Location: Longboat Key
Do Not Show Listings
4720 GULF OF MEXICO DR #Villa 2, LONGBOAT KEY, FL 34228
$599,00054 Days on yellowkey MLS ID: A4679458
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 912 Built: 1974Monthly Fee: $1,305 Tax: $1,356 (2025)Community: Windward Bay AmdVilla
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,356
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Welcome to elevated beachfront living in highly desirable Windward Bay — a premier bayside enclave offering serene coastal charm and resort-style amenities on picturesque Sarasota Bay. This fully reimagined 2-bedroom, 2-bath villa has been thoughtfully renovated from top to bottom with impeccable attention to detail and contemporary finishes throughout. Step inside to discover an open, light-filled interior featuring brand-new electrical and plumbing systems, new drywall and insulation, new kitchen and bathrooms — everything crafted for modern comfort and peace of mind. A dedicated 220-volt receptacle makes electric vehicle charging effortless, blending convenience with conscientious living. Enjoy easy walk-in access with no stairs, and take full advantage of Windward Bay’s pet-friendly policy — perfect for up to two pets — making this the ideal coastal retreat for the whole family. Relax and unwind on your private back patio overlooking lush landscaping, where tranquil sunsets frame the entrance to the beach access just steps away. Cozy evenings by the fire pit become part of your daily rhythm. Windward Bay is cherished for its park-like grounds, complete with: Nearly a half-mile of scenic walking trails. Three distinct Gulf beach access points. Two heated pools. Six pickleball/tennis courts. A well-appointed clubhouse with fitness center, sauna, library, and meeting spaces. Two marinas with boat and jet ski slips. A private fishing pier. Outdoor grilling areas, firepits, and kayak storage. This exceptional villa effortlessly combines the ease of turn-key living with premium upgrades and unparalleled community amenities — all in one of Longboat Key’s most sought-after waterfront communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Sharon Austin (678-756-4020)
3427 WINDING OAKS DR #14, LONGBOAT KEY, FL 34228
$1,150,00025 Days on yellowkey MLS ID: A4686623
0 Days Off yellowkey (back on 4/16/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2555 Built: 1988 Tax: $13,850 (2025)Community: Winding OaksSpa: NoCondo
Taxes:$13,850
Elementary School: Southside Elementary
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Privately tucked away within the private Winding Oaks community on Longboat Key, this beautifully updated three-bedroom villa offers an easy, elevated way to enjoy Sarasota’s coastal lifestyle. Overlooking the Harbourside Golf Course, the home captures peaceful water views and the scenic 5th hole, creating a backdrop that feels both open and serene. Designed for effortless living, this turnkey furnished residence blends the comfort of a single-family home with the simplicity of maintenance-free ownership—ideal for seasonal stays or extended escapes. Inside, an airy open layout, soaring ceilings, and wide-plank tile floors create a light, welcoming feel, while floor-to-ceiling sliders connect seamlessly to the outdoor living spaces. The kitchen is both stylish and functional, featuring Italian white-lacquer cabinetry, stone countertops, and premium appliances—perfect for casual evenings at home or hosting friends. The living room centers around a custom gas fireplace and flows naturally to a spacious screened lanai, where you can unwind with long water views and soft coastal breezes. The home features many new furnishings and many recent updates. A private courtyard with a heated pool adds another layer of relaxation, offering a quiet place to start the day or wind down after time on the water, golf course or tennis courts. The primary suite is a calm retreat of its own, with tranquil water views, a spa-like bath, and a generous walk-in closet. Two additional en-suite bedrooms provide flexibility for visiting guests or a comfortable home office. Ownership includes access to the Bay Isles Beach Club, where days can be spent on pristine Gulf-front sands with thoughtfully appointed amenities. Within Winding Oaks, residents enjoy a recently refreshed community pool, walking paths, and a secure, gated setting. Optional golf, tennis and social memberships are available at the Longboat Key Club. Just minutes from dining and shopping on world-renowned St. Armands Circle and the cultural amenities of downtown Sarasota, this retreat makes it easy to step into the best of the area—while always having a peaceful place to return to. Simple, sophisticated, and distinctly Longboat Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Carolyn Donnelly, Pa (941-350-9900)
3511 FAIR OAKS CT, LONGBOAT KEY, FL 34228
$1,559,00042 Days on yellowkey MLS ID: A4684840
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2579 Built: 1998Monthly Fee: $833 Tax: $17,916 (2025)Community: Bay IslesSpa: YesSingle Family
Taxes:$17,916
High School: Booker High
Middle School: Booker Middle
Remarks: Nestled behind the gates of Queens Harbour in Bay Isles, this exceptional single-story home offers a rare blend of privacy, space, and effortless Longboat Key living—perfectly positioned on a quiet cul-de-sac with sweeping views along the 4th hole of the Longboat Key Club’s Blue Heron golf course. Spanning approximately 2,579 sq. ft., the thoughtfully designed floor plan features three bedrooms, two full baths, and a half bath, with flexible spaces that adapt beautifully to your lifestyle. A large, dedicated office/den with beautiful glass French doors and custom cabinetry offers outstanding flexibility and can serve as an additional sleeping space if desired. Inside, soaring 14-foot ceilings, rich wood flooring, and an open living-and-dining layout create an airy, welcoming atmosphere. A generous great room is framed by walls of sliding glass doors, opening to the pool and patio for seamless indoor-outdoor living—ideal for entertaining or simply unwinding with tranquil golf course views. The kitchen is perfectly placed for everyday living and gathering, featuring solid wood cabinetry, stone countertops, a center island with a veggie sink, pantry storage, a gas cooktop, and stainless-steel appliances. Two generous guest suites are ideally situated in this split plan, sharing a full bath with the ability to be closed off from the main living area. The private primary suite is a true retreat with golf course views across your private pool and spa. The spa fountain’s soft, flowing water creates a soothing backdrop that drifts into the bedroom through the sliding door access to the patio. The spacious bedroom features a walk-in closet, additional wall closet and a well-appointed en-suite bath with dual sinks, a soaking tub, separate shower, and private water closet. Outdoors, enjoy the screened private pool and spa with multiple seating areas and ample room to lounge and entertain in total comfort. The home has been immaculately maintained and includes new pool equipment and pool heater, a resurfaced pool, tile roof (2020), tankless gas water heater, as well as several additional upgrades – perfect move-in condition. Queens Harbour residents enjoy a maintenance-free lifestyle with 24-hour guard-gated security, with a community heated pool and spa just across the street. Ownership also includes deeded access to the private Bay Isles Beach Club, offering Gulf-front pavilions, grilling areas, multiple beach volleyball courts and a pristine beach only minutes away. Perfectly located within the gates of the Resort at Longboat Key Club’s Harborside Golf course and 290 slip deep-water Moorings marina, and close to island dining—plus easy access to St. Armands Circle, Lido Beach, and downtown Sarasota—this golf course home delivers the space, privacy, and location that define Longboat Key at its best.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Kathy Callahan (941-900-8088)
691 TARAWITT DR, LONGBOAT KEY, FL 34228
$850,00093 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
Tax Year: 2024
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 Agent: Jodene Moneuse, Pa (941-302-4913)
536 KETCH LN, LONGBOAT KEY, FL 34228
$2,695,00030 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.
2326 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$915,00052 Days on yellowkey MLS ID: A4683180
REDUCED by $35,000 (3.7%) on 04/16/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2282 Built: 1986Monthly Fee: $143 Tax: $10,215 (2025)Community: Harbour Oaks 2Villa
Taxes:$10,215
Remarks: A rarely available END UNIT villa is located on Longboat Key within the gated Bay Isles community, offering the opportunity to embrace true island living with expansive private terrace space and tranquil pond views fed by the saltwater bay. Encompassing nearly 2,400 square feet of thoughtfully designed interiors, this residence delivers privacy, security, and effortless elegance in one of Sarasota’s most coveted coastal enclaves and just moments from Gulf beaches. Inside, soaring vaulted ceilings and inviting natural light pour in, creating an airy and refined atmosphere. The well-appointed floorplan balances sophistication with comfort, featuring multiple gathering spaces including a formal living room anchored by a charming wood-burning fireplace. Expansive sliding doors seamlessly connect the interior to an impressive 740-square-foot private terrace overlooking the serene pond waters, creating a seamless indoor-outdoor lifestyle ideal for sunset entertaining, morning coffee, or elegant evenings under the island sky. Rich wood flooring, plantation shutters, granite countertops, and updated cabinetry reflect timeless coastal luxury. A skylight enhances the kitchen with beautiful natural light, while recent improvements including a NEW AIR conditioning system (2025) and NEW ROOF (2025). Two private atriums introduce lush greenery and architectural interest, adding intimate moments within the home. A thoughtfully designed office with a built-in Murphy bed offers flexibility and can easily function as a fourth bedroom, accommodating guests with ease. The primary suite serves as a spacious sanctuary, while guest bedrooms offer privacy and comfort for family and visitors alike. The private two-car garage features organized storage for beach and recreational essentials, supporting a seamless island lifestyle. Residents of Harbour Circle enjoy a heated community pool and spa surrounded by manicured tropical landscaping, along with exclusive membership to the gated Bay Isles Beach Club — providing private Gulf-front access with convenient dedicated parking. Living on Longboat Key means enjoying easy access to world-renowned beaches, boating, fine dining, and the amenities of the Longboat Key Club, including golf, tennis, pickleball, marina access, and multiple private dining venues (membership available separately). Everyday conveniences including Publix, banks, the post office, and Longboat Key’s Town Center are just moments away. Quiet, private, and impeccably maintained, this fully furnished end-unit villa offers the feel of a single-family residence while delivering the sophistication and prestige of island living on Longboat Key. Don’t miss your opportunity—schedule your private showing today and experience elevated coastal living firsthand.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
5655 GULF OF MEXICO DR #D107, LONGBOAT KEY, FL 34228
$799,00042 Days on yellowkey MLS ID: TB8483958
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1274 Built: 1975Monthly Fee: $1,000 Tax: $3,439 (2025)Community: Cedars West Of Longboat IncCondo
Taxes:$3,439
Elementary School: None
Remarks: Experience breathtaking beach and Gulf views from this spacious, turnkey-furnished two-bedroom, two-bath residence in Cedars West. Beautifully updated with no detail overlooked, this exceptional property features elegant stone countertops, quality appliances, and a relaxed coastal ambiance that makes it highly sought after. Offering over 1,270 square feet of air-conditioned living space, the residence includes a large walkout screened lanai where you can enjoy gentle Gulf breezes and spectacular sunsets over the tranquil waters of the Gulf of Mexico. The thoughtfully designed layout provides abundant storage throughout, including generous closets in both bedrooms as well as a dedicated owner’s closet. Just steps from the unit, the pristine beach is a renowned nesting ground for sea turtles, offering the unique opportunity to watch dolphins and manatees pass by while relaxing on one of Florida’s most beautiful beaches. Cedars West residents enjoy a wide range of resort-style amenities, including a large heated and cooled swimming pool, two tennis courts, BBQ grilling areas, and convenient kayak and bike racks. Owners also have the option to generate rental income by taking advantage of Cedars West’s rare two-week minimum rental policy on Longboat Key. Don’t miss this incredible opportunity to experience the ultimate beachfront lifestyle.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: John Milkovich (727-518-5058)
524 HALYARD LN, LONGBOAT KEY, FL 34228
$5,495,000231 Days on yellowkey MLS ID: A4663499
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3737 Built: 2025Monthly Fee: $21 Tax: $17,932 (2024)Community: Country Club Shores IvSpa: YesSingle Family
Taxes:$17,932
Middle School: Brookside Middle
Remarks: One or more photo(s) has been virtually staged. Only ONE BUYER will be the FIRST OWNER! Crafted by an award winning design team, this brand-new coastal contemporary waterfront residence awaits you in the exclusive Country Club Shores community on South Longboat Key. Designed for high performance and easy maintenance, this rock-solid, all block two-story residence with a private elevator provides peace of mind while capturing the essence of easy island living. A fluid open-concept layout is ideal for seamless indoor-outdoor waterfront entertaining. Soaring ceilings with impressive transom glass over casement windows and 10-foot tall sliding glass doors illuminate the interiors with natural light. At the heart of the home, a thoughtfully created gourmet kitchen and wet bar are a showpiece, featuring tailor made modern shaker doors and full panel rift-cut white oak cabinetry. Striking elements include the waterfall island and a dramatic ceiling-height hood, both wrapped in exotic natural Quartzite. A full suite of Wolf & Sub-Zero appliances includes twin 30" refrigerator & freezer towers, an 18" wine tower, under counter beverage centers, wall ovens and a contemporary gas cooktop. The first-floor primary suite is a serene retreat featuring a warm wood-slatted ceiling, expansive glass and a gorgeous bathroom with a freestanding soaking tub, dual vanities and textured porcelain tile accents. An inviting staircase leads to an elevated private home office with a half bathroom. The second floor features a game room with a wet bar and three en-suite guest bedrooms, offering comfort and flexibility complemented by a 30 foot covered balcony overlooking the tranquil water views. Energy-efficient features include variable speed 17 SEER HVAC systems, spray foam insulation and hurricane impact-resistant ES windows and doors. Control4 Smart Home technology provides many conveniences. A host of pre-wired systems—including sound, security, shades and EV charging—can be customized to the buyer's selections. Outside, a brand-new, 100-foot-long, extra-wide seawall protects a resort-style paradise! A four piece French patterned Crema Nova marble decking surrounds the 40-foot linear pool with in-water bench seating, a large sun shelf and a 12 foot wide spa. An elevated lanai with detailed ceilings features an outdoor kitchen, complete with Naturkast marine grade cabinetry, under counter refrigerator and a 42 inch built-in grill offering the perfect retreat for alfresco dining and poolside lounging. All this is just minutes from the extraordinary shopping and dining of St. Armands Circle, the cultural richness of downtown Sarasota, and the world-renowned Gulf beaches of Longboat Key. Seller is offering generous allowances towards custom closets and boat dock design providing an opportunity for the buyer to personalize these features to meet their sytle and preferences!
Listing is courtesy of: HUNT BROTHERS REALTY, INC. (941-388-7017)
Listing Agent: Rob Hunt, Jr (941-232-2431)
6750 GULF OF MEXICO DR #163, LONGBOAT KEY, FL 34228
$500,00046 Days on yellowkey MLS ID: A4683547
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1970 Tax: $4,337 (2024)Community: Whitney BeachCondo
Taxes:$4,337
Remarks: In the sought-after Whitney Beach community on Longboat Key’s peaceful north end, this beautifully renovated two-bedroom, two-bath end unit residence offers 1,449 square feet of coastal contemporary living with tranquil water views over protected Bishop’s Bayou. Enjoy serenity of a coastal inlet sheltered from constant boat traffic of the Intracoastal Waterway, where dolphins and manatees glide past your rear Florida room, a front-row seat to nature. The versatile floor plan includes spacious bedrooms with en-suite baths (showers only), a bright 9-by-14-foot flex space with abundant windows where the washer and dryer connection is located, plus an additional 8-by-3-foot storage area. The kitchen features quartz countertops, stainless steel GE appliances and a water view that enhances everyday living. Tasteful coastal selections, a light palette and additional end unit windows create an airy, open feel throughout, complemented by storm-resistant windows for added peace of mind. Whitney Beach offers resort-style amenities including two pools, tennis court, barbecue stations, kayak storage and launch, lush recreational paths and deeded private beach access directly across the street to the turquoise Gulf waters. Boat slips are available when offered, with annual dock fees of $600 for slips up to 33 feet and $480 for slips up to 24 feet. Sublets are available. Two pets are welcome with no weight restrictions. Rentals are permitted with a one-month minimum. An exceptional opportunity to enjoy bay-to-beach living in one of Longboat Key’s charming waterfront communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Karen Whitaker (941-724-6969)
2039 GULF OF MEXICO DR #G3-203, LONGBOAT KEY, FL 34228
$499,99914 Days on yellowkey MLS ID: A4688685
REDUCED by $39,001 (7.2%) on 04/15/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1214 Built: 1974Monthly Fee: $1,170 Tax: $5,576 (2025)Community: Seaplace ISpa: YesCondo
Taxes:$5,576
Remarks: Experience the Best of Coastal Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2.5-bath residence offering a perfect blend of comfort, style, and relaxed island living. This spacious two-level layout features an inviting open-concept living and dining area with neutral coastal tones, tile flooring throughout the main level, and seamless access to a private lanai—ideal for enjoying tranquil views and Gulf breezes. The updated kitchen is designed for both functionality and style, showcasing granite countertops, white cabinetry, stainless steel appliances, and a convenient breakfast bar, perfect for casual dining or entertaining. Upstairs, you’ll find two generously sized bedrooms, each offering privacy and comfort. The primary suite serves as a relaxing retreat, while the guest bedroom is ideal for family or visitors. The additional half bath on the main level adds convenience for guests. This residence is offered in move-in ready condition and reflects pride of ownership throughout. Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an exceptional array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center, and a clubhouse with kitchen, library, and sauna. Additional features include playground areas, grilling stations, on-site management, and a 24-hour staffed gatehouse for security. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this home offers the ultimate Longboat Key lifestyle in one of the island’s most sought-after communities. Schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
2251 GULF OF MEXICO DR #301, LONGBOAT KEY, FL 34228
$5,999,000280 Days on yellowkey MLS ID: A4658325
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3921 Built: 2016Monthly Fee: $7,501 Tax: $69,970 (2024)Community: Aria Longboat KeySpa: YesCondo
Taxes:$69,970
Remarks: One or more photo(s) has been virtually staged. Are you ready to discover your very own private Gulf Oasis? Step into a slice of paradise at your dream coastal retreat located in the esteemed Aria community on Longboat Key's coveted south end. This serene haven is not just a residence; it offers an exclusive lifestyle filled with tranquility and easy access to the finest dining, arts, and cultural experiences that nearby Sarasota has to offer. Imagine living in a stunning home nestled along 300 feet of pristine private Gulf-front shoreline, where every day brings a lifestyle that is truly extraordinary. As you approach through Aria's gated entrance, you’ll be welcomed by timeless design, lush native landscaping, charming walking trails, and a lovingly preserved artesian well—a beautiful nod to the property’s storied history. Step inside your private elevator and explore nearly 4,000 square feet of meticulously crafted, light-filled living spaces. The grand foyer seamlessly flows into an open-concept layout that beautifully blends a chef’s kitchen, luxurious spa-inspired bathrooms, and elegant living areas—all thoughtfully designed for comfort and effortless entertaining. Soaring 9+ foot ceilings, floor-to-ceiling glass windows, and wrap-around terraces provide breathtaking Gulf views that you can enjoy from every angle. Relax in the inviting family room or host unforgettable gatherings in the magnificent great room. The kitchen is a culinary dream, showcasing exquisite quartz countertops, solid wood cabinetry for ample storage, and elite Wolf and Miele appliances. The primary suite is a tranquil sanctuary designed for ultimate relaxation, complete with an opulent ensuite bathroom featuring two private baths connected by a spacious walk-in shower—an indulgence you’ll cherish every day. Two additional ensuite bedrooms ensure your guests feel right at home, while a versatile home office or optional fourth bedroom adds practicality. A bonus room awaits your creative hobbies, crafts, or extra storage needs. Living in Aria means immersing yourself in a truly unparalleled lifestyle. At the community's heart lies Villa am Meer, a beautifully restored 1935 seaside mansion that forms the elegant residents' clubhouse. Whether you’re hosting friends or enjoying a peaceful evening, you can unwind in the exclusive wine cellar and choose a bottle to savor on your terrace as the sun dips below the horizon. Enjoy an array of resort-style amenities, including a beachfront pool and spa, yoga and fitness studios, a massage room, and a serene, service-oriented atmosphere. A private, oversized two-car dehumidified garage adds to your convenience, while a dedicated resident caretaker ensures that personal service is always just a phone call away. Aria is not just a home; it’s a lifestyle choice that embodies luxury and elegance. Make 2251 Gulf of Mexico Drive #301 your new address—a place where timeless sophistication meets contemporary indulgence. Embrace the extraordinary life by the sea at Aria. Don’t let this opportunity slip away!
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Rachel Woodruff, Pa (941-705-8686)
803 BAYPORT WAY #803, LONGBOAT KEY, FL 34228
$775,00031 Days on yellowkey MLS ID: A4686552
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1456 Built: 1981 Tax: $6,376 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$6,376
Remarks: Welcome to the true tropical oasis of Bayport Beach & Tennis Club, a Longboat Key Gulf to Bay community. Bayport was designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture and is recognized for its award-winning, timeless design. Bayport offers 27 lushly landscaped acres with 1,200 feet of private beach. This tastefully renovated second-floor unit offers two expansive bedrooms and two beautiful bathrooms and comes fully turn-key. This unit was curated with attention to detail and functionality in mind. The kitchen offers plenty of storage, stainless steel appliances, quartz countertops and beautiful accent details. Enjoy three patios that allow for great indoor/outdoor living. Fully equipped with Hurricane impact doors and windows. One under building parking space included, along with a locked storage closet - perfect for bikes and beach gear. When not at the beach, enjoy the meticulously kept nature trails, landscaped grounds and wildlife. Just steps away from the well appointed clubhouse is equipped with a Junior-Olympic sized heated pool, four har-tru tennis courts, a fitness center and more. In addition, Bayport residents are proud of their active social and recreational calendar. Water enthusiasts can utilize the secluded fishing pier that stretches out onto Sarasota Bay; to fish, watch the sunrise, the Manatees swim or the Egrets wading among the mangrove trees. Residents also benefit from conveniently located on-site paddle board and kayak launch and storage areas. Bayport residents enjoy an array of restaurants locally, and the convenience of a nearby supermarket, pharmacy and boutique shops. Recreational enthusiasts also benefit from the nearby Bayfront Park which offers a popular pickle-ball program, dog park and other bayside activities. The nearby Longboat Key Club offers private access to championship waterfront golf, extensive leisure activities and boating facilities. Within minutes, one can access the famous St Armand's Circle with its exceptional shopping and dining amenities. From there, cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Alexis Smith-Frady (352-225-1724)
3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228
$389,0009 Days on yellowkey MLS ID: R4911020
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1046 Built: 1970Monthly Fee: $1,457 Tax: $2,813 (2025)Community: Beach Harbor ClubCondo
Taxes:$2,813
Remarks: Longboat’s Beach Harbor club is situated on 5 Acres along the most beautiful stretch of Longboat Key Shoreline. Sugary sand and flowing seaoats beside the azure blue Gulf of Mexico. The beach Harbor club offers 133 condo units, deeded beach access with showers, umbrellas and beach chairs. Amenities also include newly constructed boat slips, rooftop decks, outdoor cook areas, heated oversized swimming pool, community area for kayaks, clubhouse, and shuffle board. Longboat Beach Harbor is a friendly community with group events and many fun times to build relationships and enjoy sense of community living. Close to Bayfront Park with Tennis, Publix/CVS shopping. This renovated condo is situated on the 3rd floor not requiring flood insurance. Air conditioned indoor hall-way with security entrance. Newly appointed appliances, bathrooms, HVAC, luxury flooring and trim. Up-scale appointed fixtures and details throughout.
Listing is courtesy of: LEN SCAVRON (908-304-5454)
Listing Agent: Len Scavron (908-304-5454)
779 SAINT JUDES DR N, LONGBOAT KEY, FL 34228
$479,000275 Days on yellowkey MLS ID: O6326464
REDUCED by $13,000 (2.6%) on 04/16/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 882 Built: 1972 Tax: $5,814 (2024)Community: Villa Dos PalmasCondo
Taxes:$5,814
Remarks: PRICED TO SELL ! Coastal Elegance Meets Effortless Island Living in Longboat Key Experience the ultimate Gulf Coast lifestyle in this beautifully maintained 2-bedroom, 1.5-bath canal-front residence, perfectly positioned within one of Longboat Key's most desirable waterfront communities. Whether you're searching for a full-time sanctuary or a refined seasonal retreat, this exceptional property delivers comfort, style, and location in perfect harmony. Inside, a thoughtfully updated kitchen takes center stage-featuring brand-new appliances, sleek contemporary countertops, and modern cabinetry designed for both everyday living and effortless entertaining. Solid block construction offers durability and peace of mind, while the newer roof enhances long-term value and security. Step outside and immerse yourself in true island living. With deeded beach access just moments away, you can transition from morning coffee to toes-in-the-sand within minutes. Enjoy leisurely strolls to some of the island's most beloved dining destinations, including Harry's Continental Kitchens, Solorzano's Pizzeria, Lazy Lobster, Lo' Key Island Café, and the iconic Euphemia Haye Restaurant. The property also includes a private 1-car carport and dedicated exterior storage-adding convenience to coastal charm. Perfectly situated on a generous canal-front lot, this residence is a short walk to the sparkling waters of the Gulf of Mexico and only 15 minutes from the sophisticated boutiques and fine dining of St. Armands Circle. Wake to peaceful bay breezes. Spend your afternoons basking on pristine white sands. End each day with spectacular Gulf sunsets painting the sky in gold and coral hues. This is more than a condo-it's a lifestyle. Don't miss your opportunity to own a piece of paradise on Longboat Key.
Listing is courtesy of: BROKERS REAL ESTATE GROUP INC (407-770-1464)
Listing Agent: Alessandro Rosa (407-460-6589)
3804 GULF OF MEXICO DR #B305, LONGBOAT KEY, FL 34228
$445,00010 Days on yellowkey MLS ID: A4689197
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1007 Built: 1970Monthly Fee: $1,347 Tax: $3,772 (2025)Community: Beach Harbor ClubCondo
Taxes:$3,772
Remarks: Experience coastal living at its absolute finest in this stunning 3rd-floor 2BR/2BA condo in Beach Harbor Club—completely redone from top to bottom with impeccable attention to detail. No surface has been overlooked in this unbelievably beautiful, fully renovated residence, offering a fresh, modern feel the moment you walk through the door. The heart of the home is a bright, open-concept kitchen featuring custom cabinetry, elegant stone countertops, and high-end appliances, perfectly designed for both everyday living and entertaining. The entire unit showcases gorgeous updated flooring throughout, creating a seamless, light, and airy coastal aesthetic. Both bathrooms have been fully redesigned with upscale finishes, mirroring the quality and style of the kitchen. Every inch of this home reflects thoughtful craftsmanship and a true top-to-bottom transformation. From the living room, enjoy a lovely view of the Gulf right from your window, bringing in natural light and a constant reminder of just how close you are to the beach. Located in the highly desirable Beach Harbor Club, this Gulf-to-bay community offers an exceptional lifestyle with private beach access just across the street, boat slips on the bay, a pool, clubhouse, gym, kayak storage, and a rooftop deck perfect for taking in breathtaking sunsets. This is not just an update—it’s a complete reimagination of the space, making B305 a standout opportunity for anyone seeking a move-in-ready coastal retreat.
Listing is courtesy of: DANIELLE GLADDING & CO. REALTY (941-539-8535)
Listing Agent: Danielle Gladding (941-539-8535)
2819 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$3,799,999175 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)
350 GULF OF MEXICO DR #211, LONGBOAT KEY, FL 34228
$938,500197 Days on yellowkey MLS ID: A4667037
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2394 Built: 1992 Tax: $9,083 (2023)Community: Tangerine Bay ClubCondo
Taxes:$9,083
Tax Year: 2023
Remarks: Experience resort-style living at Tangerine Bay Club, a gated sanctuary on the desirable south end of Longboat Key. This impeccably maintained end-unit residence offers 2,400 square feet of refined living space with lush Sarasota Bay views and unmatched proximity to the area’s top attractions. Minutes to St. Armands Circle, downtown Sarasota, and steps to Dry Dock Marina and Restaurant. No current assessments and meticulously maintained grounds. Thoughtful floor plan with multiple terrace access points to enjoy morning and afternoon sun. This three-bedroom, two-and-a-half-bath, plus den, includes an oversized private two-car garage. There is also a natural gas barbecue on the front terrace. Resort-style amenities at Tangerine Bay Club include a heated pool, lap lane, heated spa, tennis, and regulation pickleball courts, a clubhouse with a fitness center, and a vibrant social room and calendar (happy hours, pickleball, cultural excursions). Freshly renovated boat dock, two kayak launches, a fishing pier, and prime fishing directly on Sarasota Bay. Enjoy just “sittin’ on the dock of the bay” watching the dolphins roll in. Take a scenic nature walk between Sarasota Bay and Quick Point Nature Preserve. Ownership includes (optional) membership to the Bay Isles Beach Club facilities for just $600.00 per year (application required).Longboat Key is renowned for golf, tennis, fine dining, boating, and world-class fishing. Be sure to explore the newly opened St. Regis resort, just a short stroll to the north on the beach side. Ongoing management ensures a carefree ownership experience with no special assessments anticipated. Recent capital projects (painting, waterproofing, elevator rebuilds, 2024 roof replacements, exterior tile walkway updates) have been completed and funded, with milestone inspections cleared. Pet-friendly, gated entry, and a day dock for fishing. This residence offers the perfect blend of luxury, convenience, and peace of mind—an ideal retreat for those seeking sophistication and coastal living at its finest. DON’T JUST THINK ABOUT IT, COME EXPERIENCE IT FOR YOURSELF AND MAKE IT YOUR REALITY.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
757 HIDEAWAY BAY DR, LONGBOAT KEY, FL 34228
$7,488,000193 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 Agent: Andrea Cohen (786-773-0370)
435 L AMBIANCE DR #L807, LONGBOAT KEY, FL 34228
$3,500,000188 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
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!
4310 FALMOUTH DR #102, LONGBOAT KEY, FL 34228
$660,00084 Days on yellowkey MLS ID: A4679011
REDUCED by $5,000 (0.8%) on 04/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969Monthly Fee: $1,410 Tax: $6,739 (2024)Community: Longboat HarbourCondo
Taxes:$6,739
Remarks: Exceptional value for a Longboat Key condo with private beach access. Enjoy deeded Gulf access with a residents-only community beach house featuring bathrooms, indoor/outdoor showers, seating, cabana space, and parking—your personal gateway to Gulf Coast living. Experience exceptional bayfront living at 4310 Falmouth Drive, Unit 102, located in the sought-after Longboat Harbour community on Longboat Key—a premier coastal city and barrier island along Florida’s Gulf Coast, renowned for attracting year-round residents, second-home owners, seasonal residents, and visitors seeking a refined, upscale seaside lifestyle. This A-Building, direct bayfront residence captures full Sarasota Bay views from the kitchen, dining area, living room, enclosed lanai, and primary bedroom—offering a front-row seat to sunrise skies, passing boats, dolphins, manatees, eagles and all kinds of exciting wildlife just 40 feet from the tranquil water vistas. Thoughtfully updated, the home features luxury vinyl flooring, upscale LG quartz Viatera Rococo countertops in the kitchen and both bathrooms, and soft-close drawers and custom cabinetry throughout. The spacious primary suite includes double vanities and a beautifully updated walk-in shower, while the guest bath also offers a walk-in shower with quartz finishes. Significant capital improvements provide peace of mind, including new hurricane-rated windows and sliders (2024, Cat5), HVAC (2021) with approximately 8 years remaining on a 12-year warranty, and a water heater (2023). The enclosed lanai expands usable living space while maintaining sweeping Sarasota Bay views. Offered fully furnished for a seamless, move-in-ready bayfront lifestyle. Longboat Harbour is a gated, resort-style community offering an impressive array of amenities, including four heated pools, tennis and pickleball courts with active player groups, fitness center, sauna, meeting rooms, billiards, putting green, woodworking shop, kayak storage, shuffleboard, locker rooms, fishing piers, two community grills, on-site management, and a protected harbor. Boat slips are available to members of the Longboat Harbour Yacht Club (subject to availability). Enjoy the best of island living with private deeded beach access just a short walk or drive across the street—complete with seating, chair storage, cabana, restrooms, indoor and outdoor showers, parking, and a convenient car-wash area. Additional features in the condo include washer and dryer connections in a hall closet and assigned covered carport parking with abundant guest spaces nearby. In the living room, open the sliders to seamlessly expand your indoor–outdoor living space, or keep them closed and enjoy the patio as an enclosed lanai—then open the glass sliders to let in refreshing coastal breezes and salt air. Located just 7.5 miles north of St. Armands Circle, and a short drive to downtown Sarasota’s Arts District, world-class dining and shopping, with Sarasota-Bradenton International Airport nearby. Direct Sarasota Bay views and private deeded Gulf beach access make this exceptional residence the ultimate Longboat Key lifestyle opportunity.
Listing is courtesy of: MARCUS & COMPANY REALTY (941-932-8550)
Listing Agent: Kerre Allman (941-909-3095)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.