Location: Longboat Key , 34228
Do Not Show Listings
3610 BAYOU CIR, LONGBOAT KEY, FL 34228
$2,400,00020 Days on yellowkey MLS ID: A4688141
Bed: 3 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 3192 Built: 1993Monthly Fee: $104 Tax: $18,202 (2025)Community: Bay IslesSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$18,202
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to The Bayou section of beautiful Bay Isles. Tucked away from the hustle and bustle of daily life, this double-gated community, a collection of 126 homes, is the perfect place to be on Longboat Key. The pavered front circular drive delivers you to the elevated double-door entrance. Step inside and prepare to be delighted by the neutral palate throughout and an abundance of natural light. Living is easy in this updated three-bedroom home which includes high ceilings and many tasteful architectural details. Three full baths and one-half bath, a dedicated office adjacent to the primary bedroom, a large formal dining room, separate breakfast room, classy cabinet-filled kitchen with new granite counters and a 9 ft island (seats 6). The kitchen is open to a spacious great room featuring vaulted ceilings, recessed lighting, built-in surround sound and a natural gas fireplace. This step-saving layout includes a main level laundry room as well. The primary bedroom has a new primary bath with a dual control sizeable shower, a walk-in custom closet, and direct access to the heated pool and spa just outside. Every bedroom has an en-suite full bath including the one that has direct pool deck access. Three sets of sliding glass doors open to the outdoor kitchen, pool and spa, all raised to be on the same living level. This main feature, having all living space elevated well above sea level is a bonus. An extremely large non-conforming space on ground level is ideal for multiple cars and/or boat storage, plus an air-conditioned space for a workshop or weight room if desired. There is a brand- new Trane A/C system (2026) as well as a new gas pool heater (2025) With too many fine features to list, this home is a must see. Ownership includes membership into the Bay Isles Beach Club, your private spot on the white sands of the Gulf of Mexico. Also, Longboat Key Golf and Tennis Club membership is available separately. Take a short drive to shopping and dining at the famous St Armands Circle and Downtown Sarasota. Magnificent!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Mike Prisco (941-812-1291)
510 BOWSPRIT LN, LONGBOAT KEY, FL 34228
$4,400,00024 Days on yellowkey MLS ID: A4687207
REDUCED by $200,000 (4.3%) on 04/13/2026
Bed: 5 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 4389 Built: 2013Monthly Fee: $21 Tax: $35,060 (2025)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$35,060
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to this renovated waterfront luxury retreat in the highly sought-after Country Club Shores on Longboat Key. From the moment you arrive to this 5 bedroom 6.5 bathroom almost 4,400 sqft home sitting on nearly ¼ acre, the home’s striking curb appeal, tropical landscaping, and circular paver driveway set the tone for what awaits inside. Perfectly positioned on a deepwater canal with quick access to Sarasota Bay and the Gulf, this exceptional residence offers the ultimate Florida lifestyle with a private dock, 28,000-pound boat lift, and room for a large vessel currently docking a 38 ft boat. Stepping through the front entry, you’re welcomed into a stunning open-concept interior where designer finishes and natural light come together beautifully. The expansive main living area offers soaring coffered ceilings and an impressive floor-to-ceiling marble feature wall complete with an electric fireplace and custom wine display. Large sliding glass doors open wide to seamlessly blend indoor/outdoor living, allowing the waterfront views to become part of everyday living. The gourmet kitchen features top-of-the-line Thermador appliances, custom cabinetry, a wine refrigerator, quartz countertops, and an oversized island with generous seating. The kitchen flows effortlessly into the family room, while the adjacent dining area and breakfast nook offer additional space to gather, all framed by peaceful water views. Privately tucked away on the main floor, the owner’s suite serves as a true retreat. This serene space with plantation shutters offers a luxurious spa-like bathroom complete with dual vanities, quartz countertops, a soaking tub, a walk-in glass shower with a waterfall showerhead, elegant tile finishes, and a Toto Neorest toilet. Upstairs, you’ll find four generously sized bedrooms, each with its own ensuite bathroom and spacious closet, offering comfort and privacy for family or guests alike. One upstairs suite functions beautifully as a secondary primary suite with tray ceilings, dual vanities, and a large walk-in shower with dual showerheads. An upstairs media room adds flexibility and is the perfect place for movie nights, game days, or relaxed entertaining, while the upper-level terrace provides another place to unwind and take in the surrounding waterfront views. An elevator services the garage, first floor, and second floor, adding everyday ease and convenience. Outside, the backyard was designed to feel like your own private resort. The heated saltwater pool and spa are surrounded by travertine tile, tropical landscaping and spacious lounging areas, all overlooking the water for a tranquil setting. A full pool bath adds functionality for seamless indoor-outdoor living. Whether you're spending the afternoon poolside, entertaining under the sun, or heading out for a sunset cruise from your private dock, this home delivers the kind of waterfront lifestyle buyers dream about. Located in the coveted Country Club Shores community, this exceptional property also offers deeded beach access to the powder-soft Gulf beaches just moments away. Enjoy being only minutes from the world-class golf, tennis, dining, and marina amenities of Longboat Key Club, along with the upscale shopping and restaurants of St. Armands Circle, the arts and culture of downtown Sarasota, and the convenience of SRQ International Airport. This is more than just a home, it’s a luxury coastal lifestyle in one of the area’s most desirable waterfront communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kaisen Mitchell (941-726-7657)
4500 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$739,00025 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
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
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)
3240 GULF OF MEXICO DR #B402, LONGBOAT KEY, FL 34228
$895,00038 Days on yellowkey MLS ID: A4686024
REDUCED by $10,000 (1.1%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1505 Built: 1975 Tax: $8,208 (2025)Community: PortobelloSpa: NoCondo
Taxes:$8,208
Remarks: TURNKEY Furnished Portobello condo with Deeded Beach Access! TWO Balconies with Sunsets AND Sunrises included! Enjoy Beach and Bayou water access! Rarely available end unit with two balconies and lots of privacy and natural lighting. The front open balcony has unobstructed Gulf views whilst the rear balcony is glassed in with sliders/screens and faces the Bayou. This 4th Floor condo has elevator access, 1 owners storage locker, ample in unit storage and 1 assigned parking space. Condo fee includes Water, Sewer, Trash, Cable/Internet, Pest Control, on site Maintenance and Exterior Insurance. Well established social community with Community Pool, Clubhouse, Tennis Courts, Kayak storage/launch, Fishing Pier, BBQ area and ELEVATED mature landscaping. This spacious floorplan is one of the larger floorpans in the community providing you with list and bright spaces, tons of closet space and even a bonus study/den area to use as you please! Stacked Washer/Dryer located near the hallway 2nd Bathroom which has been renovated. Beautifully upgraded Kitchen with high quality cabinetry and 4 storage closets for all your pantry, cleaning and large cooking items. The Primary Bedroom has the most wonderful private bayou water views! Attached en suite full bathroom with lots of counter space. Secondary bedroom has its own separate balcony entrance. This community is located a short drive away from Publix, CVS, banks, Post office, nail salons and Golfing! New development nearby is bringing more shopping and dining! Don't miss this opportunity to own in the sough after Portobello community!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Monica Desomma (202-427-4328)
6750 GULF OF MEXICO DR #163, LONGBOAT KEY, FL 34228
$500,00049 Days on yellowkey MLS ID: A4683547
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1970 Tax: $4,337 (2024)Community: Whitney BeachCondo
Taxes:$4,337
Tax Year: 2024
Remarks: In the sought-after Whitney Beach community on Longboat Key’s peaceful north end, this beautifully renovated two-bedroom, two-bath end unit residence offers 1,449 square feet of coastal contemporary living with tranquil water views over protected Bishop’s Bayou. Enjoy serenity of a coastal inlet sheltered from constant boat traffic of the Intracoastal Waterway, where dolphins and manatees glide past your rear Florida room, a front-row seat to nature. The versatile floor plan includes spacious bedrooms with en-suite baths (showers only), a bright 9-by-14-foot flex space with abundant windows where the washer and dryer connection is located, plus an additional 8-by-3-foot storage area. The kitchen features quartz countertops, stainless steel GE appliances and a water view that enhances everyday living. Tasteful coastal selections, a light palette and additional end unit windows create an airy, open feel throughout, complemented by storm-resistant windows for added peace of mind. Whitney Beach offers resort-style amenities including two pools, tennis court, barbecue stations, kayak storage and launch, lush recreational paths and deeded private beach access directly across the street to the turquoise Gulf waters. Boat slips are available when offered, with annual dock fees of $600 for slips up to 33 feet and $480 for slips up to 24 feet. Sublets are available. Two pets are welcome with no weight restrictions. Rentals are permitted with a one-month minimum. An exceptional opportunity to enjoy bay-to-beach living in one of Longboat Key’s charming waterfront communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Karen Whitaker (941-724-6969)
1445 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$1,195,00052 Days on yellowkey MLS ID: A4684021
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2092 Built: 1982 Tax: $11,749 (2025)Community: Players Club IiiSpa: YesCondo
Taxes:$11,749
Remarks: Step into this highly desirable corner residence featuring three bedrooms, three full baths, and an expansive 36’ x 11’ sunroom at The Players Club. You’ll immediately be drawn to the impressive 31-foot balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. Inside, the sun-filled kitchen is thoughtfully designed with custom cabinetry and a built-in breakfast table that expands both workspace and storage. It flows seamlessly into the main living and dining areas, creating a warm and open environment for entertaining or daily living. Just off the kitchen, elegant French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The owner’s suite provides a private sanctuary with a spa-inspired bathroom featuring a soaking tub, separate glass-enclosed shower, dual vanities, and a spacious walk-in closet. The second bedroom functions as a true secondary master, complete with dual sinks, a full vanity, and a fitted walk-in closet, offering comfort and privacy for family or visitors. A third bedroom adds flexibility for guests, workspace, or hobbies. A unique feature of this residence is the private garage, offering rare security and convenience for residents, plus an additional covered parking space underneath the building for extra guest or secondary vehicle use. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves. Just minutes from St. Armands Circle, downtown Longboat Key, and Longboat Key Club, with championship golf, premier tennis, and a deep-water marina, this corner residence blends privacy, convenience, and resort-style coastal living. Units with this versatile layout and resort-ready features are highly sought after. Offered partially furnished. Seller is willing to discuss a subsidy on the quarterly condominium fee for reserve increase over the next two years!
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
550 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$1,295,00055 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)
4720 GULF OF MEXICO DR #Villa 2, LONGBOAT KEY, FL 34228
$599,00057 Days on yellowkey MLS ID: A4679458
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 912 Built: 1974Monthly Fee: $1,305 Tax: $1,356 (2025)Community: Windward Bay AmdVilla
Taxes:$1,356
Remarks: Welcome to elevated beachfront living in highly desirable Windward Bay — a premier bayside enclave offering serene coastal charm and resort-style amenities on picturesque Sarasota Bay. This fully reimagined 2-bedroom, 2-bath villa has been thoughtfully renovated from top to bottom with impeccable attention to detail and contemporary finishes throughout. Step inside to discover an open, light-filled interior featuring brand-new electrical and plumbing systems, new drywall and insulation, new kitchen and bathrooms — everything crafted for modern comfort and peace of mind. A dedicated 220-volt receptacle makes electric vehicle charging effortless, blending convenience with conscientious living. Enjoy easy walk-in access with no stairs, and take full advantage of Windward Bay’s pet-friendly policy — perfect for up to two pets — making this the ideal coastal retreat for the whole family. Relax and unwind on your private back patio overlooking lush landscaping, where tranquil sunsets frame the entrance to the beach access just steps away. Cozy evenings by the fire pit become part of your daily rhythm. Windward Bay is cherished for its park-like grounds, complete with: Nearly a half-mile of scenic walking trails. Three distinct Gulf beach access points. Two heated pools. Six pickleball/tennis courts. A well-appointed clubhouse with fitness center, sauna, library, and meeting spaces. Two marinas with boat and jet ski slips. A private fishing pier. Outdoor grilling areas, firepits, and kayak storage. This exceptional villa effortlessly combines the ease of turn-key living with premium upgrades and unparalleled community amenities — all in one of Longboat Key’s most sought-after waterfront communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Sharon Austin (678-756-4020)
690 FOX ST, LONGBOAT KEY, FL 34228
$725,00068 Days on yellowkey MLS ID: A4682225
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1967 Tax: $10,397 (2025)Community: Longbeach On Longboat KeySingle Family
Taxes:$10,397
Remarks: WOW, A SECOND Early Price Drop. Motivated seller, Priced for immediate sale on this fully renovated and furnished Village of Longboat Key Home. Take Advantage Today. Coastal Elegance Meets Island Ease in Longboat Key's Coveted Village. Discover a sanctuary of sophistication at the exclusive North Tip of Longboat Key. Located in the heart of historic Long Beach Village, this is more than a home; it's the ultimate island lifestyle, delivered. Just a short, serene stroll separates you from the pristine beach and the island's best waterside dining. This property has been meticulously and fully remodeled, representing a rare "move-in ready" opportunity where every detail has been elevated. From top to bottom, inside and out, virtually nothing has been untouched. A Home Designed for Seamless Living: Open Concept: Step into an airy, open-plan great room, anchored by a brand-new kitchen - perfect for hosting intimate gatherings or unwinding after a day on the water. Chef's Delight: The remodeled kitchen is a masterpiece featuring stunning marble countertops, custom cabinetry, all-new luxury appliances (including a mini wine refrigerator), and a chic island/bar. High-End Finishes: Enjoy the cohesive flow of new luxury vinyl plank flooring throughout every room, complemented by fresh, designer-selected interior paint. Peace of Mind: Recently installed, all new windows and sliding glass doors are Miami-Dade impact resistant, offering superior protection and efficiency. Also a brand new architectural three-tab shingle roof was just installed. Your Private Island Retreat: Spa-Inspired Baths: Both the master and second bathrooms have been fully renovated with premium stone shower flooring, elegant new tiles, and updated fixtures. Outdoor Oasis: Off the master suite, a new impact-resistant glass door opens to a spacious, private backyard. The highlight is the expansive, screened-in porch that wraps around the back of the house, overlooking a charming outdoor fire pit and grilling area. Beach Ready: An exterior shower and dedicated storage for your gear make rinsing off after a day at the beach effortless. The Village Lifestyle: To know The Village is to fall in love with its relaxed, yet refined rhythm. This community places everything you desire at your fingertips: secluded walking trails, Bay access, community docks, and the island's best beach access. The Village is one of the few places on Longboat Key where the golf cart isn't just legal, it's the preferred, fun, and convenient way to live. This is your unique chance to maximize a truly effortless, luxury island lifestyle. Come and see it today. * Seller has been averaging $55k Gross on seasonal rental.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228
$999,99974 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
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)
4310 FALMOUTH DR #102, LONGBOAT KEY, FL 34228
$660,00087 Days on yellowkey MLS ID: A4679011
REDUCED by $5,000 (0.8%) on 04/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969Monthly Fee: $1,410 Tax: $6,739 (2024)Community: Longboat HarbourCondo
Taxes:$6,739
Remarks: Exceptional value for a Longboat Key condo with private beach access. Enjoy deeded Gulf access with a residents-only community beach house featuring bathrooms, indoor/outdoor showers, seating, cabana space, and parking—your personal gateway to Gulf Coast living. Experience exceptional bayfront living at 4310 Falmouth Drive, Unit 102, located in the sought-after Longboat Harbour community on Longboat Key—a premier coastal city and barrier island along Florida’s Gulf Coast, renowned for attracting year-round residents, second-home owners, seasonal residents, and visitors seeking a refined, upscale seaside lifestyle. This A-Building, direct bayfront residence captures full Sarasota Bay views from the kitchen, dining area, living room, enclosed lanai, and primary bedroom—offering a front-row seat to sunrise skies, passing boats, dolphins, manatees, eagles and all kinds of exciting wildlife just 40 feet from the tranquil water vistas. Thoughtfully updated, the home features luxury vinyl flooring, upscale LG quartz Viatera Rococo countertops in the kitchen and both bathrooms, and soft-close drawers and custom cabinetry throughout. The spacious primary suite includes double vanities and a beautifully updated walk-in shower, while the guest bath also offers a walk-in shower with quartz finishes. Significant capital improvements provide peace of mind, including new hurricane-rated windows and sliders (2024, Cat5), HVAC (2021) with approximately 8 years remaining on a 12-year warranty, and a water heater (2023). The enclosed lanai expands usable living space while maintaining sweeping Sarasota Bay views. Offered fully furnished for a seamless, move-in-ready bayfront lifestyle. Longboat Harbour is a gated, resort-style community offering an impressive array of amenities, including four heated pools, tennis and pickleball courts with active player groups, fitness center, sauna, meeting rooms, billiards, putting green, woodworking shop, kayak storage, shuffleboard, locker rooms, fishing piers, two community grills, on-site management, and a protected harbor. Boat slips are available to members of the Longboat Harbour Yacht Club (subject to availability). Enjoy the best of island living with private deeded beach access just a short walk or drive across the street—complete with seating, chair storage, cabana, restrooms, indoor and outdoor showers, parking, and a convenient car-wash area. Additional features in the condo include washer and dryer connections in a hall closet and assigned covered carport parking with abundant guest spaces nearby. In the living room, open the sliders to seamlessly expand your indoor–outdoor living space, or keep them closed and enjoy the patio as an enclosed lanai—then open the glass sliders to let in refreshing coastal breezes and salt air. Located just 7.5 miles north of St. Armands Circle, and a short drive to downtown Sarasota’s Arts District, world-class dining and shopping, with Sarasota-Bradenton International Airport nearby. Direct Sarasota Bay views and private deeded Gulf beach access make this exceptional residence the ultimate Longboat Key lifestyle opportunity.
Listing is courtesy of: MARCUS & COMPANY REALTY (941-932-8550)
Listing Agent: Kerre Allman (941-909-3095)
600 SUTTON PL #104B, LONGBOAT KEY, FL 34228
$545,000399 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.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
5055 GULF OF MEXICO DR #331, LONGBOAT KEY, FL 34228
$895,000164 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)
4760 GULF OF MEXICO DR. VILLA 7, LONGBOAT KEY, FL 34228
$549,999157 Days on yellowkey MLS ID: A4671823
REDUCED by $24,501 (4.3%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 931 Built: 1974Monthly Fee: $21 Tax: $1,629 (2025)Community: Windward Bay AmdVilla
Taxes:$1,629
Remarks: UNBEATABLE VALUE! AMAZING PRICE FOR A BRAND NEW BEACH & BAY VILLA! Renovated with precision, the final finishing touches were completed in 2025 (12 weeks in living time since renovation) for this quality engineered, down to the studs, two-bedroom and two-bath beach getaway villa. From the moment you step inside, you'll be greeted by a thoughtfully designed sunny open floor plan boasting recessed lighting and an array of sleek finishes throughout the home. Distinguishing features include the true craftmanship of custom solid core doors, chic beach themed door and cabinet knobs, custom designed laundry closet housing a Full-sized front load Samsung washer & dryer, self-close solid kitchen cabinets with a bonus spice rack cabinet, pull out shelves in the pantry and below the sink, ceramic floor tiling through-out including a curb less shower entry located in the primary suite’s “ensuite bathroom. The pièce de résistance is the Cambria Quartz (lifetime warranty) kitchen countertop chosen for the beach inspired aqua accents that showcase both a breakfast bar and a dual temperature wine/beer refrigerator for added pleasure. The second bedroom is cleverly designed to serve as both an office and a guest space, complete with a comfortable “guest chest” Murphy bed cabinet. For peace of mind while away, the villa is equipped with the latest Wi-Fi enabled keyless smart lock entry system, as well as a smart remote thermostat to monitor and manage remotely. Worry free living with a New A/C (2022), Water Heater (2024) and recent Hurricane Impact Windows/Sliding Doors, Roof, & Carport (2020). Located directly across the street, with 3 beach access points (one private deeded access) is the tranquil Gulf with its crystal-clear turquoise blue waters and uncrowded sandy beaches that attract visitors from all over the world. A low-density residence and a nature lover’s delight: from captivating bird watching to the frolicking dolphins and manatees of Longboat Key. Windward Bay's unparalleled amenities include 2 tennis/pickleball courts, 2 marinas with 28 boat & jet ski slips for a low monthly fee (first come first served), barbecue grills throughout, fishing piers, 2 fish cleaning stations, kayak racks, 2 heated pools, shuffleboard, bike racks, a clubhouse with kitchen, library, fitness room, meeting room, 2 saunas, and community fire pits throughout the property. Conveniently accessible to Downtown Sarasota, St. Armands Circle, Anna Maria Island, Historic Cortez Fishing Village, Championship Golf Courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Welcome home to “Pet Friendly” Windward Bay, where TWO pets are allowed. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced. This wonderful condominium exemplifies “Florida Gulf to Bay Living” at its finest. Windward Bay: "A Special Place and A Gem of a Community." Whether you're looking for a vacation home or a permanent residence, book your private showing today. Longboat Key and Villa 7 in Windward Bay offer everything you could desire to live the life you have always dreamed of!
Listing Agent: Debby Mccaig (941-544-1713)
2039 GULF OF MEXICO DR #G3-203, LONGBOAT KEY, FL 34228
$499,99917 Days on yellowkey MLS ID: A4688685
REDUCED by $39,001 (7.2%) on 04/15/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1214 Built: 1974Monthly Fee: $1,170 Tax: $5,576 (2025)Community: Seaplace ISpa: YesCondo
Taxes:$5,576
Remarks: Experience the Best of Coastal Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2.5-bath residence offering a perfect blend of comfort, style, and relaxed island living. This spacious two-level layout features an inviting open-concept living and dining area with neutral coastal tones, tile flooring throughout the main level, and seamless access to a private lanai—ideal for enjoying tranquil views and Gulf breezes. The updated kitchen is designed for both functionality and style, showcasing granite countertops, white cabinetry, stainless steel appliances, and a convenient breakfast bar, perfect for casual dining or entertaining. Upstairs, you’ll find two generously sized bedrooms, each offering privacy and comfort. The primary suite serves as a relaxing retreat, while the guest bedroom is ideal for family or visitors. The additional half bath on the main level adds convenience for guests. This residence is offered in move-in ready condition and reflects pride of ownership throughout. Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an exceptional array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center, and a clubhouse with kitchen, library, and sauna. Additional features include playground areas, grilling stations, on-site management, and a 24-hour staffed gatehouse for security. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this home offers the ultimate Longboat Key lifestyle in one of the island’s most sought-after communities. Schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
530 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$4,795,000181 Days on yellowkey MLS ID: A4669195
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2025 Tax: $12,064 (2024)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$12,064
Remarks: New Construction - Discover the epitome of waterfront luxury with this newly built home in the heart of Longboat Key—competitively priced and move-in ready. Nestled along a private canal, this 4-bedroom plus den, 4,106 sq ft residence blends contemporary sophistication with coastal appeal. Designed for effortless indoor-outdoor living, the home boasts two spacious lanais, a private pool and spa, and an elevated foundation at 9.5 feet for added peace of mind. Boaters will enjoy concrete canal bulkhead with quick access to the Gulf of Mexico, perfect for endless days on the water. Inside, the home features engineered hardwood flooring, sleek quartz countertops throughout, a large walk-in pantry, and the convenience of dual laundry rooms. Set in a tranquil, private location just minutes from Longboat Key’s renowned beaches, golf courses, and upscale dining, this home is a rare gem. Don’t miss your opportunity to own a waterfront retreat in one of Florida’s most sought-after coastal communities.
Listing Agent: Joshua Freed (941-577-5121)
1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228
$4,750,000203 Days on yellowkey MLS ID: A4666688
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4209 Built: 1987 Tax: $16,980 (2024)Community: Bay IslesSingle Family
Taxes:$16,980
Remarks: Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast.
Listing Agent: Julie Klick (941-780-6001)
578 - 580 COMPANION WAY, LONGBOAT KEY, FL 34228
$999,00068 Days on yellowkey MLS ID: A4682264
REDUCED by $1,000 (0.1%) on 04/19/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoApartment
Taxes:$11,672
Remarks: Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Linh Pham (941-900-6789)
578 COMPANION WAY, LONGBOAT KEY, FL 34228
$999,00068 Days on yellowkey MLS ID: A4682186
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoSingle Family
2425 GULF OF MEXICO DR #14B, LONGBOAT KEY, FL 34228
$1,690,000322 Days on yellowkey MLS ID: A4654664
REDUCED by $60,000 (3.4%) on 04/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $18,495 (2024)Community: Sea Gate ClubSpa: YesCondo
Taxes:$18,495
Remarks: BREATHTAKING WATER VIEWS FROM EVERY ROOM! Enjoy nightly sunsets from your private balcony in this beautifully updated 14th-floor condominium. This highly sought-after two-bedroom, two-bath split floorplan offers the perfect blend of privacy and open living. Each bedroom is positioned on opposite sides of the unit, creating an ideal layout for guests or remote work. Recent upgrades include Hurricane Impact Windows (2021), new flooring in both bedrooms (2021), updated bathrooms, fresh paint (2021), and an A/C system replaced in 2015. The convenience of an in-unit washer and dryer, a dedicated parking space, and ample guest parking add to the comfort of this coastal retreat. The beach and heated pool are just steps from your building, creating a true resort-style experience. Enjoy premium amenities such as a tennis court, air-conditioned bike room, kayak/paddleboard storage, clubhouse with kitchen, library/meeting space, and a fully equipped fitness center. Located within walking distance to Publix, CVS, places of worship, banks, the public library, and Town Hall. Just minutes to St. Armands Circle, where you'll find world-class dining and shopping. Immerse yourself in Sarasota’s rich cultural scene with easy access to the Sarasota Opera, Ballet, Ringling Museum, Selby Gardens, and numerous art galleries and theaters. This is your chance to live the Gulf Coast lifestyle—don’t miss it!
Listing is courtesy of: ANMARK REALTY LLC (941-363-1043)
Listing Agent: Andrey Markov (941-363-1043)
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