Location: Longboat Key
Do Not Show Listings
677 LANDS END DR, LONGBOAT KEY, FL 34228
$2,790,00066 Days on yellowkey MLS ID: A4682565
REDUCED by $60,000 (2.1%) on 04/18/2026
Bed: 3 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 4182 Built: 1989Monthly Fee: $967 Tax: $33,361 (2025)Community: Lands EndSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$33,361
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: W.D. Sugg Middle
Remarks: In a rich tropical waterfront setting on Longboat Key, this unique retreat lives like a modern treehouse while evoking a sense of peace, family and comfortable, easy island living. Tucked within the island’s native landscape along a natural bayou off Sarasota Bay, the property offers a rare opportunity to experience serene waterfront living surrounded by nature, with the Gulf’s azure waters and pristine beach access just moments away. Enjoy your private backyard dock and kayak launch or secure your boat on one of the deepwater slips on the open bay. Excellent fishing and bird watching await right outside your door in this remarkable natural habitat. The spacious home is anchored by a stunning great room with vaulted cedar ceilings and exposed beams. The home features a 40-by-9-foot sunroom with bar area and handcrafted art shelves, a dedicated library, an inviting family room and a separate private office with extensive built-in cabinetry, providing warmth and functionality. Extensive decking spans the front entry and wraps around an inner atrium courtyard for alfresco dining. An elevated cabana-style shaded area invites relaxation in sun and shade. The kitchen with center island is positioned for hosting memorable gatherings. The primary suite offers a full wall of windows overlooking the tranquil bayou, two walk-in closets and an additional wall of custom storage. The split floor plan provides a separate wing for guests, featuring two additional bedrooms and baths for convenient hosting. Each guest room offers private access to the outdoor decks and views of the tropical center atrium. Two garages accommodate up to four vehicles, boats, golf carts or paddleboards. Many of the furnishings are included. In Land’s End, an intimate gated community of just 12 residences, owners enjoy maintenance-free landscaping, a heated pool, tennis and pickleball courts, and convenient deepwater boat slips, all artfully tucked among the trees for privacy. From here, it is a short visit or golf cart ride to the captivating sandy Gulf beach or local favorites, including Shore Longboat Key, Mar Vista Dockside Restaurant and Whitney’s. The adjacent plaza also offers multiple popular waterfront cafes, boutique shops, Ventura’s restaurant, and 24/7 gym or Pilates studio. Enjoy mesmerizing sunsets on the Gulf or sunrises on the bay from this waterside community. This is a rare offering in today’s marketplace, capturing the allure of Old Florida living in one of the island’s treasured enclaves.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Cindy Fischer (941-465-1124)
3610 BAYOU CIR, LONGBOAT KEY, FL 34228
$2,400,00023 Days on yellowkey MLS ID: A4688141
Bed: 3 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 3192 Built: 1993Monthly Fee: $104 Tax: $18,202 (2025)Community: Bay IslesSpa: YesSingle Family
Taxes:$18,202
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to The Bayou section of beautiful Bay Isles. Tucked away from the hustle and bustle of daily life, this double-gated community, a collection of 126 homes, is the perfect place to be on Longboat Key. The pavered front circular drive delivers you to the elevated double-door entrance. Step inside and prepare to be delighted by the neutral palate throughout and an abundance of natural light. Living is easy in this updated three-bedroom home which includes high ceilings and many tasteful architectural details. Three full baths and one-half bath, a dedicated office adjacent to the primary bedroom, a large formal dining room, separate breakfast room, classy cabinet-filled kitchen with new granite counters and a 9 ft island (seats 6). The kitchen is open to a spacious great room featuring vaulted ceilings, recessed lighting, built-in surround sound and a natural gas fireplace. This step-saving layout includes a main level laundry room as well. The primary bedroom has a new primary bath with a dual control sizeable shower, a walk-in custom closet, and direct access to the heated pool and spa just outside. Every bedroom has an en-suite full bath including the one that has direct pool deck access. Three sets of sliding glass doors open to the outdoor kitchen, pool and spa, all raised to be on the same living level. This main feature, having all living space elevated well above sea level is a bonus. An extremely large non-conforming space on ground level is ideal for multiple cars and/or boat storage, plus an air-conditioned space for a workshop or weight room if desired. There is a brand- new Trane A/C system (2026) as well as a new gas pool heater (2025) With too many fine features to list, this home is a must see. Ownership includes membership into the Bay Isles Beach Club, your private spot on the white sands of the Gulf of Mexico. Also, Longboat Key Golf and Tennis Club membership is available separately. Take a short drive to shopping and dining at the famous St Armands Circle and Downtown Sarasota. Magnificent!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Mike Prisco (941-812-1291)
510 BOWSPRIT LN, LONGBOAT KEY, FL 34228
$4,400,00027 Days on yellowkey MLS ID: A4687207
REDUCED by $200,000 (4.3%) on 04/13/2026
Bed: 5 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 4389 Built: 2013Monthly Fee: $21 Tax: $35,060 (2025)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$35,060
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to this renovated waterfront luxury retreat in the highly sought-after Country Club Shores on Longboat Key. From the moment you arrive to this 5 bedroom 6.5 bathroom almost 4,400 sqft home sitting on nearly ¼ acre, the home’s striking curb appeal, tropical landscaping, and circular paver driveway set the tone for what awaits inside. Perfectly positioned on a deepwater canal with quick access to Sarasota Bay and the Gulf, this exceptional residence offers the ultimate Florida lifestyle with a private dock, 28,000-pound boat lift, and room for a large vessel currently docking a 38 ft boat. Stepping through the front entry, you’re welcomed into a stunning open-concept interior where designer finishes and natural light come together beautifully. The expansive main living area offers soaring coffered ceilings and an impressive floor-to-ceiling marble feature wall complete with an electric fireplace and custom wine display. Large sliding glass doors open wide to seamlessly blend indoor/outdoor living, allowing the waterfront views to become part of everyday living. The gourmet kitchen features top-of-the-line Thermador appliances, custom cabinetry, a wine refrigerator, quartz countertops, and an oversized island with generous seating. The kitchen flows effortlessly into the family room, while the adjacent dining area and breakfast nook offer additional space to gather, all framed by peaceful water views. Privately tucked away on the main floor, the owner’s suite serves as a true retreat. This serene space with plantation shutters offers a luxurious spa-like bathroom complete with dual vanities, quartz countertops, a soaking tub, a walk-in glass shower with a waterfall showerhead, elegant tile finishes, and a Toto Neorest toilet. Upstairs, you’ll find four generously sized bedrooms, each with its own ensuite bathroom and spacious closet, offering comfort and privacy for family or guests alike. One upstairs suite functions beautifully as a secondary primary suite with tray ceilings, dual vanities, and a large walk-in shower with dual showerheads. An upstairs media room adds flexibility and is the perfect place for movie nights, game days, or relaxed entertaining, while the upper-level terrace provides another place to unwind and take in the surrounding waterfront views. An elevator services the garage, first floor, and second floor, adding everyday ease and convenience. Outside, the backyard was designed to feel like your own private resort. The heated saltwater pool and spa are surrounded by travertine tile, tropical landscaping and spacious lounging areas, all overlooking the water for a tranquil setting. A full pool bath adds functionality for seamless indoor-outdoor living. Whether you're spending the afternoon poolside, entertaining under the sun, or heading out for a sunset cruise from your private dock, this home delivers the kind of waterfront lifestyle buyers dream about. Located in the coveted Country Club Shores community, this exceptional property also offers deeded beach access to the powder-soft Gulf beaches just moments away. Enjoy being only minutes from the world-class golf, tennis, dining, and marina amenities of Longboat Key Club, along with the upscale shopping and restaurants of St. Armands Circle, the arts and culture of downtown Sarasota, and the convenience of SRQ International Airport. This is more than just a home, it’s a luxury coastal lifestyle in one of the area’s most desirable waterfront communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kaisen Mitchell (941-726-7657)
550 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$1,295,00058 Days on yellowkey MLS ID: A4683082
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1758 Built: 1977 Tax: $6,151 (2025)Community: Sleepy Lagoon ParkSingle Family
Taxes:$6,151
Middle School: Martha B. King Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to 550 De Narvaez Drive, a meticulously maintained WATERFRONT residence set on an ELEVATED 10,000 sq. ft. lot in the highly desirable Sleepy Lagoon neighborhood on the NORTH END of Longboat Key. This solid concrete block home has experienced NO FLOODING & NO STORM DAMAGE, offering exceptional peace of mind. Spanning 1,758 sq. ft., the light-filled interior features 3 SPACIOUS BEDROOMS and 2 beautifully RENOVATED BATHS. Generous room sizes, abundant natural light, and an inviting floor plan create a true sense of warmth throughout the home. The UPDATED KITCHEN and baths showcase contemporary finishes while maintaining comfort and functionality. Enjoy peaceful CANAL VIEWS with direct access to Sarasota Bay—perfect for boating enthusiasts and embracing the ultimate Florida waterfront lifestyle. NEW DOUBLE PANE IMPACT-RESISTANT WINDOWS and sliding glass doors provide enhanced protection and energy efficiency. Additional upgrades include NEWLY LINED PLUMBING PIPES and UPGRADED ATTIC INSULATION for lasting durability and comfort. Offered FULLY FURNISHED, all furnishings convey with the sale—making this a true TURNKEY opportunity. Simply bring your suitcase and start enjoying coastal living immediately. The expansive elevated lot offers ample space for outdoor entertaining, gardening, or FUTURE EXPANSION POTENTIAL. Ideally located near world-renown Gulf beaches with DEEDED BEACH ACCESS, exclusive dining, boutique shopping, and recreational amenities, this exceptional property is well-suited as a primary residence, seasonal retreat, or investment opportunity. Schedule your private showing today and experience refined, worry-free waterfront living at its finest.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Dean Hinterstoisser (941-726-0314)
552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228
$999,99977 Days on yellowkey MLS ID: A4680786
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1846 Built: 1960 Tax: $17,419 (2024)Community: Sleepy Lagoon ParkSingle Family
Taxes:$17,419
Tax Year: 2024
Remarks: Imagine living the coastal lifestyle only dreams are made of! Wake each morning to the sunrise over your local beach—just a short stroll down the street—where you can sink your toes into sugary white sand, take an early walk, or collect seashells along the shore. Return home to enjoy coffee outdoors by your heated pool, relaxing on the deck as tranquil water views set the tone for the day. Take a refreshing dip, then unwind as nature’s canvas unfolds before you, with shifting light and brilliant shades of blue and azure. In the evening, hop on your boat from your backyard and cruise effortlessly to waterfront restaurants and sunset destinations. With a 20,000-lb boat lift, personal watercraft lift, and a 40-foot dock on a deep-water canal, you’ll enjoy immediate access to Sarasota Bay, the Intracoastal Waterway, and the Gulf—with no fixed bridges along the way. End your days with breathtaking sunsets as the sky ignites in color, dolphins play, and manatees glide by. Inside, the home offers an optimal floor plan ready for your personal touches. The spacious eat-in kitchen features an expansive island perfect for casual entertaining, complemented by new stainless-steel appliances. A wall of sliding glass doors seamlessly blends indoor and outdoor living, filling the home with natural light and water views. All main living areas open to the pool and outdoor spaces. Recent updates include a new AC system and a recently refinished pool. The home offers three bedrooms and four baths, with the flexibility to modify the layout or easily add a fourth bedroom. A wood-burning fireplace adds warmth and charm to the living room. Located on the barrier island of Longboat Key, this exceptional property is perfectly suited for the most discerning buyers. Enjoy nearby golf, pickleball, boutique shopping, and dining, with St. Armands Circle and downtown Sarasota just minutes away. Convenient access to SRQ Airport makes this an ideal full-time residence or luxury vacation retreat. Call today to schedule your private showing and experience coastal living at its finest.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kathy Cahill (941-807-3565)
1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228
$4,750,000206 Days on yellowkey MLS ID: A4666688
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4209 Built: 1987 Tax: $16,980 (2024)Community: Bay IslesSingle Family
Taxes:$16,980
Remarks: Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast.
Listing Agent: Julie Klick (941-780-6001)
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
Taxes:$11,672
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)
612 JUAN ANASCO DR, LONGBOAT KEY, FL 34228
$22,500,000414 Days on yellowkey MLS ID: A4643123
Bed: 6 Bath: 8.0 Gar: 9 Liv Area Sq Ft: 9243 Built: 2024 Tax: $32,107 (2024)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$32,107
Remarks: Welcome to your private, gated estate on Longboat Key, where coastal luxury meets effortless sophistication. Boasting over 730 feet of water frontage, this stunning property offers panoramic views of Whitney Bayou and Harris Canal and provides the ultimate waterfront lifestyle. With 9,243 square feet of air-conditioned living space and a total of 21,562 square feet on over an acre of pristine land, this estate is a masterpiece of design and craftsmanship. Designed in the timeless British West Indies style, this home showcases vaulted ceilings, extensive trim detailing, white oak floors throughout, and two fireplaces, creating an ambiance of elegance and warmth. The expansive covered patios and porches invite you to embrace the serenity of waterfront living, while the heated pool and an impressive 13' x 13' hot tub serve as the ultimate retreats. A custom outdoor fire pit, two outdoor kitchens, and indoor and outdoor pool tables elevate the entertainment experience. For boating enthusiasts, this estate is unrivaled, featuring four low-profile boat lifts—the largest accommodating vessels up to 30,000 pounds, the second suitable for a vessel up to 20,000 pounds, and the third and fourth lifts each with a 5,000-pound capacity, ideal for jet skis, kayaks, and paddle boards. Located just 10 minutes from the Gulf of Mexico by boat and 5 minutes to Shore and Mar Vista restaurants, this is the perfect haven for life on the water. Inside, the Wolf Sub-Zero appliances provide top-tier performance in a gourmet kitchen built for culinary excellence. A Control4 smart home system offers seamless automation throughout, while HVAC-equipped garages ensure comfort year-round. The multiple garages can accommodate up to 9 cars, and the massive driveway can host 20+ vehicles. The residence boasts six spacious bedrooms, each with an en-suite bathroom, plus an additional full bath and two half baths. Designed for both productivity and leisure, the home features his and hers offices, a media/theater room, a fully equipped gym, sauna, golf simulator, tackle garage, and a workshop. A private guest suite with a separate entrance includes a kitchenette, dining room, living room, bedroom, and bathroom, offering a luxurious retreat for visitors. With two state-of-the-art elevators, expansive landscaping, and a maintenance-free turf yard, this estate blends modern convenience with natural beauty. Ideally located near pristine beaches, world-class shopping, and gourmet dining, this estate is the epitome of waterfront elegance and exclusivity. Experience the pinnacle of coastal living—this is truly paradise found.
Listing Agent: Charles Buky (941-228-6086)
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
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)
536 KETCH LN, LONGBOAT KEY, FL 34228
$2,695,00036 Days on yellowkey MLS ID: A4686553
REDUCED by $200,000 (6.9%) on 04/12/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2960 Built: 2016Monthly Fee: $10 Tax: $13,360 (2025)Community: Country Club ShoresSpa: NoSingle Family
Taxes:$13,360
Remarks: Welcome to an extraordinary south Longboat Key canal front estate in Country Club Shores, located 2 in from Sarasota Bay on a lushly landscaped 1/3 acre lot, where luxury and tranquility come together in perfect harmony. This residence is the ultimate sanctuary, blending refined modern design and extraordinary finishings with the serenity of its picturesque surroundings. Untouched by recent hurricanes, this home features impact windows and high-quality craftsmanship and is built to withstand the demands of south Florida’s climate. The completely renovated ~3,000 sq ft, 3-bedroom, 3-bathroom property is outfitted with premium finishings and an open plan that sets new standards for convenience and today’s modern lifestyle. From the cozy media room with wet bar and separate office, to the pro-outfitted chef’s kitchen and owner’s suite that is a truly an inspiring spa-like retreat, every inch of this home exudes luxury and comfort. The home has been thoughtfully renovated, featuring large plank porcelain floors and 10’ ceilings adorned with custom millwork details throughout. Plan to be impressed by the formal foyer that delivers your guests to the spectacular “Art Salon” and spacious gathering area. The gourmet kitchen is a chef's dream, featuring a stunning 9’ Dolomite Island with a vegetable sink and a 30” Fisher-Paykel dishwasher drawer adjacent to custom dual pantries. The custom built-in Thermador refrigerator/freezer columns, warming drawer, and microwave provide everything needed to prepare any culinary creation with ease. The Carrera marble backsplash complements the quartz countertops that house the commercial grade Thermador 6-burner gas range and griddle with 2 convection ovens. The kitchen area features 12-foot bifold impact door panels and 8-foot bifold impact windows, which can be fully opened to seamlessly connect the kitchen with the patio area and stunning Bay views. The owner's retreat offers a relaxing Zen atmosphere with soft tones that complement the water views. Escape to the spa inspired bathroom to indulge in a two-person freestanding hydrojet bath or relax in the spacious aroma steam shower featuring dual rain showerheads and hand showers. The blue calcite custom vanities illuminate the ethereal experience, complemented by a Toto Neorest water closet and a custom walk-in closet. The media room is perfect for movie night, featuring surround sound and wet bar with a wine captain. The two spacious guest suites feature spacious bathrooms with floor to ceiling large format porcelain tile, Hansgrohe/Gessi fixtures, marble and Cambria quartz countertops, and mosaic marble backsplashes. The baths also feature Restoration Hardware towel curios with matching pulls, oversized rain showerheads with custom finishes. Outside is a 110-foot seawall and versatile dock system, that includes an entertaining area, mooring station with shore power pedestal/water, and a floating dock perfect for launching kayaks or boarding a boat. The spacious greenhouse offers a sanctuary for relaxing and all your planting needs delivering that boujee-chic retreat embellished with orchids and herbs to further elevate the experience. Located on the highly desired south end of Longboat Key, adjacent to the Resort at Longboat Key Club and nearby St Armands Circle, this property includes deeded beach access and unrivaled convenience to Sarasota. Call now for a private tour of this bespoke property.
Listing Agent: Kathy Callahan (941-900-8088)
2819 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$3,799,999181 Days on yellowkey MLS ID: A4669533
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1173 Built: 1955 Tax: $36,688 (2024)Community: Coquina BeachSpa: NoSingle Family
Taxes:$36,688
Remarks: BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on the coveted south end of Longboat Key in Sarasota county. This charming, 1955 beach cottage sustained significant hurricane damage and is now being sold AS-IS for land value only. No HOA fees! Build your dream coastal retreat on this prime GULF-front lot and enjoy breathtaking sunsets, white-sand beaches- just steps to Publix grocery, 1.5 miles to the stunning St. Regis resort, and easy access to nearby St Armand’s dining/shopping, downtown Sarasota, golf, and marinas. You do not want to miss this opportunity to create your own piece of paradise on BEAUTIFUL Longboat Key!
Listing is courtesy of: SERHANT (646-480-7665)
Listing Agent: Jenn Flanders (941-232-0788)
757 HIDEAWAY BAY DR, LONGBOAT KEY, FL 34228
$7,488,000199 Days on yellowkey MLS ID: A4667459
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4507 Built: 2007Monthly Fee: $58 Tax: $29,603 (2024)Community: Hideaway Bay SubSpa: YesSingle Family
Taxes:$29,603
Remarks: Introducing Maison d’Azur, a custom waterfront estate in the prestigious Hideaway Bay enclave on the north end of Longboat Key. WHERE COASTAL LUXURY LIVING MEETS THE BAY! This exquisite four-bedroom, five-bath Key West-inspired residence, crafted by acclaimed builder John Cannon, seamlessly blends indoor and outdoor living to create an atmosphere of refined luxury reminiscent of a boutique hotel. Situated on over a quarter of an acre, this bayfront property commands breathtaking, unobstructed views. Enjoy the vibrant hues of sunrise and sunset over tranquil waters, with palm fronds swaying in the coastal breeze. With a newly renovated private forty-foot-deep water dock and boat lift, Maison d’Azur is a haven for boat enthusiasts and nature lovers. Spend afternoons in the saltwater pool and evenings on the loggia as the Belt of Venus rises over Sarasota Bay. Enjoy dining from your custom outdoor kitchen, surrounded by lush tropical landscaping. Step inside to experience luxury and meticulous craftsmanship, with a grand foyer featuring soaring ceilings and custom pillars. The open floor plan connects a chef’s kitchen, equipped with Sub Zero, Miele, Fisher and Paykel, and Wolf appliances, to a spacious family room with built in cabinetry, creating an inviting atmosphere for entertaining. Archways lead to elegantly decorated formal dining and living rooms. Ascend the private elevator to the second floor, where a great room with a custom entertainment center awaits, along with a study perfect for savoring a cognac on the captain’s porch. The expansive second floor offers a loggia and bedrooms with stunning panoramic views of the pool and Sarasota Bay. Maison d’Azur embodies exquisite taste and timeless beauty. With imported materials and innovative technology throughout, every detail has been curated for an elegant experience. This residence is sold fully furnished, with pieces selected to enhance each room’s design and ambiance. Hideaway Bay is located on Longboat Key, an eleven-mile island off the coast of Sarasota. This enclave of only seventeen estates is steps away from the deeded beach and boasts two private tennis courts. Residents enjoy easy access to premier country clubs, golf courses, waterfront activities, dining options, and upscale shopping. Experience coastal living where every day feels like a vacation amidst the beauty and tranquility of the Gulf Coast. This property sustained no damage from the storms/hurricanes of last year. It boasts an elevation of 10.5’, ensuring you stay high and dry.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Andrea Cohen (786-773-0370)
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
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)
510 PUTTER LN, LONGBOAT KEY, FL 34228
$2,999,000108 Days on yellowkey MLS ID: A4676878
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2253 Built: 1968 Tax: $17,343 (2024)Community: Country Club ShoresSpa: NoSingle Family
Taxes:$17,343
Remarks: Welcome to 510 Putter Lane, a stunning canal-front retreat nestled in the coveted Country Club Shores community on the south end of Longboat Key. Completely renovated with meticulous attention to detail, this turnkey furnished 3-bedroom, 2-bathroom residence offers coastal luxury and modern convenience just moments from Sarasota Bay and the Gulf of Mexico and walking distance to the beach. From the moment you arrive, the home's crisp curb appeal hints at the exceptional updates within. A brand-new 24-gauge standing seam metal roof (2025) crowns the home, complemented by all-new impact-rated windows, sliding glass doors (2024), and an elegant new front door (2024), ensuring peace of mind and energy efficiency. Step inside to find an open-concept layout bathed in natural light, where engineered hardwood flooring flows seamlessly throughout. The expansive great room features an electric fireplace set in a stacked stone lighted niche, creating a cozy yet elegant focal point. Plantation shutters, new lighting fixtures, ceiling fans, and recessed lighting add both style and comfort. The gourmet kitchen is a chef’s dream, anchored by a six-burner gas range with a pot filler, custom range hood, quartz countertops, and a suite of brand-new appliances including a refrigerator/freezer, dishwasher, microwave, and ice maker. Soft-close cabinetry offers generous storage, while the floor-to-ceiling built-in wine rack provides a striking and functional design element perfect for entertaining. Both bathrooms have been completely transformed with new tile, cabinetry, lighted mirrors, and high-end fixtures, delivering a spa-like experience. Every inch of this home has been curated for relaxed coastal living with no detail overlooked. Step outside to your private backyard oasis where a newly resurfaced pool and shell stone deck (2024) invite hours of sun-soaked enjoyment. The lush new landscaping and custom landscape lighting enhance the ambiance, while new rain gutters and a new Seawall Cao (2024) will help protect your investment year-round. Boaters will appreciate the direct, no-bridge access to Sarasota Bay. There is also the convenience of a Deed Beach Access! Whether you're spending the day on the water or relaxing poolside at home, this property delivers the quintessential Florida lifestyle. Additional updates include a recently replaced A/C system (2023), ensuring year-round comfort. Offered fully furnished and turnkey, 510 Putter Lane is move-in ready and designed for immediate enjoyment. Country Club Shores is one of Longboat Key’s most sought-after neighborhoods, known for its deepwater canals, beach access, and proximity to the Longboat Key Club, St. Armands Circle, and downtown Sarasota. Rest easy knowing this coastal dream home had no hurricane damage from 2024's storms! Whether you're seeking a primary residence, vacation getaway, or investment property, this exceptional home checks every box. Don’t miss this rare opportunity to own a completely renovated waterfront gem in one of Longboat Key’s most desired communities. 510 Putter Lane offers everything you need—style, substance, and the ultimate coastal lifestyle.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
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)
311 FIREHOUSE CT, LONGBOAT KEY, FL 34228
$2,399,000212 Days on yellowkey MLS ID: A4665445
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2352 Built: 2005Monthly Fee: $467 Tax: $29,195 (2025)Community: Conrad BeachSingle Family
Taxes:$29,195
Remarks: This is West Coast of Florida living at its finest, designed for those seeking a refined and effortless second home near the Gulf. Elevated and elegantly appointed, this custom residence is ideally located west of Gulf of Mexico Drive in the highly desirable Conrad Beach community on Longboat Key, where coastal serenity meets thoughtful design. Surrounded by lush tropical landscaping with accent lighting, the home blends timeless island architecture with modern comforts ideal for seasonal or extended stays. Inside, an open and inviting floor plan centers around a gourmet kitchen featuring a large quartz island perfect for entertaining, abundant workspace, and seamless flow into the main living areas. A full in-house generator provides peace of mind while you are away, making ownership as easy as it is enjoyable. Multiple porches and terraces, including a rooftop observation deck, create exceptional indoor-outdoor living and invite you to savor Gulf breezes and unforgettable West Coast Florida sunsets. The primary suite, located on the main living level, offers a private retreat with a spa-inspired bath and a serene balcony overlooking the tropical surroundings. Upstairs, guest bedrooms and a spacious loft-style family room provide flexible accommodations for visiting friends and family, all with access to wraparound terraces that capture the beauty of the island setting. The home comfortably sleeps ten, making it ideal for hosting while still maintaining privacy and comfort. Outdoor living is equally well designed, with expansive decks perfect for quiet mornings or relaxed gatherings. A beautifully landscaped path leads to the oversized resort-style community pool, complete with bath facilities and entertaining space, offering all the benefits of a luxury amenity without the responsibility of maintaining a private pool. From the community observation deck, enjoy glimpses of the Gulf and dramatic evening skies. Favorite features include high-impact windows and doors, full house generator and 5 minute walk to the soft powder sand beaches and beautiful Gulf waters. The award-winning Conrad Beach community enhances the lock-and-leave lifestyle with lawn care, irrigation, and landscaping services included. Just moments from pristine beaches, the charm of Longboat Key’s north end, marinas, and the dining and boutiques of St. Armands Circle, this home offers the ideal blend of privacy, convenience, and coastal living. Schedule your private showing and experience how effortless owning a second home on Florida’s West Coast can be.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-896-9981)
Listing Agent: Kathy Harman (941-900-9828)
510 WEDGE LN, LONGBOAT KEY, FL 34228
$1,990,000195 Days on yellowkey MLS ID: A4668133
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 1967Monthly Fee: $17 Tax: $14,551 (2024)Community: Country Club Shores Sec 02Single Family
Taxes:$14,551
Remarks: Welcome to your own piece of paradise in the prestigious Country Club Shores community on Longboat Key. This completely renovated 4-bedroom, 3-bath coastal retreat was taken down to the studs in 2012 and rebuilt with exceptional attention to detail—offering the rare combination of timeless style, modern infrastructure, and effortless move-in readiness on a tranquil canal. From the ground up, every major system has been upgraded for peace of mind: new water and sewer lines, updated electrical throughout, impact-rated doors and windows, a resurfaced saltwater pool and with new pool heater. Newer seawall and dock, gas that was run to the house with no propane tank to worry about. No component was overlooked. The result is a home that lives like new yet radiates refined coastal charm, with most of the beautifully curated furnishings remaining with the property. Inside, you’ll be welcomed by a bright, open-concept design featuring beautiful, engineered wood floors, custom beadboard ceilings, with beams, elevated ceiling heigh in the main living room and a soothing palette of sea-glass blues and clean whites. The heart of the home is a gourmet kitchen outfitted with stainless steel appliances, designer pendant lighting, and stylish lattice-front cabinetry. A large island anchors the space, perfect for entertaining, while the adjacent living area boasts custom-built-ins, a sleek gas fireplace, and expansive views that flow effortlessly outdoors. Each bedroom is designed for comfort and privacy, with spa-inspired bathrooms that feature elegant tile work, modern fixtures, and soft lighting. The primary suite is a retreat of its own, with custom shelving, cozy window seats, and lush garden views through plantation shutters. Step outside to experience Florida living at its finest. The spacious screened lanai surrounds a sparkling heated saltwater pool and paved deck, creating a private oasis perfect for lounging, swimming, or dining alfresco in total comfort. Just beyond, a large, newer dock awaits, offering deep-water canal access—an ideal setup for avid boaters and water lovers. The deck overlooking the canal is a peaceful setting for morning coffee or an evening cocktail This home also offers exclusive deeded beach access, just a short walk or bike ride away, where you can soak in the soft white sands and turquoise waters of the Gulf. When it’s time to explore, the renowned boutiques and fine dining of St. Armands Circle are just down the street, offering vibrant nightlife, unique shopping, and gourmet experiences in a picturesque coastal setting. A short drive over the scenic Ringling Bridge takes you to downtown Sarasota, a cultural haven known for its art galleries, theaters, opera house, and waterfront dining. Whether you're strolling through the Saturday farmers market, taking in a performance at the Sarasota Opera, or enjoying waterfront cocktails at Marina Jack, the city provides an enriching blend of sophistication and coastal charm. With its ideal location, timeless design, and luxurious updates, this home offers the very best of Longboat Key living—a rare opportunity to enjoy both boating and beachside leisure in one of Florida’s most coveted communities.
Listing Agent: Courtney Tarantino (941-893-7203)
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