Location: Longboat Key
Keyword(s): Booker High
Keyword(s) High School: Booker High
Do Not Show Listings
2089 GULF OF MEXICO DR #G1-105, LONGBOAT KEY, FL 34228
$855,000154 Days on yellowkey MLS ID: A4673060
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1974 Tax: $7,928 (2025)Community: Seaplace ISpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,928
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Wake up in This Resort-Style Living Condo located on a Barrier Island Paradise! Positioned just steps from the Gulf of Mexico on exclusive Longboat Key—where sugar-white sand beaches stretch endlessly and dolphins play in turquoise waters—this professionally redesigned ground-floor residence in Seaplace's coveted G1 building offers the rare combination of coastal luxury, modern sophistication, and effortless living. Minutes to the boutiques and dining of St. Armands Circle and Sarasota's world-class cultural scene, this is the Florida lifestyle you've been dreaming of. Step into an open-concept culinary kitchen masterpiece featuring custom cabinetry with integrated lighting, pantry, and generous extra cabinet space for all your storage needs. Premium Thermador and Bosch appliances—including an induction range and new vent hood—paired with expansive quartz countertops make this kitchen as functional as it is beautiful. Adjacent dining flows seamlessly, perfect for entertaining or intimate dinners at home. Overlooking serene garden views, the primary bedroom is a haven of calm. Custom-built closets provide abundant storage, while blackout window treatments ensure restorative sleep. The spa-inspired en-suite bath elevates everyday rituals with a double vanity, an expanded premium shower system, and stylish tile flooring with an elegant glass partition that enhances the open, airy design. This gated, 24-hour guarded community features custom wood ceiling, luxury vinyl flooring, new electrical panel and wiring, brand-new HVAC system and tankless water heater, reverse osmosis water system for pure filtered water, High-speed internet, all-new plumbing fixtures, interior doors, hardware, recessed lighting, and ceiling fans, hurricane-grade sliding doors, windows, and premium front door with keypad entry. The lanai—upgraded with beautiful new exterior tile—frames lush garden views and offers the perfect setting for morning coffee with the Gulf breeze, al fresco dining, or sunset cocktails. It's your own slice of tranquility in a tropical setting. Living at Seaplace means waking up to the sound of waves and ending each day with spectacular Gulf sunsets. This community features a newly renovated clubhouse and state-of-the-art fitness center, two sparking pools plus kiddie pool, two relaxing hot tups, three tennis courts, scenic walking trails through lush tropical landscape, covered parking beneath the building, and steps to pristine Gulf beaches. Beyond your front door lies 12 miles of unspoiled barrier island beauty—powdery beaches where sea turtles nest, championship golf courses, waterfront dining, and kayaking through peaceful mangrove tunnels. Stroll St. Armands Circle for upscale shopping, savor fresh grouper at a waterfront restaurant, or simply watch the sunset paint the sky in shades of pink and gold. This is coastal living at its finest. This home is completely renovated and ready for immediate occupancy. For ultimate convenience, beautifully curated furnishings may be available for purchase outside of the sale—allowing you to simply unlock the door and start living your dream lifestyle from day one. Whether you're seeking a sophisticated year-round retreat, a luxurious seasonal escape, or the ultimate coastal haven, this residence delivers on every front. Schedule your private showing today—and start living the life you've always imagined!
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Beverly Perez (941-323-4600)
455 LONGBOAT CLUB RD #707, LONGBOAT KEY, FL 34228
$1,999,95089 Days on yellowkey MLS ID: A4680080
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2410 Built: 1990 Tax: $9,861 (2025)Community: PierreCondo
Taxes:$9,861
Remarks: Welcome to The Pierre, a distinguished Gulf-front address behind the private gates of the Longboat Key Club, offering a rare blend of refined coastal living, privacy, and world-class resort lifestyle appeal for discerning buyers from around the globe. Located on the seventh floor, Residence 707 showcases spectacular sunset skies over the Gulf of Mexico, complemented by peaceful bay and city vistas, creating a dynamic panorama from sunrise through evening. Expansive windows fill the interiors with natural light while framing the natural beauty of Longboat Key’s shoreline and Sarasota Bay. Thoughtfully designed for both relaxed living and gracious entertaining, the residence offers generous living spaces and a seamless indoor-outdoor connection. The floor plan includes two ensuite bedrooms and a flexible third bedroom with sliding retractable wall, three full baths, and spacious living and dining areas—each with direct access to the residence’s gracious balconies. Residents of The Pierre enjoy an exceptional array of amenities, including direct private beach access, a beachfront pool, spa, fitness center,, tennis courts, a newly renovated lobby, club gathering room, meeting room and 24-hour guard security. Private guest suites are also available for visiting family and guests on a nominal rental basis. Ownership is further enhanced by secure garage parking, a private secured storage area, and onsite professional management, providing ease and confidence for both year-round and seasonal owners. Beyond the residence, membership opportunities at the renowned Longboat Key Club provide access to a celebrated resort lifestyle, featuring championship golf courses, world-class tennis, spa and wellness facilities, multiple dining venues, beach services, and an active social calendar (membership subject to application and availability). Perfectly situated near St. Armands Circle and downtown Sarasota’s cultural attractions, Residence 707 represents a rare opportunity to own within one of Longboat Key’s most prestigious waterfront communities—where international sophistication, panoramic views, and a coveted club lifestyle converge in one extraordinary coastal setting.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Judy Wright, Pa (941-232-8041)
1000 LONGBOAT CLUB ROAD #1105, LONGBOAT KEY, FL 34228
$1,050,000302 Days on yellowkey MLS ID: A4657701
1 Days Off yellowkey (back on 4/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1290 Built: 1972Monthly Fee: $209 Tax: $7,027 (2024)Community: Privateer SouthCondo
Taxes:$7,027
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Seller wants offers! Rarely available and beautifully renovated 11th floor Penthouse with breathtaking Gulf, Sunset and Bay views and ideally situated within a short beach walk between the popular Resort at Longboat Key Club and the luxurious St. Regis Resort. This island gem has brought many years of joy to the Seller based on its perfect South LBK beachside location and all it's resort style amenities. The sleek European style interior boasts carefree luxury vinyl plank flooring, along with new carpeting in both bedrooms, LED lighting, dazzling designer tile in both bathrooms, and the color scheme throughout mirrors its direct seaside setting. The open-concept kitchen makes entertaining a breeze and offers gorgeous quartz counter tops, custom backsplash, stylish GE appliances, sparkling hardware, and a customized breakfast bar. Both the primary and guest bedroom each lead to a separate balcony where you can soak up the sun while enjoying the peaceful surroundings and endless water and beach views. Residents enjoy the convenience of on-site management, an updated guest suite & additional guest quarters for your overflow visitors, a secure lobby, tennis and pickle ball, heated pool and spa, a great gym, and a refurbished lobby, hallways, social room, community bathrooms, and the landscaping create an even more exceptional experience in this world-class beach location. A membership to Longboat Key Club’s exceptional offerings will provide many hours of outdoor fun and golf & tennis enthusiasts will appreciate the two championship courses & tennis gardens. These facilities, along with professional instruction and well-appointed pro shops, cater to athletes of all levels. Outside the gates, Longboat Key offers fine & casual dining, deep water boating & fishing, 10 miles of sugar sand beaches, and a great variety of local treasures to explore. The Sarasota Opera & Ballet, Van Wezel Performing Arts, and all of Sarasota's cultural offerings including boutique shopping and popular restaurants are just minutes away, creating the perfect balance of relaxation and activity in this sought-after island paradise.
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Tina Rudek Stark, Pa (941-920-0303)
3311 SABAL COVE DR, LONGBOAT KEY, FL 34228
$2,450,000112 Days on yellowkey MLS ID: A4676501
1 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3416 Built: 2006Monthly Fee: $116 Tax: $12,784 (2025)Community: Sabal CoveSpa: NoSingle Family
Taxes:$12,784
Remarks: Expertly designed by the highly regarded John Cannon Homes, known for exceptional quality and craftsmanship, this custom 4 bedrooms plus study residence offers the comfort and convenience of expansive living on one single level within the exclusive enclave of Sabal Cove, behind the secure gates of Bay Isles on Longboat Key. The home is centered around a dramatic screened outdoor living area, where the primary gathering spaces and owner’s suite are open to a grand, tiered brick-paver patio created for easy, elegant entertaining. This resort-style environment includes a saltwater swimming pool with waterfall feature, a raised gas fire pit with lounge seating and a built-in protected summer kitchen all surrounded by architectural lighting and mature tropical plantings beyond the enclosure that ensure privacy and tranquility. Spanning more than 3,400 square feet, the interior reveals impressive architectural scale with ceiling heights ranging from 12 to 15 feet, complemented by clerestory windows that fill the home with natural light. The family room is highlighted by a newly refinished limestone and glass natural gas/electric fireplace, while seamless aquarium-style glass corner sliders retract completely, creating a fluid connection between indoor living and the outdoor retreat. Interior spaces include a formal living room, a dining room with built-in glass display shelving, and a private study featuring extensive custom cabinetry. The well-appointed kitchen with a center island and breakfast bar, quartz countertops, generous custom storage, and a six-burner Thermador gas range is ideal for culinary pursuits. Additional features include hurricane impact-rated windows, wood flooring, solid-core interior doors, detailed tray ceilings and handcrafted millwork. A side-entry brick-paver drive leads to an oversized three-car garage equipped with a 240-volt EV charging outlet. Sabal Cove is an intimate community of just 38 single-family custom homes at the southern end of Longboat Key. Bay Isles residents enjoy access to a private, gated Gulf-front beach club, with optional membership to the adjacent Longboat Key Club offering 45 holes of championship golf and a premier tennis facility. Convenient to the Longboat Key Town Center’s grocery & pharmacy, the property is also a short drive to St. Armands Circle and downtown Sarasota, known for its cultural attractions, acclaimed dining, and upscale shopping.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
2012 HARBOURSIDE DR #2104, LONGBOAT KEY, FL 34228
$895,000225 Days on yellowkey MLS ID: A4664458
Bed: 3 Bath: 3.0 Gar: 5 Liv Area Sq Ft: 2135 Built: 1985 Tax: $9,417 (2024)Community: Fairway Bay 2 Ph 2 & 3Condo
Taxes:$9,417
Remarks: Discover Refined Coastal Living at Fairway Bay Impeccably renovated from top to bottom, this three-bedroom, three-bath end-unit townhome offers the perfect blend of style, function, and coastal charm. With 2,135 square feet of thoughtfully designed living space plus an expansive 1,516-square-foot garage and storage level, the residence provides a total of 4,050 square feet under roof. The versatile loft, vaulted ceilings, and open-concept great room create a bright, welcoming ambiance, enhanced by hardwood floors, crown molding, and a wood-burning fireplace. The gourmet kitchen boasts newly updated cabinet doors (Nov. 2023), sleek appliances (2018), and an ideal flow into the dining and living areas, which open to a screened 7’ x 22’ lanai with direct access to the backyard and grill pad. Outdoor living is further enriched by private wooden decks off both the loft and the primary suite, perfect for relaxing or sunbathing. This immaculate home is move-in ready, with extensive updates including new HVAC (July 2024), vinyl plank flooring (Dec. 2023), new carpet (March 2023), a renovated shower in Bedroom 2 (Jan. 2024), updated bathroom fixtures (Jan. 2024), and a newer water heater (2018). Additional highlights include custom closets, a central vacuum system, and two inviting terraces. Fairway Bay II offers a host of amenities just steps away, including a clubhouse, swimming pool/spa, fitness center, and on-site management. Residents also enjoy access to the exclusive Bay Isles Beach Club, with private Gulf-front swimming and sunbathing. Combining elegant updates, generous storage, and a premier Longboat Key lifestyle, this home is truly a must-see.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
1922 HARBOURSIDE DR #1104, LONGBOAT KEY, FL 34228
$795,000217 Days on yellowkey MLS ID: A4666101
Bed: 2 Bath: 2.0 Gar: 5 Liv Area Sq Ft: 1316 Built: 1982 Tax: $6,750 (2024)Community: Fairway Bay 1Spa: NoCondo
Taxes:$6,750
Middle School: Pine View School
Remarks: Experience the ultimate resort lifestyle—where every day feels like a vacation. Take a refreshing dip in the pool, enjoy a tranquil walk along the bay, or bask in the warm Florida sun on the white sandy beach. This spacious 2-bedroom, 2-bath townhome offers both comfort and elegance, featuring soaring ceilings and an open-concept floor plan. The recently updated kitchen is equipped with all the modern upgrades, making it perfect for both casual meals and entertaining. The guest bedroom includes custom built-ins with ample storage and a convenient desk, ideal for a home office. The primary suite is both roomy and inviting, enhanced by built-in bookshelves and an en-suite bath filled with natural light from a skylight above the tub. Additional highlights include an interior laundry room and an oversized garage with sleek epoxy flooring, easily accommodating 4–5 vehicles. Step out onto your private lanai, where serene views of the community pool create the perfect setting for relaxation and contentment. Located in the prestigious, guard-gated community of Bay Isles, this residence is just a short stroll to shopping and the newly opened St. Regis Resort. Community amenities abound, including tennis courts, a fitness center, and onsite management. Residents also enjoy access to a private beach club offering Longboat Key’s famous white sand beaches, a shaded pavilion, restrooms, and event space. Enhancing this resort-style living, Bay Isles residents may also enjoy memberships at the exclusive Longboat Key Club, featuring a world-class marina, championship golf courses, renowned tennis gardens, and fine dining. This is more than a home—it’s a lifestyle. Welcome to your Longboat Key retreat.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Beverly St Hilaire (818-416-2505)
2800 HARBOURSIDE DRIVE DR #D-19 D-20, LONGBOAT KEY, FL 34228
$985,000387 Days on yellowkey MLS ID: A4646560
0 Days Off yellowkey (back on 3/19/2026)
Bed: Bath: 0.0 Built: 1985Monthly Fee: $1,032 Tax: $7,286 (2025)Community: Lbk Club MooringsDock-Rackominium
Taxes:$7,286
Remarks: A one of a kind boat slip available for sale with fortified pilings that are plastic coated and an extended finger pier, deep water, protected, yet easy access to Sarasota Bay and the Gulf at Longboat Key Moorings Marina. This is a 154 ft. T-dock/face dock ready to accommodate a yacht; T of D-dock has 2 50s/100 service outlets. D-19 is 74.5 feet, and D-20 is 79.5 feet, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. This only deep water marina on the West Coast of Florida is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes bath house, laundry facilities, restaurant, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. This slip will accommodate one or two vessels total 149 feet. Usable beam is 25 feet.
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
1005 BOGEY LN, LONGBOAT KEY, FL 34228
$3,300,00092 Days on yellowkey MLS ID: A4680006
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3624 Built: 2017Monthly Fee: $21 Tax: $19,847 (2025)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$19,847
Remarks: Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.
Listing Agent: Michael Nink, Pa (941-914-2805)
3617 FAIR OAKS PL, LONGBOAT KEY, FL 34228
$2,050,000234 Days on yellowkey MLS ID: A4663935
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2950 Built: 1995Monthly Fee: $746 Tax: $16,463 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$16,463
Remarks: One or more photo(s) has been virtually staged. Situated in the highly sought-after maintenance-free community of Queens Harbour, behind the gates of Bay Isles, this updated lakefront home perfectly captures the ease of Florida living. A 2023 tile roof adds peace of mind, while a smart split floor plan includes three en-suite bedrooms, a half bath, and a versatile den/office that can serve as a fourth bedroom. The interiors feel bright and welcoming with 12–15’ ceilings, neutral tones, and elegant architectural details. New wood-look porcelain tile flooring enhances the living room, dining room, den/office, and first-floor bedrooms, combining durability with style. The kitchen features stainless steel appliances, a center island with second sink, updated hardware, and a breakfast nook with bay window views of the pool and lake. The primary suite enjoys direct lanai access, tranquil water views, and a spa-like bath with dual vanities, soaking tub, and walk-in shower. Outdoors, the screened lanai offers a heated pool and spa with a peaceful lake backdrop, plus a refreshed covered sitting area with a new tongue-and-groove ceiling and accent wall—perfect for relaxing or entertaining year-round. Residents enjoy exclusive access to the Bay Isles Beach Club, with its private beachfront, cabanas, and members-only amenities, along with optional memberships for golf, tennis, and the Harbourside Marina with deepwater slips. This home sustained no hurricane damage or water intrusion. This is Longboat Key living made simple—beautiful, low-maintenance, and ready to enjoy.
2045 GULF OF MEXICO DR #M1-511, LONGBOAT KEY, FL 34228
$749,00019 Days on yellowkey MLS ID: A4689590
0 Days Off yellowkey (back on 4/12/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1076 Built: 1974Monthly Fee: $1,278 Tax: $9,430 (2025)Community: Seaplace IiCondo
Taxes:$9,430
Remarks: Experience breathtaking, full Gulf views from this beautifully maintained 5th-floor residence at Seaplace on Longboat Key. This furnished 2-bedroom, 2-bath condominium offers the perfect blend of comfort, space, and coastal charm, with expansive living and dining areas designed to capture stunning water views and natural light throughout. Step out to your private lanai and enjoy panoramic sunsets, gentle sea breezes, and the soothing sounds of the Gulf—your own peaceful retreat just steps from the beach. The spacious primary suite provides a relaxing escape, while the guest bedroom offers comfort and privacy for visitors. Seaplace residents enjoy resort-style amenities across 42 acres of lush, meticulously maintained grounds, including a half-mile of private beachfront, two heated swimming pools with spas, a fitness center, Har-Tru tennis courts, walking paths, outdoor grilling areas, and an active, well-managed association. Whether you’re seeking a full-time residence, vacation getaway, or investment opportunity, this unit is priced to sell and ready for you to start enjoying the Longboat Key lifestyle. Schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
815 BAYPORT WAY #815, LONGBOAT KEY, FL 34228
$850,00021 Days on yellowkey MLS ID: A4689278
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1601 Built: 1981 Tax: $7,370 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$7,370
Remarks: Welcome to a true hidden gem of tropical paradise at Bayport Beach and Tennis Club on Longboat Key. Designed by renowned architect Tim Seibert, this one-of-a-kind community spans 27 lush, tropical acres and offers an unmatched coastal lifestyle with 1,200 feet of pristine private beach, where chairs and umbrellas are ready for you to enjoy endless days along the Gulf. As you arrive, you’re immediately surrounded by beautifully maintained grounds and the relaxed, resort-style atmosphere that makes this community so special. Stepping inside this spacious 2 bedroom, 2 bathroom furnished residence, you’re welcomed by a light and airy interior with terracotta-look tile flooring flowing throughout the main living areas, setting a warm coastal tone. The kitchen has been thoughtfully renovated with all new cabinetry, under-cabinet lighting, quartz countertops, a modern backsplash, and stainless steel appliances, creating a clean and functional space that opens seamlessly into the living and dining areas. The expansive living room is both inviting and impressive, designed to feel like a single-family home, with stunning Sarasota Bay views that instantly capture your attention. Shutter doors provide privacy while leading into a sunroom, offering a flexible space to relax and take in the scenery. The owner’s suite is a true retreat, complete with a dedicated office nook perfectly positioned to enjoy peaceful water views. The ensuite bathroom features dual quartz-topped vanities and a walk-in closet, combining comfort and convenience. A split bedroom floorplan ensures privacy, with the guest bedroom offering its own walk-in closet and easy access to the updated guest bathroom. An in-unit laundry area adds to the everyday ease of living. Step outside onto your expansive private deck, where breathtaking views of Sarasota Bay create the perfect backdrop for morning coffee, evening wine, or entertaining guests while surrounded by nature. Bayport Beach and Tennis Club offers an incredible array of amenities, including a Junior-Olympic heated pool, four Har-Tru tennis courts, a fitness center, fishing pier, kayak storage + launch, and an active clubhouse filled with social events. Scenic walking trails wind through the property, where you’ll often spot local wildlife such as osprey, herons, ibis, and egrets, enhancing the serene, natural setting. Just moments away, Bayfront Park offers pickleball courts, green space, and stunning bay views, while St. Armands Circle provides exceptional shopping and dining. A short drive over the iconic Ringling Bridge brings you into vibrant downtown Sarasota, known for its world-class arts scene, including theaters, museums, galleries, and waterfront dining. From private beach access to unmatched amenities and breathtaking bay views, this residence offers the perfect blend of comfort, nature, and coastal elegance in one of Longboat Key’s most sought-after communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Keith Curcio (941-376-7683)
2181 HARBOURSIDE DR #1403, LONGBOAT KEY, FL 34228
$850,000307 Days on yellowkey MLS ID: A4656539
0 Days Off yellowkey (back on 4/8/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2219 Built: 1984 Tax: $9,674 (2024)Community: Harbor Oaks Ph I & IiSpa: NoCondo
Taxes:$9,674
Remarks: Under contract-accepting backup offers. PRICED TO SELL! Experience the ultimate in island living in the highly sought-after and prestigious Harbor Oaks community on Longboat Key. This one-story, 3-bedroom, 2.5-bath residence spans 2,219 sq. ft. and offers a host of desirable features—including a private pool, 2-car garage, and deeded beach access through the exclusive Bay Isles Beach Club. A new roof (2025) and fresh interior paint ensure peace of mind and a move-in-ready experience. High ceilings fill the home with natural light, enhancing the spacious feel throughout. The expansive living room, anchored by a wood-burning fireplace, seamlessly connects to the outdoor living area via pocket sliding glass doors, opening to two large screened lanais—ideal for both relaxing and entertaining. The chef’s kitchen is outfitted with granite countertops, stainless steel appliances, rich wood cabinetry, a breakfast bar, and a skylight for added brightness. The primary suite is a private retreat featuring a walk-in closet, two additional closets, updated master bath, and sliding doors leading to the terrace. A guest suite with en suite bath provides comfort and privacy for visitors. Additional highlights include an interior laundry room with sink, a newer AC unit (2018), and natural gas line for adding a pool heater. All furnishings are included. Residents of Harbour Oaks enjoy a resort-style lifestyle with access to a community pool, spa, and lushly landscaped surroundings—just minutes from Longboat Key’s vibrant Town Center. As part of Bay Isles, you’ll have exclusive access to the Bay Isles Beach Club, a private, gated Gulf-front oasis with a pavilion, picnic areas, BBQ grills, beach chairs, restrooms, and ample parking—perfect for sunset viewing or relaxing on Longboat Key’s pristine white sands. Optional membership opportunities at the Longboat Key Golf & Tennis Country Club and Harbourside Moorings deep-water slips offer even more ways to elevate your coastal lifestyle.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Sharon Morea (941-400-9300)
1932 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228
$1,200,00021 Days on yellowkey MLS ID: A4689076
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1192 Built: 1982 Tax: $9,436 (2024)Community: Fairway Bay 1Condo
Taxes:$9,436
Remarks: Welcome to this breathtaking, fully remodeled, turnkey furnished contemporary residence in Fairway Bay—nestled on picturesque Longboat Key. From the moment you enter, you're greeted by a thoughtfully redesigned open floor plan, elevated ceilings, solid core doors, and impeccable high-end finishes. IT IS TRULY ONE OF A KIND! This condominium is truly one-of-a-kind! Exceptional Kitchen features include: Bertazzoni induction range, refrigerator, and dishwasher, built-in Miele plumbed espresso machine, sleek, low-profile custom cabinetry with quartz countertops, glass tile backsplash and ambient lighting and an expansive quartz island perfect for formal dining or casual entertaining. The living room flows effortlessly from the kitchen, opening onto a covered, tiled lanai—blurring the line between indoor and outdoor living. Floor-to-ceiling impact windows frame panoramic views of Sarasota Bay, the Ringling Bridge, and the city skyline, offering million-dollar scenery from the comfort of your home. Enter the generously sized and luxurious Primary Suite with custom built-ins and ample closet space. The ensuite bath is a spa-inspired bath with dual vanities, Hansgrohe Axor faucets, Toto washlet, walk-in shower with multiple heads and elegant finishes. The guest suite features custom cabinetry and an ensuite bathroom with a Victoria & Albert volcanic limestone bathtub. Other recent upgrades include Hurricane-impact windows and doors, tankless water heater, additional upper cabinetry in kitchen and utility room, ceiling fans and more. For your convenience & comfort there is easy elevator access, coveted garage parking space and private onsite storage. Fairway Bay residents enjoy the resort-Style amenities including Deeded beach access & exclusive beach club, 24-hour gated security, pool, spa, tennis courts, and fitness center plus all the perks of Bay Isles living. Whether you're soaking in the sun, enjoying vibrant Sarasota culture and nightlife, or relaxing in your private retreat, this home is a perfect sanctuary.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Jan Jordan (941-737-4169)
2600 HARBOURSIDE DR #L-11, LONGBOAT KEY, FL 34228
$425,00022 Days on yellowkey MLS ID: A4689192
Bed: Bath: 0.0 Built: 1985Monthly Fee: $459 Tax: $3,077 (2025)Community: Bay IslesDock-Rackominium
Taxes:$3,077
Remarks: Ask an L-dock boater, they will tell you it’s the best dock in the marina. Slip mid-pier ono the north side of the dock, just a few flat steps to your parked vehicle with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This slip requires membership in the Longboat Key Club. This slip is one of the very few slips at the marina with a direct view of the Sarasota cityscape and colorfully lit Ringling bridge. This deep-water marina offers direct access to Sarasota Bay and the ICW. The marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. The Marina has everything a boater could need. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 63 LOA, usable beam is 23 ft at the head of the slip. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis and golf facilities, fitness center, with spa and beach access.
2425 GULF OF MEXICO DR #1A, LONGBOAT KEY, FL 34228
$1,595,00023 Days on yellowkey MLS ID: A4688987
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $9,602 (2025)Community: Sea Gate ClubSpa: NoCondo
Taxes:$9,602
Remarks: This is the gorgeous ground floor, walk-out unit next to the beach you've been looking for. Do you prefer to live like a single family home, no elevator, and walk straight out to the beach? Then this is the One! Welcome to Sea Gate Club on beautiful Longboat Key, perfectly positioned near mid-island, and close to shopping at Publix or CVS. As you enter this very private End Unit #1A, you're greeted by Direct and Unobstructed Gulf and beach views as far as the eye can see. Unit #1A has been extensively updated over the last few years, featuring an open kitchen with a huge island, updated cabinets and countertops, and gorgeous porcelain tile flooring. 350' of direct and private beach frontage! This unit is offered Turnkey-Fully Furnished with very tasteful furniture that you'll actually want to keep. Sea Gate Club condos are comprised of 89 units, spread across 15 floors. The building has been extensively updated over the past few years. Recent updates include a new pool and hot tub, new roof, newer hurricane rated windows, newer exterior stucco and paint, new elevator doors, climate-controlled bike storage, and paddleboard/kayak storage. Now is the perfect time to buy in this beautiful building, as there are NO current or pending assessments! Hurry before it's gone, this one is beautiful.
Listing Agent: Robert Delaney (941-315-3185)
2045 GULF OF MEXICO DR #M1-502, LONGBOAT KEY, FL 34228
$469,500131 Days on yellowkey MLS ID: A4675820
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 928 Built: 1974 Tax: $6,201 (2025)Community: Seaplace IiCondo
Taxes:$6,201
Remarks: A perfect coastal retreat located in Seaplace, and now at an unbeleivable price! This is one of Longboat Keys most desirable beachfront communities. A light and bright 2 bedroom, 1 plus bath, 5th floor condo with a beautiful Bay view. (the photos of the view just do not do it justice!) An exceptional location in the highly sought-after Gulf-front M1 building means you can have your toes in the sand in mere moments. It is beautifully turn-key furnished and meticulously maintained and is ready for its next appreciating owner. The large primary bedroom has its own private ensuite portion of the bath with a sink that can be shut off from a full bath, making it what one would call a 1 bath PLUS. The 2nd bedroom offers a perfect spot for visitors to help you enjoy this amazing way of life to the fullest. Seaplace offers resort style living with unmatched amenities that include 2 large pools and hot tubs; a kiddie pool; 3 har-tru tennis courts; a recently renovated Gulf-front clubhouse; a fitness center; library; gas grills; a one-mile paved walking path surrounding the lush 42-acre property, and a gatehouse with 24-hour security. Located near the newly opened St.Regis Resort, St.Armands Circle and the cultural epicenter of downtown Sarasota, you’ll be close to world-class restaurants, hotels, entertainment, arts, culture, and shopping. Come see this fabulous condo soon and make your island living dream a reality in 2026!
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
3576 FAIR OAKS WAY, LONGBOAT KEY, FL 34228
$3,195,000278 Days on yellowkey MLS ID: A4658145
2 Days Off yellowkey (back on 4/5/2026)
Bed: 3 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3727 Built: 1990Monthly Fee: $800 Tax: $29,357 (2024)Community: Queens HarbourSingle Family
Taxes:$29,357
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. A boater’s dream location on Longboat Key in Queens Harbour….This is the “Best” waterfront lot in Queens Harbour! Deepwater canal and no bridges to the bay and intercoastal waterway from the exclusive neighborhood on Longboat Key in Queens Harbour. 125-lb boat lift on a deepwater canal for your Dream boat. Location, Location, Location on Longboat Key with a Chef’s kitchen, contemporary interior design with three bedrooms, loft/ bonus room, 5 bathrooms, open pool deck with expansive views, and more… Also as an owner in Queens Harbor you have access to the private Bay Isles Beach Club on the Gulf of Mexico.
Listing Agent: Tom Cinquegrano (941-284-5049)
548 HORNBLOWER LN, LONGBOAT KEY, FL 34228
$4,950,000197 Days on yellowkey MLS ID: A4668463
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 02Single Family
Taxes:$47,046
Remarks: This exquisite home is sure to exceed expectations! This exceptional 4 bed/5 bath canal-front estate is located in coveted Country Club Shores, where chic architecture, thoughtful craftsmanship, and effortless coastal luxury converge. Designed by DSDG architects to maximize the contemporary sightlines and southern exposure, this Voight built custom residence offers a spectacular open floor plan and is positioned just three lots from the open waters of Sarasota Bay. This extraordinary residence is better-than-new with a recently installed metal roof, AC systems, and whole home generator and has been impeccably maintained. The home has been built to effortlessly withstand the Florida coastal environment while maintaining its magnificent beauty and clean lines. Boaters will appreciate the Trex dock equipped with a 20,000-lb boat lift, kayak and paddleboard racks, and convenient launch deck - providing quick, easy access to bay and Gulf waters. Inside, the home is both stunning and impressive with exquisite finishings and custom millwork. The first-floor owner’s suite is a luxurious retreat highlighted by soaring triple-coffered tray ceilings, tranquil views, and private pool access for a midnight swim. The spa-like bathroom is pure luxury. The chef’s kitchen is a true showpiece, featuring Viking appliances, a Sub-Zero Pro refrigerator, a walk-in pantry, expansive countertops, and a dramatic 14-foot quartz island perfect for large gatherings. The integrated dining area is framed by an aquarium window which emphasizes the tranquil water views. The family room is a natural extension of the kitchen and provides a generous area with direct access to the lanai, grille and dining areas and is perfect for enjoying movies, or just gathering with friends and family. The great room is spacious with large archways, gas fireplace, custom built-in shelving, and coffered shiplap ceilings which add to the drama of this cozy but elegant space. A wall of windows provides access to the covered lanai area and expands the feeling of openness highlighting the pool, sparkling spa, and water views. The second floor has been completely reimagined to elevate both style and function, offering three private guest suites, a versatile and spacious Florida room, wet bar, and a 300+ bottle state-of-the-art walk-in wine cellar. The enclosed upper lanai enhances ambiance and panoramic views. The Florida room provides a flexible space for enjoying sporting events or wine tastings, and includes a full bath for convenience. The 3 bedrooms on the second level are generous in size and 2 of the 3 include ensuite baths. Outdoor living is equally exceptional. The lanai with a Cypress-clad ceiling includes a new grill and dining area and pool bath, which steps down to the saltwater pool, spa, and sun deck - an ideal setting for entertaining or enjoying sunshine year-round. Additional features include a two-car garage with generous overhead storage, a rear enclosed storage compartment, and an electric vehicle charger. There is ample vertical height in the garage to add a car lift as an option. Residents of Country Club Shores enjoy private deeded beach access to the Gulf of Mexico, with optional golf and tennis memberships available at the nearby Resort at the Longboat Key Club. This is waterfront living at its finest - refined, relaxed, and designed to be enjoyed. A must-see property to fully appreciate the exceptional lifestyle, upgrades, and craftsmanship throughout.
Listing Agent: Kathy Callahan (941-900-8088)
2450 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228
$2,450,00026 Days on yellowkey MLS ID: TB8491404
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 3083 Built: 1990 Tax: $20,065 (2025)Community: Marina BayCondo
Taxes:$20,065
Remarks: Welcome to Marina Bay – the premier condominium within the gated Bay Isles Community on Longboat Key. This exceptional corner residence spans 3,578 sq ft of sunlit, sophisticated living, and shares it fourth floor lobby with only one other unit. The large, updated kitchen/dining room features extra-large windows allowing for an unobstructed view of Sarasota Bay. Exquisite floor-to-ceiling windows, in the oversized living room, frame sweeping panoramic vistas of Sarasota Bay and downtown Sarasota, while the unusually large balcony provides the perfect setting for morning coffee, evening relaxation, and observing abundant bird and marine life. A second, west-facing balcony delivers spectacular Gulf sunsets, offering the rare pleasure of both sunrise and sunset living. Marina Bay is the epitome of resort-style living, with a heated pool and spa, newly renovated tennis and pickleball courts, and well-appointed fitness room. Head to the adjacent marina or around the manicured Longboat Key Club Harbourside Golf Course. Ideally situated, this residence is in close proximity to Publix, CVS, Chase Bank, and local shops. Whether as a refined full-time residence or an elevated part-time retreat, this rare offering delivers unmatched luxury, convenience, and island living. Key Features include: Corner-end unit with 3 bedrooms and 3 ½ newly renovated baths, A walk-in double shower in main suite, New floor tile on oversized screened balcony, bathrooms, and main suite floors, Equipped with storm shutters, and access to private beach for Bay Isles residents only.
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Steven Weiss (845-242-5473)
2600 HARBOURSIDE DR #C13, LONGBOAT KEY, FL 34228
$489,50047 Days on yellowkey MLS ID: A4686064
Bed: Bath: 0.0 Monthly Fee: $411 Tax: $2,681 (2025)Community: Bay IslesDock-Rackominium
Taxes:$2,681
Remarks: 72' x 21' Boat Slip on C-Dock at Longboat Key Moorings Marina for Sale ~ AND THERE IS NO MEMBERSHIP REQUIREMENT to join The Longboat Key Club (which is now $115,000) and the annual fee of $8388 plus food & beverage fees. The beauty of this TWO-LEVEL dock is... there is no covenant BUT if you chose to join the Longboat Key Club, there are multiple membership packages to choose from which give you access to multiple restaurants, the beach club and poolside restaurants, more information can be provided upon request. The Longboat Key Moorings is strategically located on the beautiful exclusive island of Longboat Key ~ just a few minutes to St. Armands Circle, downtown Sarasota or Bradenton Beach. This amazing location provides direct access to Sarasota Bay and the ICW and the Gulf of America. The LBK Moorings is a deep water ~ state-of-the art marina ~ offering full services, with a touch of class and personal attention seldom found elsewhere. World class facilities on this spectacular island provides storm-protected deep water yacht slips, Dock Crew, Harbor Concierge, 24-hour manned Guard Gate and much more. Each slip has Cable TV, Electricity, Water and Wi-Fi. There also is an on-site service department for repair and maintenance needs, as well as, on-site fuel service, and pump out service. An amazing location with quick access to great shops and dining at St Armands Circle and from there a Classic Sarasota Trolley will take you into downtown Sarasota and back! Your Gateway to the Gulf! Imagine stepping aboard your boat just minutes from the sparkling waters of the Gulf of Mexico. This exceptional boat slip in beautiful Longboat Key offers the perfect combination of convenience, protection, and access for serious boaters and coastal lifestyle lovers alike. Perfectly positioned for effortless cruising, this dock provides quick, unobstructed access to the open waters of the Gulf—no long no-wake zones or complicated navigation. From here, you’re only moments away from world-class fishing, sunset cruises, and exploring the stunning coastline. Owning a dock in Longboat Key means more than just a place to park your boat—it’s an invitation to enjoy sun-drenched days on the water, dolphin sightings, world-class fishing, and unforgettable sunsets. Why This Location Stands Out • Quick boating access to Sarasota Bay and the Gulf • Close to waterfront dining, marinas, and fuel • Situated in one of Florida’s most sought-after boating communities Rare Opportunity Boat slips in Longboat Key are highly coveted and rarely available. Whether you’re a local boater, seasonal resident, or investor looking for premium waterfront access, this is your chance to secure a piece of paradise.
Listing Agent: Rian Carver (941-735-6010)
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