Location: Longboat Key
Keyword(s): Booker High
Keyword(s) High School: Booker High
Do Not Show Listings
3010 GRAND BAY BLVD #493, LONGBOAT KEY, FL 34228
$1,475,000270 Days on yellowkey MLS ID: A4668143
REDUCED by $404,000 (21.5%) on 07/06/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2550 Built: 1999 Tax: $16,976 (2025)Community: Grand Bay 4Spa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$16,976
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Virtually Staged. Perched just one floor below the penthouse in the sought-after Grand Bay IV community on Longboat Key, this 2,550-sq.-ft. Cayman floor plan offers an exceptional opportunity to enjoy the Grand Bay lifestyle immediately—while still allowing a future owner to complete their personal renovation plans once the building’s elevator modernization is finished. The furniture rental will extend for up to one year, giving the buyer time to enjoy the residence while preparing for future customization or construction. With ideal north–south exposure, this residence captures breathtaking sunrises over Sarasota Bay and stunning Gulf sunsets from two expansive terraces. Walls of glass and abundant natural light enhance the open-concept layout, which includes 2 bedrooms, 2.5 baths, and a den that can easily be reconfigured to include a walk-in closet for a 3rd bedroom. The primary suite opens directly to the Bayfront terrace, the second bedroom offers an en-suite bath and private Gulf-view balcony, and the den, kitchen, and third bedroom share access to a second terrace for effortless indoor-outdoor living. Two prime, side-by-side parking spaces on the upper main level sit conveniently next to the elevator, leading to a private elevator foyer. Residents of Grand Bay enjoy world-class amenities including 24-hour security, a clubhouse with library and game room, fitness center, tennis and pickleball courts, two heated pools and a spa, and deeded access to the exclusive Bay Isles Beach Club.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
2326 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$800,000133 Days on yellowkey MLS ID: A4683180
REDUCED by $99,000 (11.0%) on 06/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2282 Built: 1986Monthly Fee: $143 Tax: $10,215 (2025)Community: Harbour Oaks 2Villa
Taxes:$10,215
Remarks: PRICE IMPROVEMENT – REDUCED $99,000! Discover refined coastal living in this impeccably maintained, fully furnished end-unit villa on Longboat Key, now offered at an exceptional new value following a $99,000 price reduction. Offering nearly 2,400 square feet of thoughtfully designed living space, this residence combines the privacy and feel of a single-family home with the ease of maintenance-free living, all just moments from the Gulf's pristine beaches. Vaulted ceilings, abundant natural light, and an open floor plan create an inviting atmosphere throughout. Multiple living and entertaining areas include a formal living room with a wood-burning fireplace and expansive sliding glass doors leading to a spectacular 740-square-foot private terrace overlooking tranquil pond views. Timeless coastal finishes include rich wood flooring, plantation shutters, granite countertops, updated cabinetry, and a skylight that fills the kitchen with natural light. Recent improvements include a new roof and new air-conditioning system, both completed in 2025. Two private atriums add architectural character and natural beauty, while a versatile office with a built-in Murphy bed can easily serve as a fourth bedroom. The spacious primary suite offers a private retreat, complemented by comfortable guest accommodations. Additional features include a private two-car garage with organized storage, a heated community pool and spa, and exclusive membership to the gated Bay Isles Beach Club with private Gulf-front beach access and dedicated parking. Ideally located near world-class beaches, boating, waterfront dining, and the renowned Longboat Key Club's golf, tennis, pickleball, marina, and dining amenities, this exceptional residence offers the ultimate island lifestyle. Private, elegant, fully furnished, and now priced to sell, this is a rare opportunity to own one of Longboat Key's most desirable villa residences.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
3527 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,550,00046 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
$949,000100 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
$1,180,000130 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!
595 BOWSPRIT LN, LONGBOAT KEY, FL 34228
$3,099,000263 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)
626 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$4,495,00026 Days on yellowkey MLS ID: A4696767
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2026Monthly Fee: $50 Tax: $4,789 (2025)Community: Longboat Shores RevSpa: YesSingle Family
Taxes:$4,789
Remarks: Experience the pinnacle of coastal living in this exceptional new construction waterfront residence, ideally situated in the heart of Longboat Key. Perfectly positioned across from the community marina with direct boating access to the Gulf of Mexico, this move-in-ready home offers an extraordinary blend of modern elegance, superior craftsmanship, and the relaxed sophistication of island life. Spanning 4,106 square feet, this thoughtfully designed residence features 4 spacious bedrooms, a private office/den, and 4 luxurious bathrooms, creating an ideal setting for both everyday living and entertaining. Finished floor elevation above base flood elevation, the home provides added peace of mind while maximizing its commanding presence. Designed to embrace Florida’s indoor-outdoor lifestyle, expansive sliding glass doors seamlessly connect the interior living spaces to two generous covered lanais, overlooking a resort-style heated pool and spa. Whether hosting sunset gatherings or enjoying a quiet morning overlooking the water, every space has been crafted to capture the beauty and serenity of waterfront living. Inside, sophisticated finishes and attention to detail abound. Wide-plank engineered hardwood flooring flows throughout the home, complemented by designer quartz countertops, custom cabinetry, and an open-concept floor plan filled with natural light. The chef-inspired kitchen serves as the centerpiece of the home, featuring an oversized island, premium finishes, and a spacious walk-in pantry. The convenience of dual laundry rooms further enhances the home's thoughtful design. For boating enthusiasts, the property features a concrete seawall and marina access, offering quick and convenient access to Sarasota Bay and the Gulf waters beyond—making it easy to enjoy world-class fishing, waterfront dining, and unforgettable days on the water. A boat slip is currently leased by the owner. Tucked away on a quiet street, yet just moments from Longboat Key’s pristine white-sand beaches, championship golf courses, marinas, boutique shopping, and renowned dining destinations, this residence delivers the perfect balance of privacy and accessibility. Offering the rare combination of new construction, waterfront location, elevated construction, luxury finishes, and Gulf boating access, 626 Buttonwood Drive represents an exceptional opportunity to own a premier Longboat Key waterfront retreat in one of Florida’s most coveted coastal communities. Luxury. Boating. Beach Life. Welcome Home.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Joshua Freed (941-577-5121)
2850 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$325,0005 Days on yellowkey MLS ID: A4698791
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 532 Built: 1967 Tax: $3,248 (2025)Community: Neptune On Longboat KeyCondo
Taxes:$3,248
Remarks: Coastal Living on Longboat Key – Neptune Condominium Welcome to your island retreat at Neptune on Longboat Key, a charming boutique community just moments from the Gulf of Mexico. This beautifully updated 1-bedroom, 1-bath condominium offers the perfect blend of comfort, style, and an unbeatable Longboat Key lifestyle. Step inside to discover a bright, open floor plan featuring luxury vinyl flooring, coastal-inspired décor, crown molding, and a tastefully renovated kitchen with cabinetry, updated appliances, quartz-look countertops, and a deep stainless sink. The spacious living and dining area flows effortlessly onto a screened lanai where you can relax with a morning coffee. The generous bedroom provides a peaceful retreat with abundant natural light, while the updated bath and thoughtful finishes create a move-in-ready coastal escape. Located on the desirable south end of Longboat Key, Neptune is a small boutique community known for its quiet atmosphere and convenient location. You're just a short stroll to the beach and only minutes from St. Armands Circle, where you'll enjoy world-class dining, shopping, and entertainment. Downtown Sarasota, cultural attractions, golf, boating, and marinas are also just a short drive away. Neptune is a small, low-density community with minimal common amenities, helping keep ownership simple while offering a peaceful island setting. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, this turnkey-furnished condo offers an exceptional opportunity to own a piece of paradise on Longboat Key.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
803 BAYPORT WAY #803, LONGBOAT KEY, FL 34228
$775,000112 Days on yellowkey MLS ID: A4686552
1 Days Off yellowkey (back on 5/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1456 Built: 1981 Tax: $6,376 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$6,376
Remarks: Under contract-accepting backup offers. Welcome to the true tropical oasis of Bayport Beach & Tennis Club, a Longboat Key Gulf to Bay community. Bayport was designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture and is recognized for its award-winning, timeless design. Bayport offers 27 lushly landscaped acres with 1,200 feet of private beach. This tastefully renovated second-floor unit offers two expansive bedrooms and two beautiful bathrooms and comes fully turn-key. This unit was curated with attention to detail and functionality in mind. The kitchen offers plenty of storage, stainless steel appliances, quartz countertops and beautiful accent details. Enjoy three patios that allow for great indoor/outdoor living. Fully equipped with Hurricane impact doors and windows. One under building parking space included, along with a locked storage closet - perfect for bikes and beach gear. When not at the beach, enjoy the meticulously kept nature trails, landscaped grounds and wildlife. Just steps away from the well appointed clubhouse is equipped with a Junior-Olympic sized heated pool, four har-tru tennis courts, a fitness center and more. In addition, Bayport residents are proud of their active social and recreational calendar. Water enthusiasts can utilize the secluded fishing pier that stretches out onto Sarasota Bay; to fish, watch the sunrise, the Manatees swim or the Egrets wading among the mangrove trees. Residents also benefit from conveniently located on-site paddle board and kayak launch and storage areas. Bayport residents enjoy an array of restaurants locally, and the convenience of a nearby supermarket, pharmacy and boutique shops. Recreational enthusiasts also benefit from the nearby Bayfront Park which offers a popular pickle-ball program, dog park and other bayside activities. The nearby Longboat Key Club offers private access to championship waterfront golf, extensive leisure activities and boating facilities. Within minutes, one can access the famous St Armand's Circle with its exceptional shopping and dining amenities. From there, cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Alexis Smith-Frady (352-225-1724)
1211 GULF OF MEXICO DR #701, LONGBOAT KEY, FL 34228
$2,125,00035 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: Virtually Staged. 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
$4,950,000266 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)
455 LONGBOAT CLUB RD #PH8, LONGBOAT KEY, FL 34228
$2,700,90011 Days on yellowkey MLS ID: A4697519
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2780 Built: 1990 Tax: $23,862 (2025)Community: PierreCondo
Taxes:$23,862
Remarks: PENTHOUSE LIVING AT THE PIERRE – LUXURY GULF-FRONT RESIDENCE IN LONGBOAT KEY CLUB Welcome to The Pierre, an exclusive Gulf-front community featuring just 66 luxury residences nestled behind the private gates of the renowned Longboat Key Club. This beautifully renovated eighth-floor penthouse residence offers breathtaking panoramic views from every room, showcasing the tranquil bay waters, spectacular Gulf sunsets, and the sparkling city skyline. Designed to maximize natural light and capture the beauty of its surroundings, expansive windows frame unforgettable vistas throughout the home. Thoughtfully crafted for both everyday living and elegant entertaining, this exceptional residence features three spacious bedrooms, three-and-a-half baths, and a gourmet kitchen equipped with premium Thermador appliances, abundant cabinetry, and generous workspace for the discerning chef. The luxurious primary suite provides a peaceful retreat with stunning water views, while the additional guest suites allows for comfort and privacy for family and visitors. Residents of The Pierre enjoy an impressive collection of resort-style amenities, including: • Direct private beach access • Beachfront heated pool and spa • Fitness center • Tennis courts • Newly renovated lobby and common areas • Club gathering room and meeting facilities • 24-hour guarded security • On-site professional management Ownership also includes two private garage parking spaces, a secured storage area, and access to private guest suites available for visiting family and friends on a nominal rental basis. For those seeking an elevated lifestyle, membership opportunities at the renowned Longboat Key Club provide access to championship golf courses, world-class tennis facilities, spa and wellness services, exceptional dining venues, beach services, and a vibrant social calendar (membership subject to application and availability). Ideally located near St. Armands Circle and vibrant Sarasota, you'll enjoy convenient access to fine dining, boutique shopping, arts and cultural attractions, and some of Florida's most beautiful beaches. This is a rare opportunity to own an extraordinary Gulf-front penthouse in one of Longboat Key's most sought-after luxury communities. Schedule your private showing today and experience the unparalleled lifestyle that awaits at The Pierre.
Listing is courtesy of: REAL ESTATE BOUTIQUE LLC (941-726-8061)
Listing Agent: Maria Atkins (941-726-8061)
549 HALYARD LN, LONGBOAT KEY, FL 34228
$2,195,00015 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 Agent: Ryan Brown (941-330-7774)
1241 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228
$2,745,000252 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
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 Agent: Michael Moulton (941-928-3559)
3710 GULF OF MEXICO DR #F2, LONGBOAT KEY, FL 34228
$475,000123 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)
3301 BAYOU RD, LONGBOAT KEY, FL 34228
$1,250,00061 Days on yellowkey MLS ID: A4692818
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2827 Built: 1993Monthly Fee: $104 Tax: $12,771 (2025)Community: Bay IslesSingle Family
Taxes:$12,771
Remarks: Located within the gated and highly desirable community of Bay Isles on Longboat Key, this 4 bedroom, 3 bathroom pool home encompasses 2827 square feet of living space. The residence features a functional and spacious floor plan, including a well-appointed bedroom layout, an open kitchen and family room combo, and a formal living and dining room combo. This property is priced competitively, offering an exceptional opportunity for a buyer or investor to come in and renovate the home with their own personal style and modern finishes. The outdoor living area features a private pool, providing a quiet retreat within a stunning waterfront community. Bay Isles residents enjoy a premier island lifestyle with access to a private beach area and cabana, while separate memberships are available for those interested in world-class golf or the local marina. The location is ideal for enjoying the best of the Florida Gulf Coast, situated in close proximity to local restaurants, boutique shopping, and the famous St. Armand's Circle. Whether you are looking for a primary residence or a seasonal getaway, this home serves as the perfect canvas to create a custom masterpiece in one of Longboat Key's most sought-after enclaves.
Listing Agent: Michele Tanner (941-894-5603)
2120 HARBOURSIDE DR #623, LONGBOAT KEY, FL 34228
$975,000106 Days on yellowkey MLS ID: A4686721
REDUCED by $120,000 (11.0%) on 06/30/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988Monthly Fee: $137 Tax: $11,079 (2025)Community: Fairway Bay AtriumSpa: YesCondo
Taxes:$11,079
Remarks: Step into coastal elegance in this fully renovated three-bedroom, two-bathroom Fairway Bay residence, where every detail has been thoughtfully reimagined. A charming private lanai and seating area welcome you before entering the unit, setting the tone for relaxed waterfront living. Inside, an open-concept layout seamlessly blends the kitchen, dining, and living spaces, creating a bright, airy environment perfect for both entertaining and everyday comfort. The gourmet kitchen is outfitted with GE Profile appliances, custom soft-close cabinetry, and ample storage, offering both style and functionality. The primary suite is a serene retreat featuring a spacious walk-in closet, additional storage, and a beautifully updated en-suite bath with a large walk-in shower. From both the living room and the primary suite, step onto the expansive north-facing balcony to take in the tranquil Sarasota Bay views, where you can enjoy the morning sunrise and the soft glow of the evening sky. The second bedroom is generously proportioned and easily accommodates a king-size bed, creating a luxurious space for guests. The third bedroom is also spacious, complete with a custom built-in, ideal for a guest room, home office, or flexible living area. A thoughtfully designed guest bath ensures privacy and convenience for family or visitors. This unit also includes the ease and security of one covered parking space beneath the building. Fairway Bay residents enjoy an exceptional suite of amenities including two heated pools, a spa, a clubhouse, a fitness center, tennis and pickleball courts, and private beach access on Longboat Key. With the shops, dining, and vibrant lifestyle of St. Armands Circle just minutes away, this residence combines the best of convenience and refined waterfront living.
2301 GULF OF MEXICO DR #43N, LONGBOAT KEY, FL 34228
$1,000,000116 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Steve Nursey (941-356-7010)
775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228
$2,195,000137 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
$3,249,000271 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.
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