Location: Longboat Key , 34228
Do Not Show Listings
360 GULF OF MEXICO DR #312, LONGBOAT KEY, FL 34228
$1,100,000114 Days on yellowkey MLS ID: A4676411
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2298 Built: 1992 Tax: $13,341 (2025)Community: Tangerine Bay ClubCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,341
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Tangerine Bay Club An Island Resort-style condo located at the premier location on Longboat Key. This professionally painted 2 bedroom, 2.5bath with office/den features views of Sarasota Bay. It is in close proximity to New Pass and the pristine beaches of the Gulf of Mexico. Upgraded Ergon Fall White stone ceramic tile flooring is as beautiful as it is durable. The kitchen will satisfy your culinary desires an features; European cabinetry, lavish corian counters, Ge Profile Stainless steel appliances, Gas cooktop including an 18-bottle wine cooler and double oven. The chef's kitchen desk space will help you plan your extravagant meals. It is conveniently located near the breakfast nook and view of your courtyard. The open floor isilluminated by natural direct and indirect sunlight. Catch breathtaking sunrises over Sarasota Bay or relax by the gas fireplace during the winter. Hang out on the patio enjoying your favorite beverage and enjoy the lush exotic view. Mahogany doors through the residence give the condo a splendid feel. Stay cool all summer long with the brand- new Comfort Maker A/C unit that was just installed. Cleanses and refresh in your spa-like remodeled master bathroom with a new vanity, separate sinks, new toilet, new jacuzzi tub, tile quartz counters, and spacious neutral tile shower. Come enjoy the outrageous serenity of a LBK sunset. Maybe you will be lucky enough to witness a Flash of Green or Bioluminescence lights. Tangerine Bay offers resort-style amenities centered around one of the luxurious private pools on all of Longboat Key. The amenities include a cabana, fitness center, library, hot tub, and pool surroundedby tropical landscape. The resort also features tennis courts, pickleball courts, and a clubhouse. Organized social including group happy hours in the Cabana, scheduled group pickleball games, and planned excursions to local cultural happenings. Come hang out at Your Private Beach Access at Bay Isles Beach Club for only $250 per year. The privacy and island feel of Tangerine Bay is highlightedby its Bay front living enjoy the recently renovated boat dock which is a secret fishing spot or slip into your kayak and launch out for some peace and serene calm. Longboat key is one of the top destinations for enthusiasts of golf, tennis, fine dining, world-class fishing, and boating. In addition, Tangerine Bay Club is positioned at the southernmost point of theisland, walking distance to Quick Point Nature Preserve located on the New Pass and Sarasota Bay. Come check out all the tropical birds and enjoy a stroll through the nature path. Bring your fishing pole or picnic lunch. Tangerine Bay is located across from the famous Longboat Key Club Golf Course . Come enjoy fine dining in downtown Sarasota, St Armands Cir, or many highly rated island restaurants.Just over the bridge is City Island, Mote Aquarium, Ken Thompson Park, and Sarasota Sailing Squadron marina. The St. Armand's Circle shopping district and Lido Key Beach are just a few minutes drive.
Listing is courtesy of: SUNREAL ESTATE INC (941-376-7653)
Listing Agent: Karl Helbig (941-376-7653)
4900 GULF OF MEXICO DR #205, LONGBOAT KEY, FL 34228
$698,000166 Days on yellowkey MLS ID: A4671087
1 Days Off yellowkey (back on 2/18/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1312 Built: 1975 Tax: $6,787 (2024)Community: Windward BayCondo
Taxes:$6,787
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Breathtaking full bay views greet you as you enter this delightful 2 Bedroom 2 bath condo at Windward Bay. The interior has been freshly painted and fully updated with brand new Luxury Vinyl Plank flooring and Moen plumbing fixtures. The Unit boasts granite countertops and Brookhill custom wood cabinets in kitchen and baths, GE Profile double oven, Bosch stacking washer/dryer, Hunter Douglas window treatments, large walk-in master bed closet, hurricane impact windows, and Honeywell WiFi thermostat with humidity control. Enjoy the stunning waterfront views as you dine or relax on your private lanai. Windward Bay is a low density, pet friendly community nestled on 26 acres with 1/2 mile of waterfront trails and 3 adjacent beach accesses. (1deeded,2public). It enjoys a prime mid key location near dining, shopping, and world class entertainment in St Armand's Circle, Sarasota, and Anna Maria Island. The property has many recent updates including new roofs, painting of the mid-rises and extensive landscaping. Its numerous amenities include 2 heated pools, tennis and pickleball courts, 2 marinas with 28 boat slips, kayak racks and launches, covered parking, grills, firepits, and seating areas throughout, and a clubhouse with kitchen, meeting room, fitness center, 2 saunas, and a library. One of the very few units at Windward Bay with ALL of its assessments having been fully paid, including the 15 year Community Capital Improvement and the 30 year Longboat Key undergrounding. For added security, the State of Florida Milestone Inspection on all buildings is complete and Windward Bay is certified for an additional 10 years. Whether your're considering a getaway, a new home, or a rental property, don't miss this great opportunity to own your piece of paradise.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Richard Perlman (941-228-8580)
3408 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,645,000183 Days on yellowkey MLS ID: A4667842
REDUCED by $50,000 (1.9%) on 04/01/2026
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4510 Built: 1992 Tax: $20,206 (2024)Community: Coreys LandingSingle Family
Taxes:$20,206
Remarks: Elegant 5BR/5BA home in the gated community of Corey’s Landing within Bay Isles on Longboat Key. With over 4,500 sq ft, this spacious two-story residence offers open living areas, soaring ceilings, and refined design for both comfort and style. The light-filled great room with 22-ft ceilings opens to a gourmet kitchen with stone countertops, breakfast bar, and stainless-steel appliances. The main-level primary suite features pool access, dual vanities, soaking tub, and walk-in shower. A fifth bedroom or office, full bath, laundry room, and elevator complete the first floor. Upstairs includes three en-suite bedrooms, including a guest suite with private balcony and golf course and bay views. Outdoor living includes a screened lanai, heated pool and spa, and lush tropical landscaping. Updates include 2018 roof, new A/C (2023), tankless water heaters, and new pool/spa motors. Owners enjoy deeded beach access at the Bay Isles Beach Club plus community tennis, pool, spa, kayak launch, and 24-hour gated security. Close to the Longboat Key Club, offering world-class golf, tennis, marina facilities, dining, and a private Gulf-front beach experience, as well as the shops and restaurants of St. Armands Circle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
4350 CHATHAM DR #106, LONGBOAT KEY, FL 34228
$409,00029 Days on yellowkey MLS ID: A4687361
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $2,272 (2025)Community: Longboat HarbourCondo
Taxes:$2,272
Elementary School: Anna Maria Elementary
High School: Manatee High
Middle School: W.D. Sugg Middle
Remarks: Light, bright, charming and ready to move into! Kitchen gutted to studs, totally updated. Tile floors, lots of closet space throughout. Updated baths, Enclosed Lanai with tile floors and electric shades overlooks lovely water view. Lovely updated decor. Furnishings are negotiable . Longboat Harbour is amenity packed- 4 heated pools, tennis/pickleball, At the clubhouse/communinity center there is a full equipped gym with sauna and lockers, library, wood shop, kayak float/launch, social room, billiards room, shuffleboard. Great location! The community laundry room and pool are just around the corner and this unit in Building E has the shortest walk to the deeded beach access across the street, where there are restrooms and showers. Longboat Harbour is a very vibrant community with many social activites. An excellent rental as well. Call me for a showing. No water intrusions post-hurricanes 2024.
Listing Agent: Michael Yawitz (941-587-8091)
3070 GRAND BAY BLVD #632, LONGBOAT KEY, FL 34228
$724,900534 Days on yellowkey MLS ID: A4627468
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1276 Built: 1995 Tax: $7,802 (2024)Community: Grand Bay 6Condo
Taxes:$7,802
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Move in ready and beautifully updated two bedroom two bath Bimini model in Grand Bay nestled within the secure gated enclave of Bay Isles. Located on the third living level of the four level over parking building 6, you will enjoy panoramic views of Sarasota Bay as you gaze out from your almost 400 foot wrap around terrace offering sunrise and sunset views. This particular condo has been tastefully updated with new variable speed HVAC with humidity control & Wi-Fi thermostat in 2024; new water heater & significantly updated kitchen in 2026; new refrigerator, washer & dryer, Hunter Douglas battery operated remote-controlled window treatments, lighting & plumbing fixtures & freshly painted all in 2023. Nothing more to do but to move in and enjoy everything Grand Bay, Longboat Key and Sarasota have to offer especially with the recently renewed transferable Home-Tech service contract! Your amenities include two large resort style heated swimming pools and spas, tennis courts, state of the art fitness center and expansive clubhouse with social activities as well as access to the private white sandy well maintained beach at the Bay Isles Beach Club on the Gulf of Mexico. You will also have access to beautiful peaceful walking trails winding along the bay front, marina and golf courses. A short drive will lead you to choice eateries along Gulf of Mexico Drive or over the bridge to St Armands Circle and downtown Sarasota.
3040 GRAND BAY BLVD #213, LONGBOAT KEY, FL 34228
$1,550,00092 Days on yellowkey MLS ID: A4678941
Bed: 2 Bath: 3.5 Liv Area Sq Ft: 2550 Built: 1996 Tax: $8,474 (2025)Community: Grand Bay 2Condo
Taxes:$8,474
Remarks: Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance, residents enjoy resort-style amenities, deeded beach access, and a lifestyle defined by location, comfort, and waterfront elegance. The spacious primary suite offers a tranquil retreat with direct terrace access, peaceful water views, a large walk-in closet, and a spa-like bath featuring dual vanities, a soaking tub, and a walk-in shower. The generous kitchen featuring a Sub-Zero refrigerator and causal eat-in dining, den, and guest suite each open to a second terrace that overlooks Bay Isles’ beautifully landscaped grounds and tennis courts. The den offers versatility for a home office or additional living space, while the guest suite features an en-suite bath and private access to the expansive terrace. A dedicated wine and storage room adds a thoughtful layer of convenience and elegance, blending seamlessly into the home’s well-planned layout. Grand Bay residents enjoy an array of resort-style amenities, including two pools, a fitness center, tennis courts, a clubhouse, and deeded beach access through the Bay Isles Beach Club. Set behind the secure gates of Bay Isles, this residence offers the perfect blend of space, privacy, and the coveted Longboat Key lifestyle.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Dianne Anderson (941-350-3513)
2155 HARBOURSIDE DR #804, LONGBOAT KEY, FL 34228
$775,00072 Days on yellowkey MLS ID: A4681778
1 Days Off yellowkey (back on 3/31/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2119 Built: 1984 Tax: $6,299 (2025)Community: Harbor Oaks Ph I & IiCondo
Taxes:$6,299
Remarks: Under contract-accepting backup offers. Situated behind gates of the coveted Bay Isles on Longboat Key is the private enclave of Harbour Oaks. This meticulously renovated second floor residence offers an effortless blend of comfort, refinement, and coastal living. Offering an expansive 3 bedrooms, 2 bathrooms as well as a 2-car garage overlooking one of the most pristine Longboat Key Club golf courses. Furniture conveys with a few personal exceptions. Vaulted ceilings as well as skylights allow natural light to flood through the entire space. The custom modern kitchen is well-appointed with KitchenAid appliances including a 36-inch induction cooktop, built-in oven, refrigerator and dishwasher as well as a dedicated wine refrigerator within the expansive kitchen island. The master bedroom offers vaulted ceilings with a connected terrace to enjoy your morning coffee or watch beautiful Gulf sunsets. The primary bath exudes a sense of being at a spa with its tiled shower, glass shower door and double sink vanity. The third bedroom is currently being used as an office and gym, however could easily be set up as a bedroom. Harbour Oaks is also pet friendly and close to shopping, golf, tennis, beach and bay. Walks and bike rides can be enjoyed in one of the most scenic areas on Longboat Key. Bay Isles offers an exceptional coastal lifestyle including two fully staffed, 24-hour security entrances and exclusive access to a private, gated Gulf-front beach club. Residents have access to a thoughtfully appointed beachside retreat featuring a shaded pavilion, picnic spaces, restrooms, dedicated beach chair storage, grilling stations, and generous parking. Within minutes, access the famous St Armand’s Circle with its exceptional shopping and dining amenities. Cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining. Additional amenities are available within Bay Isles upon joining the Longboat Key Club.
Listing Agent: Alexis Smith-Frady (352-225-1724)
1241 GULF OF MEXICO DR #203, LONGBOAT KEY, FL 34228
$1,999,000190 Days on yellowkey MLS ID: A4668344
0 Days Off yellowkey (back on 3/31/2026)
Bed: 3 Bath: 4.0 Liv Area Sq Ft: 3045 Built: 1996 Tax: $25,305 (2025)Community: Water Club 01 At Longboat KeyCondo
Taxes:$25,305
Remarks: Under contract-accepting backup offers. Design your dream beachfront retreat at the Water Club on Longboat Key. This spacious three-bedroom, four-bath residence offers 3,000-plus square feet of living space with Gulf views and a flexible layout, ideal for creating your custom coastal masterpiece. The private primary suite features dual baths, walk-in closet and beachfront terrace. A generous guest suite sits on opposite end, and a den/office easily serves as a third bedroom with full bath nearby. The gourmet kitchen includes white cabinetry, stone counters, center island and a cozy breakfast nook overlooking the beach. The expansive great room opens to the main balcony, ideal for entertaining or relaxing. Additional highlights include semi-private elevator access and two desired garage parking spaces. Enjoy world-class amenities such as an 18,000-square-foot clubhouse, concierge, fitness center, spa, Har-Tru tennis courts, game room, beachfront pool and spa, fire pit and 24-hour gated security. Set on 16 lush beachfront acres with 680 feet of private shoreline. Pet-friendly. Just minutes to St. Armands, golf, marinas and downtown Sarasota.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Jo Rutstein (941-587-9156)
1241 GULF OF MEXICO DR #207 S, LONGBOAT KEY, FL 34228
$1,500,000189 Days on yellowkey MLS ID: A4668589
0 Days Off yellowkey (back on 12/12/2025)
Bed: 2 Bath: 4.0 Liv Area Sq Ft: 2965 Built: 1996 Tax: $15,546 (2024)Community: Water Club 01 At Longboat KeyCondo
Taxes:$15,546
Remarks: PRICE REDUCED! This beautifully furnished, move-in-ready residence at The Water Club stands among the best values in one of Longboat Key's most sought-after gulf-front addresses. Featuring two bedrooms plus a den and four baths, this refined coastal retreat offers an ideal combination of comfort, style, and convenience. Spanning 2,965 square feet, this residence welcomes you with new designer flooring, an open-concept layout, and abundant natural light. The spacious 2024 custom kitchen renovation showcases premium white cabinetry, quartz countertops, an island with bar seating, and Cafe' appliances-perfectly blending modern style with everyday functionality. Enjoy serene views of tropical landscaping and partial ocean views from the private terraces throughout. The primary master suite is a peaceful retreat featuring a spa-inspired bath with soaking tub, bidet, and glass-enclosed shower. The second bedroom also includes its own en-suite bath and terrace, while the open den provides flexible space for work or relaxation. This unit also has a separate controlled climate storage area and convenient ground-level garage parking. At the Water Club, residents enjoy resort-style living with 24-hour gated security, full concierge service, and a 17,000 square foot clubhouse featuring a spa, state-of-the-art fitness center, library, catering kitchen, and grand ballroom. Ideal for entertaining! Outdoors, residents can enjoy the Olympic-sized heated pool and Har-Tru tennis courts. The 600 feet of private white-sand beachfront is perfect for morning walks, sunset views, or relaxed days by the water. All this is just minutes from St. Armands Circle and downtown Sarasota. With its refined updates, including new flooring and a custom kitchen, this move-in-ready residence stands out as one of the best opportunities at The Water Club at Longboat Key.
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Lisa O'Hara (941-302-1688)
2600 HARBOURSIDE DR #J-04, LONGBOAT KEY, FL 34228
$350,000219 Days on yellowkey MLS ID: A4665164
Bed: Bath: 0.0 Monthly Fee: $420 Tax: $2,532 (2025)Community: Longboat Key Moorings Marina 2Dock-Rackominium
Taxes:$2,532
Remarks: Unique location on the lawn at Longboat Key Club Moorings! A 70 x 21 slip that is conveniently located near the Marina Village. One of the boaters favorite location. Club membership is not required. 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 marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 65 LOA; beam depends on the vessel. Call to discuss
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
230 SANDS POINT RD #3703, LONGBOAT KEY, FL 34228
$1,875,00023 Days on yellowkey MLS ID: A4687684
0 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1394 Built: 1982 Tax: $21,015 (2025)Community: Inn On The Beach Ph ICondo
Taxes:$21,015
Remarks: Under contract-accepting backup offers. Rarely available renovated corner two bedroom at The Resort at Longboat Key Club. Full gulf views from this 7th floor vantage are enjoyed from every room and the corner position offers extra square footage with extra windows. Located behind the gates of the Longboat Key Club, owners will enjoy the coastal contemporary finishes and excellent income history. As an owner, you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship golf, the award-winning Tennis Gardens, spa/wellness center, white sand beach with umbrellas and waitstaff and a full-service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying the Longboat Life today!
Listing Agent: Ian Addy, Pa (941-961-8850)
1425 GULF OF MEXICO DR #308, LONGBOAT KEY, FL 34228
$1,140,000111 Days on yellowkey MLS ID: A4676606
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2149 Built: 1983 Tax: $12,342 (2025)Community: Players Club IvCondo
Taxes:$12,342
Remarks: Enjoy the best of Gulf-front living in one of the largest units, this 3-bedroom, 3-bath residence with a flexible study/den/4th bedroom, in a gated community located on the sought-after south end of Longboat Key. This residence offers sweeping views of the Gulf of Mexico and includes an enclosed lanai with new telescopes, hurricane windows, and a spacious interior with tile floors in the main living areas and a neutral color palette. A wall of sliding glass doors in the living room opens to a spacious enclosed terrace—perfect for relaxing, dining, and enjoying the sounds of the surf through the new telescoping hurricane windows. The kitchen is large enough for all the chefs in the family. Corian countertops, a tile backsplash, and a breakfast bar that connects easily to the living space. The primary suite includes a king-size bed, wake up to view of the Gulf, access to the terrace, and an en-suite bath with a large walk-in shower. For your guests, the second bedroom has an en-suite bathroom. The third bedroom provides a great space for guests or a home office. The private terrace offers views of the beautifully maintained grounds, the beach, and the Gulf beyond. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, 4 Har-Tru pickleball courts, a putting green, and a heated saltwater pool and spa. Players Club is located just a short drive to St. Armands Circle, where you will enjoy the shopping and dining experiences. Just over the Ringling Bridge, there are many theater options downtown Sarasota. Additional conveniences include on-site management and a 24-hour staffed gate, ensuring comfort and peace of mind.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Diane Smith (941-313-4957)
1955 GULF OF MEXICO DR #G6-311, LONGBOAT KEY, FL 34228
$1,049,00024 Days on yellowkey MLS ID: A4687954
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1978 Tax: $8,677 (2025)Community: Seaplace IvCondo
Taxes:$8,677
Remarks: Experience the coastal gulf front living lifestyle to its fullest, in this 3-bedroom 2 bath condo with views of the Gulf from inside as well as the 2 balconies. Make this your new oasis and enjoy the sunsets off one of your two separate balconies (one off the main living area and another private balcony for the primary bedroom). Start experiencing this 3-bedroom condo at Seaplace which is located on a pristine beach area of Longboat Key. There is an array of amenities across the 42 beautifully landscaped acres, including two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center and a new gulf front firepit area. The clubhouse offers a kitchen, library, fitness area and sauna. Additional features include playground, grilling areas, on-site management, and a 24-hour staffed gatehouse.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Bruce A Meyer, Pa (941-266-8152)
825 TARAWITT DR, LONGBOAT KEY, FL 34228
$1,599,00048 Days on yellowkey MLS ID: A4684674
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1882 Built: 1982 Tax: $19,384 (2025)Community: Longboat KeySingle Family
Taxes:$19,384
Remarks: Welcome to Your Beach House Sanctuary on Longboat Key! Experience the ultimate coastal lifestyle in this beautifully renovated island retreat, ideally situated just four homes from Tarawitt Point on a deep-water canal. Set on an expansive 125x90 ft lot, this waterfront property offers 125 feet of seawall with dockage for a boat up to 30 feet, a jet ski lift, and additional space for all your water toys. With the Intracoastal Waterway just 50 yards from the canal’s end, you’ll enjoy direct, no-bridge access to Sarasota Bay—perfect for fishing, cruising, or sunset boating. Catch bait and be fishing in under 30 minutes! Inside, this meticulously maintained home features: 3 spacious bedrooms, 2 full baths + 1 half bath, 1-car garage, Open-concept floor plan with stunning bay views! The oversized primary suite offers a comfortable seating area, TV space, a generous walk-in closet, and a beautifully updated bath with dual vanities and a large walk-in shower. The kitchen and living area flow seamlessly onto a porch overlooking the bay—ideal for morning coffee or evening cocktails. Renovated in 2022, the home boasts a new roof, new windows and doors, granite countertops, new appliances, updated bathrooms, new flooring, fresh interior and exterior paint, and even a relaxing hot tub. Deeded beach access sits directly across Tarawitt Drive, offering effortless enjoyment of the Gulf’s turquoise waters and sugar-sand beaches. Enjoy walkable access to some of the island’s favorite dining destinations, including: Harry's Restaurant, Euphemia Haye, The Lazy Lobster, A short bike ride takes you to: The Shore Restaurant, Mar Vista Dockside Restaurant And you’re just an easy drive to Anna Maria Island, St. Armands Circle, and downtown Sarasota. This is more than a home—it’s a waterfront lifestyle defined by boating, beach days, and breathtaking bay views.
Listing is courtesy of: BRISTA REALTY LLC (941-373-0500)
Listing Agent: Ian Greenberg, Llc (941-724-4003)
6322 LAGUNA DR #1, LONGBOAT KEY, FL 34228
$2,499,900180 Days on yellowkey MLS ID: A4669170
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2886 Built: 2001 Tax: $12,100 (2024)Community: Laguna Yacht Village A CondoSingle Family
Taxes:$12,100
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Welcome to Laguna Yacht Village on beautiful Longboat Key- a gated waterfront community located across the street from the beach, with private bay access. This fully furnished turnkey home is perfectly positioned to embrace the island lifestyle, with fantastic gulf views from almost every room. The home includes a deeded deep-water dock (Slip #6- boat lift included), located in a protected lagoon just minutes from the Intracoastal Waterway and Gulf of Mexico with no fixed bridges, making it a boater’s dream. This modern Key West inspired three story single residence with an oversized 3-car garage features four bedrooms, three full baths, and over 2,886 square feet of beautifully designed living space. Perfectly positioned to embrace the island lifestyle, this home includes a deeded deep-water dock (Slip #6) located in a protected lagoon just minutes from the Intracoastal Waterway and Gulf of Mexico — with no fixed bridges, making it a boater’s dream. Step inside and experience a harmonious blend of coastal elegance and comfort. Expansive living areas feature soaring ceilings, an abundance of natural light, and sophisticated finishes throughout. The culinary-inspired kitchen, designed in timeless style, boasts custom cabinetry, quartz countertops, and an oversized central island — the ideal space for hosting and entertaining. The primary suite, complete with a study, serves as a serene retreat with dual vanities, a hydro-massage soaking tub, and a walk-in glass-enclosed shower for the ultimate spa-like experience. Multiple balconies, including an elevated screened patio off the main level, provide refreshing sea breezes and captivating water views of the Gulf. A ground-floor patio further extends the outdoor living experience. The oversized garage provides ample storage for beach gear and boating essentials. The gated community features a resort-style pool offering a true lock-and-leave lifestyle. Residents will appreciate convenient proximity to Longboat Key’s pristine beach, award-winning island restaurants, boutique shopping, and parks — all while being a short drive from the cultural heart of downtown Sarasota and St. Armands Circle.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Brandy Loebker (941-404-4737)
2800 HARBOURSIDE DR #F-06, LONGBOAT KEY, FL 34228
$339,00049 Days on yellowkey MLS ID: A4684822
Bed: Bath: 0.0 Built: 1985Monthly Fee: $573 Tax: $3,032 (2025)Community: Bay IslesDock-Rackominium
Taxes:$3,032
Remarks: Slip F-06 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 70 X 26, and a usable beam of 23 feet and a 32 FT long finger pier. This location provides close proximity to parking with a view of the west side of the marina and golf courses. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis and golf facilities, fitness center, with spa and beach access. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 65 feet. Beam; on the vessel type and measure. Membership in the Longboat Key Club is required.
1085 GULF OF MEXICO DR #404, LONGBOAT KEY, FL 34228
$950,00030 Days on yellowkey MLS ID: A4686960
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1503 Built: 1981 Tax: $5,482 (2025)Community: Beachplace IiiCondo
Taxes:$5,482
Remarks: Coveted Southern exposure offering morning sun with a very tropical feel over looking the Longboat Key Club golf course. With palm trees and beautifully landscaped grounds right outside your windows and privacy on your balcony. Featuring two bedrooms and two bathrooms, this spacious residence is open and airy with a beautifully updated kitchen, bathrooms and impact windows, this is the largest two bedroom available at Beachplace offering 1503 sq. ft. This residence also includes TWO under building parking spaces and one outside parking space that convey with the property. Beachplace offers a very nice fitness center, a guard gated entry, a Junior Olympic sized swimming pool, a splash pool, hot tub, tennis, pickle ball, grilling area and the beach is equipped with lounge chairs and umbrella's. Beachplace offers a Jr. Olympic sized swimming pool with swim lanes, a splash pool, hot tub, fitness center, grilling area, tennis, pickle ball and a 24 hour guard gated entrance. All furnishings are included and this would make a great rental.
Listing Agent: Maggie Hicks (941-321-1759)
669 SPANISH DR N #21, LONGBOAT KEY, FL 34228
$339,000329 Days on yellowkey MLS ID: A4653816
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1087 Built: 1969 Tax: $5,733 (2024)Community: Spanish Main Yacht Club CondoCondo
Taxes:$5,733
Remarks: One or more photo(s) has been virtually staged. Priced to sell - Fully renovated villa ready for immediate occupancy! Welcome to Spanish Main Yacht Club, a sought-after 55+ waterfront community on Longboat Key, where coastal living meets exceptional value. This 2-bedroom, 2-bath villa-style condo offers 1700 SqFt of interior living space, 1087 of it under air, with endless potential to make it your dream home. This stand-alone condo has undergone FEMA-approved storm mitigation and a full rebuild. Bring your vision and decorate to suit your personal style—below market value! Step inside to find a spacious open-concept living and dining area, perfect for entertaining. The adjoining Florida room offers additional flexible space, bathed in natural light—ideal for morning coffee or quiet evenings. The primary suite features an en-suite bathroom, closet and indoor laundry room. Enjoy private beach access just steps away, or take advantage of the community marina with first-come, first-served boat slips, kayak racks, and direct access to Sarasota Bay. Amenities include a heated outdoor pool, shuffleboard courts, a clubhouse with game room, library, and frequent community events. This pet-friendly community offers covered carport parking, guest spaces, and maintenance-free living, all set within beautifully maintained, palm-lined grounds. Just minutes from St. Armand’s Circle and Anna Maria Island, this location offers world-class shopping, dining, and entertainment, plus access to some of Florida’s finest white sand beaches. Whether you're looking for an investment, full-time residence or a vacation getaway, this villa offers endless potential in one of Longboat Key’s most desirable communities. Seller says bring offers—don’t miss your chance to own a piece of paradise!
Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)
Listing Agent: Geoff Scalera (941-321-4158)
1105 GULF OF MEXICO DR #401, LONGBOAT KEY, FL 34228
$999,99976 Days on yellowkey MLS ID: A4680369
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1172 Built: 1981Monthly Fee: $1,600 Tax: $8,733 (2025)Community: Beachplace IiCondo
Taxes:$8,733
Remarks: Direct Ocean view from this Bright Airy corner unit in desirable building five. Catch the view of the Gulf of Mexico and Sunsets from your balcony. To see this property is to fall in love with easy living! You need to visit this unit to get a sense of the remarkable views , especially the amount of light that permeates the entire interior. Beachplace is a perfect get away on the south end of Longboat Key, and comprise many amenities. Pickle Ball, Tennis, two exercise facilities, Olympic pool, with designated lap lanes, over size hot tub , covered baby pool . Electric car chargers, gas grill
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: James Weingart (440-623-9068)
4825 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
$839,900203 Days on yellowkey MLS ID: A4667044
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $11,897 (2024)Community: Westchester AptsCondo
Taxes:$11,897
Remarks: Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The pool area is currently undergoing a transforamtion and will include a new spa, a tiki hut and new landscaping when complete. Also important: The Westchester has completed its Milestone Inspection and all assessments have been paid in full.
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
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