Location: Longboat Key, Longboat Key
Do Not Show Listings
578 COMPANION WAY, LONGBOAT KEY, FL 34228
$999,00071 Days on yellowkey MLS ID: A4682186
REDUCED by $1,000 (0.1%) on 04/19/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,672
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Linh Pham (941-900-6789)
636 TARAWITT DR, LONGBOAT KEY, FL 34228
$799,000386 Days on yellowkey MLS ID: TB8368182
1 Days Off yellowkey (back on 3/19/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1248 Built: 1961 Tax: $6,715 (2024)Community: Longboat KeySingle Family
Taxes:$6,715
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. A NEW PRICE!! Wake up to tranquil canal views and end your day with sunsets just steps from the Gulf — all on Longboat Key! Priced UNDER $1M & Renovation Loan Eligible! Opportunities like this are rare, and this property is priced to sell fast. Featuring 2 bedrooms, 2 bathrooms, and a 1-car garage, this home also includes a separate 1-bedroom, 1-bathroom GARAGE APARTMENT with its own entrance—perfect for SHORT TERM RENTALS or guest accommodations. Sitting directly on a CANAL with room to dock a boat, this home is a dream for boaters and beach lovers alike. The 120 feet of reinforced seawall ensures lasting waterfront stability. Enjoy DEEDED BEACH ACCESS, just a short stroll away, where you can witness the magic of turtle nesting season. Walk to dog-friendly Durante Park, the scenic shores of Sarasota Bay, and some of Longboat Key’s most popular restaurants, including Lo’Key and Harry’s Continental Kitchen. Cannon’s Marina is nearby for all your boating needs, and the trolley provides easy access to Anna Maria Island. The home boasts a 2024 AC and a 5-year-old tile roof, giving you peace of mind on major updates. The private outdoor space is perfect for soaking up Florida’s year-round sunshine. Renovation Loan Eligible – Plus an Incredible Build Opportunity! This property qualifies for a renovation loan, allowing you to finance both the purchase and renovations—an incredible opportunity to customize your dream home while keeping costs manageable. Waterfront. Deeded beach access. Room for a boat. Rental potential. And all for UNDER $1 MILLION! This is an **unbeatable opportunity** in one of the most desirable locations on the Gulf Coast. Don’t miss out—schedule your showing today!
Listing is courtesy of: JT REALTY & ASSOCIATES (352-279-2640)
Listing Agent: Sarah Beth Mayer (941-779-5690)
691 TARAWITT DR, LONGBOAT KEY, FL 34228
$850,00099 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
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)
435 L AMBIANCE DR #L807, LONGBOAT KEY, FL 34228
$3,500,000194 Days on yellowkey MLS ID: A4668015
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2525 Built: 1994 Tax: $29,083 (2024)Community: L Ambiance At Longboat Key Club Ph 02Spa: YesCondo
Taxes:$29,083
Elementary School: Southside Elementary
High School: Riverview High
Middle School: Pine View School
Remarks: Discover Your Coastal Paradise at L'Ambiance!** Step into a world of instant enjoyment. Nestled along the stunning Gulf of Mexico, L'Ambiance offers you a front-row seat to Sarasota's dramatic sunrises and captivating sunsets. This exceptional corner residence is a rare gem, designed to help you create a lifetime of cherished memories. As you glide off your private elevator into the foyer, prepare to be mesmerized by panoramic views that seamlessly blend the indoors with the stunning outdoors. Meticulously crafted by a professional decorator, this residence is a masterpiece of elegant living, featuring expansive glass walls that invite the beach's natural beauty into your home. Enjoy the custom kitchen and luxurious bathrooms, all adorned with travertine flooring in the main living areas and plush carpeting in the bedrooms. Imagine sipping your morning coffee on the east terrace, soaking in the breathtaking sunrise, or toasting to the magical afterglow of sunset with a glass of champagne on the southwest terrace. This spacious 2-bedroom (plus den or 3-bedroom) and 3.5-bathroom residence exemplifies the pinnacle of beachside luxury. Your maintenance fee ensures a stress-free lifestyle, covering everything from the building's exterior and cable service to flood insurance and on-site management so that you can immerse yourself fully in the extraordinary island living experience. With concierge services, a resort-style pool and spa, guest suites for visitors, and a state-of-the-art fitness center, L'Ambiance offers amenities that elevate your everyday life. Sarasota's pristine white, sugar-sand beaches are just the beginning! Dive into a vibrant cultural scene to enjoy the Sarasota Opera, the Sarasota Ballet, and the West Coast Symphony. Explore the renowned Ringling Museum of Art, wander through charming art galleries and antique shops, or indulge in exquisite dining at world-class restaurants. Whether you crave the excitement of marinas and golf courses or the casual charm of local cafes, Sarasota truly has it all. Make this luxurious beachfront residence your new home and embrace the unparalleled lifestyle that awaits you at L'Ambiance. Your dream of extraordinary living is just a step away!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
726 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$1,090,00049 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)
761 TARAWITT DR, LONGBOAT KEY, FL 34228
$1,499,000160 Days on yellowkey MLS ID: A4672164
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2377 Built: 1981 Tax: $10,693 (2024)Community: Longboat KeySpa: NoSingle Family
Taxes:$10,693
Remarks: This fabulous waterfront Longboat Key pool home has it all! It is situated on an oversized 11,250sf lot on the canal with 125 feet of seawall, so you can truly enjoy hopping on your boat or kayak or paddle board right outside your back door! It was built strong with steel and precast slab and all of the windows and doors are storm rated or have shutters. Two large garages allow for plenty of storage space, and one of them flows through to the backyard which allows for all your water toys to be easily at the ready. The first floor has 1 of the 3 bedrooms and baths and a large open area for gathering and enjoying the gorgeous backyard. The 2nd floor features the other 2 bedrooms and 2 baths, an open kitchen and living area plus a lovely, light filled dining space overlooking the canal. A large deck area over top one of the garages looks over the sparkling salt water pool with picturesque views and steps down for your refreshing swim. The home has been meticulously kept and is set up for a perfect balance of indoor/outdoor living. All of this plus deeded beach access down the street mean you have covered all the bases to be living the true island lifestyle that Longboat Key is known for.
519 ROUNTREE DR, LONGBOAT KEY, FL 34228
$6,488,0008 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)
5965 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$38,450,00048 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
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)
2800 HARBOURSIDE DRIVE DR #D-19 D-20, LONGBOAT KEY, FL 34228
$985,000381 Days on yellowkey MLS ID: A4646560
0 Days Off yellowkey (back on 3/19/2026)
Bed: Bath: 0.0 Built: 1985Monthly Fee: $1,032 Tax: $7,286 (2025)Community: Lbk Club MooringsDock-Rackominium
Taxes:$7,286
High School: Booker High
Middle School: Booker Middle
Remarks: A one of a kind boat slip available for sale with fortified pilings that are plastic coated and an extended finger pier, deep water, protected, yet easy access to Sarasota Bay and the Gulf at Longboat Key Moorings Marina. This is a 154 ft. T-dock/face dock ready to accommodate a yacht; T of D-dock has 2 50s/100 service outlets. D-19 is 74.5 feet, and D-20 is 79.5 feet, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. This only deep water marina on the West Coast of Florida is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes bath house, laundry facilities, restaurant, 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. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. This slip will accommodate one or two vessels total 149 feet. Usable beam is 25 feet.
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
3710 GULF OF MEXICO DR #F2, LONGBOAT KEY, FL 34228
$475,00048 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)
6851 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$1,775,00083 Days on yellowkey MLS ID: A4675356
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2643 Built: 1986 Tax: $9,196 (2024)Community: Longbeach On Longboat KeySingle Family
Taxes:$9,196
Remarks: Welcome to 6851 Longboat Drive South, a completely renovated waterfront retreat offering the best of Longboat Key living. This exceptional residence features four bedrooms and four baths, including a private guest suite above the garage, and office/gym space, making it ideal for hosting family and friends in comfort and style. Designed with coastal elegance in mind, the home showcases light-filled living spaces, a modern open layout and high-quality finishes throughout. The seamless indoor-outdoor flow leads to tranquil waterfront views, ideal for entertaining or unwinding after a day on the water. Boaters will appreciate the private dock, providing direct access to the bay and making it easy to enjoy fishing, cruising or sunset rides right from your backyard. Every detail has been thoughtfully updated, offering peace of mind and turnkey convenience. Just minutes from the Gulf beaches, St. Armands Circle and Longboat Key Club, this property delivers a rare opportunity to own a move-in-ready waterfront home in one of Florida’s sought-after island communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Barbara Szumski (941-232-8776)
3710 GULF OF MEXICO DR #F1, LONGBOAT KEY, FL 34228
$139,900161 Days on yellowkey MLS ID: A4671498
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 620 Built: 1974Monthly Fee: $290 Tax: $2,407 (2025)Community: Gulfshore Of Longboat KeySpa: NoMobile Home
Taxes:$2,407
Remarks: READY FOR REMODELING: This unit in beautiful Gulfshore of Longboat Key, is waiting for a buyer with imagination. This unit will require restoration to make it the beautiful beach bungalow that it once was. As such, they are offering a dramatically reduced asking price to make restoration economically feasible. The home features 620 square feet of living space, with a kitchen, living room, one primary bedroom (L-shaped) and a full bath. There is also an outside bath with shower (needs renovation) that is perfect for when you return from the beach. This unit is close to the clubhouse and the marina. The community of Gulfshore, is truly a tropical paradise and is just six miles from world-famous St. Armands Circle in Sarasota. It offers ownership of approximately 450 feet of beach on the beautiful Gulf of Mexico. The Gulf is known for its wonderful sand beaches and turquoise waters. In addition, Gulfshore has a marina on Sarasota Bay (currently being rebuilt), a large community swimming pool, and a clubhouse for hosting social events. Gulfshore is proud of their financial management and the affordable cost of living that has resulted. Gulfshore is a 55+ community that does not allow rentals or pets. The combination of a beach bungalow with the amenities offered by Gulfshore, truly make this a home in paradise. Please call for your personal showing.
Listing is courtesy of: EDGEWATER REAL ESTATE, INC (941-778-8104)
Listing Agent: Bill Shuttleworth (941-779-8877)
6841 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$1,050,000126 Days on yellowkey MLS ID: A4674302
0 Days Off yellowkey (back on 4/9/2026)
REDUCED by $45,000 (4.1%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1380 Built: 1935 Tax: $13,113 (2025)Community: Longbeach On Longboat KeySpa: NoSingle Family
Taxes:$13,113
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Rarely does a property offer this much land, waterfront, and location value within the cherished Longbeach community of Longboat Key. Located on the desirable Manatee County side of the island, this original 1935 coastal cottage sits on an oversized .34+ acre waterfront lot with approximately 78 feet of frontage and an impressive 192-foot depth—dimensions increasingly difficult to find on Longboat Key. Enjoy direct, bridge-free boating to the Intracoastal Waterway, Sarasota Bay, and the Gulf of America, making it an exceptional opportunity for boaters, investors, or those looking to build a future waterfront estate. All just moments from the beach and within walking distance of the charm and character of Longbeach Village. Enjoy a short walk to the beach, no HOA fees, and flexible rentals with one-month minimums allowed up to 12 times per year. RSF-6 zoning (buyer to verify) allows up to six units per acre, offering potential for a primary home with guest house, pool, and spa. An existing dock (currently damaged) already has water and electric, and the lot provides ample space for a large lap pool and outdoor entertaining. Over $100,000 in capital improvements include a shingle roof (2023), and extensive interior updates completed in 2025 following storm remediation, including all new flooring, paint, cabinetry, and drywall. Additional upgrades include a new 2.5-ton AC system (2024), electrical improvements with a 200-amp panel and grounding, water heater (2025), hurricane impact windows in most rooms, including the primary bedroom, kitchen, both bathrooms, and living room, a sizable upgrade to the home. Private irrigation well, providing peace of mind, long-term efficiency and conveniences of moving right in to enjoy this exceptional home and property! Offering two bedrooms, two bathrooms, and approximately 1,180 square feet, the home retains timeless island character with original cypress walls and ceilings, abundant windows, and a wood-burning fireplace that anchors the living space. A standout feature is the 15x33 rear-facing covered and screened lanai, providing approximately 510 square feet of under-roof outdoor living with pitched ceilings, fans, sun shades, and fully pocketing sliding glass doors, with the flexibility to incorporate this space into additional interior living if desired. The updated half-galley kitchen features shaker wood cabinetry, soft-close drawers, light quartz countertops, an LG stainless steel appliance package, deep stainless sink, pull-outs, and lazy Susan, all overlooking the front stoop and lawn. The spacious primary ensuite measures approximately 10x22 and includes room for seating or office use, dual sinks, his-and-hers closets, and a shower/tub combination. A shared full bath offers inlaid tile flooring and a walk-in shower with marble step. Wood flooring runs throughout with tile in the bathrooms, offering NO carpeting. Additional features include a shell and paver driveway, French front door, expansive fully pocketed sliding glass doors, gutters, fenced yard, and a one-car carport (that houses the washer, dryer and hot water heater). One of the last remaining original cottages in the Whitney Beach / LongBeach area, this property offers a compelling opportunity to restore historic charm, reimagine the footprint, or create a refined waterfront estate defined by location, land, boating, beach access, flexibility, and vision. SELLER financing terms available upon request.
Listing is courtesy of: CORCORAN DWELLINGS REALTY (941-200-4663)
Listing Agent: Shayla Twit (941-544-7690)
765 SAINT JUDES DR N, LONGBOAT KEY, FL 34228
$1,499,90062 Days on yellowkey MLS ID: A4683420
REDUCED by $80,100 (5.1%) on 04/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1900 Built: 1963 Tax: $14,125 (2025)Community: Longboat KeySpa: NoSingle Family
Taxes:$14,125
Remarks: Best Waterfront Value on Longboat Key – CANAL-FRONT Home with Deeded Private Beach Access. Exceptional opportunity to own a fully renovated CANAL-FRONT residence on highly sought-after Longboat Key. Notably, the property was appraised prior to renovation completion for more than the original asking price, creating a rare built-in equity opportunity. This 4-bedroom, 2-bathroom coastal retreat offers the perfect blend of luxury, location, and lifestyle, complete with DEEDED PRIVATE BEACH ACCESS to the Gulf of America. Positioned along 132 linear feet of canal frontage, the property features a seawall and kayak launch (2020) and provides direct boating access to Sarasota Bay and beyond. The home has undergone a comprehensive interior and exterior renovation, with virtually everything NEW apart from the home’s foundation, delivering exceptional move-in-ready peace of mind. 2025 Improvements Include: • New roof (2025) • New flooring (2025) • New interior walls (2025) • Full home renovation – interior & exterior (2025) • New AC systems (2025) • New decking (2025) • New cabinets (2025) • New landscaping (2025) • New electrical systems (2025) Major System & Feature Upgrades: • Electrical panel (2022) • New plumbing (2022) • Commercial-grade whole-home surge protector (2022) • Tankless gas water heater (2022) • New sliding glass doors (2022) • New impact windows (2022–2023) • Impact-rated garage doors (2022) • New pavers (2022) • New ductwork (2020) • Seawall & kayak launch (2020) PGT high-impact sliding glass doors, new impact windows, and impact-rated French doors enhance storm protection, energy efficiency, and natural light. Interior highlights include vaulted ceilings, expansive water views, two electric fireplaces, and elegant wood-look ceramic tile flooring throughout. The bright, open layout is designed for effortless coastal living. The beautifully updated kitchen features solid wood cabinetry, soft-close hardware, marble-look quartz countertops, a gas stove, premium stainless-steel appliances, a copper hood, and a copper farmhouse sink. Updated bathrooms showcase sophisticated Italian marble-look ceramic tile, including an alcove soaking tub in the primary suite and a walk-in rain shower. Outdoor living is elevated by a spacious screened porch overlooking the canal and backyard. The yard is enclosed with sleek black aluminum fencing and offers ample room for a future pool. Additional Highlights: • Higher elevation than many ground-level Longboat Key homes • 132 ft of canal frontage • Direct boating access • Deeded PRIVATE beach access Ideally located near Cedars East Tennis Resort & Club, offering nine tennis courts, three pickleball courts, and a large community lap pool, as well as Joan Durante Park (34 acres). Dining, shopping, and island amenities are all within close proximity. Offered fully furnished / TURNKEY, this home is ready for immediate enjoyment as a primary residence, vacation retreat, or investment opportunity. Boating + Beach + Extensive 2025 Renovation = Rare Longboat Key Opportunity. Schedule your private tour today!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Kalison Nix (941-900-9189)
1581 GULF OF MEXICO DR #406, LONGBOAT KEY, FL 34228
$6,750,00044 Days on yellowkey MLS ID: A4685503
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2347 Built: 2024 Tax: $50,055 (2025)Community: St. RegisSpa: NoCondo
Taxes:$50,055
High School: Sarasota High
Remarks: Perched above the shimmering shoreline, this exquisite two-bedroom, two-and-a-half-bath residence at The St. Regis Longboat Key Resort offers breathtaking panoramic views of the turquoise waters of the Gulf of Mexico and the resort’s serene saltwater lagoon. Designed for both refined comfort and effortless coastal living, the residence showcases exceptional craftsmanship and sophisticated design throughout. A defining feature of this residence is the expansive private terrace, where all principal rooms open seamlessly to the outdoors. Complete with a gas grill, this exceptional outdoor living space provides sweeping views of the Gulf of Mexico and the tranquil lagoon—creating the perfect setting for al fresco dining, entertaining, or simply enjoying spectacular sunsets over the water. The gourmet kitchen is a true showpiece, appointed with sleek Poggenpohl cabinetry and premium appliances including Wolf double ovens, a gas cooktop, microwave, icemaker, and wine refrigerator. A generously sized island provides abundant built-in storage, making the space as functional as it is beautiful. This thoughtfully designed floor plan features two luxurious owner’s suites. The primary suite enjoys stunning views of the Gulf of Mexico and opens directly onto the large terrace. The spa-inspired bathroom features a large double vanity with elegant lighted mirrors plus a separate makeup vanity, two private water closets, a seamless glass shower, and a freestanding soaking tub. Electronic sheers and blackout shades provide effortless ambiance and privacy, while a custom-built closet offers exceptional storage. The second owner’s suite also captures captivating Gulf views and opens onto the terrace. Its spacious bath includes dual vanities with lighted mirrors, a water closet, and custom-built closets. Electronic sheers and blackout shades add both convenience and luxury. Additional highlights include a large laundry room with sink, cabinetry, and hanging rack, as well as an elegantly designed powder room for guests. Offered completely turnkey, the residence is beautifully furnished and enhanced with custom light fixtures throughout, creating a sophisticated yet inviting coastal retreat. 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lynn Morris, Pllc (941-400-4526)
1561 GULF OF MEXICO DR #304, LONGBOAT KEY, FL 34228
$13,000,00043 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
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!
1591 GULF OF MEXICO DR #412, LONGBOAT KEY, FL 34228
$3,950,00093 Days on yellowkey MLS ID: A4679040
3 Days Off yellowkey (back on 3/24/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2154 Built: 2024 Tax: $34,330 (2025)Community: St. Regis Longboat KeySpa: NoCondo
Taxes:$34,330
Remarks: Spectacular Sarasota Bay and city skyline views set the stage for this exquisite and private two-bedroom, two-bath residence at the prestigious St. Regis Longboat Key. Offered fully furnished and thoughtfully designed by Studio G Interiors, the home showcases an elegant coastal aesthetic throughout. A large wraparound terrace with a private gas grill provides the perfect setting for indoor-outdoor living and entertaining. The spacious owner’s suite enjoys breathtaking Sarasota Bay views and features a spa-like bathroom appointed with Poggenpohl cabinetry and quartz countertops. The en suite guest bedroom offers privacy and comfort with custom-designed closets, making it ideal for visitors or extended stays. Additional highlights include electronic blinds throughout, a built-in office area, and a sophisticated wet bar with designer tile, custom shelving, a wine refrigerator, and an ice maker—perfect for entertaining. The gourmet kitchen is beautifully appointed with Poggenpohl cabinetry, a Sub-Zero refrigerator, Wolf double ovens and six-burner cooktop, and a Cove dishwasher. A dedicated laundry room with sink is equipped with an Electrolux washer and dryer. Completing this exceptional residence is a private two-car garage, offering rare convenience and security. Beyond the residence, The St. Regis Longboat Key Resort offers a curated collection of world-class amenities designed exclusively for residents. The private clubhouse includes a state-of-the-art fitness center, a resident-only pool and spa, and access to the signature St. Regis Butler and Concierge services that redefine luxury living. Indulge in the oceanfront spa, diverse dining venues, and beachfront cabanas, or enjoy family-friendly experiences such as a lazy river and saltwater lagoon teeming with tropical fish, stingrays, and resident tortoises. Set on 17 acres of pristine beachfront, and just 3.5 miles from St. Armands Circle’s renowned shopping and dining, this residence represents more than a home—it’s an invitation to embrace the legendary St. Regis lifestyle, where elegance, comfort, and unparalleled service define every moment. Begin your journey to Live Exquisite at The St. Regis Longboat Key.
1591 GULF OF MEXICO DR #216, LONGBOAT KEY, FL 34228
$2,750,000217 Days on yellowkey MLS ID: A4665247
Bed: 1 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1556 Built: 2025 Tax: $25,560 (2025)Community: St. Regis Longboat KeySpa: NoCondo
Taxes:$25,560
Remarks: Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home. St. Regis Longboat Key offers a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail. An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds. Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents. This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulf side living.
7149 LONGBOAT DR N, LONGBOAT KEY, FL 34228
$2,595,00026 Days on yellowkey MLS ID: A4687604
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3230 Built: 1967 Tax: $19,370 (2025)Community: Longbeach On Longboat KeySpa: YesSingle Family
Taxes:$19,370
Remarks: Fully Renovated in Coveted Longbeach Village, This Waterfront Retreat Captures the Rare Blend of Old Longboat Key Charm and Like-New Coastal Luxury...Extensively Overhauled From Top to Bottom, the Residence Showcases a Refined Interior, a Stunning Floating Staircase Connecting the Levels, a Newly Added True Fourth Bedroom on the First Floor, and a Spacious Second Floor Chef’s Kitchen Appointed with Built-In Appliances Including Refrigerator, Microwave, Wall Oven, and Cooktop with Vent Hood, a Large Island with Basin Sink, Quartz Countertops, Soft-Close Drawers, and Under-Cabinet Lighting...Ceramic Tile Flooring, Thick Foam Insulation in the Attic and Interior Walls for Energy Efficiency and Added Sound Control, a Sleek First Floor Entertaining Bar with Built-In Draft Beer System, and Integrated Audio Throughout the Interior and Outdoor Living Spaces Further Elevate the Experience...Since Ownership, the Improvements Have Continued with a Replaced Roof, All New Impact Windows, Doors, and Sliders, a Saltwater Tiled Pool and Spa, Premium Landscaping, Extensive Landscape Lighting, and Clear View Screening for Uninterrupted Pool and Canal Views...Designed for Buyers Who Value Both Elegance and Utility on the Water, the Outdoor Experience Is Equally Compelling with a New Seawall, a New Dock with Trex Decking, an 8,000-Lb Boat Lift, Dual PWC Accommodations, Dock Lighting and Electrical, and Speakers at the Dock for Effortless Days Enjoying the Longboat Key Lifestyle...Offered Turnkey and Ideally Positioned Near Mar Vista Dockside Restaurant & Pub, Shore, Whitney’s, the Beach, and the Open Water Beyond the Canal, This Is a Rare Opportunity to Own a Substantially Enhanced Waterfront Property in One of Longboat Key’s Most Coveted Settings...Book Your Private Tour Today and Live a Fuller Life on Longboat Key.
Listing is courtesy of: FULLER GROUP (941-961-3100)
Listing Agent: Bo Fuller (941-961-3100)
2600 HARBOURSIDE DR #C13, LONGBOAT KEY, FL 34228
$489,50041 Days on yellowkey MLS ID: A4686064
Bed: Bath: 0.0 Monthly Fee: $411 Tax: $2,681 (2025)Community: Bay IslesDock-Rackominium
Taxes:$2,681
Remarks: 72' x 21' Boat Slip on C-Dock at Longboat Key Moorings Marina for Sale ~ AND THERE IS NO MEMBERSHIP REQUIREMENT to join The Longboat Key Club (which is now $115,000) and the annual fee of $8388 plus food & beverage fees. The beauty of this TWO-LEVEL dock is... there is no covenant BUT if you chose to join the Longboat Key Club, there are multiple membership packages to choose from which give you access to multiple restaurants, the beach club and poolside restaurants, more information can be provided upon request. The Longboat Key Moorings is strategically located on the beautiful exclusive island of Longboat Key ~ just a few minutes to St. Armands Circle, downtown Sarasota or Bradenton Beach. This amazing location provides direct access to Sarasota Bay and the ICW and the Gulf of America. The LBK Moorings is a deep water ~ state-of-the art marina ~ offering full services, with a touch of class and personal attention seldom found elsewhere. World class facilities on this spectacular island provides storm-protected deep water yacht slips, Dock Crew, Harbor Concierge, 24-hour manned Guard Gate and much more. Each slip has Cable TV, Electricity, Water and Wi-Fi. There also is an on-site service department for repair and maintenance needs, as well as, on-site fuel service, and pump out service. An amazing location with quick access to great shops and dining at St Armands Circle and from there a Classic Sarasota Trolley will take you into downtown Sarasota and back! Your Gateway to the Gulf! Imagine stepping aboard your boat just minutes from the sparkling waters of the Gulf of Mexico. This exceptional boat slip in beautiful Longboat Key offers the perfect combination of convenience, protection, and access for serious boaters and coastal lifestyle lovers alike. Perfectly positioned for effortless cruising, this dock provides quick, unobstructed access to the open waters of the Gulf—no long no-wake zones or complicated navigation. From here, you’re only moments away from world-class fishing, sunset cruises, and exploring the stunning coastline. Owning a dock in Longboat Key means more than just a place to park your boat—it’s an invitation to enjoy sun-drenched days on the water, dolphin sightings, world-class fishing, and unforgettable sunsets. Why This Location Stands Out • Quick boating access to Sarasota Bay and the Gulf • Close to waterfront dining, marinas, and fuel • Situated in one of Florida’s most sought-after boating communities Rare Opportunity Boat slips in Longboat Key are highly coveted and rarely available. Whether you’re a local boater, seasonal resident, or investor looking for premium waterfront access, this is your chance to secure a piece of paradise.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Rian Carver (941-735-6010)
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