Location: Longboat Key
Keyword(s): Bayshore High
Keyword(s) High School: Bayshore High
Do Not Show Listings
6489 GULFSIDE RD, LONGBOAT KEY, FL 34228
$13,995,000108 Days on yellowkey MLS ID: A4677413
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 6616 Built: 2026 Tax: $42,641 (2025)Community: Sleepy LagoonSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$42,641
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability. In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive. The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs. The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views. Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Nicholle Mckiernan (941-928-2922)
4485 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228
$1,095,00014 Days on yellowkey MLS ID: A4690646
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1175 Built: 1973 Tax: $6,115 (2025)Community: Arbomar AptsCondo
Taxes:$6,115
Remarks: 2BR/2BA full Gulf-front condo in Longboat Key. 8th-floor unobstructed sunset views, updated interior, pets allowed. Direct Gulf-front condo with unobstructed views rarely available on Longboat Key! This 8th-floor residence at The Arbomar delivers panoramic views of the Gulf of Mexico, white sand beaches and sunsets that fill the horizon year-round. This 2-bedroom, 2-bath home offers 1,175 sq. feet and the kind of setting buyers often wait years to find. Inside the renovated kitchen features wood cabinetry, quartz countertops, under-cabinet lighting, and stainless-steel appliances. Ceramic tile flooring runs through the main living areas, while crown molding plantation shutters and custom built-ins add clean, timeless detail throughout. Electric hurricane shutters ensure peace of mind and long-term value. Wake to open water views and end the day with the changing colors of the sunset from your private 8th-floor vantage point. Whether used as a full-time residence or seasonal retreat, this home offers the everyday ease that draws buyers to beachfront living in the first place. Most recent improvements include fully renovated kitchen, updated bathrooms, a newer HVAC system, and a tankless water heater. The Arbomar also completed major exterior upgrades including new roof, hurricane-rated insulated windows, new entry and storm doors, and water-resistant Gemstone concrete coating on lanais and common area breezeways. Community amenities include a Gulf-front heated pool, fitness room, club room, community kitchen, kayak storage, and climate-controlled storage lockers. The condominium association is well-managed and well-funded, with low quarterly fees of $4,000. Ownership details include one-month minimum rentals permitted up to four times per year after the required ownership holding period. Pets are permitted for owners, while rentals are pet-free. The residence conveys unfurnished and includes one assigned carport space with additional guest parking available. Located on Gulf of Mexico Drive, this Longboat Key address places you near island dining, golf, boating, shopping, St. Armands Circle, and downtown Sarasota. For buyers seeking a true beachfront position, updated condition, and views that never get old, this residence stands apart.
Listing is courtesy of: WHITE SANDS REALTY GROUP FL (941-260-3350)
Listing Agent: Julie Larson, Llc (941-284-9826)
550 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$1,295,00069 Days on yellowkey MLS ID: A4683082
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1758 Built: 1977 Tax: $6,151 (2025)Community: Sleepy Lagoon ParkSingle Family
Taxes:$6,151
Remarks: One or more photo(s) has been virtually staged. Welcome to 550 De Narvaez Drive, a meticulously maintained WATERFRONT residence set on an ELEVATED 10,000 sq. ft. lot in the highly desirable Sleepy Lagoon neighborhood on the NORTH END of Longboat Key. This solid concrete block home has experienced NO FLOODING & NO STORM DAMAGE, offering exceptional peace of mind. Spanning 1,758 sq. ft., the light-filled interior features 3 SPACIOUS BEDROOMS and 2 beautifully RENOVATED BATHS. Generous room sizes, abundant natural light, and an inviting floor plan create a true sense of warmth throughout the home. The UPDATED KITCHEN and baths showcase contemporary finishes while maintaining comfort and functionality. Enjoy peaceful CANAL VIEWS with direct access to Sarasota Bay—perfect for boating enthusiasts and embracing the ultimate Florida waterfront lifestyle. NEW DOUBLE PANE IMPACT-RESISTANT WINDOWS and sliding glass doors provide enhanced protection and energy efficiency. Additional upgrades include NEWLY LINED PLUMBING PIPES and UPGRADED ATTIC INSULATION for lasting durability and comfort. Offered FULLY FURNISHED, all furnishings convey with the sale—making this a true TURNKEY opportunity. Simply bring your suitcase and start enjoying coastal living immediately. The expansive elevated lot offers ample space for outdoor entertaining, gardening, or FUTURE EXPANSION POTENTIAL. Ideally located near world-renown Gulf beaches with DEEDED BEACH ACCESS, exclusive dining, boutique shopping, and recreational amenities, this exceptional property is well-suited as a primary residence, seasonal retreat, or investment opportunity. Schedule your private showing today and experience refined, worry-free waterfront living at its finest.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Dean Hinterstoisser (941-726-0314)
552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228
$999,99988 Days on yellowkey MLS ID: A4680786
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1846 Built: 1960 Tax: $17,419 (2024)Community: Sleepy Lagoon ParkSingle Family
Taxes:$17,419
Tax Year: 2024
Remarks: Imagine living the coastal lifestyle only dreams are made of! Wake each morning to the sunrise over your local beach—just a short stroll down the street—where you can sink your toes into sugary white sand, take an early walk, or collect seashells along the shore. Return home to enjoy coffee outdoors by your heated pool, relaxing on the deck as tranquil water views set the tone for the day. Take a refreshing dip, then unwind as nature’s canvas unfolds before you, with shifting light and brilliant shades of blue and azure. In the evening, hop on your boat from your backyard and cruise effortlessly to waterfront restaurants and sunset destinations. With a 20,000-lb boat lift, personal watercraft lift, and a 40-foot dock on a deep-water canal, you’ll enjoy immediate access to Sarasota Bay, the Intracoastal Waterway, and the Gulf—with no fixed bridges along the way. End your days with breathtaking sunsets as the sky ignites in color, dolphins play, and manatees glide by. Inside, the home offers an optimal floor plan ready for your personal touches. The spacious eat-in kitchen features an expansive island perfect for casual entertaining, complemented by new stainless-steel appliances. A wall of sliding glass doors seamlessly blends indoor and outdoor living, filling the home with natural light and water views. All main living areas open to the pool and outdoor spaces. Recent updates include a new AC system and a recently refinished pool. The home offers three bedrooms and four baths, with the flexibility to modify the layout or easily add a fourth bedroom. A wood-burning fireplace adds warmth and charm to the living room. Located on the barrier island of Longboat Key, this exceptional property is perfectly suited for the most discerning buyers. Enjoy nearby golf, pickleball, boutique shopping, and dining, with St. Armands Circle and downtown Sarasota just minutes away. Convenient access to SRQ Airport makes this an ideal full-time residence or luxury vacation retreat. Call today to schedule your private showing and experience coastal living at its finest.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kathy Cahill (941-807-3565)
4420 EXETER DR #303, LONGBOAT KEY, FL 34228
$625,00098 Days on yellowkey MLS ID: TB8455704
REDUCED by $24,900 (3.8%) on 04/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970Monthly Fee: $1,412 Tax: $3,678 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$3,678
Remarks: Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (727-342-3800)
Listing Agent: Jerry Gemmecke (317-445-2434)
4380 EXETER DR #H-103, LONGBOAT KEY, FL 34228
$649,900133 Days on yellowkey MLS ID: A4675171
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970 Tax: $7,333 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$7,333
Remarks: Welcome to this beautifully updated first-floor waterfront condominium offering two bedrooms, two bathrooms, and a glass-enclosed lanai, all sold for effortless coastal living. Enjoy tranquil canal views with passing boats and frequent manatee sightings, delivering an authentic Florida waterfront experience right outside your door. The open-concept kitchen has been fully remodeled and features granite countertops, new cabinetry, stainless steel appliances, ceramic tile flooring, and fresh interior paint. Tile floors extend throughout the main living areas, while new carpeting enhances the comfort of the second bedroom. Both bathrooms were tastefully renovated in 2022, and a new A/C system installed in 2021, Hurricane Windows and Doors , ensure year-round comfort and peace of mind. Offered fully furnished, this inviting residence includes tasteful décor, artwork, and kitchenware, making it ideal for immediate occupancy, seasonal use, or investment. Located within Longboat Harbour, a gated waterfront community, residents enjoy an impressive collection of resort-style amenities. Highlights include deeded private beach access with a beachfront pavilion featuring gated Gulf access, restrooms, hot showers, lockers, parking, and a convenient car wash area. Additional amenities include boat docks, four heated pools, a recently updated clubhouse with banquet hall, library, arts and crafts room, billiards and card rooms, a fully equipped fitness center, tennis and pickleball courts, barbecue grills, kayak storage, and additional storage rooms. When available, boat slips accommodating vessels up to 34 feet are offered for a nominal annual fee. This is a rare opportunity to own a turnkey waterfront residence on the ground floor with exceptional amenities in one of Longboat Key’s most desirable communities. Call today to set up your private showing!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Andrew Haddad (941-313-1218)
4500 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$739,00039 Days on yellowkey MLS ID: A4685838
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1975 Tax: $2,843 (2025)Community: Windward Bay AmdCondo
Taxes:$2,843
Remarks: GORGEOUS BAYFRONT PENTHOUSE VIEWS Nestled in the heart of a vibrant Longboat Key Community, this stunning two-bedroom, two-bathroom condo offers unparralled water views of Sarasota bay, creating a great backdrop for both sunrises and sunsets. Step inside and be captivated by the breathtaking scenery and spacious design that blends coastal living with sophistication. Beautifully renovated with new floor to ceiling hurricane windows, this condo seamlessly integrates the living and dining areas with an open kitchen featuring stone countertops, custom cabinets and new Stainless steel appliances. The light-filled primary bedroom boasts two closets, one being a walkin complete with built in ample storage. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Take in manatee and dolphin viewing from the expansive Florida Room or relax in style looking out the huge picture window as the sun rises over the bay. This professionally managed, pet friendly community offers an array of amenities including 26 acres of landscaped ground, 2 marinas, 2 heated pools, tennis courts, pickle ball courts, state-of-the art Fitness Center, library and Community Clubhouse. Take advantage of the Deeded Beach Access just steps away. With its prime location, stunning views and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living. Schedule your private showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Marcela Terrell (941-929-3010)
528 FOREST WAY, LONGBOAT KEY, FL 34228
$595,000257 Days on yellowkey MLS ID: A4662713
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1440 Built: 1989 Tax: $3,072 (2025)Community: Cedars East Sec 2Townhouse
Taxes:$3,072
Remarks: New Price! Seize the opportunity to acquire a prime, elevated townhome in Cedars East on beautiful Longboat Key. This location is arguably the closest Cedars East property to the pristine, sugar-white sands of the Gulf. This Large Pet-friendly townhome is an Elevated structure, positioned well above the flood plain, ensuring peace of mind. Offer turn-Key Furnished excluded a few personal items. The interior exudes sophistication, featuring stunning crown molding and newer tile flooring throughout the main living areas. The kitchen has undergone beautiful updates, including shaker cabinets, granite countertops, stainless steel appliances, and a beautiful stone backsplash. These premium materials are consistently applied across all three bathrooms, enhancing the home's cohesive design. Ideally open floor plan, The kitchen, complete with a convenient snack bar, seamlessly transitions into the dining ,family room & lanai. The primary bedroom is generously proportioned, featuring a wall of windows for abundant natural light and picturesque views. Its en-suite bathroom is equally spacious, boasting dual vanities. The guest bedroom is ample & includes a walk-in closet. A full-sized laundry room is conveniently located adjacent to the bedroom space. This meticulously maintained residence presents an ideal proposition for both personal enjoyment & lucrative rental income, boasting a flexible two-week minimum rental allowance. With an approximate gross annual income of $50,000, even with several months of owner occupancy or vacancy, this property offers substantial returns. A rare asset on Longboat Key, the oversized garage includes a substantial storage closet, perfect for accommodating hobbies and recreational gear. The exterior received a comprehensive upgrade in 2018 with the installation of low-maintenance Hardi Board Siding and all new High-Impact Windows. In 2023, a brand-new hurricane-rated garage door was installed, further enhancing the home's resilience. Both air conditioning units were replaced in 2021, ensuring optimal comfort and efficiency. Finally, 2024 brought a brand new roof. Cedars East offers the convenience of on-site rental management, if desired. This 66-acre village-like townhome community is enveloped by nature, providing effortless access to both the beach and the bay on the beautiful north end of Longboat Key. The spacious and tropical community features lit boardwalks winding through mangroves, leading to an array of exceptional amenities including a heated Jr. Olympic Size Pool, nine Har-Tru Tennis Courts, three Pickleball courts, a Clubhouse with a Pro-Shop, a 24-hour Fitness Center, a Tiki bar, a restaurant, a fishing pier, and a kayak launch. Please note that some amenities require an additional club membership. The property is within walking distance to a variety of local attractions, such as Harry's Deli & Continental Kitchen, the true island gem that is Joan Durante Park, Euphemia Haye Restaurant & The Haye Loft, and, of course, Longboat Key's globally renowned sugary white sand beaches. Furthermore, it offers convenient proximity to other major attractions and cultural venues, including St. Armand's Circle, Mote Aquarium, the Asolo Repertory Theatre, Van Zel Performing Arts Center, Marie Selby Gardens, Anna Maria Island, the Ringling Museum complex, and numerous dining options on Longboat Key and in downtown Sarasota. Lots to love here, come see it today.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (941-387-8888)
Listing Agent: Jesse Griffin (941-822-6165)
4234 GULF OF MEXICO DR #G2, LONGBOAT KEY, FL 34228
$849,000351 Days on yellowkey MLS ID: A4653045
REDUCED by $46,000 (5.1%) on 04/21/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1636 Built: 1973 Tax: $13,273 (2024)Community: Pelican Harbour & Beach ClubCondo
Taxes:$13,273
Remarks: Motivated Seller—Priced to Sell! Enjoy sweeping Sarasota Bay views from this refreshed 3-bedroom, 2-bath end-unit condo in the highly sought-after Pelican Harbour & Beach Club on Longboat Key. This light-filled second-floor residence offers over 1,600 sq ft of coastal living with panoramic water views from the living room, primary suite, and private screened balcony. The spacious floor plan includes a bright living area, tranquil dining space, and a serene owner’s suite with lanai access and a beautifully renovated ensuite bath. Recent improvements include new carpet, recessed lighting, interior paint, mounted TVs, and a new AC (2025), water heater (2024) and roof (2023). Additional conveniences include in-unit laundry and covered parking and private Beach Access directly across the street. Pelican Harbour provides resort-style amenities: 200 ft of private deeded beach with new lounge chairs, heated pool and clubhouse, marina with boat slips (up to 28 ft) and kayak launch, plus tennis and pickleball courts. Pet-friendly community allowing up to two pets (dog/cat combinations permitted). Professionally managed with new roofs and hurricane-rated carports. Ideally located mid-key, just minutes to St. Armands Circle, Bayfront Park, and the new St. Regis Resort. Perfect as a full-time residence, seasonal retreat, or investment property—this bayside condo offers an unbeatable combination of location, amenities, and motivated-seller value.
Listing is courtesy of: BLUESRQ REAL ESTATE INC (941-894-7248)
Listing Agent: Shauna Ruby (941-544-2070)
6700 GULF OF MEXICO DR #117, LONGBOAT KEY, FL 34228
$550,00020 Days on yellowkey MLS ID: A4687787
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1969 Tax: $2,348 (2025)Community: Whitney BeachSpa: NoCondo
Taxes:$2,348
Remarks: Welcome to 6700 Gulf of Mexico Drive #117, a beautifully reimagined end-unit 2-bedroom, 2 full bath residence in the sought-after Whitney Beach community on Longboat Key. Taken down to the studs and completely renovated, this waterfront condominium offers coastal living with sweeping views of Bishop’s Bayou, abundant natural light, and exceptional privacy. A private front courtyard welcomes you inside, where new high-end luxury vinyl plank flooring flows throughout, and a bright, open layout immediately draws your eye to the water. As an end unit, additional windows enhance the airy feel, while hurricane-impact windows and sliding doors frame tranquil bayou views. From the main living space—and even from the primary bedroom upon waking—you’ll enjoy peaceful scenes of dolphins, manatees, and glowing sunsets reflecting across the water. The fully redesigned kitchen is both stylish and functional, featuring granite countertops, soft-close cabinetry, custom glass-front accents, classic subway tile backsplash, designer pendant lighting, peninsula seating for four, and a full suite of GE stainless steel appliances—all positioned to capture the water views. Both bathrooms have been completely renovated with glass walk-in showers, elegant tilework, and quartz-topped vanities, offering a clean, modern aesthetic. A new Whirlpool stackable washer and dryer adds everyday convenience. Whitney Beach is a unique beach-to-bay community with deeded private access to the Gulf just across the street. Residents enjoy resort-style amenities including pools, tennis courts, shuffleboard, barbecue areas, kayak storage and launch, walking paths, and a tranquil bayfront pavilion. Boat slips are available when offered, and the community pier provides a charming setting for fishing or relaxing by the water. Ideally located on the north end of Longboat Key, this residence offers easy access to Anna Maria Island, as well as the dining, shopping, and cultural attractions of Sarasota. Whether as a full-time home, seasonal retreat, or investment, this is an exceptional opportunity to enjoy the best of bay-to-beach living. Professional photos coming soon.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kelly Sallee (941-914-0400)
651 BROADWAY ST, LONGBOAT KEY, FL 34228
$2,795,000163 Days on yellowkey MLS ID: A4672952
2 Days Off yellowkey (back on 3/19/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3320 Built: 2003 Tax: $26,362 (2025)Community: Longbeach On Longboat KeySpa: YesSingle Family
Taxes:$26,362
Remarks: Under contract-accepting backup offers. Experience island living at its finest in this exquisite coastal retreat in the historic Village on Longboat Key. This home offers a refined blend of relaxed coastal charm and timeless sophistication throughout more than 3,300 heated square feet. The meticulously designed interior includes elegant crown molding, coffered ceilings, custom doors, impact windows and an elevator from the garage to each level. The great room features dramatic ceiling height and opens to a large covered terrace overlooking an exceptionally private backyard, creating an ideal setting for quiet evenings and effortless entertaining. The gourmet kitchen is a chef’s dream with rich wood cabinetry, granite countertops, natural gas cooktop, a pot filler, center island with sink and second cooktop, and a bright breakfast nook that opens to a covered terrace, ideal for morning coffee. Adjacent dining and living areas flow seamlessly and are enhanced by a coffered ceiling and French doors to the charming terrace. The second-level primary suite serves as a serene retreat with polished wood floors, an intricate coffered ceiling, a comfortable seating area, and a private covered balcony for enjoying peaceful moments under the morning or evening sky. Elevated views and sound of ospreys add to the sense of tranquility. The suite also features a spacious en-suite bath with soaking tub and two walk-in closets. Three additional bedrooms provide comfort and flexibility for guests or work needs. Outdoors, a resort-style saltwater pool and spa with integrated features are surrounded by lush landscaping and generous lounging space. The expansive ground-floor lanai and outdoor kitchen further enrich the indoor-outdoor living experience. A circular brick drive accommodates more than 10 vehicles, and the oversized two-and-a-half-car garage and first-level area offer abundant storage, ideal for bicycles, golf carts, kayaks and more. The home and pool are centered on a 12,000-square-foot lot, and an adjacent 6,000-square-foot parcel is also available from the same owner for those interested in expanding or creating a larger compound. This unique golf cart friendly community is surrounded by waterfront restaurants, quaint shops, cafés, fitness centers, fishing piers, a boat ramp on Sarasota Bay, kayak launch areas and a pristine Gulf beach just moments away with no mandatory HOA. We invite you to experience this remarkable home in person to fully appreciate its beauty and lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Cindy Fischer (941-465-1124)
509 SPANISH DR N, LONGBOAT KEY, FL 34228
$369,00021 Days on yellowkey MLS ID: N6143864
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1357 Built: 1967 Tax: $6,955 (2024)Community: Spanish Main Yacht Club CondoVilla
Taxes:$6,955
Remarks: STEPS FROM THE BEACH.....WATERFRONT COMMUNITY......DEEDED BEACH ACCESS......FULLY RENOVATED..........IMPACT WINDOWS..........COMMUNITY POOL...........Just **432 steps from the beach**, this is where coastal living stops being a dream and becomes your daily rhythm. Morning walks on soft sand, sunset returns under glowing skies, and the constant sense that the water is always just around the corner. **Fully renovated and never lived in**, this Longboat Key retreat feels brand new in every way — a clean, beach-inspired design with effortless flow and natural light throughout. Featuring **quartz countertops, impact windows, and a brand new water heater**, every detail has already been perfected so you can arrive and immediately exhale. Set within a **quiet waterfront community with deeded beach access**, life here feels unhurried and private, yet connected to everything that defines coastal luxury. From **boating access and a nearby pool** to the walkable, relaxed atmosphere residents cherish, it’s a setting designed for ease, not effort. With your own **covered parking and driveway**, and just minutes to **St. Armands Circle, Sarasota, and Anna Maria Island**, you’re positioned in one of the most desirable corridors on the Gulf. This is the rare combination buyers wait for — **newly finished, never occupied, and this close to the shoreline** — where every day feels like a quiet escape, and every return home reminds you why you chose it.
Listing Agent: Garrett Sedlacek (913-461-6882)
5055 GULF OF MEXICO DR #412, LONGBOAT KEY, FL 34228
$565,00067 Days on yellowkey MLS ID: A4683419
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $8,183 (2024)Community: Club Longboat Beach & TennisSpa: YesCondo
Taxes:$8,183
Remarks: Discover an exceptional value opportunity in Club Longboat on Longboat Key, one of the island’s most desirable beachside communities known for its active lifestyle and resort style amenities. This three bedroom, two bathroom ground floor walkout residence is currently the least expensive unit in the community and presents a rare chance to create a fully customized coastal retreat. With a solid existing layout and desirable ground level access that enhances indoor / outdoor living, the residence offers tremendous flexibility. Buyers have the opportunity to redesign and expand the third bedroom to add additional square footage, whether to create a more spacious primary suite, an inviting guest retreat, or a dedicated office or flex space. The potential to transform this residence into a personalized showpiece is exceptional. Club Longboat is ideal for tennis, pickleball, and beach enthusiasts, offering eight Har Tru tennis courts with three lined for pickleball, two heated swimming pools, and 750 feet of private Gulf front beachfront complete with lounge chairs and umbrellas. The serene waterfront setting enhances the peaceful atmosphere and scenic surroundings. The residence includes a covered parking space directly in front of the unit along with abundant guest parking. On site management serves the 85 residences, providing convenience and peace of mind within a welcoming, all ages community. Owners enjoy a pet friendly environment with no weight restrictions and a flexible rental policy allowing one month minimum rentals up to twelve times per year, creating excellent income potential. Conveniently located near shopping and fine dining, this is a rare opportunity to secure a value driven property in an amenity rich Longboat Key beachfront community and make it entirely your own.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
6810 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$2,250,000188 Days on yellowkey MLS ID: A4669890
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2848 Built: 2024Monthly Fee: $83 Tax: $7,410 (2024)Community: LongbeachSpa: YesSingle Family
Taxes:$7,410
Remarks: Significant Price Reduction on this NEW in 2024, dream retreat that is uniquely positioned in the highly sought after “Village” of Longboat Key, a neighborhood known for its quaint charm and vibrant community atmosphere. Featuring 4 bedrooms and 4 and a half baths in open and light filled rooms, a backyard oasis with a pool and outdoor kitchen, high impact windows and doors throughout, 1230 sq ft of porches and balconies and an amazing rooftop top deck with spectacular water views: this is truly the epitome of luxury island living! The stunning chefs kitchen features high end appliances, including a 6 burner gas range, double ovens and a large center island. A perfect open flow into the inviting dining and living area, allows for exceptional entertaining with picturesque views out to the backyard oasis, seamlessly connecting indoor and outdoor spaces. This rare offering of NEW construction in this wonderful neighborhood is hard to come by. It affords its owner peace of mind, whether this is your forever home, your part time vacation retreat or a fabulous investment rental property. The community features multiple restaurants, a couple of Bayfront docks and even a community boat ramp. The gorgeous Gulf of Mexico is within a short walk, bike or golf cart ride away and is one of the nicest beaches on the island. It stretches for miles and is the perfect spot to spend the day before returning to watch the sunset from your rooftop deck. Come savoir the laid back island lifestyle that Longboat Key is known for and make this tranquil coastal retreat your own.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
619 CEDARS CT, LONGBOAT KEY, FL 34228
$430,000535 Days on yellowkey MLS ID: A4629084
Bed: 1 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1244 Built: 1988 Tax: $5,555 (2024)Community: Cedars East Sec 1Spa: NoTownhouse
Taxes:$5,555
Remarks: Welcome to your cozy island townhome at the north end of Longboat Key. Perfect as a fulltime residence, seasonal retreat, or investment property, this one-bedroom, two-bath unit fits your needs. This two-story property weathered three hurricanes in 2024, sustaining only minor flooding in the garage during Hurricane Helene and a cracked top-floor window during Hurricane Milton. The HOA will cover and replace the window. On the ground floor, enjoy your private parking garage and storage space. The main living area on the first floor features an open-concept living room and kitchen, ideal for relaxing or entertaining. Step out onto the screened balcony to enjoy the natural beauty of Florida or unwind with your morning coffee. This floor also has a full bathroom and a pull-out sofa for hosting guests. The second floor boasts a spacious master bedroom with a king-sized bed and two walk-in closets, filled with natural light from large windows. This level includes a second bathroom and a sun deck with an outdoor shower, offering peaceful views of a natural reserve. It’s the perfect spot to soak up the sun or enjoy a good book in a hammock. Short-term rentals with a 14-day minimum stay are allowed, adding investment potential. From July 2024 - July 2025, the home already has booked rental income booked totaling $45,0000. With some cosmetic upgrades, this could be even more! The unit is part of a top-notch tennis club that now includes two pickleball courts. You'll be close to the pool and the island’s beaches. Pet-friendly and welcoming, the community features a Junior Olympic-sized pool, a Tiki Bar, and a restaurant for a resort-like feel. Nature trails wind through the property, leading to a dock with stunning views of Sarasota Bay— perfect for launching your kayak to explore mangrove tunnels or paddle alongside manatees and dolphins. Whether you're into kayaking, tennis, pickleball, cycling, or jogging in nearby John Durante Community Park, this condo offers the perfect balance of luxury and leisure. Your island paradise is waiting—make it yours today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Simone Schaerf (941-260-1550)
597 SUTTON PL, LONGBOAT KEY, FL 34228
$530,000182 Days on yellowkey MLS ID: A4669989
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1008 Built: 1972 Tax: $2,379 (2025)Community: Sutton PlaceSpa: NoHalf Duplex
Taxes:$2,379
Remarks: Experience the best of Longboat Key living at Sutton Place, ideally positioned mid-island with convenient access to both Sarasota Bay and the Gulf of Mexico. Enjoy deeded beach access just moments away—perfect for daily beach outings, sunset walks, and the pristine Gulf shoreline. Active living comes naturally here. Bike to Bayfront Park for pickleball or tennis, or visit the nearby dog parks where neighbors and pets gather. When it’s time to relax, choose from two community pools, including one overlooking the marina and peaceful Bay waters. The community also offers multiple BBQ areas, creating ideal spaces for gatherings with friends and family in a beautifully maintained coastal setting. This two-story townhome offers 2 bedrooms and a full bathroom upstairs, with a second bathroom conveniently located on the main level. The eat-in kitchen features a charming dining nook, and the adjoining screened porch provides a tranquil outdoor retreat. A private one-car garage adds convenience and storage for a vehicle, golf cart, or beach essentials. Additional highlights include first-come, first-served dock slips available for a nominal fee and a setting that offers comfort and peace of mind. Seller reports the property had no flooding during Hurricane Helene. Live the Longboat Key lifestyle—sun, sand, coastal breezes, and effortless island living.
624 SAINT JUDES DR, LONGBOAT KEY, FL 34228
$749,900165 Days on yellowkey MLS ID: A4672840
REDUCED by $15,000 (2.0%) on 04/20/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1387 Built: 1957 Tax: $8,692 (2025)Community: Longboat KeySingle Family
Taxes:$8,692
Remarks: Wow, Excellent New Price! Your opportunity to own a piece of Longboat Key paradise just got even better. The stunning Cali-Modern residence has a new, more attractive price! Presenting an amazing opportunity for this stunning, fully renovated residence where Cali-Modern design meets the tranquil elegance of Longboat Key. Presenting a stunning, fully renovated residence where Cali-Modern design meets the tranquil elegance of Longboat Key. This sophisticated, move-in ready home offers an abundance of good vibes and professional quality, available now on the highly sought-after North End of exclusive Longboat Key. Sleek, chic, and absolutely move-in ready, this property is an instant atmosphere setter. From the moment you step inside, you'll feel the coastal modern bliss. Enjoy the clean, modern lines, vaulted ceilings, and stunning stone tile floors, all bathed in gorgeous southern sun light. The upgraded kitchen and bathrooms sparkle with new features, complemented by new appliances. This home has been lovingly and extensively renovated, offering quality and style that goes well beyond the expected. You will find thoughtful design and premium features in every corner. Step outside to your own private backyard oasis, the perfect spot to sip a sunset cocktail. Fully fenced and private this oasis sets up perfectly for the future pool. And talk about location! You are literally steps from both Gulf and Bay access. This home boasts unbeatable walkability to island favorites like Harry's Deli and The Continental Kitchen, Euphymya Haye and the Hayloft, Lo-Key Island Grille, Cedars East Tennis and Fitness Resort and many others. The best-kept secret? A private back gate leads you directly into the 32 acres of Joan Durante Park, offering pure, natural Florida coastal hammock. This park is a true gem filled with nature walking trails, fishing piers, playground for the kids and multiple Bay access points (perfect for the kayak launch) No fuss, no stress. With a standing seam metal roof, Hardi board siding, newer double-pane windows, New interior, new appliances and offered fully furnished, this charmer is ready for your island life to begin immediately. Don't wait, come feel the charm for yourself!
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
5055 GULF OF MEXICO DR #331, LONGBOAT KEY, FL 34228
$895,000178 Days on yellowkey MLS ID: A4670624
REDUCED by $90,000 (9.1%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $5,337 (2024)Community: Club LongboatSpa: YesCondo
Taxes:$5,337
Remarks: One or more photo(s) has been virtually staged. Welcome to your coastal retreat in paradise — a stunning third-floor waterfront residence in Club Longboat Beach and Tennis, offering expansive Gulf views and one of the largest floor plans in the community. This exceptional 2-bedroom plus 3rd bedroom/study layout perfectly blends elegance, comfort, and functionality, ideal for full-time living or as a refined vacation escape. With 750 feet of pristine Gulf frontage, this home immerses you in the beauty and serenity of coastal living. Beautiful engineered white oak wood floors flow throughout the open, sun-filled living space, which seamlessly extends to your private balcony’s, the perfect spot to enjoy the tranquil sound of the waves and stunning sunsets. The updated kitchen features stone countertops, white cabinetry, and has been opened up to create a larger, more connected floor plan ideal for entertaining. The primary suite is a private sanctuary, boasting a remodeled marble bath with high-end fixtures and a spa-like ambiance. The guest suite provides equal comfort and privacy, featuring a beautifully appointed travertine-floored bathroom. A custom wall of California closets offers exceptional storage and style. The Club Longboat Beach and Tennis community offers amazing amenities, including private beach access with lounge chairs and beach umbrellas, eight professional har-tru tennis courts, pickleball, fitness center, shuffleboard, barbeque area, clubhouse with regular social events, sauna, spa and two heated swimming pools. Club Longboat is a pet-friendly community allowing up to two pets with fees that include exterior maintenance and insurance, cable, water, sewer and trash. Perfect as a full-time residence or an income-producing rental, with one-month minimum leases permitted up to 12 times per year. Only a short drive to many fine restaurants, boutiques, Anna Maria Island, St. Armands Circle and the City of Sarasota. Sarasota is a well-known center for arts and culture including the Asolo Theater, Van Wezel Performing Arts Center and Ringling Museum. Schedule your showing today and make resort style living a reality.
Listing Agent: Ryan Heers (941-726-1703)
600 SUTTON PL #104B, LONGBOAT KEY, FL 34228
$545,000413 Days on yellowkey MLS ID: A4644920
REDUCED by $25,000 (4.4%) on 04/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1144 Built: 1973 Tax: $6,737 (2024)Community: Sutton PlaceCondo
Taxes:$6,737
Remarks: Incredible FULL BAY VIEW! This tranquil and beautifully renovated island retreat located in the beach to bay community of Sutton Place offers that and so much more. This 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous, remodeled kitchen is open to the living/dining area across an expanse of granite that includes a custom made dining table with lots of storage underneath and seating all around! Porcelain tile flooring makes the journey from one room to another a seamless and beautiful transition. These smart owners have converted the lanai into finished square footage and it is the perfect spot to enjoy a morning coffee or an evening beverage while watching the fish jump or the birds fly by. They also upgraded to IMPACT RESISTANT SLIDING DOORS AND WINDOWS throughout. The Primary bedroom has this same gorgeous view and a renovated ensuite bath. The once walk-in closet was converted to a small office space, (which could easily be changed back) but it’s current use is rather genius. When guests are not in town, the 2nd bedroom is another tranquil space to enjoy. Did I mention this is a 2 pets friendly community?! Sutton Place also offers its own PRIVATE BEACH CLUB and includes an abundance of amenities including 2 pools, a clubhouse, and an onsite marina with slips for a nominal fee of only $300 per year. The community recently completed a number of updates including repainting, reroofing and passing the milestone inspection and securing a 10 year certification. This owner has paid for all of those upgrades in full. The unit is being offered furnished with exceptions. Here you will find a remarkable quality of laid-back island life but if you're ready for more, enjoy the multitude of restaurants, shopping and the cultural mecca of downtown Sarasota, all within a short drive away.
7105 GULF OF MEXICO DR #21, LONGBOAT KEY, FL 34228
$895,000231 Days on yellowkey MLS ID: A4665082
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1170 Built: 1974 Tax: $10,071 (2024)Community: LongbeachSpa: NoCondo
Taxes:$10,071
Remarks: Gulfside Condo on north Longboat Key with direct beach access: This 2-bedroom, with bonus room, second floor condo offers the island lifestyle you've been searching for—a waterfront community, stunning sunset views from the lanai, and steps to the beach. Located in Longbeach Condo community on Longboat Key, this turnkey furnished, coastal Florida condo features 2 bedrooms, 2 bathrooms,and a bonus room currently used as a den. The comfortable floorplan features a bonus room for bunks, an office, or a reading room, a wide galley kitchen with Corian counters and tossed marble tile backsplash, in-unit washer/dryer, tile floors throughout, and a private balcony with views of the Gulf. At 19.5 foot base flood elevation, this unit was well above the storm surge of previous hurricanes. Longboat Key Living means beach access, world-class golf courses, world class tennis and waterfront dining just minutes away. The Longbeach Condo community offers 9.2 acres of gulf front, beach property, amenities like heated pool, club house, open parking, private beach access, kayak storage and private tennis. You're 15 minutes to St. Armands Circle shopping, 20 minutes to downtown Sarasota, and close to world-class fishing charters from Cortez Fishing Village. This barrier island property is perfect for full-time Florida living, a vacation home, a snowbird retreat or investment rental property. Rental history/projections available. The location puts you near Coquina Beach, Marina Jack, and easy access to Sarasota-Bradenton International Airport. Nationally ranked medical facilities located within minutes and all LBK first responders are EMTs!
Listing Agent: Diana Kryszak (941-993-4078)
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