet, and custom-built closets. Electronic sheers and blackout shades add both convenience and luxury. Additional highlights include a large laundry room with sink, cabinetry, and hanging rack, as well as an elegantly designed powder room for guests. Offered completely turnkey, the residence is beautifully furnished and enhanced with custom light fixtures throughout, creating a sophisticated yet inviting coastal retreat. Nestled within the first branded residential community and ultra-luxe 5 star resort on the Gulf of Mexico. The Residences at The St. Regis Longboat Key blend legendary service with the allure of a seaside getaway. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in residence dining. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
842 BAYPORT WAY, LONGBOAT KEY, FL 34228
$675,00071 Days on yellowkey MLS ID: A4687058
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983 Tax: $5,662 (2025)Community: Bayport Bch & Ten Ph FSpa: NoCondo
Taxes:$5,662
High School: None
Remarks: Poised within the Gulf to Bay community of Bayport Beach and Tennis Club, 842 Bayport Way offers 1570 square feet of effortless indoor-outdoor living. This first floor corner residence brings added natural light and extra privacy, giving the feeling of a private home with the ease of low maintenance living. The open layout includes a spacious kitchen, a primary bedroom with office space, walk-in closet and ensuite bath with dual vanities, as well as convenient in-unit laundry, covered parking and private storage closet. A combined dining and living area opens to a screened lanai and extended brick patio. This is a favorite spot for morning coffee, afternoon siestas and al fresco dining watching sunset skies. A garden gate leads to a direct side path to deeded beach access across the road. For pet owners, Bayport is small-pet friendly, and this walk-out location makes dog-walking especially easy. Spanning 27 acres of exquisitely landscaped tropical grounds, Bayport is celebrated for its timeless Tim Seibert architecture, exceptional amenities, and easy resort lifestyle. Residents enjoy a heated Jr. Olympic pool, clubhouse, fitness center, tennis, bocce ball, and shelled walking paths. Along the bay shoreline, a fishing pier, kayak launch and storage is perfect for morning paddles or simply enjoying nature . On the Gulf side, 1,200 feet of deeded beach access, complete with loungers and umbrellas, makes enjoying Longboat Key’s famously uncrowded beaches effortless. The condo’s split floor plan works well for year round living or a seaside escape. A favorable rental policy offers excellent income opportunity. Located mid-key, Bayport keeps you close to shopping, daily conveniences, great island dining, and the vibrance of Sarasota, all while feeling tucked away and serene. Settle in and enjoy a slice of true paradise on Longboat Key.
Listing Agent: Rosemarie Mckee (941-504-9396)
1211 GULF OF MEXICO DR #301, LONGBOAT KEY, FL 34228
$1,590,000225 Days on yellowkey MLS ID: A4669896
REDUCED by $85,000 (5.1%) on 04/19/2026
Bed: 2 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2100 Built: 1985 Tax: $14,792 (2025)Community: PromenadeSpa: YesCondo
Taxes:$14,792
Remarks: Rarely available north-side corner residence at The Promenade showcases panoramic views of the Gulf of Mexico, Sarasota Bay, white sandy beaches, and the sparkling city skyline. This beautifully designed 2,100 sq. ft. “E” floor plan features two bedrooms plus a den/3rd bedroom (with an en-suite full bath) and three bathrooms, with a spacious split layout that captures natural light and breathtaking vistas from every room. The expansive living and dining areas flow seamlessly to two private terraces—set your morning coffee down as you watch the sunrise over the bay, and end the day with a glass of wine while taking in the sunset over the Gulf. A stylish wet bar adds the perfect touch for entertaining. The kitchen is a showpiece, featuring 2022 installed Sub Zero refrigerator/freezer, GE Monogram stainless-steel induction cooktop and oven, ASCO dishwasher and GE Monogram microwave / convection oven combo, a white subway tile backsplash, quartz countertops, sleek contemporary white cabinetry, and an eat-in area overlooking the bay. Engineered white oak hardwood floors extend throughout, adding warmth and sophistication. The primary suite offers stunning Gulf views, built-in cabinetry, and two walk-in closets, while the guest suite enjoys downtown views and a private bath. The third bedroom/den opens to a terrace overlooking the Gulf. Includes one deeded parking space and access to resort-style amenities—concierge, 24-hour security, fitness center, an Olympic-size heated pool, four Har-Tru tennis courts, and more.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
2425 GULF OF MEXICO DR #2E, LONGBOAT KEY, FL 34228
$1,400,00043 Days on yellowkey MLS ID: A4691707
3 Days Off yellowkey (back on 6/1/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $14,160 (2025)Community: Sea Gate ClubSpa: NoCondo
Taxes:$14,160
Remarks: Amazing and Unobstructed 2nd Floor Gulf, Beach, and Pool Views! This is your perfect Direct beachfront condo, with floor to ceiling updated windows throughout! Nearly 1,500 sq. ft,. Tile floors in the main living areas, split bedroom floor plan, and amazing views from every room! Just move right in and enjoy, or bring your own creative ideas. The Sea Gate Club building has been completely remodeled! New roof, new windows, new railings, gorgeous 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. Priced for a quick sale, hurry to come see this gorgeous condo in paradise today!
4127 GULF OF MEXICO DR #N102, LONGBOAT KEY, FL 34228
$4,700,000131 Days on yellowkey MLS ID: A4680618
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3521 Built: 2007 Tax: $30,723 (2025)Community: La FirenzaSpa: NoCondo
Taxes:$30,723
Remarks: Spectacular Gulf of Mexico views define this exceptional three-bedroom, three-and-a-half-bath residence that lives like a single-family home. A large wraparound terrace with a built-in grill offers seamless indoor-outdoor living, and private steps leading directly to the sandy beach – perfect for sunset entertaining or morning walks along the shore. Enter the home through a private elevator into a formal foyer with double door entry into the residence. The gracious living room is framed by expansive windows showcasing endless water views and exceptional sunsets flowing effortlessly to a built-in wet bar complete with wine refrigerator, ice maker, and a dedicated desk area—ideal for entertaining or casual work-from-home moments. A formal dining room with elegant ceiling detail makes hosting a dinner party a treat. Plantation shutters throughout the residence add a coastal and private touch. The gourmet kitchen is designed for both function and style, offering a large island for gathering, side-by-side Sub-Zero refrigerator and freezer, Wolf gas cooktop, Wolf oven with warming drawer, generous pantry, and a cozy desk area for browsing favorite recipes. A large center island and charming breakfast nook are the perfect spots for morning coffee or casual meals. Adjacent to the kitchen, the inviting keeping room opens to a private east-facing terrace with beautiful sunrise and views of Sarasota Bay. The expansive owner’s suite is a true retreat, featuring its own breakfast bar with sink and refrigerator for enjoying morning coffee while overlooking the Gulf. Two oversized, custom-built walk-in closets provide exceptional storage. The spa-inspired bath includes double vanities, a glass-enclosed shower, a private water closet with bidet, and refined finishes throughout. Two en-suite guest bedrooms with large custom-built closets open onto a private terrace with views of Sarasota Bay, ensuring comfort and privacy for family and guests alike. This rare beachfront residence combines luxury, privacy, and the ease of coastal living, all with breathtaking views and thoughtfully designed spaces for everyday enjoyment and elegant entertainment. Residents of La Firenza enjoy a boutique, gated setting with private beach access, a heated beachfront pool and spa, fitness facilities and secure garage parking.
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