Location: Longboat Key
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
806 BAYPORT WAY #806, LONGBOAT KEY, FL 34228
$949,00016 Days on yellowkey MLS ID: TB8489326
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981 Tax: $5,917 (2025)Community: Bayport Bch & Ten Ph ECondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,917
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Welcome to this beautifully appointed ground floor residence that combines modern elegance with functional design. Newly remodeled in 2025, this residence features high-end finishes and modern amenities, making it an ideal retreat for those seeking luxury in a serene environment. Upon entering, you are greeted by a bright and spacious interior filled with natural light, thanks to strategically placed additional windows featured in corner/end units of this community. The subtle elegance of the interior is complemented by sleek flooring that enhances the flow from room to room. The kitchen is a true highlight, featuring quality cabinetry, elegant quartz counters, and modern stainless-steel appliances, which allow a harmonious flow, delivering both functionality and sophistication. The open-concept layout continues through the dining and living areas, combining a blend of textures and stylish finishes to cohesively create an environment of relaxed elegance. An abundance of natural light floods this space through large retractable sliding glass doors, which provide the option of extending the outdoors in. A private outdoor patio showcases a beautiful backdrop of lush tropical landscaping, adding to the property’s overall appeal. The bedrooms within the property are thoughtfully designed, each offering generous space and natural light. The primary suite offers a restful retreat, complete with an ensuite bathroom featuring modern fixtures and thoughtful design, ensuring comfort and privacy. This property will continue to amaze, as beauty extends beyond its walls into an amenity-rich community of 27 acres of picturesque tropical landscaping. This gulf-to-bay community offers an active island lifestyle with 4 Har-Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court, and amazing nature trails. A distinct advantage and unique selling point of this property is its proximity to a private, deeded beach. This property offers future owners not just exclusive beach access, but a revitalizing retreat amidst the hustle and bustle of life—truly a valuable benefit that amplifies the charm of this residence. Close to local amenities yet precisely positioned to offer privacy and quietude, this property represents an excellent opportunity for discerning buyers. Experience the best of coastal living in this beautiful home, where modern comfort meets natural beauty. Welcome home!
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Antonietta Car (813-684-9500)
803 BAYPORT WAY #803, LONGBOAT KEY, FL 34228
$775,00028 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)
536 KETCH LN, LONGBOAT KEY, FL 34228
$2,695,00027 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Kathy Callahan (941-900-8088)
3511 FAIR OAKS CT, LONGBOAT KEY, FL 34228
$1,559,00039 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
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.
1445 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228
$924,90050 Days on yellowkey MLS ID: A4683660
REDUCED by $65,000 (6.6%) on 04/12/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1933 Built: 1982 Tax: $10,149 (2025)Community: Players Club IiiCondo
Taxes:$10,149
Remarks: Welcome to Residence #103 at 1445 Gulf of Mexico Drive, located within the prestigious Players Club on Longboat Key. This exceptional 550-foot Gulf-front community offers an unparalleled coastal lifestyle, and this residence presents a rare opportunity—available for the first time in 37 years. Originally the building’s model home, this thoughtfully designed condominium combines timeless elegance with spacious comfort. This beautifully maintained residence features three bedrooms, two and a half baths. The third bedroom/den is complete with twin Murphy beds and built-in storage. The spacious living and dining area opens to a wall of sliding glass doors leading to an expansive 30-foot open-air balcony, where you will enjoy sweeping views of the Gulf of Mexico, overlooking the 70-foot heated saltwater swimming pool, spa, lush tropical landscaping, and breathtaking sunsets. Just steps from the pristine beach, this outdoor retreat invites you to relax, read, listen to the waves, and savor spectacular evening skies. Inside, the home offers a seamless blend of style and functionality. The spacious primary suite features sliding glass doors to the balcony, a generous walk-in closet, and a split en-suite bath with dual vanities, a spa-like soaking tub and shower, and a large window that fills the space with natural light. The second en-suite bedroom, privately positioned off the front hallway, is generously sized, offers abundant natural light, and includes a large walk-in closet—perfect for guests. Additional conveniences include a powder room, in-unit laundry, interior storage, and a private storage closet just outside the front door. The residence also includes assigned under-building parking and access to bike storage. Residents of Players Club enjoy resort-style amenities, including a newly renovated clubhouse with a state-of-the-art fitness center, library, catering kitchen, and inviting indoor and outdoor social spaces. Four Har-Tru tennis courts, pickleball, a putting green, beautifully maintained grounds, a security gate, and on-site management provide both luxury and peace of mind. Ideally situated on the desirable south end of Longboat Key, this community is just minutes from Publix, the renowned St. Regis Longboat Key Resort, the upscale boutiques and fine dining of St. Armands Circle, and the vibrant cultural attractions of downtown Sarasota. This is a rare opportunity to own a distinguished Gulf-front residence in one of Florida’s most sought-after coastal communities—where luxury, location, and lifestyle come together beautifully.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Steve Nursey (941-356-7010)
1918 HARBOURSIDE DR #902, LONGBOAT KEY, FL 34228
$1,299,00061 Days on yellowkey MLS ID: A4680710
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1748 Built: 1982Monthly Fee: $146 Tax: $11,598 (2025)Community: Fairway Bay 1Spa: YesTownhouse
Taxes:$11,598
Remarks: Welcome to a masterfully reimagined two-bedroom, 2.5-bath FURNISHED town home offering breathtaking, full open views of Sarasota Bay and the vibrant city skyline with its OWN PRIVATE BOAT SLIP. Arguably the most exquisite residence in the esteemed Fairway Bay community at Bay Isles on Longboat Key. The property underwent a meticulous down-to-the-studs renovation in 2020 that included filling in the 100 square foot atrium on the second floor, blending high-end craftsmanship with its unparalleled waterfront setting. The interior is a showcase of custom artistry, featuring warm wood ceilings, solid White Oak stairway treads, an elegant custom iron stairway railing, inset cabinets, Sonos sound system and a Lutron smart lighting system for effortless ambiance control. The gourmet kitchen is a chef’s dream, anchored by a custom White Oak island with quartz tops, Fisher Paykel built-in appliances, and charming built-in banquet seating breakfast niche. Sophisticated touches continue throughout, including a custom iron wine rack, grass wallpaper, designer light fixtures and sleek tile flooring in every room. Retreat to the primary suite, where soaring wood ceilings and a custom walk-in closet provide a sanctuary of comfort. The bath is light, bright and features a furniture-quality inset vanity and an enclosed wet room complete with a standalone soaking tub. The other bedroom on the second floor also has an en-suite bath that features furniture-quality vanity and beautiful walk-in shower. The second-floor laundry with full size LG front-loaded machines makes doing laundry a breeze. For ultimate peace of mind, the home features an impact-rated bayfront living room window and rear exterior door, complemented by a Garrison Hammerhead Aluminum Flood Barrier System installed in 2025. This system includes reinforced cement pilings just inside the garage door with easy-to-use slide-in aluminum slats designed to prevent water intrusion. As part of the Bay Isles community, residents enjoy world-class amenities including 24-hour gated security, swimming pools, tennis and pickleball courts, and exclusive access to the private Bay Isles Beach Club. Just minutes from the cultural heart of downtown Sarasota and upscale shopping of St. Armands Circle, this home offers a lifestyle of effortless elegance.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Liz Nason (941-350-2243)
1005 BOGEY LN, LONGBOAT KEY, FL 34228
$3,300,00077 Days on yellowkey MLS ID: A4680006
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3624 Built: 2017Monthly Fee: $21 Tax: $19,847 (2025)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$19,847
Remarks: Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.
Listing Agent: Michael Nink, Pa (941-914-2805)
1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228
$4,750,000197 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
Tax Year: 2024
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)
3617 FAIR OAKS PL, LONGBOAT KEY, FL 34228
$2,050,000219 Days on yellowkey MLS ID: A4663935
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2950 Built: 1995Monthly Fee: $746 Tax: $16,463 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$16,463
Remarks: One or more photo(s) has been virtually staged. Situated in the highly sought-after maintenance-free community of Queens Harbour, behind the gates of Bay Isles, this updated lakefront home perfectly captures the ease of Florida living. A 2023 tile roof adds peace of mind, while a smart split floor plan includes three en-suite bedrooms, a half bath, and a versatile den/office that can serve as a fourth bedroom. The interiors feel bright and welcoming with 12–15’ ceilings, neutral tones, and elegant architectural details. New wood-look porcelain tile flooring enhances the living room, dining room, den/office, and first-floor bedrooms, combining durability with style. The kitchen features stainless steel appliances, a center island with second sink, updated hardware, and a breakfast nook with bay window views of the pool and lake. The primary suite enjoys direct lanai access, tranquil water views, and a spa-like bath with dual vanities, soaking tub, and walk-in shower. Outdoors, the screened lanai offers a heated pool and spa with a peaceful lake backdrop, plus a refreshed covered sitting area with a new tongue-and-groove ceiling and accent wall—perfect for relaxing or entertaining year-round. Residents enjoy exclusive access to the Bay Isles Beach Club, with its private beachfront, cabanas, and members-only amenities, along with optional memberships for golf, tennis, and the Harbourside Marina with deepwater slips. This home sustained no hurricane damage or water intrusion. This is Longboat Key living made simple—beautiful, low-maintenance, and ready to enjoy.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228
$389,0006 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
Elementary School: None
Remarks: Longboat’s Beach Harbor club is situated on 5 Acres along the most beautiful stretch of Longboat Key Shoreline. Sugary sand and flowing seeds oats 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)
2326 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$950,00049 Days on yellowkey MLS ID: A4683180
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: Perfectly positioned end-unit villa is located on prestigious Longboat Key within the gated Bay Isles community, offering the rare 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 world-renowned 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 brand-new air conditioning system (2025) and new roof (2025) provide peace of mind. 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. Schedule your private showing today and experience the elevated coastal lifestyle that awaits.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rachel Tritschler (941-993-5892)
3710 GULF OF MEXICO DR #F2, LONGBOAT KEY, FL 34228
$475,00039 Days on yellowkey MLS ID: A4681154
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 740 Built: 2026Monthly Fee: $290 Tax: $2,070 (2025)Community: Gulfshore Of Longboat KeyManufactured Home
Taxes:$2,070
Remarks: Island Living at Its Finest – Brand New Home on Longboat Key. Welcome to Gulfshore of Longboat, a highly desirable waterfront co-op community offering private beach access, boat docks, and sweeping views of the Gulf of Mexico and Sarasota Bay. This beautifully built 2-bedroom home combines modern efficiency with relaxed coastal living. An outdoor bathroom with a shower is a wonderful convenience for those enjoying the pool or boating. Step inside to an open, sun-filled floor plan featuring soaring ceilings with tray accents in both the living room and the primary bedroom, creating a bright, spacious atmosphere throughout. The kitchen is designed for everyday comfort and entertaining, complete with a center island, hardwood shaker cabinetry with soft-close doors and drawers, and a full stainless appliance package including refrigerator with ice and water, range, dishwasher, microwave, and garbage disposal. Built to current HUD hurricane standards and Energy Star certified, the home offers peace of mind with 2x6 construction, upgraded insulation, and low-E vinyl windows for year-round comfort and efficiency. Enjoy mornings at the private beach, afternoons at the heated pool, and evenings watching sunsets over the water. The community clubhouse hosts regular activities, making it easy to relax and connect with neighbors in a friendly coastal setting. Whether you’re looking for a winter retreat or full-time residence, this move-in-ready island home delivers comfort, security, and the lifestyle Longboat Key is known for. No pets (except for service animals or emotional support animals with appropriate paperwork) or Rentals permitted. Schedule your private showing today and start living the Gulf Coast dream.
Listing is courtesy of: WAGNER REALTY (941-751-0670)
Listing Agent: Marsha Winegarden (248-563-2820)
2045 GULF OF MEXICO DR #M1-511, LONGBOAT KEY, FL 34228
$749,0004 Days on yellowkey MLS ID: A4689590
0 Days Off yellowkey (back on 4/12/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1076 Built: 1974Monthly Fee: $1,278 Tax: $9,430 (2025)Community: Seaplace IiCondo
Taxes:$9,430
Remarks: Experience breathtaking, full Gulf views from this beautifully maintained 5th-floor residence at Seaplace on Longboat Key. This furnished 2-bedroom, 2-bath condominium offers the perfect blend of comfort, space, and coastal charm, with expansive living and dining areas designed to capture stunning water views and natural light throughout. Step out to your private lanai and enjoy panoramic sunsets, gentle sea breezes, and the soothing sounds of the Gulf—your own peaceful retreat just steps from the beach. The spacious primary suite provides a relaxing escape, while the guest bedroom offers comfort and privacy for visitors. Seaplace residents enjoy resort-style amenities across 42 acres of lush, meticulously maintained grounds, including a half-mile of private beachfront, two heated swimming pools with spas, a fitness center, Har-Tru tennis courts, walking paths, outdoor grilling areas, and an active, well-managed association. Whether you’re seeking a full-time residence, vacation getaway, or investment opportunity, this unit is priced to sell and ready for you to start enjoying the Longboat Key lifestyle. Schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228
$950,000100 Days on yellowkey MLS ID: A4676681
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1966 Tax: $3,929 (2025)Community: Sands PointCondo
Taxes:$3,929
Remarks: SELLER IS MOTIVATED AND WILL ENTERTAIN ALL REASONABLE OFFERS! GREAT PRICE REDUCTION !!!! MUST SEE ARCHITECTURAL GEM on Longboat Key! Be in your new home to enjoy summer activities and gorgeous sunsets.Sands Point Condominium is a best kept secret along the beautiful crystal white sands of Longboat Key. This community blends gorgeous mid-century architecture with the stunning location tucked away next to Longboat Key Club. Sands Point offers everything you need to relax and unwind under the Florida sun and all the amenities you could ask for including a private marina. Whether you are a vacationer or full- time resident, you will find this New Pass location one of the best on the island encompassing stunning sunset views. This two bedroom unit is filled with sunlight and has had extensive renovations/remodel (2023) throughout. The beautiful luxury flooring and tall baseboards extend throughout the entire unit. The expansive combination living/dining spaces offer room for large groups or to allow for separate seating areas; all without giving up glorious sunny views. The gorgeous kitchen offers stainless steel Samsung appliances including a French door refrigerator with 2 freezer drawers range and microwave. The double stainless steel sink is a plus for those who love to cook. Beautiful stone countertops top fresh white cabinetry with soft-close doors and drawers. A generous pantry holds all the supplies you need for cooking and entertaining. Dual sides cabinetry forms the breakfast bar offering even more storage. The interior laundry room has GE Insignia washer and dryer and add cabinetry and shelving for storage. Both bathrooms are updated with new cabinetry and countertops. The Primary bedroom is a huge space with a wall of windows; a bright, airy space with ample room for a desk and has both a built-in and a walk-in closet. Both the Primary Suite and the large great room space have stunning views of the Marina. Mid-century charm exudes from the social room gathering space; terrazzo floors and complementing furnishings make this a fun space to gather and entertain. The space includes a kitchen and library area. There is onsite management housed in this building as well. A short walk takes you to the stunning beach-exactly what you come here for! Expansive white sand beach area wraps around the complex. Palapas, beach chairs and a newly renovated pool area overlooks New Pass. Watch the dolphin and enjoy spectacular sunsets. The marina complex offers boat slips on a first come/first serve basis and offers a kayak launch, fishing pier, storage and bicycle storage areas. HVAC new in 2020,. The condo offers an assigned covered parking spot right and a separate assigned storage unit. St Armands Circle, with a variety of restaurants and shops is a short drive away. Easy access to downtown Sarasota and its cultural and entertainment venues. You must see this home to fully appreciate the charm, history and expansive coveted location on the beach of Sands Point. Don't fight the crowds and traffic to enjoy the beach; you are here!!! AMAZING LOCATION near St Armand's Circle, downtown Sarasota and all of the white sand gulf beaches. Own a piece of paradise today!
Listing Agent: Donna Turnbaugh (410-382-4692)
3802 GULF OF MEXICO DR #A203, LONGBOAT KEY, FL 34228
$399,000194 Days on yellowkey MLS ID: A4667199
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1007 Built: 1970Monthly Fee: $1,347 Tax: $2,774 (2024)Community: Beach Harbor ClubCondo
Taxes:$2,774
Remarks: Super value on 2nd floor 2br/2ba condo in Beach Harbor Club. This beautifully maintained Gulf-to-bay community offers boat slips on the bay and private beach access on the Gulf side, as well as pool, clubhouse, gym and private beach access just accross the street! Just bring your bathing suit and flip flops as this two-bedroom and two-bath unit has been beautifully updated to include an all-new bright open kitchen with custom cabinetry, stone counters and high-end appliances, including a Fisher & Paykel fridge, a two-drawer Cafe dishwasher, and a Cafe two-oven, six-burner stove. Flooring throughout was updated with a light blond luxury vinyl plank. Both baths had updates including cabinetry and countertops found in the kitchen. The AC was replaced in 2024. This home also has a sweet view of the Gulf from the outdoor seating area in the front. Beach Harbor Club is an active and amenities-rich community with boat docks, a pool, a gym, private beach access, kayak storage, a ground-level storage closet for beach gear, a beautiful clubhouse and just upstairs from this unit is a wonderful rooftop deck for sunset viewing.
Listing Agent: Holly Switow (941-735-3186)
1050 LONGBOAT CLUB RD #204, LONGBOAT KEY, FL 34228
$850,000238 Days on yellowkey MLS ID: A4662463
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1974Monthly Fee: $209 Tax: $8,541 (2024)Community: Privateer NorthCondo
Taxes:$8,541
Remarks: **Price Improvement ~ Motivated Seller** Step into the island lifestyle you’ve always imagined at Privateer North, located behind the gates of the Longboat Key Club. This CORNER residence with over 1,400 sq. ft. invites you to wake each morning to the sound of waves and natural light streaming through wide glass doors. Sip your coffee on the balcony as Gulf breezes drift in, and in the evening, watch the sky transform with unforgettable Longboat Key sunsets. Inside, thoughtful UPDATES create a fresh, welcoming home. The owners have recently installed a NEW ELECTRIC PANEL, added NEW LIGHTING, FRESH PAINT in areas where needed, and are offering the property FULLY FURNISHED — so you can start enjoying it from day one. The OPEN LIVING AND DINING area flows easily for entertaining, while the SPLIT-BEDROOM design ensures privacy. The spacious primary suite features a WALK-IN CLOSET and SPA-STYLE BATH, while the guest suite provides a comfortable retreat for family and friends. Privateer North has just completed a STUNNING MODERNIZATION of its common areas and elevators, complementing its prime beachfront setting. Amenities include a BEACHFRONT POOL AND SPA, FITNESS CENTER, SAUNA, TENNIS and PICKLEBALL courts, CONCIERGE service, and DIRECT BEACH ACCESS — everything you need for a true resort lifestyle. With the new St. Regis Resort just minutes away, and St. Armands Circle and downtown Sarasota within easy reach, this home blends relaxation and sophistication in one of the Gulf Coast’s most desirable locations. Whether a seasonal retreat or full-time residence, Unit 204 offers the perfect balance of LUXURY, LIFESTYLE, and ISLAND CHARM. Call the listing agent today for a V.I.P. tour!
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)
Listing Agent: Chris Carpenter (941-599-2277)
815 BAYPORT WAY #815, LONGBOAT KEY, FL 34228
$850,0006 Days on yellowkey MLS ID: A4689278
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1601 Built: 1981 Tax: $7,370 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$7,370
Remarks: Welcome to a true hidden gem of tropical paradise at Bayport Beach and Tennis Club on Longboat Key. Designed by renowned architect Tim Seibert, this one-of-a-kind community spans 27 lush, tropical acres and offers an unmatched coastal lifestyle with 1,200 feet of pristine private beach, where chairs and umbrellas are ready for you to enjoy endless days along the Gulf. As you arrive, you’re immediately surrounded by beautifully maintained grounds and the relaxed, resort-style atmosphere that makes this community so special. Stepping inside this spacious 2 bedroom, 2 bathroom furnished residence, you’re welcomed by a light and airy interior with terracotta-look tile flooring flowing throughout the main living areas, setting a warm coastal tone. The kitchen has been thoughtfully renovated with all new cabinetry, under-cabinet lighting, quartz countertops, a modern backsplash, and stainless steel appliances, creating a clean and functional space that opens seamlessly into the living and dining areas. The expansive living room is both inviting and impressive, designed to feel like a single-family home, with stunning Sarasota Bay views that instantly capture your attention. Shutter doors provide privacy while leading into a sunroom, offering a flexible space to relax and take in the scenery. The owner’s suite is a true retreat, complete with a dedicated office nook perfectly positioned to enjoy peaceful water views. The ensuite bathroom features dual quartz-topped vanities and a walk-in closet, combining comfort and convenience. A split bedroom floorplan ensures privacy, with the guest bedroom offering its own walk-in closet and easy access to the updated guest bathroom. An in-unit laundry area adds to the everyday ease of living. Step outside onto your expansive private deck, where breathtaking views of Sarasota Bay create the perfect backdrop for morning coffee, evening wine, or entertaining guests while surrounded by nature. Bayport Beach and Tennis Club offers an incredible array of amenities, including a Junior-Olympic heated pool, four Har-Tru tennis courts, a fitness center, fishing pier, kayak storage + launch, and an active clubhouse filled with social events. Scenic walking trails wind through the property, where you’ll often spot local wildlife such as osprey, herons, ibis, and egrets, enhancing the serene, natural setting. Just moments away, Bayfront Park offers pickleball courts, green space, and stunning bay views, while St. Armands Circle provides exceptional shopping and dining. A short drive over the iconic Ringling Bridge brings you into vibrant downtown Sarasota, known for its world-class arts scene, including theaters, museums, galleries, and waterfront dining. From private beach access to unmatched amenities and breathtaking bay views, this residence offers the perfect blend of comfort, nature, and coastal elegance in one of Longboat Key’s most sought-after communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Keith Curcio (941-376-7683)
3488 MISTLETOE LN, LONGBOAT KEY, FL 34228
$3,980,000167 Days on yellowkey MLS ID: A4670010
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3341 Built: 1989Monthly Fee: $1,083 Tax: $25,296 (2025)Community: Coreys LandingSpa: NoSingle Family
Taxes:$25,296
High School: Sarasota High
Remarks: Discover an exceptional opportunity to live behind the gates of the Longboat Key Club in the highly coveted Corey’s Landing neighborhood — one of the island’s premier bayfront addresses. Set within an intimate, established enclave there is a difference in this property vs. others in the neighborhood: it’s a free-standing residence which means you don’t share any common elements with an attached neighbor necessitating joint decisions on when to paint or replace a roof. There are only four free standing homes such as this, the rest are attached. This home welcomes you through double doors into a showplace of light, style, and space with immediate expansive bay views. Step outside to the expansive screened lanai — an inviting oasis for relaxing or entertaining by the pool while taking in mesmerizing bay views and the twinkling lights of downtown Sarasota. Enjoy immediate bay access with the private boat dock and lift. Inside, soaring transom windows, walls of glass, and rich wood floors enhance the open great-room design — a perfect setting for entertaining around the elegant fireplace. The updated kitchen connects seamlessly to the dining and living areas, showcasing sleek white cabinetry, a striking tile backsplash, solid-surface countertops, stainless steel appliances, and a generous breakfast bar ideal for casual gatherings. The first-floor primary suite is a private retreat with walls of glass, a cozy sitting area, custom built-ins, dual closets, and a luxurious remodeled bath featuring dual vanities, a large walk-in shower, and a separate water closet. Also on the main level are a private guest suite, second bedroom, full bathroom, a study/den, and a convenient outdoor dog space. Upstairs, a versatile loft provides the flexibility for a gym, library, or additional guest accommodations. The attached two-car garage offers ample storage, while Corey’s Landing residents enjoy access to a community pool, spa, Har-Tru tennis courts, and the private Bay Isles Beach Club. Ideally located near world-class shopping, dining, and the renowned St. Armands Circle, this residence captures the essence of the Longboat Key lifestyle — elegant, relaxed, and effortlessly connected to both land and sea.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
1932 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228
$1,200,0006 Days on yellowkey MLS ID: A4689076
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1192 Built: 1982 Tax: $9,436 (2024)Community: Fairway Bay 1Condo
Taxes:$9,436
Remarks: Welcome to this breathtaking, fully remodeled, turnkey furnished contemporary residence in Fairway Bay—nestled on picturesque Longboat Key. From the moment you enter, you're greeted by a thoughtfully redesigned open floor plan, elevated ceilings, solid core doors, and impeccable high-end finishes. IT IS TRULY ONE OF A KIND! This condominium is truly one-of-a-kind! Exceptional Kitchen features include: Bertazzoni induction range, refrigerator, and dishwasher, built-in Miele plumbed espresso machine, sleek, low-profile custom cabinetry with quartz countertops, glass tile backsplash and ambient lighting and an expansive quartz island perfect for formal dining or casual entertaining. The living room flows effortlessly from the kitchen, opening onto a covered, tiled lanai—blurring the line between indoor and outdoor living. Floor-to-ceiling impact windows frame panoramic views of Sarasota Bay, the Ringling Bridge, and the city skyline, offering million-dollar scenery from the comfort of your home. Enter the generously sized and luxurious Primary Suite with custom built-ins and ample closet space. The ensuite bath is a spa-inspired bath with dual vanities, Hansgrohe Axor faucets, Toto washlet, walk-in shower with multiple heads and elegant finishes. The guest suite features custom cabinetry and an ensuite bathroom with a Victoria & Albert volcanic limestone bathtub. Other recent upgrades include Hurricane-impact windows and doors, tankless water heater, additional upper cabinetry in kitchen and utility room, ceiling fans and more. For your convenience & comfort there is easy elevator access, coveted garage parking space and private onsite storage. Fairway Bay residents enjoy the resort-Style amenities including Deeded beach access & exclusive beach club, 24-hour gated security, pool, spa, tennis courts, and fitness center plus all the perks of Bay Isles living. Whether you're soaking in the sun, enjoying vibrant Sarasota culture and nightlife, or relaxing in your private retreat, this home is a perfect sanctuary.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Jan Jordan (941-737-4169)
1581 GULF OF MEXICO DR #406, LONGBOAT KEY, FL 34228
$6,750,00035 Days on yellowkey MLS ID: A4685503
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2347 Built: 2024 Tax: $50,055 (2025)Community: St. RegisSpa: NoCondo
Taxes:$50,055
Remarks: Perched above the shimmering shoreline, this exquisite two-bedroom, two-and-a-half-bath residence at The St. Regis Longboat Key Resort offers breathtaking panoramic views of the turquoise waters of the Gulf of Mexico and the resort’s serene saltwater lagoon. Designed for both refined comfort and effortless coastal living, the residence showcases exceptional craftsmanship and sophisticated design throughout. A defining feature of this residence is the expansive private terrace, where all principal rooms open seamlessly to the outdoors. Complete with a gas grill, this exceptional outdoor living space provides sweeping views of the Gulf of Mexico and the tranquil lagoon—creating the perfect setting for al fresco dining, entertaining, or simply enjoying spectacular sunsets over the water. The gourmet kitchen is a true showpiece, appointed with sleek Poggenpohl cabinetry and premium appliances including Wolf double ovens, a gas cooktop, microwave, icemaker, and wine refrigerator. A generously sized island provides abundant built-in storage, making the space as functional as it is beautiful. This thoughtfully designed floor plan features two luxurious owner’s suites. The primary suite enjoys stunning views of the Gulf of Mexico and opens directly onto the large terrace. The spa-inspired bathroom features a large double vanity with elegant lighted mirrors plus a separate makeup vanity, two private water closets, a seamless glass shower, and a freestanding soaking tub. Electronic sheers and blackout shades provide effortless ambiance and privacy, while a custom-built closet offers exceptional storage. The second owner’s suite also captures captivating Gulf views and opens onto the terrace. Its spacious bath includes dual vanities with lighted mirrors, a water closet, and custom-built closets. Electronic sheers and blackout shades add both convenience and luxury. Additional highlights include a large laundry room with sink, cabinetry, and hanging rack, as well as an elegantly designed powder room for guests. Offered completely turnkey, the residence is beautifully furnished and enhanced with custom light fixtures throughout, creating a sophisticated yet inviting coastal retreat. Nestled within the first branded residential community and ultra-luxe 5 star resort on the Gulf of Mexico. The Residences at The St. Regis Longboat Key blend legendary service with the allure of a seaside getaway. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in residence dining. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!
Listing Agent: Lynn Morris, Pllc (941-400-4526)
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