Location: Longboat Key
Do Not Show Listings
1000 LONGBOAT CLUB RD #403, LONGBOAT KEY, FL 34228
$974,500165 Days on yellowkey MLS ID: A4680791
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972Monthly Fee: $1,565 Tax: $9,673 (2025)Community: Privateer SouthCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,673
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Experience refined coastal living behind the gates of the Longboat Key Club at Privateer South — a serene waterfront retreat where the Gulf sets the rhythm of each day. This exclusive Longboat Key enclave blends timeless Old Florida charm with resort-style amenities. Residents enjoy access to the Longboat Key Club’s championship golf, tennis, deep-water marina, fine dining, and private beach club, while Privateer South offers intimate beachfront living in a 12-story tower at 1000 Longboat Club Road. This fourth-floor corner residence is a fully renovated two-bedroom, two-bath home that captures the essence of coastal elegance. Floor-to-ceiling windows and sliding glass doors open to wraparound balconies with eastern, southern, and partial Gulf views. Begin your mornings with sunrise over Sarasota Bay and the Intracoastal Waterway, as soft hues of pink and gold fill the open living and dining spaces. By afternoon, enjoy sweeping southern views of powder-white sand and turquoise Gulf waters, accompanied by the gentle sound of waves. The interior renovation reflects modern sophistication and comfort. A sleek galley kitchen with quartz countertops, stainless steel appliances, and custom cabinetry flows seamlessly into the bright living-dining area. Neutral tones, shiplap accents, and high-end finishes create an inviting, light-filled space ideal for entertaining or relaxing. The primary suite features desirable southern exposure and a refreshed en-suite bath with dual vanities and a walk-in shower. The second bedroom offers flexibility as a guest room, office, or private retreat, with the guest bath refreshed as well, in a clean, contemporary style. Daily living feels effortlessly indulgent. From the lobby, take the elevator to the heated Gulf-front pool and spa, complete with lounge seating overlooking the shoreline. Manicured pathways lead to private beach access, where dunes, complimentary chairs and umbrellas, and uncrowded sands create the perfect setting for sunset walks and frequent dolphin and pelican sightings. Residents also enjoy beachside grilling, on-site tennis, and the simple pleasures of Gulf coastal living. Gated security, covered parking, and the low-density South tower — with approximately 62 residences — provide both privacy and a welcoming community atmosphere shared by seasonal and full-time residents alike. Evenings on the balcony are unforgettable, with brilliant sunsets fading into star-filled skies over the Gulf. Inside, the open layout invites relaxed dinners, quiet reading, and peaceful nights accompanied by the sound of the water. This beautifully renovated corner residence offers the perfect balance of comfort, elegance, and breathtaking scenery in one of Florida’s most sought-after barrier island communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
4825 GULF OF MEXICO DR #504, LONGBOAT KEY, FL 34228
$825,00077 Days on yellowkey MLS ID: A4689724
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970Monthly Fee: $1,656 Tax: $12,908 (2025)Community: Westchester AptsCondo
Taxes:$12,908
Remarks: Discover coastal living at its finest in this beautifully positioned 2-bedroom, 2-bath condominium on one of Longboat Key’s most sought-after stretches. This residence offers spectacular, breathtaking views from both private lanais—perfect for enjoying sunrise coffee or evening sunsets over the water. Inside, the layout is bright and inviting, with seamless indoor-outdoor flow that maximizes the scenery from multiple vantage points. Whether you’re looking for a full-time residence or a serene getaway, this condo delivers both comfort and location. The community is elevating its appeal with exciting enhancements, including upcoming clubhouse renovations featuring a boutique fitness center, newly refreshed landscaping, and a hot tub addition to the pool deck—creating a true resort-style atmosphere with two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan FURNISHED 5th floor panoramic view, master en-suite unit awaits YOU! Enjoy the best of island living with pristine beaches, nearby dining, and a relaxed yet refined lifestyle—all just moments from your door. R&R IS THE PACE, LBK IS THE PLACE!!!!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Toni Giliberti (941-284-9208)
4835 GULF OF MEXICO DR #106, LONGBOAT KEY, FL 34228
$749,900161 Days on yellowkey MLS ID: A4677656
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $6,331 (2024)Community: Westchester AptsSpa: NoCondo
Taxes:$6,331
Tax Year: 2024
Remarks: Waterfront Living on Longboat Key – Direct Gulf Access Experience the best of coastal living on beautiful Longboat Key. This first-floor residence offers effortless access and an unbeatable connection to the water, with direct access to the stunning Gulf of Mexico just steps from your door. Recently updated, the home features brand-new flooring throughout, along with all-new hurricane-impact windows, sliding glass doors, and a hurricane front door—providing peace of mind and modern comfort. Enjoy seamless indoor-outdoor living with easy walk-out access, perfect for morning beach strolls, sunset views, or simply embracing the relaxed Gulf Coast lifestyle. Whether you’re looking for a full-time residence, vacation getaway, or investment opportunity, this property offers exceptional value in a highly sought-after location. Year after year, The Westchester has been considered to be the most sought after location on Gulf of Mexico Drive. This two bedroom, two bath 1,393 sq. ft. condominium holds many family memories, which could now be yours. Experience the beautiful views of the Emerald waters from both lanais. Unit has recently been completely painted. Unit is move-in ready to be enjoyed! Both bathrooms contain generous walk-in closets, with a washer/dryer installed in the guest closet. Come witness Resort Style amenities of two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan, first floor, master en-suite unit awaits your TLC. Kitchen includes side-by-side beverage refrigerators. R&R IS THE PACE, LBK IS THE PLACE!!!!!
5920 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$1,749,500429 Days on yellowkey MLS ID: A4652254
Bed: 2 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2823 Built: 1973 Tax: $8,478 (2024)Community: Longboat KeySpa: YesSingle Family
Taxes:$8,478
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: DEEDED BEACH ACCESS AND DEEP WATER CANAL at this beautifully renovated mid-key beach house on the barrier island of Longboat Key. You can enjoy a 3-minute walk to the beach using your private beach access or step outside and enjoy the canal on your trex dock. The uncrowded beach with natural surroundings, fine sand beaches, warm breezes, and clear turquoise waters is truly a special place. Entering the home, you are greeted by terrazzo floors, stunning 2 story foyer and a water view of the canal. All new wood kitchen cabinets including island and coffee bar with quartz countertops making this a great area to entertain guests. All 3 bathrooms have been completely renovated and include custom tile showers. Large master bedroom with en-suite bathroom. An enclosed lanai overlooking the canal is a perfect spot for an office or tropical retreat. Large living room with wood burning fireplace and new tile flooring provides a relaxing space. New kitchen and bath fixtures throughout. Ceiling fans in each room. Being in the middle of LBK provides easy access to Anna Maria Island and Bradenton to the north, St. Armands and Sarasota to the south. SRQ airport is less than 45 minutes. Completely restored home by licensed general contractor and professionally mitigated after hurricane Helene flood damage. The house shares a driveway, deeded beach and canal access with 5924 Gulf of Mexico Drive making it a perfect guest house or family compound when purchased together (or use one as a rental for an ongoing revenue stream}. The property is being sold as-is. Please use AS IS Residential Contract for Sale and Purchase_FloridaRealtors-FloridaBar-ASIS-7.xdp
Listing is courtesy of: JOHN DONATO REAL ESTATE INC (941-504-4987)
Listing Agent: John Donato (941-504-4987)
5924 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$849,500429 Days on yellowkey MLS ID: A4651805
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1359 Built: 1955 Tax: $11,764 (2024)Community: Fractional SubSingle Family
Taxes:$11,764
Remarks: Sought after mid-key cottage home with DEEDED BEACH ACCESS on the barrier island of Longboat Key. Entering the home, you are greeted by terrazzo floors, wood beam ceilings and a tile accented gas fireplace in the large living room. An additional room overlooking screened in pool can be used as an office, exercise room or extra space for guests. Newly renovated kitchen with wood cabinets, quartz countertops, new sink and fixtures. Bathrooms have been completely renovated with beautiful walk-in tiled showers. A built-in bookcase in the living room adds charm with plantation shutters, accent lighting and ceiling fans throughout. Completely restored home by licensed general contractor and professionally mitigated after hurricane Helene flood damage. The house shares a driveway and deeded beach access with 5920 Gulf of Mexico Drive making it a perfect guest house or family compound when purchased together. Another possibility is to use one as as a rental for an ongoing revenue stream. The property is being sold As-Is (use FAR-BAR-ASIS-7.
562 RANGER LN, LONGBOAT KEY, FL 34228
$3,499,900210 Days on yellowkey MLS ID: A4675541
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3149 Built: 1995Monthly Fee: $20 Tax: $27,065 (2024)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$27,065
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: One or more photo(s) has been virtually staged. A rare opportunity to own a single-family waterfront home with 100 feet of canal frontage and direct access to Sarasota Bay. Located in Country Club Shores on the desirable southern end of Longboat Key, 562 Ranger Lane offers 4 bedrooms, 3 full baths, and approximately 3,149 square feet of living space designed for relaxed coastal living. The property features a sunny southern rear exposure overlooking the canal, with a north-facing street frontage, providing balanced natural light throughout the day. The home underwent a comprehensive renovation in 2018, including a tile roof, paver driveway, two Trane A/C units, tankless water heater, updated sprinkler system, railings, pool equipment, and a Pebble Tec refinished pool positioned to maximize the southern exposure. The interior features an open great-room layout with 16-foot ceilings, porcelain tile flooring throughout, plantation shutters, LED lighting, and a spacious kitchen with Starmark solid-wood soft-close cabinetry, Cambria quartz countertops, and stainless-steel appliances. An 8-foot arched iron front door introduces abundant natural light and an open, functional floor plan. The current configuration includes an upper-level primary suite with solid oak flooring, walk-in closets, and a well-appointed bath, while the first level offers three large bedrooms, including an office with custom built-ins, and two full baths with handcrafted cabinetry, quartz countertops, and glass-enclosed showers. The flexible layout provides the opportunity to create a first-floor primary suite to suit individual lifestyle needs. Boating amenities include a new seawall, a 70-foot private Trex dock with 50-amp shore power, and a recently serviced 10,000-pound boat lift. Outdoor living is enhanced by a covered lanai and a two-level travertine deck ideal for entertaining and enjoying the canal setting. Residents enjoy access to a private deeded beach on the Gulf of Mexico and proximity to Longboat Key Club golf, dining, and shopping at St. Armands Circle, with downtown Sarasota’s cultural arts and dining scene just minutes away. Schedule a private showing to experience this waterfront home, its flexible living options, and direct access to Sarasota Bay
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-748-6300)
Listing Agent: Cheri Mazan Castro (941-400-3777)
2181 HARBOURSIDE DR #1403, LONGBOAT KEY, FL 34228
$850,000386 Days on yellowkey MLS ID: A4656539
0 Days Off yellowkey (back on 4/8/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2219 Built: 1984 Tax: $9,674 (2024)Community: Harbor Oaks Ph I & IiSpa: NoCondo
Taxes:$9,674
Middle School: Pine View School
Remarks: Under contract-accepting backup offers. PRICED TO SELL! Experience the ultimate in island living in the highly sought-after and prestigious Harbor Oaks community on Longboat Key. This one-story, 3-bedroom, 2.5-bath residence spans 2,219 sq. ft. and offers a host of desirable features—including a private pool, 2-car garage, and deeded beach access through the exclusive Bay Isles Beach Club. A new roof (2025) and fresh interior paint ensure peace of mind and a move-in-ready experience. High ceilings fill the home with natural light, enhancing the spacious feel throughout. The expansive living room, anchored by a wood-burning fireplace, seamlessly connects to the outdoor living area via pocket sliding glass doors, opening to two large screened lanais—ideal for both relaxing and entertaining. The chef’s kitchen is outfitted with granite countertops, stainless steel appliances, rich wood cabinetry, a breakfast bar, and a skylight for added brightness. The primary suite is a private retreat featuring a walk-in closet, two additional closets, updated master bath, and sliding doors leading to the terrace. A guest suite with en suite bath provides comfort and privacy for visitors. Additional highlights include an interior laundry room with sink, a newer AC unit (2018), and natural gas line for adding a pool heater. All furnishings are included. Residents of Harbour Oaks enjoy a resort-style lifestyle with access to a community pool, spa, and lushly landscaped surroundings—just minutes from Longboat Key’s vibrant Town Center. As part of Bay Isles, you’ll have exclusive access to the Bay Isles Beach Club, a private, gated Gulf-front oasis with a pavilion, picnic areas, BBQ grills, beach chairs, restrooms, and ample parking—perfect for sunset viewing or relaxing on Longboat Key’s pristine white sands. Optional membership opportunities at the Longboat Key Golf & Tennis Country Club and Harbourside Moorings deep-water slips offer even more ways to elevate your coastal lifestyle.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Sharon Morea (941-400-9300)
7147 LA LENAIRE DR, LONGBOAT KEY, FL 34228
$5,000,000241 Days on yellowkey MLS ID: TB8448347
REDUCED by $235,000 (4.5%) on 05/07/2026
Bed: 5 Bath: 5.5 Liv Area Sq Ft: 3503 Built: 1990Monthly Fee: $283 Tax: $33,963 (2023)Community: Jewfish KeySpa: YesSingle Family
Taxes:$33,963
Tax Year: 2023
Middle School: W.D. Sugg Middle
Remarks: A rare offering on Florida’s coveted west coast, this private island sanctuary feels worlds away yet remains moments from the region’s most beloved coastal destinations. Set on the exclusive 38-acre island of Jewfish Key (accessible only by boat), this remarkable 1.35-acre estate commands its own secluded shoreline and uninterrupted views of crystal clear waters. Inspired by Polynesian architecture and designed to dissolve the boundaries between indoors and out, this estate home unfolds through airy pavilions connected by elevated walkways. Towering palms and lush tropical landscaping envelop the home, while its 18-foot elevation ensures both peace of mind and panoramic, horizon-level vistas. Inside, the freshly reimagined kitchen serves as the gathering heart of the home, with sleek quartz countertops, modern cabinetry, and a spacious oversized island that effortlessly bridges culinary function and relaxed entertaining. Expansive sliding glass doors draw natural light into the living space and frame sweeping views of the sandbar and bay, perfect for sunset watching. The main residence includes four bedrooms and four-and-a-half baths, plus a separate guest suite offering an additional bedroom, kitchen, and full bath, ideal for hosting with comfort and privacy. The primary suite is where the pace of the island truly settles in. Wake up to wide-open bay views, linger with coffee in the sitting area, or enjoy a glass of wine as the sun sinks toward the horizon. The ensuite feels fresh and spa-like, with a soaking tub, walk-in shower, and water views. A series of screened porches and wraparound decks encourage slow living, morning yoga on the deck, afternoon reading in the shade, sunset grilling and cocktails overlooking the Gulf. Outdoors, a newly installed pool and spa with a sun shelf and expansive sundeck overlook the storied Jewfish Key Sandbar. A private dock with jet ski lift offers instant access to calm waters perfect for fishing, snorkeling, paddle boarding, or exploring neighboring Longboat Key and Anna Maria Island, both just minutes away by boat and beloved for dining, boutique shopping, and laid-back coastal culture. Equal parts island hideaway and refined coastal home, this one-of-a-kind property offers the rare combination of true privacy, effortless access, and natural beauty, set against a backdrop of turquoise water, powder soft sand, and endless sky. Here, relaxation, adventure, and natural beauty converge in a setting that feels almost like an escape, yet unmistakably home.
Listing is courtesy of: SIGHT REAL ESTATE, LLC (877-361-0878)
Listing Agent: Chase Moore (727-325-7272)
578 - 580 COMPANION WAY, LONGBOAT KEY, FL 34228
$900,000156 Days on yellowkey MLS ID: A4682264
REDUCED by $99,000 (9.9%) on 05/07/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoApartment
Taxes:$11,672
Remarks: Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value.. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Linh Pham (941-900-6789)
578 COMPANION WAY, LONGBOAT KEY, FL 34228
$900,000156 Days on yellowkey MLS ID: A4682186
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoSingle Family
Remarks: Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.
1241 GULF OF MEXICO DR #506, LONGBOAT KEY, FL 34228
$3,850,00072 Days on yellowkey MLS ID: A4689658
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2650 Built: 1996 Tax: $27,928 (2025)Community: Water Club 01 At Longboat KeyCondo
Taxes:$27,928
Remarks: Welcome to coastal luxury redefined at the Water Club on Longboat Key. This fully reimagined residence at 1241 Gulf of Mexico Dr, Unit 506 has undergone a complete, top-to-bottom renovation completed in 2025, offering a like-new living experience in one of Florida’s most sought-after beachfront communities. No detail was overlooked—featuring a brand-new designer kitchen with premium finishes, fully renovated bathrooms, new flooring throughout, updated trim, modern lighting, and fresh interior paint. The home is further elevated by a whole-home Lutron system, delivering effortless, customizable lighting control and a true smart-luxury experience. Positioned in the highly desirable south building and an even-numbered unit (ideal for sunset views over the Gulf), this residence captures some of the most breathtaking winter sunset views—where the sun sets between the buildings, creating a rare and unforgettable coastal backdrop. Residents enjoy an unparalleled resort lifestyle at The Water Club, featuring an exceptional collection of amenities including Har-Tru tennis courts, a resort-style beachfront pool and spa, state-of-the-art fitness center, saunas, locker rooms, elegant clubhouse, library, and private event spaces. With 24-hour security, concierge-level services, and meticulously maintained grounds, The Water Club offers the ultimate in privacy, comfort, and luxury coastal living. Whether as a full-time residence or seasonal retreat, this is Gulf-front living at its absolute finest.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Tyler Sajan (877-366-2213)
5311 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228
$799,00084 Days on yellowkey MLS ID: A4691314
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1110 Built: 1973 Tax: $3,363 (2025)Community: Mccalls Beach CastleSpa: YesCondo
Taxes:$3,363
Remarks: Turnkey furnished and positioned just steps from the Gulf’s sandy shoreline, this first-floor residence at Beach Castle on Longboat Key offers a compelling combination of coastal living and proven rental potential. With flexible daily or weekly rental allowances, this two-bedroom retreat presents an exceptional opportunity for personal use, income generation, or both. The light-filled interior features an open layout designed for ease and comfort, where the kitchen, dining, and living areas flow together naturally. Oversized tile flooring, updated impact glass, and sliding doors enhance both durability and livability, while the kitchen is well-appointed with granite countertops, solid wood cabinetry, stainless steel appliances, and built-in shelving—creating a functional space for everyday living or hosting. Floor-to-ceiling sliders lead to a private patio and screened lanai, offering a seamless transition to the outdoors and placing you just moments from the beach. The split-bedroom plan provides added privacy, with the primary suite enjoying direct access to the outdoor space, while the guest bedroom is comfortably sized with its own en-suite bath. Set within the boutique Beach Castle community, residents enjoy a unique beach-to-bay lifestyle with deeded Gulf access, a heated swimming pool and spa, grilling areas, and a fishing pier with day dock on Sarasota Bay. Lush landscaping and well-maintained grounds create a relaxed, resort-style setting that enhances both owner enjoyment and guest appeal. Located on the desirable north end of Longboat Key, this property is just minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic biking and walking paths. A short drive south brings you to the Longboat Key Club, St. Armands Circle’s dining and boutiques, and downtown Sarasota’s renowned cultural venues, waterfront parks, and year-round events. With strong rental history, immediate beach access, and a turnkey presentation, this Beach Castle residence offers a rare opportunity to enjoy the best of Longboat Key—whether as an investment, a private getaway, or a combination of both.
Listing Agent: Roger Pettingell (941-387-1840)
847 EVERGREEN WAY, LONGBOAT KEY, FL 34228
$599,000303 Days on yellowkey MLS ID: A4665172
REDUCED by $10,000 (1.6%) on 05/04/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1440 Built: 1991 Tax: $8,510 (2024)Community: Cedars East Sec 3Townhouse
Taxes:$8,510
Remarks: Refined Coastal Living with Proven Income Potential – Experience the best of Longboat Key in this impeccably appointed, turnkey furnished residence within the coveted Cedars East Tennis Resort. This elegant 2BR/2.5BA townhome spans 1,440 square feet of thoughtfully curated living space, where tasteful coastal design meets modern comfort. The gourmet kitchen is adorned with granite surfaces and flows seamlessly into a bright, open living area designed for effortless entertaining. A tranquil, private lanai invites you to unwind amid lush tropical surroundings. The primary suite serves as a serene retreat, complete with dual vanities and a spa-inspired ambiance, while upstairs laundry enhances everyday ease. With a strong history of rental performance, this property offers a rare opportunity to blend lifestyle with investment. Residents and guests enjoy an array of resort-caliber amenities, including championship Har-Tru tennis courts, a heated Olympic-style pool, fitness center, and exclusive bayfront features such as a kayak launch, fishing pier, and scenic mangrove boardwalks. An on-site dining option adds to the effortless luxury. Ideally located just moments from the beautiful beaches of Longboat Key, the boutiques and dining of St. Armands Circle, downtown Sarasota, and Anna Maria Island. A distinctive offering for the discerning buyer seeking both coastal elegance and exceptional return on investment. No flood damage | New A/C (2025)
Listing Agent: Kiki Bowers (941-718-3435)
2295 GULF OF MEXICO DR #23S, LONGBOAT KEY, FL 34228
$1,295,000268 Days on yellowkey MLS ID: A4669226
REDUCED by $100,000 (7.2%) on 04/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $9,812 (2024)Community: Islander Club Of LongboatSpa: NoCondo
Taxes:$9,812
Remarks: Set directly on the shores of the Gulf of Mexico, this beautifully renovated residence in the Islander Club captures the essence of Longboat Key beachfront living. Located in the desirable South Tower, this 2BR/2BA home showcases a fresh coastal design with wide-plank flooring, crown molding, recessed lighting, and an open layout oriented to the water. The kitchen exudes coastal charm with stone countertops, shaker cabinetry, stainless-steel appliances, and a sea-glass tile backsplash. Both baths have been redone with refined finishes, glass-enclosed showers, and clean modern tilework. Floor-to-ceiling sliders open to an expansive covered terrace—perfect for outdoor dining, lounging, and taking in sweeping Gulf views. The primary suite also enjoys terrace access and an endless horizon of turquoise water. Residents of the Islander Club enjoy 400 feet of private beach, a Gulf-front pool, fitness center, tennis courts, pickleball, library, social lounge, and on-site management within two secure towers and gated entry. The recently updated common areas - including the elegant lobby and clubroom - offer a stylish, contemporary ambiance overlooking the Gulf. Ideally positioned near St. Armands Circle and Sarasota’s world-class dining, shopping, and cultural attractions, this residence offers an effortless blend of comfort, sophistication, and beachfront tranquility.
Listing Agent: Bruce Myer (941-376-5311)
535 SANCTUARY DR #C807, LONGBOAT KEY, FL 34228
$3,750,000165 Days on yellowkey MLS ID: A4680240
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2580 Built: 1990 Tax: $25,298 (2025)Community: Sanctuary IvSpa: YesCondo
Taxes:$25,298
Remarks: Sanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Sarasota. *Now Unfurnished*. Total renovations completed in 2023 with nothing overlooked, including but not limited to EFCO turtle-approved glass, high-impact double pane hurricane sliders and windows, crystal custom kitchen cabinets by SRQ Custom Cabinetry, Thermador appliances including induction cooktop, wall-mounted microwave and convection oven, side-by-side Thermador refrigerator, Wi-Fi enabled dryer and hood fan, laundry room with added pantry features and a newly created breakfast bar. Complete water filtration system and quartz countertops throughout, with 5.5-inch baseboards with custom-milled crown molding and trim, solid wood doors, rectified 12-by-60-inch porcelain tile flooring, and custom built-ins in living room and primary bedroom. Hunter Douglas remote-controlled blinds, 10-foot-high ceilings complete with skylights, tankless hot water system, and two zoned air conditioning units installed in 2019 and 2023. Amenities include cable, water and internet. New roof in 2024. Storage locker with under-building parking. Nearly 18 acres with 1,200 feet of Gulf of Mexico beachfront, an Olympic-sized heated pool and spa with extensive pool decks, a fire pit and gazebos to provide shade. A 24/7 guard gate, Har-Tru tennis courts, on-site management, and a two-story clubhouse come complete with a fitness center, showers, saunas and a large entertaining room with catering facilities. Membership to the Longboat Key Club is available which would include six restaurants, 45 holes of golf, 20 tennis courts plus other amenities. You are close to shopping, Publix, CVS, places of worship, a library, town hall and banks, St. Armands Circle along with Sarasota and all it offers.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Dennis Girard (941-809-0041)
4380 EXETER DR #H202, LONGBOAT KEY, FL 34228
$499,000249 Days on yellowkey MLS ID: A4671530
REDUCED by $21,000 (4.0%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970 Tax: $6,314 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$6,314
Remarks: Experience the ultimate Bay-to-Beach lifestyle in this turnkey 2-bedroom, 2-bath condo at Longboat Harbour, where nearly every room offers sparkling water views and a sense of calm that only waterfront living can bring. Perfect for investors or seasonal residents, this home combines desirable updates with a lifestyle that’s hard to beat. Fully updated in 2025, this home blends modern luxury with coastal charm. LVP flooring, textured ceilings, and fresh paint flow throughout, while the brand-new kitchen boasts with all-white cabinetry, coffee bar, coastal glass backsplash, and quartz countertops. The master suite features custom closet doors, a new porcelain shower with frameless glass, porcelain flooring, and a quartz-top vanity with Bosch washer/dryer in the bath. The hall bath includes a new porcelain shower/tub combo, stylish vanity with quartz countertops, and contemporary Euroflush toilets. Every detail is designed to make the interior as inviting as the stunning views outside. Every update you could hope for in a ready-to-enjoy condo! Step outside and enjoy the resort-style amenities of a vibrant waterfront community. Longboat Harbour offers four heated pools, tennis and pickleball courts, a recreation hall, billiards, game rooms, docks with sailboat access (no bridges to the bay), and a fitness center. Social committee events, on-site grills, and beautiful landscaping surround you at every turn. For beach lovers, the private deeded beach access at 4415 Gulf of Mexico includes a beach house with restrooms, showers, and reserved parking. A short drive from Longboat Key, St. Armands Circle, and downtown Sarasota, you’ll find boutique shops, delightful dining, arts, festivals, and the wonder of Selby Botanical Gardens. Watch Gulf sunsets paint the sky while manatees, ospreys, and egrets play in the waters below… this condo is all about a life of fun, relaxation, and unforgettable moments.
Listing Agent: Ryan Skrzypkowski (941-328-8307)
948 SPANISH DR S, LONGBOAT KEY, FL 34228
$1,199,000128 Days on yellowkey MLS ID: A4685572
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1399 Built: 1968 Tax: $4,945 (2025)Community: Spanish Main Yacht Club CondoVilla
Taxes:$4,945
Remarks: Stunning full bay views as you enter this jaw-dropping magnificent, completely custom renovated stand-alone villa on Sarasota Bay. Professionally designed starting with an 18-by-11-foot gourmet kitchen. With 10-12-foot wood beam ceilings, a beautiful 12-foot quartz island that seats 10-plus people, solid wood cabinetry, Café’ brand double oven, refrigerator with two additional drawers, stainless steel appliance, huge undermount sink, glass backsplash, separate wet bar and more. The 2-by4-foot white porcelain rectangular tile flows seamlessly from room to room with water views that entertain you every moment of every day. With the Intracoastal Waterway just beyond the brick paver back patio, the wildlife is abundant, more than you can imagine, with morning sunrises that softly greet you as you awaken to a true slice of paradise. The entire glass-enclosed 23-by-12-foot lanai brings so much light, brightness and cheerfulness that it makes your heart smile. The end unit offers privacy and protection with lush green mangroves creating a protected area plus easy access for entering the water, going for a swim, fishing or kayaking. Back to the renovations, the main bedroom en suite offers privacy with upscale bath appointments, a double sink, and large designer shower. The enclosed laundry area right off the bedroom was carefully crafted with a walk-in closet, extra storage room and a rare whole-house water purification system. Not to mention all hurricane windows and doors throughout with additional footings, foam support and steel beams under the sliding doors to ensure structural integrity and peace of mind. All appliances are 2025, LG Thin Q washer and dryer, Café kitchen appliances, tankless hot water tank, custom fan and lights, all new plumbing and electrical as the home was taken down to the studs. PVC sewer lines completely replaced all cast iron pipes. New tile roof in 2025. There is nothing to do except move in and relax. You will not be disappointed. All FEMA regulations have been completed, including inspections. Vibrant waterfront 55-plus community with 40-slip marina and deeded beach access to gorgeous beaches of Longboat Key. Close to restaurants, shops, renowned St. Armands Circle, plus 30 minutes to Sarasota International Airport. Take a look.
Listing Agent: Kimberly Freiwald (941-256-6775)
2039 GULF OF MEXICO DR #G3-207, LONGBOAT KEY, FL 34228
$550,000379 Days on yellowkey MLS ID: A4657767
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1974 Tax: $5,281 (2024)Community: SeaplaceSpa: NoCondo
Taxes:$5,281
Remarks: THIS IS THE LARGEST 2 BEDROOM 2 BATH FLOOR PLAN IN SEAPLACE! Located on the second floor (elevator access on the north end) of the G3 building, this home is move in ready! The previous den has been enclosed for a proper bedroom and updated! The primary bedroom and bathroom have both been updated. Updated lighting, updated baseboards, crown molding, no popcorn ceilings, no carpet, new hurricane rated sliders and windows! Plantation shutters are added for easy care and the coastal vibe! This building is located directly adjacent to the Har-Tru tennis courts, perfect for the avid player! Seaplace is a Gulf front community situated on lushly maintained grounds and offers not only tennis courts, a secure guarded gated entry, clubhouse, two heated pools/spas, fitness, Gulfside BBQ, organized social functions, onsite management and the icing on the cake is direct beach access! Residence comes completely furnished, assigned parking space #115, (north side of the building) Perfect for your second home and income protection, with a 2-month minimum rental period. Seaplace is located on beautiful Longboat Key convenient to grocery shopping, banking, and the best shopping on St. Armand's Circle! Or make a reservation at any number of first-class restaurants on the Key, and dine waterside, or find a nice cozy quiet booth inside and take in one of nature's most beautiful gifts of a sunset, and if you are lucky, you just may see the dolphins diving and playing! Come off the beach at the south end and you are immediately in downtown Sarasota, where you can catch any number of plays, or a live band for evening entertainment. The weekend offers a sidewalk Farmer's Market, with an assortment of vendors! Whatever time you have planned to be here, may just not be enough!!!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Diane Fogo Harter (941-445-2431)
1065 GULF OF MEXICO DR #201, LONGBOAT KEY, FL 34228
$629,000266 Days on yellowkey MLS ID: A4669086
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1172 Built: 1981 Tax: $7,875 (2024)Community: Beachplace IiiCondo
Taxes:$7,875
Remarks: One or more photo(s) has been virtually staged. One or more video(s) was virtually staged. Sunny and rarely available 2-bedroom, 2-bath corner residence in BeachPlace III on Longboat Key. This desirable end unit offers a wraparound terrace and open views of lush tropical landscaping, the Longboat Key Club’s Links Golf Course, and partial Gulf views—providing excellent natural light and a true coastal feel. The residence features brand-new, impact-rated floor-to-ceiling sliding glass doors that brighten the living and dining areas and enhance indoor-outdoor living. The open-concept layout connects the kitchen, dining, and living spaces, making it well suited for everyday living or entertaining. A split-bedroom floor plan provides privacy, with the primary suite offering direct access to the terrace. One assigned parking space is included, and the unit is ready for personalization or updating. BeachPlace is a gated, Gulf-front condominium community offering 24-hour security and resort-style amenities, including a clubhouse, heated beachfront pool and spa, tennis courts, fitness center, and a private boardwalk with direct beach access. Seasonal beach service with lounge chairs and umbrellas is provided. Conveniently located near golf, marinas, dining, and shopping, and just a short drive to downtown Sarasota, this property offers flexibility as a full-time residence, seasonal getaway, or investment opportunity.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: John Esser (515-306-8505)
350 GULF OF MEXICO DR #211, LONGBOAT KEY, FL 34228
$938,500288 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
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.
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