Location: Longboat Key
Do Not Show Listings
2425 GULF OF MEXICO DR #14B, LONGBOAT KEY, FL 34228
$1,690,000389 Days on yellowkey MLS ID: A4654664
REDUCED by $60,000 (3.4%) on 04/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $18,495 (2024)Community: Sea Gate ClubSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$18,495
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: BREATHTAKING WATER VIEWS FROM EVERY ROOM! Enjoy nightly sunsets from your private balcony in this beautifully updated 14th-floor condominium. This highly sought-after two-bedroom, two-bath split floorplan offers the perfect blend of privacy and open living. Each bedroom is positioned on opposite sides of the unit, creating an ideal layout for guests or remote work. Recent upgrades include Hurricane Impact Windows (2021), new flooring in both bedrooms (2021), updated bathrooms, fresh paint (2021), and an A/C system replaced in 2015. The convenience of an in-unit washer and dryer, a dedicated parking space, and ample guest parking add to the comfort of this coastal retreat. The beach and heated pool are just steps from your building, creating a true resort-style experience. Enjoy premium amenities such as a tennis court, air-conditioned bike room, kayak/paddleboard storage, clubhouse with kitchen, library/meeting space, and a fully equipped fitness center. Located within walking distance to Publix, CVS, places of worship, banks, the public library, and Town Hall. Just minutes to St. Armands Circle, where you'll find world-class dining and shopping. Immerse yourself in Sarasota’s rich cultural scene with easy access to the Sarasota Opera, Ballet, Ringling Museum, Selby Gardens, and numerous art galleries and theaters. This is your chance to live the Gulf Coast lifestyle—don’t miss it!
Listing is courtesy of: ANMARK REALTY LLC (941-363-1043)
Listing Agent: Andrey Markov (941-363-1043)
691 TARAWITT DR, LONGBOAT KEY, FL 34228
$850,000163 Days on yellowkey MLS ID: A4678131
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1500 Built: 1960 Tax: $13,845 (2024)Community: Longboat KeySingle Family
Taxes:$13,845
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Presenting the perfect waterfront island getaway! Uniquely situated on an extra large 11,250 sf lot on a canal with easy access to the intracoastal waterway, making a day out on the water an easy escape. This completely remodeled home offers a new kitchen with all new appliances and is done up in seaside hues; Beautiful new wood look tile flooring flows seamlessly from room to room; New water resistant Enduroboard surrounds the living area lower walls and creates an extra added artistic detail to this already charmingly decorated home. Used primarily as a beach escape (with deeded beach access) for this Florida owner, it also presents a great opportunity for monthly rental income. In only a short walk or bike ride down the street, you have access to multiple restaurants, shopping, 12 miles of bike paths and the beautiful nature trails of Joan Durante Park. Just a short drive off island and over the bridge is world famous St. Armands Circle and just beyond that, the culture rich city of downtown Sarasota. This is truly what laid back island life on Longboat Key is all about. Make an appointment to see this home today and start enjoying your piece of island paradise.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
3810 GULF OF MEXICO DR #F206, LONGBOAT KEY, FL 34228
$325,00092 Days on yellowkey MLS ID: A4686238
5 Days Off yellowkey (back on 4/16/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1007 Built: 1970 Tax: $3,657 (2025)Community: Beach Harbor ClubCondo
Taxes:$3,657
Tax Year: 2025
Remarks: Under contract-accepting backup offers. Start living the Longboat Key lifestyle from day one in this furnished coastal condominium at Beach Harbor Club with serene bay views. This spacious two bedroom, two bath residence is ideally located in a sought after beach to bay community along Gulf of Mexico Drive. Positioned on the second floor with convenient elevator access, the residence is filled with natural light and offers a comfortable, easy flowing layout. The living and dining areas feel bright and inviting, with soft views of Sarasota Bay creating a calm, coastal backdrop. Beautiful luxury vinyl flooring extends throughout much of the residence, adding a fresh and cohesive feel. The kitchen provides ample space and storage, features an InSinkErator replaced in 2024, and a separate laundry room with a Maytag stackable washer and dryer adds everyday convenience. Both bedrooms are generously sized and well situated, with the primary bedroom being ensuite. Both bathrooms feature tubs, offering comfort and flexibility for owners and guests alike. A 2 ton Trane HVAC system installed in 2024 adds significant value and peace of mind. All furniture and furnishings are included, making this a truly move in ready opportunity. The residence experienced no damage or flooding from recent storms. Beach Harbor Club stretches from the Gulf to Sarasota Bay, offering the best of both worlds with a private deeded beach for stunning sunsets and Bayfront amenities include a marina with fishing pier, kayak storage. The community also features a heated pool, cabanas and grilling and picnic areas, a clubhouse, and a fitness center. Covered carport parking is included. You are a short drive to SRQ airport, with easy access to nearby beaches including Siesta Key, Lido Beach, and Anna Maria Island, as well as the shopping, dining, and boutiques of St. Armand's Circle and the vibrant downtown Sarasota scene. Simply arrive, unpack, and start enjoying your place in the sun.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Pam Bailey (941-777-5039)
726 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$1,090,000113 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
Taxes:$15,835
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 Agent: Steve Walter (941-809-0907)
519 ROUNTREE DR, LONGBOAT KEY, FL 34228
$6,488,00072 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
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
$1,550,00072 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
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)
408 GULF OF MEXICO DR #1214, LONGBOAT KEY, FL 34228
$99,00074 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)
1445 GULF OF MEXICO DR #501, LONGBOAT KEY, FL 34228
$1,499,00088 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)
340 GULF OF MEXICO DR #112, LONGBOAT KEY, FL 34228
$1,775,000240 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
$2,795,000130 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.
2089 GULF OF MEXICO DR #G1-108, LONGBOAT KEY, FL 34228
$675,000124 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
$13,000,000107 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
$995,000146 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
$6,100,00084 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
$425,00080 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
$425,00081 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)
100 SANDS POINT RD #114, LONGBOAT KEY, FL 34228
$2,100,000112 Days on yellowkey MLS ID: A4685212
3 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2094 Built: 1966 Tax: $14,826 (2025)Community: Sands PointSpa: YesCondo
Taxes:$14,826
Remarks: Completely updated and offered furnished, this spectacular direct Gulf-front residence at Sands Point delivers the rare combination of expansive living space, modern design, and immediate beach access. True three-bedroom, three-bath Gulf-front residences are seldom available in this sought-after Longboat Key community, making this nearly 2,100-square-foot getaway a standout opportunity. This residence has undergone an extensive renovation that reimagines the interior with a bright, open layout designed to showcase panoramic Gulf views. Floor-to-ceiling glass sliders and expansive windows frame the turquoise waters and sugar-white shoreline beyond, while opening directly to the beachfront patio—placing the sand and surf just steps from your door. Major improvements throughout the residence include impact windows and sliders, new drywall, updated electrical and plumbing systems, newer ductwork, and a new HVAC system—creating a move-in ready coastal retreat where every detail has already been thoughtfully addressed. Inside, the thoughtfully redesigned interior blends coastal comfort with modern finishes. Wide-plank porcelain tile flooring with a warm wood finish flows throughout the residence, connecting each space with a clean contemporary aesthetic. The open great-room layout seamlessly links the chef’s kitchen, dining area, and living room, creating a welcoming environment for entertaining or relaxed beachfront living. The gourmet kitchen serves as the centerpiece of the home, featuring an oversized waterfall-edge island with dine-in seating, custom cabinetry, quartzite countertops, striking Sea Glass tile backsplash, and high-end stainless steel appliances. With the kitchen positioned to overlook the living area and Gulf beyond, every gathering benefits from a dramatic waterfront backdrop. The primary suite occupies the south side of the residence, offering privacy, tranquil water views, and a spacious walk-in closet. Its spa-inspired quartzite bathroom includes dual sinks and a large walk-in shower designed with modern finishes. Two guest bedrooms are arranged on the north side of the residence, each with access to beautifully updated quartzite bathrooms, providing comfort and privacy for visitors. The residence also includes a covered parking space conveniently located just outside the front door. Sands Point is a private Gulf-front enclave located behind the gates of the prestigious Longboat Key Club. Residents enjoy a relaxed resort setting with a beachfront geothermal-heated pool and spa, private clubhouse, shaded tiki huts along the shoreline, and beautifully maintained grounds. A short stroll leads to the community marina, where boat slips are available on a waitlist basis. Positioned on the southern end of Longboat Key, this location places you minutes from championship golf and tennis at the Longboat Key Club, the boutiques and restaurants of St. Armands Circle, and the vibrant arts and dining scene of downtown Sarasota. From boating and beach walks to waterfront dining and cultural events, this exceptional residence offers effortless access to the best of the Gulf Coast lifestyle.
Listing Agent: Roger Pettingell (941-387-1840)
3010 GRAND BAY BLVD #482, LONGBOAT KEY, FL 34228
$1,845,000492 Days on yellowkey MLS ID: A4640667
11 Days Off yellowkey (back on 1/19/2026)
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2250 Built: 1999 Tax: $15,440 (2024)Community: Grand Bay 4Condo
Taxes:$15,440
Middle School: Pine View School
Remarks: Under contract-accepting backup offers. This FURNISHED waterfront residence offers panoramic views of Sarasota Bay and the Gulf of Mexico, seamlessly complementing its neutral, sophisticated interior. An elegant double-door entry leads to an open floor plan with gleaming ceramic tile floors and floor-to-ceiling glass that highlights the stunning scenery. BRAND NEW IMPACT WINDOWS THROUGHOUT. The split layout ensures privacy, with a guest en-suite featuring bay views. The bright, modern kitchen includes a striking tile backsplash, white cabinetry, stainless steel appliances, stone countertops, and a tray ceiling. A breakfast bar connects to an informal dining space, perfect for daily use. The great room provides ample space for both relaxation and entertaining. The primary suite offers terrace access, his-and-hers bathrooms, and a walk-in closet with custom shelving. The wraparound terrace showcases expansive water views, ideal for enjoying both sunrises and sunsets. Residents enjoy top-tier amenities, including a 24-hour guard-gated entry, secure under-building parking, a clubhouse, a fitness center, two Har-Tru tennis courts, and two heated pools with a spa. Deeded access to a private beach and membership to the Bay Isles Beach Club enhance this exceptional lifestyle. Located just minutes from Downtown Sarasota and St. Armands Circle, this home offers luxury, convenience, and breathtaking waterfront living.
2800 HARBOURSIDE DR #E-07, LONGBOAT KEY, FL 34228
$300,00085 Days on yellowkey MLS ID: A4688599
Bed: Bath: 0.0 Built: 1985Monthly Fee: $372 Tax: $2,230 (2025)Community: Longboat Key Moorings MarinaDock-Rackominium
Taxes:$2,230
Remarks: A favorite dock in the Marina with ample turning radius. This 55 x 21 foot slip at Longboat Key Club Moorings is located on the west side of the Marina. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 50 LOA; beam depends on the vessel. Call to discuss!
2295 GULF OF MEXICO DR #64S, LONGBOAT KEY, FL 34228
$625,000188 Days on yellowkey MLS ID: A4675582
0 Days Off yellowkey (back on 3/1/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $6,088 (2025)Community: Islander Club Of LongboatCondo
Taxes:$6,088
Remarks: Under contract-accepting backup offers. PRICE REDUCED! Don’t miss this opportunity, schedule your showing today! Beachfront Living at Islander Club on Longboat Key Experience relaxed beachfront living at the Islander Club, one of Longboat Key’s most established and sought-after Gulf-front communities. Located directly on the Gulf of Mexico, this beautifully updated 2-bedroom, 2-bath residence offers true resort-style living in a premier island setting. Situated on the 6th floor along the desirable south/southeast side of the building, the residence spans more than 40 feet, capturing stunning Gulf views and refreshing coastal breezes. Inside, the home has been thoughtfully refreshed with new luxury engineered wood flooring, fresh coastal-inspired paint, and updated lighting throughout. The open floor plan creates a bright, airy atmosphere, with the kitchen flowing seamlessly into the main living area. Large impact windows in the primary bedroom bring in abundant natural light while framing uninterrupted Gulf views. The primary suite includes a private ensuite bath, a full-size washer and dryer are conveniently located inside the unit, and additional storage off the living room adds everyday functionality. Residents of the Islander Club enjoy an impressive collection of resort-style amenities set on an expansive stretch of private beachfront. Community features include over 400 feet of private beach frontage, two fishing jetties, Har-Tru tennis courts, a beachfront heated pool and spa, a fitness center, saunas, and a newly renovated clubhouse with a full kitchen, library, billiards, and table tennis. The community also offers secure gated entry, elevators, professional on-site management, and 24/7 maintenance, providing both comfort and peace of mind. The location is equally exceptional. The Longboat Key Club is just a short bike ride or drive away, offering world-class golf, dining, tennis, and pickleball. The boutiques and restaurants of St. Armands Circle are less than four miles away, with downtown Sarasota’s cultural attractions, shopping, and dining just beyond. This turnkey beachfront condominium offers the perfect opportunity to enjoy effortless coastal living in one of Longboat Key’s most desirable Gulf-front communities. Simply bring your flip-flops and start enjoying the island lifestyle.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Harold Kaufman (508-525-5938)
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