Location: Longboat Key
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
626 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$4,395,00039 Days on yellowkey MLS ID: A4696767
REDUCED by $100,000 (2.2%) on 07/17/2026
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,789
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
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, quality 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 beautiful 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)
3606 FAIR OAKS PL, LONGBOAT KEY, FL 34228
$4,999,00055 Days on yellowkey MLS ID: A4694394
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3842 Built: 2000Monthly Fee: $833 Tax: $29,486 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$29,486
Remarks: Nestled behind the gates of the highly celebrated Bay Isles community, this exceptional five-bedroom waterfront residence at 3606 Fair Oaks Lane offers the perfect blend of luxury, comfort, and peace of mind with an impressive list of recent upgrades and improvements. Designed for effortless coastal living, this beautifully updated home showcases refined interiors, expansive outdoor living spaces, and direct boating access, all within one of Longboat Key’s most sought-after neighborhoods. From the moment you arrive, the home’s meticulous maintenance and thoughtful renovations are immediately apparent. A roof just two years old, hurricane shutters on all windows and doors, and multiple updated mechanical systems provide exceptional value and confidence for years to come. Inside, the residence has been extensively renovated in 2026 with stunning new engineered wood flooring flowing throughout the home, creating a warm and welcoming coastal aesthetic. The spacious floor plan offers five generously sized bedrooms, ideal for accommodating family and guests while maintaining privacy and flexibility for today’s lifestyle needs. The heart of the home is the beautifully refreshed kitchen, complete with brand-new KitchenAid appliances installed in 2026, blending modern functionality with timeless design. Adjacent living and dining areas are filled with natural light and seamlessly connect to the outdoor entertaining spaces, creating an inviting atmosphere perfect for both everyday living and hosting gatherings. Every bathroom in the home was completely renovated in 2026 with stylish finishes and contemporary details that elevate the home’s overall elegance. Extensive system upgrades include three HVAC systems replaced in 2022, 2023, and 2026, along with a new hot water heater installed in 2026, ensuring maximum efficiency and comfort throughout the property. Outdoor living is equally impressive and designed to embrace the Florida waterfront lifestyle. The pool area underwent a significant transformation in 2025 with new pool decking, a resurfaced pool finish, updated waterline tile, and a new gas pool heater, creating a true private resort setting. In 2026, the addition of a fully equipped outdoor kitchen elevated the entertaining experience even further, offering the perfect backdrop for waterfront dining and sunset gatherings. Boating enthusiasts will appreciate the new 10,000-pound boat lift installed in 2025 along with a beautifully updated dock and deck, providing quick and convenient access to Sarasota Bay and the Gulf waters beyond. Combining luxury updates, exceptional outdoor amenities, and a premier location within the coveted Bay Isles community, with private beach club access, this extraordinary Longboat Key residence presents a rare opportunity to enjoy refined waterfront living with every major improvement already completed.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
548 GUNWALE LN, LONGBOAT KEY, FL 34228
$2,100,000168 Days on yellowkey MLS ID: A4680965
REDUCED by $100,000 (4.5%) on 06/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1853 Built: 1967Monthly Fee: $17 Tax: $9,801 (2025)Community: Country Club Shores Sec 1Spa: YesSingle Family
Taxes:$9,801
Remarks: Country Club Shores - Completely renovated 3-bedroom, 2-bath canal-front home just three houses from the Bay. Updates include a new flat tile roof (2025), Carrier A/C and A.O. Smith water heater (2024), Pebble Tec pool and paver deck (2024), and newer seawall, dock, and 16,000 lb. boat lift (2.5 years). Enjoy Bay views from the 18 foot x 16 foot Trex dock with lighting and water, plus a 3 foot x 36 foot Trex dock with power and water. Interior features NuCORE waterproof flooring, plantation shutters, Silestone quartz countertops, and new Bosch and GE stainless appliances. The primary suite includes a walk-in closet with built-ins, dual sinks, whirlpool tub, and large shower. Split floor plan with guest bedrooms featuring walk-in closets; one includes a built-in office area. Move-in ready and ideally located for boaters seeking the best of Longboat Key waterfront living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: John August (941-320-9795)
510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228
$4,395,000251 Days on yellowkey MLS ID: A4671696
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5080 Built: 1996Monthly Fee: $208 Tax: $42,201 (2024)Community: Bay IslesSpa: YesSingle Family
Taxes:$42,201
Tax Year: 2024
Remarks: A Waterfront Work of Art. Experience a one-of-a-kind waterfront residence on Longboat Key — now offered at an exceptional new value. Designed around three interconnected circular "pods," the residence flows like a choreographed dance. There are no awkward hallways, no wasted corners, no spaces that feel like afterthoughts. Curved walls carry throughout every room — even into the garage — creating a cohesive design statement that's genuinely rare in residential construction at any price point. This architectural masterpiece is a sculptural composition of flowing living spaces connected by custom corridors, delivering remarkable privacy, abundant natural light, and seamless indoor–outdoor living. The dramatic Great Room pod showcases soaring wood-paneled ceilings and expansive walls of glass that frame tranquil water views. The circular primary suite is a private retreat featuring a spa-inspired bath with dual showers, a lounge area, private office, and direct access to the pool and spa terrace. At the heart of the home, the striking circular kitchen is both artful and functional, centered around a curved island beneath a two-story ceiling and skylight, with a thoughtfully designed radial appliance layout. Two en-suite guest bedrooms open to private patios, while the fully self-contained Secondary Primary Suite above the impressive 32' x 23' three-car garage offers independent HVAC, a luxury bath with steam shower and sauna, and flexible living space ideal for extended guests or multigenerational living. Outdoors, the property embraces the waterfront lifestyle with protected deep sailboat water, a private dock with a 12,000-pound lift, and a resort-style pool and spa designed for entertaining and relaxation. Located behind the 24-hour guarded gates of Bay Isles, residents also enjoy exclusive access to the Bay Isles Beach Club on the Gulf of Mexico.
562 RANGER LN, LONGBOAT KEY, FL 34228
$3,499,900213 Days on yellowkey MLS ID: A4675541
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3149 Built: 1995Monthly Fee: $20 Tax: $27,065 (2024)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$27,065
Remarks: Virtually Staged. A rare opportunity to own a single-family waterfront home with 100 feet of canal frontage and direct access to Sarasota Bay. Located in Country Club Shores on the desirable southern end of Longboat Key, 562 Ranger Lane offers 4 bedrooms, 3 full baths, and approximately 3,149 square feet of living space designed for relaxed coastal living. The property features a sunny southern rear exposure overlooking the canal, with a north-facing street frontage, providing balanced natural light throughout the day. The home underwent a comprehensive renovation in 2018, including a tile roof, paver driveway, two Trane A/C units, tankless water heater, updated sprinkler system, railings, pool equipment, and a Pebble Tec refinished pool positioned to maximize the southern exposure. The interior features an open great-room layout with 16-foot ceilings, porcelain tile flooring throughout, plantation shutters, LED lighting, and a spacious kitchen with Starmark solid-wood soft-close cabinetry, Cambria quartz countertops, and stainless-steel appliances. An 8-foot arched iron front door introduces abundant natural light and an open, functional floor plan. The current configuration includes an upper-level primary suite with solid oak flooring, walk-in closets, and a well-appointed bath, while the first level offers three large bedrooms, including an office with custom built-ins, and two full baths with handcrafted cabinetry, quartz countertops, and glass-enclosed showers. The flexible layout provides the opportunity to create a first-floor primary suite to suit individual lifestyle needs. Boating amenities include a new seawall, a 70-foot private Trex dock with 50-amp shore power, and a recently serviced 10,000-pound boat lift. Outdoor living is enhanced by a covered lanai and a two-level travertine deck ideal for entertaining and enjoying the canal setting. Residents enjoy access to a private deeded beach on the Gulf of Mexico and proximity to Longboat Key Club golf, dining, and shopping at St. Armands Circle, with downtown Sarasota’s cultural arts and dining scene just minutes away. Schedule a private showing to experience this waterfront home, its flexible living options, and direct access to Sarasota Bay
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-748-6300)
Listing Agent: Cheri Mazan Castro (941-400-3777)
842 BAYPORT WAY, LONGBOAT KEY, FL 34228
$625,000111 Days on yellowkey MLS ID: A4687058
REDUCED by $50,000 (7.4%) on 06/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983 Tax: $5,662 (2025)Community: Bayport Bch & Ten Ph FSpa: NoCondo
Taxes:$5,662
High School: None
Remarks: Don’t miss this opportunity for a prime location in the celebrated Bayport Beach and Tennis Club. This first floor corner residence with a west-facing patio offers maximum privacy and 1570 square feet of effortless indoor-outdoor living. A favorite feature is the screened lanai opening to an extended brick patio, perfect for easy mornings and catching brilliant sunsets. Step out to landscaped grounds and a direct path to deeded beach access across the road. The condo's open layout features a spacious kitchen, living and dining space, a primary bedroom with dual vanity bath, walk-in closets and nice little office nook overlooking the patio. Full sized laundry, covered under unit parking and a private storage closet add convenience. Offered fully furnished with a brand new high efficiency AC, this property is poised and ready to be a low maintenance island escape, year round residence or a smart rental, allowing 12 monthly rentals each year. Bayport is well known for it's timeless architecture, exceptional amenities, and easy resort lifestyle. Residents enjoy a heated and cooled Jr. Olympic pool, clubhouse, fitness center, tennis, bocce ball, and shelled walking paths among 27 acres of exquisitely landscaped tropical grounds. Along the bay shoreline, a fishing pier, kayak launch and storage is perfect for morning paddles or simply enjoying nature . On the Gulf side, 1,200 feet of deeded beach access, complete with loungers and umbrellas, makes enjoying Longboat Key’s famously uncrowded beaches effortless. The mid-key location puts you close to shopping, daily conveniences, Duarante Park, great island dining, and the vibrance of Sarasota, all while feeling tucked away and serene. Settle in and enjoy a slice of true paradise.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Rosemarie Mckee (941-504-9396)
2326 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$800,000146 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: Welcome to effortless coastal living in this beautifully maintained, fully furnished end-unit villa on Longboat Key. Offering nearly 2,400 square feet of thoughtfully designed living space, this exceptional residence combines the spaciousness and privacy of a single-family home with the convenience of maintenance-free living—all just moments from the Gulf's renowned white-sand beaches. From the moment you step inside, soaring vaulted ceilings, abundant natural light, and an open, airy floor plan create a warm and inviting atmosphere. Designed for both comfortable everyday living and effortless entertaining, the home offers multiple gathering spaces, including a formal living room with a charming wood-burning fireplace and expansive sliding glass doors that open to an impressive 740-square-foot private terrace overlooking peaceful pond views. The kitchen is both stylish and functional, featuring granite countertops, updated cabinetry, rich wood flooring, plantation shutters, and a skylight that fills the space with natural light. Recent upgrades, including a new roof and new air-conditioning system completed in 2025, provide added comfort and peace of mind. Adding to the home's unique character are two private atriums that bring the outdoors in, creating bright, tranquil spaces throughout the residence. A versatile office with a built-in Murphy bed offers the flexibility to easily serve as a fourth bedroom, while the spacious primary suite provides a relaxing retreat with comfortable accommodations for family and guests. Additional highlights 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, where residents enjoy private Gulf-front beach access and dedicated parking. Perfectly located near world-class beaches, boating, waterfront restaurants, boutique shopping, and the renowned Longboat Key Club's golf, tennis, pickleball, marina, and dining amenities, this residence places the very best of island living right at your doorstep. Beautifully furnished, impeccably maintained, and move-in ready, this is an exceptional opportunity to enjoy the relaxed elegance and coastal lifestyle that make Longboat Key one of Florida's most sought-after destinations.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
560 HARBOR COVE CIR, LONGBOAT KEY, FL 34228
$7,900,000249 Days on yellowkey MLS ID: A4672059
REDUCED by $800,000 (9.2%) on 05/06/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3485 Built: 1981Monthly Fee: $517 Tax: $28,036 (2024)Community: Bay IslesSingle Family
Taxes:$28,036
Remarks: An exceedingly rare offering within the exclusive Bay Harbour enclave of Bay Isles on Longboat Key, this extraordinary peninsula estate delivers exceptional privacy, dramatic Sarasota Bay views, and direct boating access to both the Intracoastal Waterway and the Gulf of Mexico. Positioned at the end of a quiet cul-de-sac on a three-sided waterfront peninsula, the property features two private docks with water and electric, including one with a 15,000-lb lift designed for easy access. The Gulf is reachable through the nearby jetty with drawbridge, with an additional route via the John Ringling Bridge. The seawall was newly capped in 2020, and the pier deck and boat lift controls were replaced in 2025, ensuring superior waterfront infrastructure. Extensively rebuilt and structurally engineered, the residence is warm, refined, and filled with natural light, capturing sweeping bay views from nearly every room. The chef-inspired kitchen showcases custom rare wood cabinetry, an extended breakfast bar, a three-sink layout, double dishwashers, Sub-Zero refrigerator, Wolf warming drawer, standalone ice maker, and beautifully finished wood ceilings. The living and dining areas feature a custom jazz club floor and open seamlessly to a wraparound screened lanai, fully reconstructed with multilayer waterproof construction, a rich teak ceiling, and an open-sky section ideal for coastal breezes and stargazing. Multiple seating and dining areas create effortless indoor-outdoor living with uninterrupted water views. Outdoors, the pool area offers a private retreat surrounded by tropical landscaping and expansive travertine decking designed for both relaxation and entertaining. A custom palm-terrace garden enhances the tranquil ambiance along the east side of the deck. All bathrooms have been fully remodeled with premium finishes, floor-to-ceiling tilework, and frosted glass shower doors. The primary suite features an elegant, spa-like bath designed with refined materials. Additional upgrades include hurricane-rated windows and doors, 5-ton A/C units installed in 2024 and 2025, all-new plumbing, electrical, and HVAC ductwork, a whole-house water purification system, a full security camera system, and extensive structural improvements completed under engineering oversight. Exterior enhancements include landscape lighting, a resurfaced epoxy garage floor with mini-split A/C, and cell-foam insulation for efficiency. Residents of Bay Isles enjoy private Gulf beach access at the Bay Isles Beach Club, offering tiki huts, restrooms, BBQ areas, and gathering spaces. The gated community provides 24/7 security, community pools, and miles of shaded sidewalks ideal for walking and cycling. With its unrivaled peninsula setting, exceptional boating amenities, unmatched privacy, and sweeping water views at every turn, this estate represents one of Longboat Key’s most remarkable waterfront opportunities—an extraordinary residence defined by craftsmanship, luxury, and coastal elegance.
2301 GULF OF MEXICO DR #45N, LONGBOAT KEY, FL 34228
$625,00014 Days on yellowkey MLS ID: A4698596
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $4,789 (2025)Community: Islander Club Of LongboatCondo
High School: Sarasota High
Remarks: Experience exceptional Gulf-front living in this beautifully maintained two-bedroom, two-bath residence at the highly desirable Islander Club on Longboat Key. Enjoy peaceful views of the manicured grounds, entrance, and tennis courts from the expansive wraparound terrace offering more than 60 feet of private outdoor living space—perfect for relaxing or entertaining. Inside, the light-filled open floor plan features floor-to-ceiling sliding glass doors, a well-appointed kitchen with KitchenAid appliances, and spacious living and dining areas. The primary suite offers terrace access and an en-suite bath, while the guest bedroom provides comfortable accommodations for visitors or a home office. Recent updates include hurricane-impact windows and doors, a Bosch HVAC (2016), water heater (2020), in-unit humidistat, assigned parking, and extensive community improvements including new elevators, roof, porte cochère, fitness center, clubhouse, locker rooms with saunas, recreation room, and landscaping. End-window replacements have also been ordered. The Islander Club offers over 400 feet of private Gulf beach frontage, a heated beachfront pool, fitness center, Har-Tru tennis court, two pickleball courts, two fishing piers, on-site management, and 24/7 maintenance staff. Just minutes from St. Armands Circle and Downtown Sarasota, this is your opportunity to enjoy the very best of Longboat Key beachfront living.
Listing Agent: Paul Bachmann (813-786-6242)
597 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$4,125,000518 Days on yellowkey MLS ID: A4640902
INCREASED by $235,000 (6.0%) on 07/08/2026
Bed: 5 Bath: 6.0 Gar: 5 Liv Area Sq Ft: 4176 Built: 2025 Tax: $7,998 (2024)Community: Buttonwood HarborSpa: YesSingle Family
Taxes:$7,998
Remarks: Completed New Construction – Best-Priced Luxury New Construction on Longboat Key! Gulf & Bay Views | Private Tropical Oasis | Three Outdoor Living Areas Move in today and experience the best value in luxury new construction on Longboat Key. Built by Floridian Crafted Homes, this completed coastal contemporary residence combines exceptional craftsmanship, hurricane-resilient construction, and an unbeatable location just steps from the beach. Elevated approximately 13 feet above sea level, this stunning home offers 4,176 square feet of thoughtfully designed living space with 5 bedrooms, 5 full bathrooms, and 2 half bathrooms. An elevator shaft has already been framed and is ready for elevator installation. Designed for effortless indoor-outdoor living, the home features three expansive outdoor entertaining spaces, including two private balconies and an incredible rooftop terrace showcasing panoramic Gulf and Bay views with unforgettable sunset vistas. Inside, the spacious open-concept great room seamlessly connects to the designer gourmet kitchen, creating the perfect setting for entertaining family and friends. A second-floor club room provides additional flexible living space ideal for a media room, game room, or private retreat. Step outside to your own private tropical oasis, where lush landscaping surrounds a sparkling resort-style pool and spa, creating a secluded backyard retreat rarely found in new construction on Longboat Key. The oversized 5+ car garage provides abundant space for vehicles, golf carts, water toys, and beach equipment. Perfectly situated just a short walk to the Gulf beaches and the exciting new retail and dining destination anticipated to open nearby, this home also offers access to a community marina with available boat slips, making it an exceptional choice for boating enthusiasts. With completed construction, premium finishes, breathtaking Gulf and Bay views, a private tropical backyard, and one of the most competitive prices for luxury new construction on Longboat Key, this is an extraordinary opportunity to own a truly exceptional island home.
2850 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$325,00018 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)
545 SANCTUARY DR #B305, LONGBOAT KEY, FL 34228
$2,495,000166 Days on yellowkey MLS ID: A4681142
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2580 Built: 1991 Tax: $25,314 (2025)Community: Sanctuary IiiCondo
Taxes:$25,314
Remarks: The Sanctuary behind the gates of the Longboat Key Club located on the beachfront is one of the most desirable addresses on Longboat Key, Florida. New to the market, this full on, direct Gulf view residence B305 in Building III at 545 Sanctuary Drive offers about 3,000 square feet with three bedrooms & 2 ½ bathrooms providing spacious and elegant beach front living. From the handsome double door entry, the gleaming marble floor dining area invites you into this luxurious condominium home. Then, you will be treated to a sparkling like diamonds daytime Gulf water views or in the evening, breathtaking sunsets in shades of purple & orange. These magnificent direct Gulf views can be enjoyed from the attractively furnished living room and the serene primary bedroom & of course from the 21-foot-long covered Gulf side terrace. This unique Carlyle floorplan also features a second, east facing private terrace which can be accessed through the guest bedroom as well as from the handsome kitchen as you enjoy morning sunrises with a cup of coffee. This beach retreat is in impeccable condition with high quality furnishings plus electric storm shutters on all sliding doors. This unit also has one under building garage space #150 plus a climate controlled storage cage. Decorated in neutral tones, this home offers coastal elegant style throughout. The cozy eat in kitchen has custom built light wood cabinetry, high end finishes, cream colored granite counter tops, tile backsplash & double ovens. The gracious, large primary bedroom suite is a tranquil retreat with Gulf water views, a large walk-in closet & a spa like En Suite bathroom with double sinks, a soaking tub & a walk-in shower. The Sanctuary offers an exclusive resort lifestyle. The beautiful beach front measures 1200 feet of pristine white sand. The resort style, heated Olympic sized swimming pool includes a 25 meter lap lane plus there is a separate outdoor whirlpool & fire pit area. Amenities include two lighted Har-Tru tennis courts & a state of the art fitness center with saunas located in the newly redecorated clubhouse which offers a fully equipped kitchen & entertainment room. On site management, 24 hour security & 18 acres of meticulously maintained grounds & beach enhance the sense of exclusivity & security.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Maruta Miluns (941-374-9702)
1095 GULF OF MEXICO DR #102, LONGBOAT KEY, FL 34228
$625,00069 Days on yellowkey MLS ID: A4693425
REDUCED by $100,000 (13.8%) on 07/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981 Tax: $9,531 (2025)Community: Beachplace IiSpa: YesCondo
Taxes:$9,531
Remarks: A rare private walk-down residence in the highly sought-after Beachplace community on Longboat Key. This property offers the convenience of direct terrace access to the beautifully landscaped grounds below, overlooking a serene pond with fountains and offering a charming peekaboo view of the Gulf. Spacious and largely original, presenting the perfect canvas for a buyer to customize and create their ideal coastal retreat while enjoying the exceptional location and layout. The light-filled interior features an open living and dining area with walls of glass that connect seamlessly to the outdoor living space, creating an inviting indoor-outdoor lifestyle just moments from the beach. The split-bedroom floor plan offers privacy and functionality, while the terrace provides a peaceful setting to relax and enjoy the lush tropical surroundings. Whether updating immediately or renovating over time, this residence offers tremendous potential within one of Longboat Key’s premier Gulf-front communities. Beachplace is renowned for its resort-style amenities and beautifully maintained grounds. Residents enjoy 24-hour guard-gated entry, on-site management, a clubhouse, fitness center, tennis and pickleball courts, heated swimming pool and spa, private beach access, walking paths, and expansive tropical landscaping throughout the community. Ideally positioned on the south end of Longboat Key, Beachplace is just minutes from the fine dining, boutiques, and waterfront charm of St. Armands Circle, as well as downtown Sarasota’s cultural attractions, marinas, golf clubs, and world-class beaches. Whether you are searching for a seasonal getaway, investment opportunity, or full-time coastal residence, this property presents exceptional value and the opportunity to create a personalized beachfront retreat in one of Longboat Key’s most desirable locations.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Rich Polese (941-914-7115)
2850 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228
$324,00082 Days on yellowkey MLS ID: A4691701
REDUCED by $24,000 (6.9%) on 07/16/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 657 Built: 1967 Tax: $4,601 (2025)Community: Neptune On Longboat KeySpa: NoCondo
Taxes:$4,601
Remarks: A renovated condo directly across from public beach access under $350,000. on Longboat Key? This is the one you've been looking for! Perfectly positioned for both personal enjoyment and strong rental income potential. Whether you're seeking a low-maintenance vacation escape or an income-generating property, this location checks all the boxes. Walk across the street to watch sunset on the sand, then stroll to Publix, Bayfront Park's tennis & pickleball courts, the library, or one of the island’s cozy dining spots. Everything your guests—or you—could want is right at your doorstep. The unit features a bright, open living space with tile flooring, a spacious bedroom, walk-in closet and parking. The well-maintained community offers low HOA fees and a relaxing island vibe that keeps guests coming back. Don’t miss out on this rare opportunity to own on Longboat Key—whether you're investing in your future or your lifestyle.
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
3060 GRAND BAY BLVD #174, LONGBOAT KEY, FL 34228
$1,798,000196 Days on yellowkey MLS ID: R4910478
REDUCED by $141,000 (7.3%) on 05/17/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2550 Built: 1994Monthly Fee: $2,617 Tax: $17,500 (2024)Community: Grand Bay 1Spa: YesCondo
Taxes:$17,500
Elementary School: None
Remarks: PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings
Listing is courtesy of: LEN SCAVRON (908-304-5454)
Listing Agent: Len Scavron (908-304-5454)
3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228
$369,000103 Days on yellowkey MLS ID: R4911020
REDUCED by $20,000 (5.1%) on 06/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1046 Built: 1970Monthly Fee: $1,457 Tax: $2,813 (2025)Community: Beach Harbor ClubCondo
Taxes:$2,813
Remarks: Longboat’s Beach Harbor club is situated on 5 Acres along the most beautiful stretch of Longboat Key Shoreline. Sugary sand and flowing seaoats beside the azure blue Gulf of Mexico. The beach Harbor club offers 133 condo units, deeded beach access with showers, umbrellas and beach chairs. Amenities also include newly constructed boat slips, rooftop decks, outdoor cook areas, heated oversized swimming pool, community area for kayaks, clubhouse, and shuffle board. Longboat Beach Harbor is a friendly community with group events and many fun times to build relationships and enjoy sense of community living. Close to Bayfront Park with Tennis, Publix/CVS shopping. This renovated condo is situated on the 3rd floor not requiring flood insurance. Air conditioned indoor hall-way with security entrance. Newly appointed appliances, bathrooms, HVAC, luxury flooring and trim. Up-scale appointed fixtures and details throughout.
2819 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$3,590,000269 Days on yellowkey MLS ID: A4669533
REDUCED by $109,999 (3.0%) on 07/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1173 Built: 1955 Tax: $36,688 (2024)Community: Coquina BeachSpa: NoSingle Family
Taxes:$36,688
Remarks: BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on the coveted south end of Longboat Key in Sarasota county. This charming, 1955 beach cottage sustained significant hurricane damage and is now being sold AS-IS for land value only. No HOA fees! Build your dream coastal retreat on this prime GULF-front lot and enjoy breathtaking sunsets, white-sand beaches- just steps to Publix grocery, 1.5 miles to the stunning St. Regis resort, and easy access to nearby St Armand’s dining/shopping, downtown Sarasota, golf, and marinas. You do not want to miss this opportunity to create your own piece of paradise on BEAUTIFUL Longboat Key!
Listing is courtesy of: SERHANT (646-480-7665)
Listing Agent: Jenn Flanders (941-232-0788)
1211 GULF OF MEXICO DR #701, LONGBOAT KEY, FL 34228
$2,125,00048 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 is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Maggie Hicks (941-321-1759)
525 SLOOP LN, LONGBOAT KEY, FL 34228
$1,999,0007 Days on yellowkey MLS ID: A4699685
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2934 Built: 1962Monthly Fee: $13 Tax: $12,725 (2025)Community: Country Club ShoresSingle Family
Taxes:$12,725
Remarks: Discover an exceptional chance to complete a vision of waterfront luxury in the highly sought-after community of Country Club Shores on Longboat Key. This canal-front home offers the rare opportunity to pick up where the current owner left off—finishing a sophisticated coastal residence with the majority of major structural work already completed. For discerning buyers seeking to capture immediate equity and create a bespoke waterfront retreat, this property represents outstanding value in prime Longboat Key real estate. Set on a spacious 110’ x 110’ canal-front lot, the home features a fully reconstructed seawall and a private dock equipped with a 13,000-pound Platinum Series boat lift, providing effortless access to Sarasota Bay and the sparkling Gulf of Mexico. The residence is framed for approximately 3,089 square feet under air, offering 5 bedrooms and 3 bathrooms in an elegant coastal ranch-style layout designed for seamless indoor-outdoor living. Substantial improvements have already been executed to the highest standards: a brand-new roof, complete framing, exterior walls, plumbing and electrical rough-ins, natural gas lines, insulation, HVAC ductwork, and impact-resistant windows and doors. Premium materials and finishes—including custom Italian cabinetry, Miele appliances, designer fixtures, and additional high-end components—convey with the property. Engineer-prepared plans provide a clear roadmap for completion, empowering the next owner to personalize the final touches while benefiting from the extensive work already invested. Located in one of the best positions within the desirable Country Club Shores community, this fixer-upper presents the perfect canvas to realize the seller’s vision of an amazing luxury waterfront home. Imagine waking to serene water views, launching your boat from your private dock, and enjoying the effortless Florida lifestyle that defines Longboat Key. Just moments away, enjoy world-class amenities and recreation: championship golf at the prestigious Longboat Key Club, pristine Gulf beaches for sun-soaked days, and the vibrant dining and shopping scene at St. Armands Circle. Explore Sarasota’s renowned fine and performing arts venues, upscale boutiques, and waterfront restaurants—all while residing in this sought-after enclave. Whether you crave boating adventures, cultural experiences, or relaxed coastal living, this location delivers unparalleled convenience and luxury. Don’t miss this unique opportunity to complete a standout waterfront property and unlock its full potential in one of Florida’s most desirable communities.
Listing Agent: Steve Walter (941-809-0907)
2800 HARBOURSIDE DR #E-08, LONGBOAT KEY, FL 34228
$250,000143 Days on yellowkey MLS ID: A4683624
Bed: Bath: 0.0 Built: 1985Monthly Fee: $405 Tax: $2,400 (2025)Community: Bay IslesDock-Rackominium
Taxes:$2,400
Remarks: access on the south side of the pier! A 60 ft. x 21 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club.. Direct access to Sarasota Bay and the ICW. The deep water 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. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. 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 for approval prior to entering the marina. Max length of vessel allowed is 55 LOA, usable beam is 19 ft at the head of the slip.
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
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