Location: Longboat Key
Do Not Show Listings
726 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$1,090,00085 Days on yellowkey MLS ID: A4684733
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1384 Built: 1963 Tax: $15,835 (2024)Community: Longboat KeySpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$15,835
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: W.D. Sugg Middle
Remarks: Coastal Living Perfected on Longboat Key Discover the ultimate island retreat at 726 Jungle Queen Way, a beautifully reimagined 2-bedroom, 2-bath waterfront home where modern comfort meets timeless Florida charm. Tucked away on a peaceful canal just steps from the Gulf of Mexico, this residence offers the rare privilege of deeded beach access, 125ft canal frontage, and a resort-style saltwater pool - everything you need to live each day like a vacation. Wake up to soft morning light glistening off the water and ease into your day with coffee poolside, surrounded by lush tropical landscaping and the hush of palm fronds swaying in the breeze. Launch your boat from the private dock pilings on the deep-water canal and explore Sarasota Bay or head out toward Egmont Key. After a day on the water, rinse off in the outdoor shower, slip into the saltwater pool, or unwind on the travertine deck beneath wide island skies that glow at sunset. Evenings invite laid-back luxury - cocktails by the firepit, good company, and a canopy of stars overhead. Inside, this home blends classic coastal character with thoughtful, high-end updates throughout. The light-filled living spaces feel open yet intimate, with plantation shutters, fresh neutral tones, new baseboards and trim that anchors the living room with style. The redesigned kitchen shines with quartz countertops, stainless-steel appliances, and sleek cabinetry, while both bathrooms echo a spa-inspired sensibility with crisp, elegant finishes. The family room’s canal views beyond the French doors provide a quiet reminder that you’re always connected to the water. Recent updates lend peace of mind with new HVAC (2019), refreshed interior paint, new interior doors, and professional flood mitigation - including new drywall and rewired electrical. The exterior is equally turnkey, with manicured landscaping, a paver driveway, and a shaded carport for convenience. Living on Longboat Key means embracing an effortless, elegant coastal lifestyle. From here, you’re minutes to St. Armands Circle, Anna Maria Island, and downtown Sarasota, with boutique shopping, fine dining, dog-friendly parks, and beach paths all within easy reach. Boat in the morning. Beach at sunset. Poolside under the stars. This is more than a home - it’s the Longboat Key lifestyle realized.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
519 ROUNTREE DR, LONGBOAT KEY, FL 34228
$6,488,00044 Days on yellowkey MLS ID: A4690210
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3554 Built: 2025Monthly Fee: $250 Tax: $9,330 (2024)Community: Longboat Key EstatesSpa: YesSingle Family
Taxes:$9,330
Elementary School: None
High School: None
Middle School: None
Remarks: BUILT TO LAST. 519 Rountree is new construction built entirely of concrete block (CBS) across every level—unlike many barrier island homes that transition to wood-frame construction above the flood elevation. The residence has already experienced recent hurricanes without damage. NEW CONSTRUCTION. 519 ROUNTREE is a privately positioned coastal residence offering over 6,400 square feet of indoor and outdoor living, including approximately 5,200 square feet under roof and a 1,100 square foot elevator-accessible rooftop terrace, located within Longboat Key Estates. GULF LIVING EXPERIENCE. At 519 Rountree, days begin with morning air carrying the salt-kissed character of the Gulf and conclude with glowing sunsets that define the Florida coastline. This is not simply proximity to the beach — it is immersion in it. Positioned just moments from the sand, the home offers balcony and rooftop experiences designed for sunset entertaining, open-air dining, and the effortless rhythm of Gulf living from morning through evening. WATERFRONT LIVING. A waterside deck is currently in process, transforming the canal setting into a true extension of the home’s outdoor living experience, subject to permitting. Flexibility remains for a variety of dock and lift configurations, tailored to buyer preference. DESIGN AND EXECUTION. The newly constructed residence has withstood three recent hurricanes without damage, a testament to its quality, elevation, and thoughtful execution. Each level is purposeful in both design and function, delivering a vertical lifestyle that feels intuitive, private, and refined. FURNISHINGS. For buyers seeking the residence exactly as photographed, the complete furnishings and curated design package may be acquired separately. FINAL NOTE. 519 Rountree delivers the atmosphere buyers seek when they say they want Gulf living — quietly, privately, and without excess.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Colby Lengel (941-779-6227)
2425 GULF OF MEXICO DR #8C, LONGBOAT KEY, FL 34228
$1,550,00044 Days on yellowkey MLS ID: A4688797
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $17,374 (2025)Community: Sea Gate ClubCondo
Taxes:$17,374
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Welcome to the prestigious Sea Gate community on world renowned Longboat Key! With direct views of the Gulf of Mexico from every room and situated perfectly on the 8th floor, this stunning 2-bedroom, 2-bathroom residence offers just under 1500 square feet of refined coastal living on pristine white shores, endless turquoise waters and vibrant sunsets that create a truly extraordinary backdrop that is postcard worthy! This beautifully appointed residence has been meticulously maintained by the owners and showcases expansive glass sliders that flood the home with natural light, seamlessly connecting the indoor living spaces to a private balcony and your front-row seat to one of Florida’s most coveted coastlines.Thoughtfully enhanced for both comfort and style, the residence features fresh interior paint, a new HVAC system and Hot Water Tank and some new kitchen appliances, delivering a modern and move-in-ready experience. The addition of an in-unit washer and dryer provides a rare and highly desirable level of convenience within the building. The spacious layout offers an effortless flow between the living, dining and kitchen areas for both everyday living and entertaining.The primary suite serves as a peaceful retreat, complete with generous proportions, ample storage and a calming ambiance inspired by the surrounding Gulf views, walk- in closet and ensuite. A well-appointed guest bedroom boasts a private balcony and large closet, while the guest bath provides comfort and privacy for visitors. Residents of Sea Gate enjoy an intimate, resort-style lifestyle with direct beach access, a beachfront pool, tennis courts, a fitness center, and beautifully maintained grounds, all within a private, boutique community setting. Additionally, Sea Gate offers covered parking, ample guest parking and a large storage unit! The building has undergone major capital improvements in recent years, including impact-rated windows (2021), a full exterior restucco and repaint (2022), a new roof (2023) and upgrades to the pool, spa, sundeck and elevator doors. Residents enjoy resort-style amenities including a Gulf front pool and hot tub, fitness center, clay tennis court, library, and a social room with catering kitchen. Shaded tiki huts, outdoor showers, and climate-controlled storage for bikes, kayaks, and paddleboards complete the experience of true beachfront living. All fully paid for by current owners, totaling over $100K/unit. Ideally located near daily shopping, Longboat Key offers a lifestyle defined by elegance and ease, with world-class golf, waterfront dining, boating, and the upscale shops and restaurants of St. Armands Circle just moments away, along with the cultural attractions of Sarasota. With monthly rentals allowed, a unit of this stature could rent for 10k a month in season offering potential income. Option to be sold turnkey furnished as well. Don't hesitate, this unit is a beaut and easy to show!
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Melissa Killion (941-248-6840)
2341 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$1,399,99052 Days on yellowkey MLS ID: A4688219
0 Days Off yellowkey (back on 4/15/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2282 Built: 1986Monthly Fee: $1,617 Tax: $11,814 (2025)Community: Harbour Oaks 2Spa: NoVilla
Taxes:$11,814
Remarks: Welcome to your elevated and relaxed Longboat Key lifestyle—where everything has already been beautifully updated - all that’s left to do is move in and enjoy. Tucked behind the gates of Bay Isles in the charming Harbour Oaks enclave, this bright and open end-unit villa offers gorgeous golf course views, peaceful water features and those unforgettable sunset skies that make every evening feel like a getaway. Inside, the home has a Serena & Lilly feel - its fresh, comfortable and thoughtfully designed. With 2,282 square feet, three en-suite bedrooms and a light-filled open layout - it’s ideal for both relaxed everyday living and hosting friends and family. New luxury vinyl plank flooring runs throughout, while vaulted ceilings, skylights and a garden atrium brings in beautiful natural light. The kitchen has been fully updated with quartz countertops, a marble backsplash, stainless appliances and a casual breakfast bar—perfect for morning coffee before heading to the beach. There’s also a separate dining space for more intimate dinners. Outdoor living is where this home really shines. Sliding doors open to a spacious, two-level screened lanai with a newly pavered deck, electric awning for shade and a newly resurfaced and retiled PebbleTec saltwater pool. It’s your own private retreat—perfect for lounging, entertaining or simply soaking in the peaceful golf course views. The bathrooms have been beautifully reimagined with marble showers, Kohler fixtures and clean, modern finishes. Additional updates include a new roof (2025), newer AC and water heater (2021) and a two-car garage for convenience. Upgrades are plentiful - including Hunter Douglas window treatments and plantation shutters - which add a polished but easygoing feel. Living in Bay Isles means enjoying a true resort lifestyle, with access to a private beach club, marina and scenic walking paths—all in a gated, maintenance-free community. You’re just minutes from the Longboat Key Club and Tennis Center, Publix, everyday conveniences - and a short drive to the shops and restaurants of St. Armands Circle and downtown Sarasota.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Monica Verinder (941-704-4040)
408 GULF OF MEXICO DR #1214, LONGBOAT KEY, FL 34228
$99,00046 Days on yellowkey MLS ID: A4689763
Bed: Bath: 0.0 Built: 2006 Tax: $563 (2025)Community: Boathouse On LongboatDock-Rackominium
Taxes:$563
Remarks: Welcome to Slip #1214 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities PLUS the price includes a 2018 Robalo R18 with a Yamaha 150 motor, recently detailed tuned up for one-stop shopping! This premium slip accommodates boats up to 31.5 feet in length, with a maximum height of 8' 4" and an 8' 6" beam (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and even the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Daniel Treiman (917-657-7495)
1085 GULF OF MEXICO DR #205, LONGBOAT KEY, FL 34228
$999,000111 Days on yellowkey MLS ID: A4681713
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1819 Built: 1981 Tax: $8,830 (2025)Community: Beachplace IiiSpa: YesCondo
Taxes:$8,830
Remarks: Spacious 3-Bedroom End-Unit Residence in Sought-After Beachplace Welcome to this beautifully maintained three-bedroom, two-bath end-unit condominium offering exceptional natural light, generous living spaces, and serene views in one of South Longboat Key’s most desirable beachfront communities. The open living and dining areas are thoughtfully designed for comfort and entertaining, featuring expansive sliders and windows that flood the space with sunlight and create seamless indoor-outdoor flow. A spacious living room opens to a south-facing screened lanai—perfect for enjoying morning light, golf course views, and gentle coastal breezes. The kitchen is bright and functional, offering ample cabinetry, full appliance package, and convenient in-unit laundry tucked neatly into a dedicated closet. Adjacent dining space provides flexibility for everyday living or hosting guests. The primary suite is generously sized and enjoys tranquil views, abundant natural light, and direct access to the lanai. Two additional bedrooms are versatility for guests, family, or a home office, all thoughtfully laid out to maximize privacy and comfort. Being an end unit, this residence benefits from additional windows and enhanced light throughout, creating an airy, welcoming atmosphere. Neutral finishes and tasteful furnishings allow for immediate enjoyment while offering an excellent canvas for personalization. Residents of Beachplace enjoy resort-style amenities, including a heated pool with lap lanes, spa, tennis courts, a fully equipped clubhouse with gathering spaces, on-site management, and private deeded beach access complete with lounge chairs and umbrellas. The community’s prime location places you moments from St. Armands Circle, Longboat Key Club, and downtown Sarasota’s dining, shopping, and cultural attractions. This well-cared-for residence presents an outstanding opportunity—whether as a primary home, vacation retreat, or income-producing investment in a premier Gulf-front community.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
1445 GULF OF MEXICO DR #501, LONGBOAT KEY, FL 34228
$1,499,00060 Days on yellowkey MLS ID: A4687339
0 Days Off yellowkey (back on 4/10/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2642 Built: 1982 Tax: $19,801 (2025)Community: Players Club IiiCondo
Taxes:$19,801
Remarks: This stunning corner penthouse spans over 2,800 sq. ft. and boasts breathtaking views of the Gulf, Bay, and city skyline. Key features include elegant stone floors, storm-resistant windows, custom cabinetry, skylights, raised ceilings, and indirect lighting. The kitchen offers a breakfast bar and an adjacent Solarium, perfect for enjoying your morning coffee while taking in both Gulf and city vistas. The spacious sitting room/office adjacent to the primary bedroom features built-in desk and shelving, with expansive glass walls overlooking the pool and Gulf. For entertaining, the impressive 800 sq. ft. private courtyard includes a large fountain and a summer kitchen. This residence also includes a private garage and an additional assigned under building parking space. Residents of The Players Club enjoy a guarded entrance, on-site management, a resort-style saltwater pool and cabanas, spa, Har-Tru tennis courts, pickleball, putting green, a fitness center, renovated clubhouse with catering kitchen, outdoor entertainment area with fire pits, barbecue grills, and direct access to a white sand beach. All of this is just minutes away from the vibrant shops, restaurants, theaters, and art galleries of St. Armands Circle and Downtown Sarasota.
Listing Agent: Ian Addy, Pa (941-961-8850)
5965 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$38,450,00084 Days on yellowkey MLS ID: A4681869
Bed: 11 Bath: 15.0 Gar: 7 Liv Area Sq Ft: 17199 Built: 2026 Tax: $82,342 (2025)Community: Longboat KeySpa: YesSingle Family
Taxes:$82,342
Middle School: Martha B. King Middle
Remarks: Under Construction. Set on nearly two private Gulf-front acres, this visionary estate is emerging as one of the most architecturally significant residences ever conceived on Longboat Key. Designed by the internationally acclaimed firm Sweet Sparkman Architecture & Interiors, the home represents a rare convergence of sculptural design, coastal sensitivity, and modern livability. Bold in concept yet timeless in execution, the main residence unfolds with intention. A dramatic foyer introduces expansive living spaces designed to capture light, scale, and uninterrupted Gulf views. The primary suite is conceived as a private sanctuary, complete with dual spa-inspired baths and bespoke dressing rooms. A stately office, refined lounge, formal dining room, and temperature-controlled wine cellar complement the open-concept great room, which transitions seamlessly to a sweeping Gulf-front terrace. Dual kitchens, a showpiece entertaining kitchen and a separate chef’s kitchen, elevate both daily living and grand-scale hosting. The estate continues upward to a rooftop deck with panoramic coastal vistas, while other levels offer a private cinema, multiple guest suites, and a dedicated guest-level kitchenette. A thoughtfully designed guest house and separate pool house provide additional privacy and flexibility for extended stays or staff accommodations. Outdoors, the setting transforms into a private coastal resort. Lush, layered landscaping surrounds a dramatic resort-style pool and spa, expansive entertaining terraces, tranquil water features, and potential for a private tennis and pickleball court — all oriented toward the Gulf’s endless horizon. Positioned along one of the most coveted stretches of Longboat Key, the property offers both seclusion and proximity to the best of the region, including The Resort at Longboat Key Club, The St. Regis Longboat Key Resort, St. Armand's Circle, and the cultural vibrancy of downtown Sarasota. With construction advancing and pricing evolving accordingly, this is a rare opportunity to secure a generational Gulf-front legacy estate at a pivotal stage. Longboat Key’s global recognition, including its inclusion among Forbes Travel Guide’s Top 12 Destinations, further underscores the enduring value of this extraordinary offering.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
615 DREAM ISLAND PL #105, LONGBOAT KEY, FL 34228
$995,00045 Days on yellowkey MLS ID: A4689957
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1293 Built: 1985Monthly Fee: $2,208 Tax: $4,735 (2025)Community: Harbour Villa Club At The BuccaneerSpa: YesCondo
Taxes:$4,735
Remarks: Welcome to Paradise Found at Harbour Villa Club, a waterfront luxury condo that is truly a slice of heaven on earth. This stunning property offers breathtaking views of the glistening water and is situated in a prime location that is peaceful, serene, and truly one-of-a-kind. A true Longboat Key gem. As you step inside this luxurious, fully renovated (2025) condo, you'll be greeted by a spacious and open floor plan that is perfect for entertaining guests or simply relaxing in style. The living area is bathed in natural light, thanks to the open plan, high ceilings, and large sliders that offer stunning views of the Bay, the Intercostal Waterway, and protected Sister Keys. The gourmet kitchen is a chef's dream. Built completely custom, featuring top-of-the-line appliances, ample counter space, and plenty of creative storage. The primary bedroom is designed with your comfort in mind, offering tremendous space, ample dual closets, and unparalleled views of the water. The primary bathroom is equally luxurious, featuring high-end fixtures, beautiful tile work, and a spacious shower. Entertain with ease and impress your guests with a sleek and stylish wet bar, perfect for any occasion. The secondary bedroom with a large space is ideal for a great flex space, depending on your needs. But perhaps the most impressive feature of this luxury condo is the covered and screened lanai. This space is perfect for hosting guests, sipping your morning coffee, or evening cocktail, or simply taking in the beauty of your surroundings. For the boating enthusiasts, this condo conveys a deeded boat slip #14, which includes electric, water, and new composite decking. This slip is 40ft in length and can dock up to a 55'+/- vessel and is positioned directly outside the unit, which is rare. This community is flush with mature tropical landscaping and grounds. Other amenities include a heated pool, hot tub, outdoor grill, kayak storage/launch, boat ramp, climate-controlled bicycle/locker storage, Brand New tennis courts, two Brand New pickleball courts, and one covered parking space. Harbour Villa Club is one of the few Longboat Key communities that has the ability to rent on a weekly basis. This gives you options and flexibility to carve out your formula of ownership and use. Located within a short distance to nearby popular beaches, restaurants, clubs, and parks, and just a short drive to St. Armands Circle and Downtown Sarasota. This property is more than just a luxury condo - it's a lifestyle. So why wait? Come see for yourself what makes this property so special and start living your Longboat Key dream today.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
455 LONGBOAT CLUB RD #707, LONGBOAT KEY, FL 34228
$1,999,950119 Days on yellowkey MLS ID: A4680080
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2410 Built: 1990 Tax: $9,861 (2025)Community: PierreCondo
Taxes:$9,861
Remarks: Welcome to The Pierre, a distinguished Gulf-front address behind the private gates of the Longboat Key Club, offering a rare blend of refined coastal living, privacy, and world-class resort lifestyle appeal for discerning buyers from around the globe. Located on the seventh floor, Residence 707 showcases spectacular sunset skies over the Gulf of Mexico, complemented by peaceful bay and city vistas, creating a dynamic panorama from sunrise through evening. Expansive windows fill the interiors with natural light while framing the natural beauty of Longboat Key’s shoreline and Sarasota Bay. Thoughtfully designed for both relaxed living and gracious entertaining, the residence offers generous living spaces and a seamless indoor-outdoor connection. The floor plan includes two ensuite bedrooms and a flexible third bedroom with sliding retractable wall, three full baths, and spacious living and dining areas—each with direct access to the residence’s gracious balconies. Residents of The Pierre enjoy an exceptional array of amenities, including direct private beach access, a beachfront pool, spa, fitness center,, tennis courts, a newly renovated lobby, club gathering room, meeting room and 24-hour guard security. Private guest suites are also available for visiting family and guests on a nominal rental basis. Ownership is further enhanced by secure garage parking, a private secured storage area, and onsite professional management, providing ease and confidence for both year-round and seasonal owners. Beyond the residence, membership opportunities at the renowned Longboat Key Club provide access to a celebrated resort lifestyle, featuring championship golf courses, world-class tennis, spa and wellness facilities, multiple dining venues, beach services, and an active social calendar (membership subject to application and availability). Perfectly situated near St. Armands Circle and downtown Sarasota’s cultural attractions, Residence 707 represents a rare opportunity to own within one of Longboat Key’s most prestigious waterfront communities—where international sophistication, panoramic views, and a coveted club lifestyle converge in one extraordinary coastal setting.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Judy Wright, Pa (941-232-8041)
3311 SABAL COVE DR, LONGBOAT KEY, FL 34228
$2,450,000142 Days on yellowkey MLS ID: A4676501
1 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3416 Built: 2006Monthly Fee: $116 Tax: $12,784 (2025)Community: Sabal CoveSpa: NoSingle Family
Taxes:$12,784
Remarks: Expertly designed by the highly regarded John Cannon Homes, known for exceptional quality and craftsmanship, this custom 4 bedrooms plus study residence offers the comfort and convenience of expansive living on one single level within the exclusive enclave of Sabal Cove, behind the secure gates of Bay Isles on Longboat Key. The home is centered around a dramatic screened outdoor living area, where the primary gathering spaces and owner’s suite are open to a grand, tiered brick-paver patio created for easy, elegant entertaining. This resort-style environment includes a saltwater swimming pool with waterfall feature, a raised gas fire pit with lounge seating and a built-in protected summer kitchen all surrounded by architectural lighting and mature tropical plantings beyond the enclosure that ensure privacy and tranquility. Spanning more than 3,400 square feet, the interior reveals impressive architectural scale with ceiling heights ranging from 12 to 15 feet, complemented by clerestory windows that fill the home with natural light. The family room is highlighted by a newly refinished limestone and glass natural gas/electric fireplace, while seamless aquarium-style glass corner sliders retract completely, creating a fluid connection between indoor living and the outdoor retreat. Interior spaces include a formal living room, a dining room with built-in glass display shelving, and a private study featuring extensive custom cabinetry. The well-appointed kitchen with a center island and breakfast bar, quartz countertops, generous custom storage, and a six-burner Thermador gas range is ideal for culinary pursuits. Additional features include hurricane impact-rated windows, wood flooring, solid-core interior doors, detailed tray ceilings and handcrafted millwork. A side-entry brick-paver drive leads to an oversized three-car garage equipped with a 240-volt EV charging outlet. Sabal Cove is an intimate community of just 38 single-family custom homes at the southern end of Longboat Key. Bay Isles residents enjoy access to a private, gated Gulf-front beach club, with optional membership to the adjacent Longboat Key Club offering 45 holes of championship golf and a premier tennis facility. Convenient to the Longboat Key Town Center’s grocery & pharmacy, the property is also a short drive to St. Armands Circle and downtown Sarasota, known for its cultural attractions, acclaimed dining, and upscale shopping.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
340 GULF OF MEXICO DR #112, LONGBOAT KEY, FL 34228
$1,775,000212 Days on yellowkey MLS ID: A4670120
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2298 Built: 1991 Tax: $12,180 (2024)Community: Tangerine Bay ClubSpa: YesCondo
Taxes:$12,180
Remarks: Perfectly positioned on Sarasota Bay at the southern end of Longboat Key, this beautifully renovated 3BR/3BA, 2,298± sq. ft. residence with a private 2-car garage at Tangerine Bay Club combines luxury, comfort, and a premier location just moments from St. Armands Circle and downtown Sarasota. A private front courtyard welcomes you inside, where rich wood floors, custom doors, and neutral tones complement the panoramic bay views. Redesigned from its original layout, the home offers an open flow through the main living areas. The reimagined chef’s kitchen features stone countertops, custom cabinetry, stainless-steel appliances, a wine fridge, and center island. The living room’s corner fireplace and full wall of glass highlight the sparkling water views. The spacious terrace is ideal for relaxing or entertaining. The primary suite offers terrace access and a beautifully updated bath with dual vanities, glass shower, and private water closet. Tangerine Bay residents enjoy a lagoon-style pool with waterfalls, spa, tennis and pickleball courts, day dock, fishing pier and membership to the Bay Isles Beach Club with private beach access, cabanas and more. Across from the Longboat Key Club, optional membership includes access to golf, tennis, beach and pool facilities, marina, spa, and fine dining.
Listing Agent: Bruce Myer (941-376-5311)
5970 EMERALD HARBOR DR, LONGBOAT KEY, FL 34228
$2,795,000102 Days on yellowkey MLS ID: A4681905
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3098 Built: 1977Monthly Fee: $63 Tax: $12,915 (2024)Community: Emerald Harbor Unit 1 RevSpa: NoSingle Family
Taxes:$12,915
Remarks: Set at the peaceful end of a wide, deep canal on the north end of Longboat Key, this waterfront residence in Emerald Harbor offers a rare combination of space, privacy and effortless boating access. With long views straight down the canal and quick entry to Sarasota Bay, the setting feels calm, open and ideally positioned for life on the water. A circular paver brick drive framed by meticulously maintained landscaping leads to the front entrance, where a barrel tile roof and timeless exterior details create a welcoming first impression. Inside, 3,098+/- sq. ft. of thoughtfully planned living space unfolds in soft neutral tones, complemented by abundant natural light, large tile flooring, crown molding and expansive windows throughout the main living areas. The living room is designed for seamless indoor-outdoor living, featuring a full wall of pocket sliders that open completely to a covered sitting area accented by a pecky cypress ceiling. From here, the view extends across the pool, private dock and calm canal beyond, creating a natural backdrop for both entertaining and everyday enjoyment. The kitchen anchors the home with ease and functionality, offering a center island with breakfast bar, wood cabinetry, stone countertops, stainless steel appliances, tile backsplash and pendant lighting. Its placement allows the home to flow comfortably for gatherings or quiet evenings alike. The floor plan offers exceptional flexibility, with two generously sized suites. The main primary suite features a tray ceiling, a large custom walk-in closet and a beautifully updated bath with dual vanities, glass-enclosed shower and convenient access to the outdoor living area. A second suite includes its own custom walk-in closet and en suite bath, making it ideal for guests or extended family. Two additional bedrooms and a study overlooking the water complete the layout, along with three and a half total baths. Outdoors, the setting feels private yet expansive, with a sparkling pool and a private dock equipped with a boat lift. The canal offers excellent boating water with no-bridge access to the Intracoastal Waterway, Sarasota Bay and the Gulf. Emerald Harbor is a bayside enclave of just 82 homes, known for its broad lagoon-style canals and deeded private beach access located one block away.
729 SAINT JUDES DR S #3, LONGBOAT KEY, FL 34228
$449,00078 Days on yellowkey MLS ID: A4685189
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 1966 Tax: $1,994 (2025)Community: Saint Judes AptsSpa: NoCondo
Taxes:$1,994
Remarks: Live that Longboat Key waterfront lifestyle and have your own boat lift without the multi-million dollar price. Cute and conveniently located, this on-grade one bedroom condominium unit that is located on a saltwater canal on Longboat Key, features its own 10,000 lb boat lift, and is one block to the gulf beaches and adjacent to Durante Park. Everything new in 2025, including a washer and dryer and hot water demand unit. The condo is completely furnished with an updated living space, complete with open kitchen that features granite countertops, stainless steel appliance and plenty of storage. The modern wood-look tile and updated sliders and windows make for an open feeling living area. There is a paver patio and dock behind the condo for enjoying the sunsets on the canal. A number of shops and restaurants within walking distance. Schedule your showing today!
Listing Agent: Steven Schield (941-650-1010)
2089 GULF OF MEXICO DR #G1-108, LONGBOAT KEY, FL 34228
$675,00096 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 (941-739-6777)
Listing Agent: David Denardo (203-321-9109)
1561 GULF OF MEXICO DR #304, LONGBOAT KEY, FL 34228
$13,000,00079 Days on yellowkey MLS ID: A4685495
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4891 Built: 2024 Tax: $94,589 (2025)Community: St. Regis Longboat KeySpa: NoCondo
Taxes:$94,589
High School: Sarasota High
Remarks: Experience the pinnacle of coastal luxury in the highly sought-after Armand building at The St. Regis Longboat Key, where breathtaking Gulf of Mexico views set the stage for an extraordinary living experience. This residence is absolutely breathtaking and is a must see. Designed for both grand entertaining and effortless everyday living, the expansive great room showcases a sophisticated wet bar and wine refrigerator, all enhanced by striking designer light fixtures and elegant sheers that create a soft, ethereal ambiance. Accordion glass doors seamlessly extend the space onto a sprawling wraparound terrace—complete with a private gas grill and unforgettable sunset vistas. Thoughtfully designed, this gracious room transitions beautifully between formal gatherings and relaxed coastal living. The chef’s kitchen is a true centerpiece, featuring premium Poggenpohl cabinetry, a Sub-Zero refrigerator, Wolf double ovens and gas cooktop, dual dishwashers, and a separate breakfast area with bar and microwave. A large island offers additional seating, making it as functional as it is elegant. Or just order room service! The owner’s suite is a private sanctuary, offering stunning Gulf views and a wet bar perfect for morning coffee or evening unwinding. Dual spa-inspired bathrooms provide two luxurious and private retreats—one with custom closets, an oversized vanity, seamless glass shower, and private water closet; the other with a large vanity, dedicated makeup area, custom closets, seamless shower, and private water closet. A spacious and comfortable club room creates an additional venue for entertaining, complete with a wet bar and beverage refrigerator. Two additional guest bedrooms are equally well-appointed, each opening onto a private terrace. One offers Gulf views, custom closets, and a luxurious bath with a large vanity, makeup area, seamless glass shower, and private water closet. The third bedroom is thoughtfully designed for comfort and privacy, featuring accordion doors to the terrace and a beautifully finished bathroom with a large vanity and makeup area, freestanding soaking tub, seamless glass shower, and private water closet. An elegant powder room adds convenience for guests. Additional highlights include a large laundry room with sink, built-in cabinetry, and hanging rack. The residence is offered fully turnkey, with exquisite furnishings curated by the renowned Marc-Michaels Interior Design—featuring designer-selected finishes, statement lighting, refined furniture pieces, and custom window treatments that create a cohesive, sophisticated aesthetic throughout. Modern living is elevated by fully integrated smart home technology, including iPad-controlled systems, electronic sheers, and blackout shades—delivering both convenience and ambiance at the touch of a button. Nestled within the first branded residential community and ultra-luxe 5 star resort on the Gulf of Mexico. The Residences at The St. Regis Longboat Key blend legendary service with the allure of a seaside getaway. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in residence dining. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!
Listing Agent: Lynn Morris, Pllc (941-400-4526)
4401 GULF OF MEXICO DR #601, LONGBOAT KEY, FL 34228
$995,000118 Days on yellowkey MLS ID: A4679728
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1524 Built: 1972 Tax: $14,214 (2024)Community: Longboat Harbour TowersCondo
Taxes:$14,214
Remarks: Two-bedroom, two-bath residence offering sweeping sixth-floor views of the Gulf of Mexico from Longboat Harbor Towers. This rare southwest corner condominium has completely unobstructed views west and south providing one of the most interesting and protected waterfront visages available anywhere on the key. In largely original condition, this spacious property presents an exceptional opportunity for renovation and customization in one of Longboat Key’s most coveted waterfront locations. Few properties combine this level of potential with such a remarkable setting. Positioned directly on the Gulf with more than 400 feet of pristine beach frontage, this fully amenitized community also enjoys eastern views of Sarasota Bay and the downtown Sarasota skyline—delivering breathtaking sunrises and sunsets from the same home. The southwest exposure also provides much more to view and enjoy with site lines extending down the entire length of the key. Common areas have been recently renovated and include a beachfront, heated, saltwater pool, a complete exercise room and spacious lounge with pool baths. Longboat Key is a sought-after barrier island community known for its relaxed coastal lifestyle, pristine beaches, and upscale residential atmosphere. Ideally located just minutes from the cultural and social energy of Sarasota, residents enjoy convenient access to world-class arts, dining, and entertainment while maintaining a sense of privacy and tranquility. A short drive south leads to iconic St. Armands Circle, renowned for its eclectic mix of boutiques, fine dining, cafés, and year-round events. Beyond St. Armands, downtown Sarasota offers theaters, galleries, live music, waterfront parks, and a thriving culinary scene, making Longboat Key an exceptional blend of island serenity and vibrant city living. This seller also has a BOAT SLIP for sale at The Boathouse, adjacent to the Dry Dock Restaurant just minutes away. Buy the condo and the slip for a complete Florida lifestyle!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: David Jennings (941-650-7354)
415 L AMBIANCE DR #A301, LONGBOAT KEY, FL 34228
$6,100,00056 Days on yellowkey MLS ID: A4688759
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3380 Built: 1992 Tax: $46,418 (2025)Community: L Ambiance 1Spa: YesCondo
Taxes:$46,418
Remarks: Rare corner Gulf-front residence with expansive wraparound terrace and views. An exceptional residence in L’Ambiance, where sweeping water views and refined coastal design converge. This light-filled corner home is defined by an expansive wraparound terrace, offering multiple seating areas and uninterrupted vistas of the Gulf - creating a seamless connection between indoor and outdoor living. Walls of glass frame the horizon from the main living spaces, enhanced by high-impact glass throughout, where generous scale and an open layout provide an effortless setting for both intimate living and entertaining. The kitchen is thoughtfully designed with extensive custom cabinetry, stone surfaces, and a functional layout complemented by a dedicated dining area. A private split-bedroom plan enhances comfort and separation, while a flexible den or media room offers additional space for guests or a home office. Throughout the residence, polished flooring and plantation shutters add a layer of understated sophistication. This residence includes two garage parking spaces, a private wine locker, and additional storage, offering both convenience and security. L’Ambiance offers a boutique beachfront setting with concierge service, a well-appointed fitness center, three guest suites for visiting family and friends, two Har-Tru tennis courts, and an expansive resort-style pool and spa set within beautifully maintained tropical grounds, all with direct beach access. Ideally positioned on the south end of Longboat Key and adjacent to the Longboat Key Club, with optional membership offering access to championship golf, tennis, marina, dining, and a full-service spa, this is a rare opportunity to experience elevated beachfront living.
2600 HARBOURSIDE DR #L-11, LONGBOAT KEY, FL 34228
$425,00052 Days on yellowkey MLS ID: A4689192
Bed: Bath: 0.0 Built: 1985Monthly Fee: $459 Tax: $3,077 (2025)Community: Bay IslesDock-Rackominium
Taxes:$3,077
Remarks: Ask an L-dock boater, they will tell you it’s the best dock in the marina. Slip mid-pier ono the north side of the dock, just a few flat steps to your parked vehicle with easy in/out access. A 68 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina. This slip requires membership in the Longboat Key Club. This slip is one of the very few slips at the marina with a direct view of the Sarasota cityscape and colorfully lit Ringling bridge. This deep-water marina offers direct access to Sarasota Bay and the ICW. The marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. The Marina has everything a boater could need. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 63 LOA, usable beam is 23 ft at the head of the slip. 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.
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
96 TWIN SHORES BLVD, LONGBOAT KEY, FL 34228
$425,00053 Days on yellowkey MLS ID: A4688151
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 758 Built: 2026Monthly Fee: $280 Tax: $815 (2025)Community: Twin Shores Mobile HomeManufactured Home
Taxes:$815
Remarks: Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can only make you smile. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated 2-bedroom, 2 bath, open floorplan home. The home is built by Skyline, highly regarded in the industry, winning "America's Most Trusted Manufactured Homebuilder" for six consecutive years (2021-2026). Bring your boat as you are only footsteps away from your own private marina. If you prefer the beach, go the opposite direction. You don't even have to worry about a chair. Twin Shores Beach and Marina have their own deeded entrance with brand new Tiki Hut and complimentary chairs to watch the sunset. All of this is located in the middle of Historic Longboat Key. Down the street, Bayfront Park has pickle ball, tennis, basketball, playground, swings, picnic pavilions, big dog and little dog fenced parks with new turf, walking paths, kayak launch/storage and bathrooms. Go south and find your grocery and liquor store, banks, pharmacy and newly added large outdoor pavilion with bathrooms. Wonderful restaurants, shopping, golf, and fishing make island living incredible. See you soon!!! Hurry, paradise awaits!
Listing is courtesy of: EVENTIDE REALTY LLC (941-799-9190)
Listing Agent: Kyle Adams (941-799-9190)
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