Location: Longboat Key
Do Not Show Listings
744 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$975,000187 Days on yellowkey MLS ID: TB8463320
1 Days Off yellowkey (back on 7/1/2026)
REDUCED by $150,000 (13.3%) on 06/29/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1688 Built: 1963 Tax: $7,142 (2024)Community: Longboat KeySpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,142
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. Laid-back Living on Longboat Key -- A Boater's Paradise! Welcome to 744 Jungle Queen Way, a fully renovated, FURNISHED 3-bedroom, 2-bathroom coastal retreat on the stunning Longboat Key! Whether you're a boating enthusiast, a beachcomber, or someone who just loves the island life, this home delivers the ultimate Florida lifestyle. ***Prime Location & Waterfront Living Nestled just seven homes away from Sarasota Bay, this property is a boater's dream with two boat lifts, offering quick access to the Gulf of Mexico's crystal-clear waters. Spend your days fishing, cruising, or island-hopping--all from your backyard! ***Deeded Beach Access - Just 777 Steps to Paradise... take a short stroll across Gulf of Mexico Drive and find yourself on the powdery sands of Longboat Key's legendary beaches. Enjoy sun-soaked days, breathtaking sunsets, and gentle Gulf breezes right outside your door. ***Close to Local Favorites & Hidden Gems. In just a short walk, you'll find island hotspots like the Lo'Key Island Grille, Guppy's Restaurant, and the award-winning Euphemia Haye. A short boat ride, you can enjoy The Shore, Cortez Kitchen, Swordfish Grille, Tide Tables, Anna Maria Oyster Bar, Bridgetenders and Dockside restaurants. ***Modern Updates with Coastal Charm. Step inside to an open-concept layout featuring a spacious, upgraded kitchen with solid wood cabinetry and stone countertops -- perfect for entertaining. The home's split-bedroom design ensures privacy, while the extra-wide lot provides a natural buffer between properties for peace and tranquility. ***Take a short scenic 1-mile stroll from your front door to enjoy the beauty of Florida's coastal landscape at Joan M. Durante Park and the Sarasota Bay overlook dock for a peaceful escape. This 32-acre bay front nature preserve features winding boardwalks, shaded trails, and scenic waterfront views, perfect for birdwatching, peaceful walks, or catching a sunrise over the mangroves. ***Your Slice of Island Paradise Awaits! Whether you're looking for a full-time residence, a vacation getaway, or an investment property, this home captures the essence of laid-back luxury. Don't miss your chance to live the dream on Longboat Key! ***Schedule your private showing today!
Listing is courtesy of: YOUR HOMETOWN REALTY, INC. (813-645-7007)
Listing Agent: Teddi Aberle (813-645-7007)
1211 GULF OF MEXICO DR #109, LONGBOAT KEY, FL 34228
$975,00059 Days on yellowkey MLS ID: A4694082
5 Days Off yellowkey (back on 6/30/2026)
REDUCED by $25,000 (2.5%) on 06/26/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1827 Built: 1985 Tax: $6,388 (2025)Community: PromenadeSpa: YesCondo
Taxes:$6,388
Tax Year: 2025
Remarks: Under contract-accepting backup offers. Virtually Staged. Experience beachfront living at its finest at The Promenade on Longboat Key. This beautifully positioned residence showcases sweeping Gulf Views expansive terraces, and a seamless connection between indoor and outdoor living. Floor-to-ceiling windows fill the home with natural light while framing spectacular sunsets, pristine beaches and lush tropical surroundings. Thoughtfully designed with custom woodwork and an open , flowing layout, the residence offers exceptional comfort and flexibility. The kitchen enjoys water views and a unique connection to celebrated culinary icon, Marcella Hazan. Often called "the godmother of Italian cuisine', her award-winning documentary premiered at the Sarasota Film Festival! Residents enjoy resort-style amenities including concierge services, a staffed gatehouse, over-sized heated pool and spa, tennis courts, men's & women's fitness facilities, the Sunset and Sunrise club rooms, beachside gathering areas and direct access to the Gulf. Ideally located on the coveted south end of Longboat Key, The Promenade offers convenient access to St Armands Circle, downtown Sarasota , premier golf, dining, shopping, arts and cultural attractions. A rare opportunity to enjoy an exceptional beachfront lifestyle in one of Longboat's most sought after communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Bill Blume (941-525-6257)
549 HALYARD LN, LONGBOAT KEY, FL 34228
$2,195,00025 Days on yellowkey MLS ID: A4696535
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1594 Built: 1965Monthly Fee: $23 Tax: $20,602 (2025)Community: Country Club ShoresSingle Family
Taxes:$20,602
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: This is the one * PERFECTLY POSITIONED ON A QUIET CUL DE SAC STREET AT THE PREFERRED SOUTH END OF LONGBOAT KEY * Located on the QUIET END OF THE CANAL with OPEN WATER JUST BEYOND YOUR DOCK and the PRIVATE BEACH ACCESS ONLY MINUTES AWAY * A quick 3 minute cruise to Sarasota Bay & the ICW & The GULF * This coveted Country Club Shores IV home has been LOVINGLY RENOVATED with a NEW Kitchen & modern amenities while retaining its classic charm * NEW KITCHEN CABINETS * NATURAL GAS STOVE * GE CAFE APPLIANCES * NEW Solid Core Doors * FULL HURRICANE PROTECTION * NEW TILE Flooring throughout * 2 Car Garage has a NEW Mini Split A/C * Primary Suite with a Spa-style Bath featuring a LARGE Walk-in Shower * BEAUTIFUL VIEWS OF YOUR POOL & PRIVATE CANAL * This THOUGHTFULLY CURATED HOME is an open floor plan * The additional Bedrooms are well-appointed and located in a way that allows for guest privacy * Impact Sliding Glass Doors surround the Outdoor Area * ROOF IS 9 YEARS YOUNG * WATER HEATER IS 3 YEARS YOUNG * All of this wraps your Caged Pool with Paver Decking and a Paver Walkway to your 2021 NEW SEAWALL & COMPOSITE DOCK with a 10,000lb Boat Lift & 2 Additional NEW Jetski Lifts PLUS a 2-step down Kayak Dock Launch with Power & Water * THIS IS A BOATER'S DREAM * The PERFECT HOME & OUTDOOR OASIS to entertain family & friends or just simply relaxing in your slice of paradise * PRIDE OF OWNERSHIP SHOWS IN THIS IMMACULATE HOME * Furniture is available * Just bring your suitcase * Country Club Shores is a well established waterfront neighborhood offering DEEDED BEACH ACCESS with a convenient south end location close to ST ARMAND'S CIRCLE, The new ST REGIS, and even downtown Sarasota * Join the Longboat Key Club offering 45 holes of championship golf & world class tennis * Your family will love this home * One look & you'll fall in love! *
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Ryan Brown (941-330-7774)
1241 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228
$2,745,000262 Days on yellowkey MLS ID: A4669837
0 Days Off yellowkey (back on 6/26/2026)
REDUCED by $10,000 (0.4%) on 06/23/2026
Bed: 3 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3045 Built: 1996 Tax: $25,341 (2024)Community: Water Club 01 At Longboat KeyCondo
Taxes:$25,341
Remarks: Welcome to The Water Club at Longboat Key, where privacy, spaciousness, and resort-style amenities complement the natural beauty of the setting at the edge of the sparkling waters of the Gulf of Mexico. Residents benefit from a semi-private elevator that opens directly into an impressive foyer, offering sweeping views of Sarasota Bay and the city skyline through floor-to-ceiling windows. This residence is on the north side of the south building, the sunset view side, overlooking the beautiful pool deck amenity of the community. This eighth-floor Brighton residence is highly coveted for its three-bedroom configuration with panoramic vistas of the Gulf, beach, and bay from two expansive terraces. Features include ten-foot ceilings, extensive glass walls, and storm protection shutters , enhancing both comfort and sophistication. The living room is designed to maximize openness and showcase sunsets over the Gulf. The primary suite offers a private terrace, den, walk-in closet, and dual bathrooms. With a split-bedroom plan, privacy is maintained for two generous guest suites, each featuring an en-suite bath. The kitchen is efficiently appointed with significant storage and a breakfast area overlooking the water. The Water Club stands as Longboat Key’s premier gated beachfront community, situated on 16 acres of meticulously landscaped grounds. Amenities include a 17,000-square-foot clubhouse, well-equipped fitness center and spa, heated lap pool and hot tub, four Har-Tru tennis courts, concierge services, and versatile gathering spaces such as a library, billiards room, ballroom, firepit, and grilling area. Additional conveniences include under-building parking, climate-controlled storage, on-site management, and 24-hour security. Ideally located on the south end of Longboat Key, residents enjoy proximity to Longboat Key Club golf facilities, Publix shopping center, exclusive St. Armands Circle, downtown Sarasota’s cultural offerings, and Sarasota International Airport, just 20 minutes away. The Water Club is pet-friendly and impeccably maintained, providing the pinnacle of coastal luxury living. You must live on the side of this building where this residence is located to see the sunset.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Michael Moulton (941-928-3559)
612 JUAN ANASCO DR, LONGBOAT KEY, FL 34228
$22,500,000499 Days on yellowkey MLS ID: A4643123
0 Days Off yellowkey (back on 6/30/2026)
Bed: 6 Bath: 8.0 Gar: 9 Liv Area Sq Ft: 9243 Built: 2024 Tax: $32,107 (2024)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$32,107
Remarks: Under contract-accepting backup offers. Welcome to your private, gated estate on Longboat Key, where coastal luxury meets effortless sophistication. Boasting over 730 feet of water frontage, this stunning property offers panoramic views of Whitney Bayou and Harris Canal and provides the ultimate waterfront lifestyle. With 9,243 square feet of air-conditioned living space and a total of 21,562 square feet on over an acre of pristine land, this estate is a masterpiece of design and craftsmanship. Designed in the timeless British West Indies style, this home showcases vaulted ceilings, extensive trim detailing, white oak floors throughout, and two fireplaces, creating an ambiance of elegance and warmth. The expansive covered patios and porches invite you to embrace the serenity of waterfront living, while the heated pool and an impressive 13' x 13' hot tub serve as the ultimate retreats. A custom outdoor fire pit, two outdoor kitchens, and indoor and outdoor pool tables elevate the entertainment experience. For boating enthusiasts, this estate is unrivaled, featuring four low-profile boat lifts—the largest accommodating vessels up to 30,000 pounds, the second suitable for a vessel up to 20,000 pounds, and the third and fourth lifts each with a 5,000-pound capacity, ideal for jet skis, kayaks, and paddle boards. Located just 10 minutes from the Gulf of Mexico by boat and 5 minutes to Shore and Mar Vista restaurants, this is the perfect haven for life on the water. Inside, the Wolf Sub-Zero appliances provide top-tier performance in a gourmet kitchen built for culinary excellence. A Control4 smart home system offers seamless automation throughout, while HVAC-equipped garages ensure comfort year-round. The multiple garages can accommodate up to 9 cars, and the massive driveway can host 20+ vehicles. The residence boasts six spacious bedrooms, each with an en-suite bathroom, plus an additional full bath and two half baths. Designed for both productivity and leisure, the home features his and hers offices, a media/theater room, a fully equipped gym, sauna, golf simulator, tackle garage, and a workshop. A private guest suite with a separate entrance includes a kitchenette, dining room, living room, bedroom, and bathroom, offering a luxurious retreat for visitors. With two state-of-the-art elevators, expansive landscaping, and a maintenance-free turf yard, this estate blends modern convenience with natural beauty. Ideally located near pristine beaches, world-class shopping, and gourmet dining, this estate is the epitome of waterfront elegance and exclusivity. Experience the pinnacle of coastal living—this is truly paradise found.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Charles Buky (941-228-6086)
3030 GRAND BAY BLVD #PH3101, LONGBOAT KEY, FL 34228
$7,999,000133 Days on yellowkey MLS ID: A4685052
2 Days Off yellowkey (back on 6/30/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4413 Built: 1998 Tax: $36,728 (2025)Community: Grand Bay 3Spa: YesCondo
Taxes:$36,728
Remarks: Under contract-accepting backup offers. Breathtakingly gorgeous PENTHOUSE level condominium recently and meticulously redesigned to a clean-line ultra-luxury residence with advanced ultra smart-home technology managing the entire home. This rarely available opportunity offers a refined coastal lifestyle with the highest quality for the discerning buyer. The 4400-square foot custom residence features a dramatic private 5300-square foot wraparound terrace with outdoor kitchen and panoramic 270-degree sunrise-to-sunset views of the area including Sarasota Bay, the golf course, Sarasota city skyline, marina, Gulf of Mexico and beach area of Longboat Key. At an understated tasteful level of luxury living, the thoughtfully designed space now offers 3 ensuite bedrooms, an entertainment room, a den or office, living room, dining area, and a large functional kitchen featuring Cucine Ricci cabinetry, Dornbracht fixtures, high-end appliances, and a discreet area containing the butler's pantry, dry bar, and extensive storage. A premium Lutron smart-home system manages lighting, air conditioning, doors, window treatments, plumbing fixtures and electronics enhancing home convenience and elegance. The impressive primary bedroom suite is complete with stunning views, a fabulous dressing room with multiple built-ins, expansive personalized and automated bathroom with heated tile floors & towel racks, and sleek clean-finish tile & minimalist easy-cleaning cabinetry. Each private and spacious guest suite is thoughtfully planned with a complete built-in beverage center, bathrooms with heated floors and private balcony. As an extra bonus this sophisticated penthouse is sold fully furnished with high-end custom furniture tailored to the design. Words cannot describe this extraordinary residence purposefully created with no expense spared and where nothing has been overlooked. It must be experienced to be appreciated. Also included are two deeded parking spaces with Tesla charging station and air-conditioned storage unit. Grand Bay is among Longboat Key’s premier gated communities, offering resort-style amenities including two heated pools, Har-Tru tennis courts, a well-equipped fitness center, clubhouse, and social activities. Residents benefit from on-site management and 24-hour security. Ownership includes deeded access to the private Bay Isles Beach Club, featuring a Gulffront pavilion, grilling areas, and beautiful sandy beaches. Located within the Longboat Key Club, residents have the option to join golf, tennis, and social memberships, all just minutes from the boutiques and dining on world-renowned St. Armands Circle, downtown Sarasota’s cultural attractions and Harbourside Marina. Appraisal available.
Listing Agent: Carolyn Donnelly, Pa (941-350-9900)
3710 GULF OF MEXICO DR #F2, LONGBOAT KEY, FL 34228
$475,000133 Days on yellowkey MLS ID: A4681154
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 740 Built: 2026Monthly Fee: $290 Tax: $2,070 (2025)Community: Gulfshore Of Longboat KeyManufactured Home
Taxes:$2,070
Remarks: Island Living at Its Finest – Brand New Home on Longboat Key. Welcome to Gulfshore of Longboat, a highly desirable waterfront co-op community offering private beach access, boat docks, and sweeping views of the Gulf of Mexico and Sarasota Bay. This beautifully built 2-bedroom home combines modern efficiency with relaxed coastal living. An outdoor bathroom with a shower is a wonderful convenience for those enjoying the pool or boating. Step inside to an open, sun-filled floor plan featuring soaring ceilings with tray accents in both the living room and the primary bedroom, creating a bright, spacious atmosphere throughout. The kitchen is designed for everyday comfort and entertaining, complete with a center island, hardwood shaker cabinetry with soft-close doors and drawers, and a full stainless appliance package including refrigerator with ice and water, range, dishwasher, microwave, and garbage disposal. Built to current HUD hurricane standards and Energy Star certified, the home offers peace of mind with 2x6 construction, upgraded insulation, and low-E vinyl windows for year-round comfort and efficiency. Enjoy mornings at the private beach, afternoons at the heated pool, and evenings watching sunsets over the water. The community clubhouse hosts regular activities, making it easy to relax and connect with neighbors in a friendly coastal setting. Whether you’re looking for a winter retreat or full-time residence, this move-in-ready island home delivers comfort, security, and the lifestyle Longboat Key is known for. No pets (except for service animals or emotional support animals with appropriate paperwork) or Rentals permitted. Schedule your private showing today and start living the Gulf Coast dream.
Listing is courtesy of: WAGNER REALTY (941-751-0670)
Listing Agent: Marsha Winegarden (248-563-2820)
2425 GULF OF MEXICO DR #14E, LONGBOAT KEY, FL 34228
$1,675,000122 Days on yellowkey MLS ID: A4686539
REDUCED by $25,000 (1.5%) on 06/25/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $13,728 (2025)Community: Sea Gate ClubSpa: YesCondo
Taxes:$13,728
High School: Riverview High
Remarks: Under contract-accepting backup offers. Back on the market, buyer's financing fell through. Home inspection already completed and all good, and appraisal from bank already completed with no issues. Amazing and Unobstructed 14th Floor Gulf and Beach Views! This is the perfectly remodeled unit you've been waiting for, with stunning sky views! Open floor plan, tile floors throughout, gorgeous open kitchen, and split bedroom floor plan. Just move right in and enjoy the views and amenities. The building has been completely remodeled. New roof, new windows, new railings, new pool, new storage lockers, updated elevators, new parking lot paving. NO PENDING SPECIAL ASSESSMENTS! Every owner has paid over $130K in the last 5 years to update the building and facilities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Robert Delaney (941-315-3185)
450 GULF OF MEXICO DR #B207, LONGBOAT KEY, FL 34228
$650,000286 Days on yellowkey MLS ID: A4667364
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1474 Built: 1970 Tax: $6,830 (2024)Community: Bay Harbour AptsCondo
Taxes:$6,830
Remarks: Where can you find an exquisite 3-bedroom waterfront condo on the coveted South End of Longboat Key under $700,000? Discover the ultimate island lifestyle in this beautifully furnished end unit located in the highly sought-after Bay Harbour community. Boasting a desired southern exposure, lower maintenance fees, and a pet-friendly policy, this condo is the perfect blend of comfort and convenience. Even better, the 2023 special assessment of $23,000 has been paid in full, covering a new roof, total building painting, and internal pipe lining. This immaculate home features a bright, coastal interior with a serene, open layout and spectacular bay and pool views through the multiple windows only an end unit can offer. The living room and third bedroom are elevated by beautiful moldings and updated ceilings, while the newer kitchen is a chef’s dream with all under-cabinet pull-out drawers and a clever corner turn-around for maximum storage. The bathrooms present an excellent opportunity for a new owner to customize and enhance the space with contemporary finishes. The primary suite is a true retreat, offering breathtaking water views and exceptional closet space with his-and-her built-ins. A unique design feature allows the hallway door to close, transforming the master entry into a private dressing room complete with a full-length mirror. For guests, the hallway is equipped with a pocket door to provide more privacy. The master bedroom also is equipped with a pocket door. Whether you use the expansive third bedroom for visiting family or as a home office, the versatility of the space is unmatched. Step outside and immerse yourself in the beauty of Sarasota Bay, where you'll enjoy direct access to a kayak launch and optional boat slips just steps from your front door. For boating and nature enthusiasts, Bay Harbour is a true gem. Enjoy direct access to a kayak launch and optional boat slips just steps from your front door. With no bridges to Sarasota Bay and just one to the Gulf, you'll have unrestricted access to deep waters for boats up to 42 feet. The remodeled marina is fully equipped with electrical, freshwater, and a fish cleaning station, while the seawall offers frequent visits from dolphins and playful manatees. This unparalleled location is just minutes from world-renowned St. Armands Circle and downtown Sarasota, and it is walkable to the Longboat Key Club, Dry Dock, and Charthouse. Whether you're seeking a permanent residence or a seasonal retreat, this waterfront oasis offers the perfect combination of location, luxury, and lifestyle.
Listing Agent: Mairead Smialek (847-334-4848)
2945 PYRULA DR, LONGBOAT KEY, FL 34228
$3,125,00063 Days on yellowkey MLS ID: O6408404
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4340 Built: 2024 Tax: $36,325 (2025)Community: Coquina BeachSpa: YesSingle Family
Taxes:$36,325
Remarks: A contemporary masterpiece awaits Your going to love this house !, constructed in 2024 and completed in December of 2025 this newly built residence blends contemporary architecture with uncompromising craftsmanship. The craftsmanship, and finishing touches puts this property in a class by itself when making your buying comparisons. Worth repeating….Your going to love this house! Step into more than 4300 square feet of modern design perfection ideally located in one of Longboat Keys most coveted neighborhoods. Just minutes on foot brings you to pristine beach access or a tee time at the prestigious Longboat Keys club. Seamless indoor- Outdoor living, a stunning floor to ceiling glass wall sets the tone from the moment you walk in revealing a private courtyard that feels like your own luxury resort, complete with an elegant pool, a relaxing spa, and a fully equipped outdoor kitchen and dining area. This harmonious flow creates an exceptional living experience where the outdoors becomes an extension of the home . Refined interiors inside , warm oak wood flooring runs throughout the home beautifully paired with stone accents , sleek cabinetry , and high end finishes. The chef designed kitchen is crafted for culinary excellence and features quartzite countertops prized for their durability, beauty, and unmistakably high end character. The primary suite is a serene retreat with glass walls overlooking the courtyard , a soaking tub , a separate shower, and generous storage. Spaces designed for comfort the home offers five bedrooms including An in law suite with a kitchenette, private laundry, spacious bedroom, and walk in shower. An additional bedroom on the main level with its own private balcony . Upstairs two guest suites connected by a bright relaxation area with courtyard views through the floor to ceiling glass. Striking modern architecture, the exterior showcases clean contemporary lines enhanced by rare hand selected stone and rich custom woodwork. Come visit this spectacular offering. ..
Listing is courtesy of: PROPERTIO (888-817-3383)
Listing Agent: Alin Zdroba (888-817-3383)
2089 GULF OF MEXICO DR #G1-108, LONGBOAT KEY, FL 34228
$675,000145 Days on yellowkey MLS ID: A4683552
REDUCED by $24,000 (3.4%) on 04/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 933 Built: 1974Monthly Fee: $1,250 Tax: $6,817 (2025)Community: Seaplace ICondo
Taxes:$6,817
Remarks: Welcome to G1-108, a recently remodeled and fully-furnished residence in Seaplace! Overlooking the pristine sands and sunsets of the Gulf, this first-floor 2 bedroom/2 bathroom residence offers unparalleled access to the beach and resort-style amenities. In early 2025, this residence was extensively remodeled, including impact-resistant hurricane door, new bathrooms and a new kitchen with stainless steel appliances and modern cabinetry. The master suite is a cozy, spacious retreat with a walk-in closet and bathroom. The second bedroom is the perfect space for family and guests, featuring 2 twin beds and a full bathroom. The home also features a new lanai, a comfortable place to relax and soak in the views. Sliding door and all windows are hurricane impact rated. Complimentary with the residence is one parking spot and a designated storage space - perfect for storing any extra beach gear. This residence is being offered furnished. Seaplace is a premier, 24-hour gated and guarded community on Longboat Key. The community boasts 2 swimming pools and hot tubs, a clubhouse and fitness center, fire pit, playground, grilling station, outdoor showers and three Har-Tru tennis courts. Perhaps the most stand-out amenity of this community is its direct beach access already set with lounge chairs and umbrellas. All you have to bring is yourself, your sunscreen and your towel! Going to the beach could not get any easier. Just a short distance from grocery shopping, local boutiques and first-class restaurants and entertainment, G1-108 is perfectly situated to give you that beachfront lifestyle you’ve been looking for. Everything that Longboat Key, St. Armand’s Circle, Anna Maria Island and Downtown Sarasota have in store is at your fingertips. Whether as your primary residence, second home or investment opportunity, G1-108 cannot be missed!
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: David Denardo (203-321-9109)
4400 EXETER DR #305, LONGBOAT KEY, FL 34228
$324,90085 Days on yellowkey MLS ID: A4691085
0 Days Off yellowkey (back on 5/15/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 837 Built: 1970 Tax: $2,819 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$2,819
Remarks: Under contract-accepting backup offers. Welcome to coastal living on coveted Longboat Key. Priced to move, this beautifully maintained 1-bedroom residence at 4400 Exeter Dr Unit 305J offers an exceptional opportunity to own in one of the island’s most desirable waterfront communities. Inside, you’ll find a bright open floor plan with warm wood flooring, an updated kitchen featuring stone countertops, stainless appliances, breakfast bar seating, and abundant custom storage. The spacious living area flows seamlessly to the enclosed lanai where tranquil water and tropical garden views create the perfect setting for morning coffee or evening relaxation. The generous primary suite includes large windows, great natural light, and access to a beautifully updated bath with dual vanities and modern finishes. Enjoy resort-style amenities including waterfront grounds, boat docks, pool, lush landscaping, and close proximity to deeded beach access, golf, tennis, dining, and shopping. Whether you’re seeking a seasonal retreat, investment property, or year-round island lifestyle, this value-priced Longboat Key residence is ready for immediate enjoyment. Opportunities at this price on Longboat Key do not last. Schedule your private showing today.
Listing is courtesy of: SVN COMMERCIAL ADVISORY GROUP (941-387-1200)
Listing Agent: Larry Starr (941-914-6869)
4485 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228
$1,025,00088 Days on yellowkey MLS ID: A4690646
1 Days Off yellowkey (back on 6/29/2026)
REDUCED by $50,000 (4.7%) on 06/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1175 Built: 1973 Tax: $6,115 (2025)Community: Arbomar AptsCondo
Taxes:$6,115
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Under contract-accepting backup offers. Renovated direct Gulf-front 2BR/2BA on Longboat Key. End-unit 8th-floor condo at The Arbomar, panoramic sunset views, pets allowed, hurricane-protected. For buyers seeking a move-in-ready beachfront residence on Longboat Key, this renovated direct Gulf-front end unit at The Arbomar delivers updated condition and views that don't quit. The 8th-floor 2-bedroom, 2-bath floor plan offers 1,175 square feet, with panoramic Gulf views from the balcony and partial bay views from the bedrooms. Inside, the renovated kitchen features wood cabinetry, quartz countertops, under-cabinet lighting, and stainless-steel appliances. Ceramic tile flooring extends through the main living areas, paired with crown molding, plantation shutters, and custom built-ins. Electric hurricane shutters provide added protection. Recent owner improvements include the renovated kitchen, updated bathrooms, a newer HVAC system, and a tankless water heater. At the building level, The Arbomar has invested in major upgrades including a new roof, hurricane-rated insulated windows, new entry and storm doors, and water-resistant Gemstone concrete coating on lanais and common breezeways. Amenities include a Gulf-front heated pool, fitness room, club room, community kitchen, kayak storage, and climate-controlled storage. The association is well-managed and well-funded, with quarterly HOA fees of $4,000. Rentals are permitted at one-month minimum, four times per year, after the required ownership holding period; pets are permitted for owners, rentals are pet-free. The residence conveys unfurnished, with one assigned carport space. On Gulf of Mexico Drive near island dining, golf, boating, shopping, St. Armands Circle, and downtown Sarasota.
Listing is courtesy of: WHITE SANDS REALTY GROUP FL (941-260-3350)
Listing Agent: Julie Larson, Llc (941-284-9826)
2600 HARBOURSIDE DR #C11, LONGBOAT KEY, FL 34228
$479,50029 Days on yellowkey MLS ID: A4697476
Bed: Bath: 0.0 Built: 1983 Tax: $2,837 (2025)Community: Longboat Key MooringsDock-Rackominium
Taxes:$2,837
Remarks: Club membership is NOT required and Owner Financing IS available for this rare 72' x 21' deep water boat slip on C-Dock at Longboat Key Moorings Marina, allowing for a 67' x 19' boat. Enjoy a premier deep-water, storm-protected marina location with direct access to Sarasota Bay, the ICW, and the Gulf. Longboat Key Moorings offers full-service amenities including dock crew, harbor concierge, 24-hour manned guard gate, cable TV, electricity, water, Wi-Fi, on-site fuel, pump-out service, and repair/maintenance services. Ideally located just minutes from St. Armands Circle, downtown Sarasota, Bradenton Beach, waterfront dining, shopping, and world-class boating. While membership to the Longboat Key Club is optional, it is not required to own this slip. A rare opportunity to secure premium waterfront access in one of Florida's most desirable boating communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Daniel Treiman (917-657-7495)
2301 GULF OF MEXICO DR #43N, LONGBOAT KEY, FL 34228
$1,000,000126 Days on yellowkey MLS ID: A4686190
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $10,915 (2025)Community: Islander Club Of LongboatCondo
Taxes:$10,915
Remarks: Virtually Staged. Perfectly positioned in the sought-after Islander Club Condominium, this 2-bedroom, 2-bath residence offers commanding Gulf and beach views from the living room, dining room, and both bedrooms. Expansive windows frame the sparkling waters of the Gulf of Mexico, creating a breathtaking backdrop for everyday living while showcasing spectacular sunset skies each evening. Situated front and center on the 4th floor, the residence enjoys one of the most desirable vantage points in the building, elevated enough for panoramic shoreline views yet close enough to feel immersed in the beauty and rhythm of the beach below. Competitively priced, the condominium presents a rare opportunity for the next owner to create their own vision of coastal living. Whether designing a sophisticated modern retreat or a relaxed island escape, the residence offers a blank canvas ready to be transformed to your personal taste and style—truly a chance to make it your own. Residents of the Islander Club enjoy a collection of resort-style amenities including direct access to the pristine Gulf Beach, a beachfront Olympic size swimming pool, tennis courts, fitness center, clubhouse, library, and beautifully landscaped tropical grounds. Located on the coveted south end of Longboat Key, the community offers convenient access to Publix, the world-class shopping and dining of St. Armands Circle as well as the vibrant arts, cultural venues, and waterfront restaurants of downtown Sarasota. Go ahead – Make it your own and have it your way!
Listing Agent: Steve Nursey (941-356-7010)
775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228
$2,195,000147 Days on yellowkey MLS ID: A4683021
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2122 Built: 1984 Tax: $17,930 (2025)Community: Beaches Of Longboat KeyCondo
Taxes:$17,930
Remarks: Behind the gates of the Longboat Key Club, this exceptional residence at The Beaches captures sweeping, unobstructed views of the Gulf of Mexico and its pristine shoreline, where vivid sunsets paint the horizon each evening. Perched on the eighth floor, this coveted Star floor plan is ideally positioned as a spacious end residence, offering 2,122 square feet of thoughtfully designed living space with 3 bedrooms and 3 full baths. Walls of glass frame panoramic water vistas and invite natural light to pour into the main living areas. Newly installed impact-rated sliders enhance both storm protection and seamless indoor-outdoor living, while oak engineered hardwood flooring flows beautifully through the living room, dining area, and kitchen, creating a warm yet sophisticated coastal aesthetic. The generous layout provides an effortless blend of comfort and refinement, with well-proportioned bedrooms and baths designed to accommodate both everyday living and gracious entertaining. The Beaches is recognized as one of the premier beachfront addresses within the Longboat Key Club, offering direct access to the sugar-white sands and turquoise waters of the Gulf. Residents enjoy an elevated level of service and amenities, including a 24-hour concierge, resort-style pool, fitness center, tennis courts, and impeccably maintained grounds. Ideally located on the southern end of Longboat Key, this gated community affords convenient access to the fine dining and boutiques of St. Armands Circle, the vibrant arts and culture of downtown Sarasota, and the exclusive offerings of the Longboat Key Club. This is a rare opportunity to secure a front-row seat to the Gulf and embrace the effortless elegance of Florida’s most sought-after coastal lifestyle.
Listing Agent: Lenore Treiman (941-356-9642)
6489 GULFSIDE RD, LONGBOAT KEY, FL 34228
$13,995,000182 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
Taxes:$42,641
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. Come and witness the cutting edge of enhanced hurricane construction, wander and enjoy the exquisite staging by Clive Daneil Homes. 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 Agent: Nicholle Mckiernan (941-928-2922)
1241 GULF OF MEXICO DR #803, LONGBOAT KEY, FL 34228
$3,249,000281 Days on yellowkey MLS ID: A4667938
REDUCED by $101,000 (3.0%) on 06/29/2026
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3045 Built: 1996 Tax: $31,926 (2025)Community: Water Club 01 At Longboat KeySpa: YesCondo
Taxes:$31,926
Remarks: The epitome of beachfront luxury awaits in this meticulously renovated 8th-floor residence at the prestigious Water Club on Longboat Key. This stunning 3-bedroom plus oversized study, 4-bath home is a rare offering in one of the Gulf Coast’s premier direct beachfront communities. From the moment you step off the private elevator into the foyer, you’re greeted by serene neutral tones, 10-foot ceilings, and wide-plank engineered hardwood floors that set the tone for elegant coastal living. Walls of glass frame spectacular, unobstructed views of the Gulf of Mexico, filling the expansive living spaces with natural light and breathtaking scenery. The open-concept floor plan seamlessly blends comfort and sophistication, enhanced by recessed lighting and a calming contemporary palette. The spacious living room flows onto a generous beachfront terrace—perfect for soaking in mesmerizing views and the soothing sounds of the surf. The designer kitchen is a showcase of modern design, featuring white glass subway tile backsplash, solid wood cabinetry, an induction cooktop with pot filler, Sub-Zero refrigerator, and premium stainless-steel appliances. A large center island and adjacent breakfast area provide the perfect setting for casual meals with sweeping water views. Each guest suite is a luxurious haven, including one with double queen beds and an en suite bath with soaking tub and separate shower. The third bedroom is currently configured as an office, yet spacious enough to accommodate a queen-size bed, and offers beautiful views of downtown Sarasota. The primary suite is a private retreat, featuring its own beachfront terrace, a separate sitting area, custom-fitted dual closets, and a spacious study with built-in office space. The spa-inspired primary bath is the essence of indulgence with white marble floors and walls, a freestanding soaking tub, and a glass-enclosed walk-in shower. Additional highlights include two under-building covered garage parking spaces, a private storage closet, and access to all the amenities of the Water Club—24-hour security, full concierge service, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and over 16 acres of pristine beachfront grounds. This is beachfront living redefined! Located just a short distance to St. Armands and downtown Sarasota's shopping, dining & cultural events.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1935 GULF OF MEXICO DR #G7-304, LONGBOAT KEY, FL 34228
$455,00098 Days on yellowkey MLS ID: TB8496217
REDUCED by $10,000 (2.2%) on 06/29/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 933 Built: 1979Monthly Fee: $1,633 Tax: $4,940 (2025)Community: Seaplace ViCondo
Taxes:$4,940
Remarks: Experience the best of coastal living in this beautifully maintained 2-bedroom, 1-bathroom condominium, perfectly situated on the third floor of the desirable Seaside community on Longboat Key. Set within a secure, 24-hour guard-gated enclave, this charming residence offers both privacy and peace of mind. Step inside to discover a light and airy interior that was tastefully repainted in April 2021, along with stylish updates to the kitchen and bathroom completed at the same time. The functional layout includes a spacious living area that opens to a generously sized screened-in patio—an ideal space for enjoying morning coffee, evening breezes, or simply soaking in the serene surroundings. A brand-new air conditioning system was installed in October 2024, ensuring year-round comfort and energy efficiency. The building’s exterior also received a fresh coat of paint in April 2021, enhancing its curb appeal and overall charm. This coastal retreat offers direct access to the soft sands and crystal-clear waters of the Gulf, making beach days effortless and spontaneous. Residents also enjoy an array of resort-style amenities, including two heated swimming pools with relaxing spas, a well-equipped fitness center, a playground, three tennis courts, a welcoming clubhouse, and tranquil walking trails that wind through the community. Located just a short drive from the boutique shops, fine dining, and vibrant atmosphere of St. Armands Circle, this property is ideal for full-time residents, seasonal getaways, or investment opportunities. Leasing is allowed with a twomonth minimum lease period, up to six times per year, offering flexibility for owners. Don’t miss your chance to own a piece of paradise on Longboat Key!
Listing is courtesy of: EATON REALTY (813-672-8022)
Listing Agent: Alie Espinoza (813-382-6465)
2301 GULF OF MEXICO DR #12N, LONGBOAT KEY, FL 34228
$1,225,27744 Days on yellowkey MLS ID: A4695851
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $9,496 (2025)Community: Islander Club Of LongboatSpa: NoCondo
Taxes:$9,496
Remarks: A rare opportunity to own a beautifully reimagined Gulf-front residence at the prestigious Islander Club on South Longboat Key. Completely renovated with sophisticated coastal elegance, this exceptional beachfront condominium offers the convenience of first-floor walk-out living with direct access to the resort-style beachfront pool and the pristine white sands of the Gulf of Mexico. Walls of glass frame breathtaking panoramic Gulf views while filling the residence with natural light and spectacular sunsets. Thoughtfully redesigned with high-end finishes, the residence features a luxurious open-concept floor plan, a stunning chef's kitchen, beautifully appointed baths, and seamless indoor-outdoor living. The private beachfront terrace serves as an extension of the living space, creating the perfect setting for morning coffee, sunset cocktails, and effortless entertaining. Ideally positioned on the coveted south end of Longboat Key, this residence offers the privacy and comfort of a beachfront home with the convenience of luxury condominium living. Residents enjoy an impressive collection of amenities including 400 feet of private beachfront, an Olympic-size beachfront pool, a newly renovated fitness and community center, Har-Tru tennis courts with planned pickleball additions, on-site management, gated entry, and a highly desirable owner-to-owner rental program. Located just minutes from St. Armands Circle and vibrant downtown Sarasota, this exceptional residence places world-class dining, boutique shopping, cultural attractions, and marina amenities within easy reach. An extraordinary opportunity to experience refined Gulf-front living at one of Longboat Key's most sought-after beachfront addresses.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Leah George (941-780-0597)
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