Location: Longboat Key
Do Not Show Listings
1000 LONGBOAT CLUB RD #403, LONGBOAT KEY, FL 34228
$974,500117 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)
775 LONGBOAT CLUB RD #203, LONGBOAT KEY, FL 34228
$1,750,000236 Days on yellowkey MLS ID: A4667025
3 Days Off yellowkey (back on 5/12/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2122 Built: 1984 Tax: $14,781 (2024)Community: Beaches Of Longboat Key Ph-1Spa: YesCondo
Taxes:$14,781
Tax Year: 2024
Remarks: Welcome to your dream beachfront retreat, nestled behind the exclusive gates of the prestigious Longboat Key Club. This exquisite 3-bedroom, 3-bathroom Gulf-front residence captures breathtaking, unobstructed views of the sparkling turquoise waters of the Gulf from every room—an ever-changing canvas of sunlight, sea, and sky. From the moment you enter, you're greeted by expansive walls of glass that bathe the interiors in natural light and frame the stunning panoramic seascape. Every corner of this residence is infused with the tranquil energy of the ocean, from the shimmering waves to the soft sea breezes that drift through the impact-rated sliding glass doors and windows. The spacious open-concept living and dining area is designed for effortless entertaining, offering a front-row seat to the water. Whether hosting friends or enjoying a quiet evening at home, you'll savor the endless horizon stretching beyond your wraparound balcony—a perfect place to sip morning coffee at sunrise or unwind at sunset. The Kitchen has abundant counter space, generous storage, a built-in desk, and a charming breakfast nook overlooking the beach. Each of the three expansive bedroom suites offers privacy and comfort, with en-suite bathrooms, ample closet space—including dual closets in the primary suite. Freshly painted interiors, electronic shades in every room and new carpeting in the primary suite add a fresh, move-in-ready feel. Unlike many condominiums, this residence offers the space and storage of a single-family residence, including in-unit laundry and generous closets throughout. And with no neighboring buildings in sight, you'll enjoy uninterrupted views and a sense of peaceful seclusion rarely found in beachfront living. Step outside and indulge in resort-style amenities at The Beaches, including 24-hour concierge services, two Har-Tru tennis courts, a heated beachfront pool and spa, fitness center, and a club room with catering kitchen. Mere steps from your door lie the powdery white sands and warm waters of the Gulf—perfect for sunbathing, shelling, or a sunset stroll. For the ultimate in luxury, residents may also join the renowned Longboat Key Club, offering access to two championship golf courses, a world-class spa & wellness center, tennis courts, fine dining restaurants, and a deep-water marina. Located on the coveted south end of Longboat Key, you're just minutes from the chic boutiques and dining of St. Armands Circle and the vibrant arts and culture of downtown Sarasota. This is more than a home—it’s a lifestyle. A rare opportunity to own a slice of paradise where the Gulf meets the sky. Welcome to beachfront living at its most luxurious.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Courtney Tarantino (941-893-7203)
843 BAYPORT WAY #843, LONGBOAT KEY, FL 34228
$670,00025 Days on yellowkey MLS ID: TB8505224
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983 Tax: $5,838 (2025)Community: Bayport Bch & Ten Ph FSpa: NoCondo
Taxes:$5,838
Remarks: This exceptionally clean and well maintained 2-bedroom, 2-bath residence in Bayport Beach and Tennis Club is offered turnkey (with a few exclusions), ready for immediate enjoyment. Currently the lowest-priced unit in the community, it also presents a rare opportunity for a new owner to customize and renovate at their own pace—adding personal style while building value. Ideally positioned as a bright and private second-floor end unit with no neighbors above, this home is filled with natural light. Kitchen, dining, living room open design with split bedrooms for privacy. The primary suite features a walk-in closet and a dedicated office niche—perfect for today’s work-from-home lifestyle. Two inviting outdoor living spaces—a private open-air deck and a screened lanai overlooking the tropical gardens—create the perfect setting to relax and unwind. Additional highlights include covered parking, ample guest parking, two private storage areas plus an owner’s closet, and the convenience of an in-unit full-size washer and dryer. Set on 27 acres of beautifully landscaped grounds on Longboat Key, Bayport is a sought-after gulf-to-bay community designed by renowned architect Tim Seibert. Residents enjoy 1,200 feet of deeded private beach access along the Gulf of Mexico. Community amenities are exceptional, including a Junior Olympic-size heated pool—one of the largest on the Key—four Har-Tru tennis courts, a fitness center, fishing pier, and kayak launch. Beach chairs and umbrellas are provided, and a full calendar of seasonal social activities fosters a vibrant yet relaxed coastal lifestyle. Meandering shell pathways and meticulously maintained tropical landscaping complete the serene setting. Experience the best of island living with breathtaking sunrises over the bay, unforgettable sunsets on the beach, and everything in between.
Listing is courtesy of: HOME SOLD REALTY LLC (833-700-2782)
Listing Agent: Camilo Perez (833-700-2782)
4485 GULF OF MEXICO DR #402, LONGBOAT KEY, FL 34228
$745,000163 Days on yellowkey MLS ID: A4675789
REDUCED by $15,000 (2.0%) on 05/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1022 Built: 1973Monthly Fee: $1,050 Tax: $4,183 (2024)Community: Arbomar AptsCondo
Taxes:$4,183
Remarks: Experience exceptional beachfront living in this beautiful Gulf-front residence at Arbomar on Longboat Key. Unit 402 is a 2-bedroom, 2-bath condominium offering direct, unobstructed Gulf of Mexico views and immediate beach access, making it the most affordable 2-bedroom, 2-bath opportunity on Longboat Key with true Gulf frontage. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways, updated carports, and new doors and impact-rated windows throughout the community. Inside, the home is move-in ready with a newer AC system and newer appliances, ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. Arbomar offers elevator access, a heated beachfront pool, fitness center, and a welcoming, well-maintained community. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions, and world-class golf—while delivering the rare luxury of direct Gulf views and private beach access at an exceptional value.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Richard Tyson (941-999-1179)
741 OLD COMPASS RD, LONGBOAT KEY, FL 34228
$1,895,00085 Days on yellowkey MLS ID: A4684578
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2173 Built: 1969Monthly Fee: $63 Tax: $11,776 (2024)Community: Emerald HarborSpa: YesSingle Family
Taxes:$11,776
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: W.D. Sugg Middle
Remarks: Exceptional opportunity to own a Longboat Key waterfront home in the highly desired community of Emerald Harbor. This 3BR/2BA, 1,926-sf canal front home with pool sits on an oversized 100x155-ft lot along one of Longboat’s widest canals (~110 ft) offering deep-water boating access just a half mile to the Intracoastal Waterway. Private beach access with parking is less than half a mile away. The property experienced storm-related water damage in 2024 and is ready for renovation or a brand-new custom home build. Enjoy island living close to The St. Regis Longboat Key Resort, The Resort at Longboat Key Club, St. Armands Circle, and North Longboat Village favorites—Shore, Mar Vista, Whitney’s, and Lazy Lobster. Emerald Harbor Longboat Key home for sale combines boating, beach access, and the ultimate Florida lifestyle—an unbeatable fixer-upper Longboat Key canal-front opportunity in one of the island’s premier neighborhoods.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
5005 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$7,495,000163 Days on yellowkey MLS ID: A4673495
REDUCED by $305,000 (3.9%) on 05/08/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4630 Built: 2018Monthly Fee: $572 Tax: $30,971 (2024)Community: Bonaire At Longboat KeySpa: YesSingle Family
Taxes:$30,971
Remarks: Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes. Walk in to this fully furnished home which is steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and balconies. A beautiful foyer, large family room, and home gym are featured on the ground floor, along with an oversized three-car garage and storage room. The quality of the home’s design and construction are matched by the charm of the interior finishes and amenities. The living areas incorporate beautiful ceiling elevations, along with custom wide-plank hardwood, Italian porcelain tile, and custom plantation shutters and drapes. The Great Room flows into the chef’s kitchen which features custom cabinetry, quartz countertops, Wolf and SubZero appliances, and a temperature-controlled 275 bottle wine room. Designed for easy entertaining, the Great Room opens onto a large lanai with its gas fireplace and grill, and gorgeous Gulf and sunset views. Adjoining the kitchen is a perfect dining room with its own balcony and Gulf views, as well as a large family office/bonus room with custom cabinetry and bookshelves. The Lutron system controls both the lighting and the custom drapes and shades. The home’s elegant chandeliers and sconces bathe its interior with gracious warmth. The beautiful master suite on the main floor includes a bedroom cathedral ceiling and access to the outdoor lanai. The master bath features custom cabinetry, porcelain tile, a large steam shower, and is plumbed for a master bathtub. Three spacious guest suites, a gathering lounge, and balconies with Gulf views are found on the second living floor. A private elevator connects all levels. Both the home and exterior grounds are designed for year-round, low-maintenance living. An extensive landscape refresh in 2023 included new turf and lighting, an outdoor shower, and a great fire pit area for entertaining. Lush landscaping and a tranquil pool setting provide both screening and privacy. The home features remote controlled screening and storm shutters, extensive use of Azek composite, and other low-maintenance materials, along with a gas generator, whole-house water filtration system, central vacuum, and much more. With miles of pristine beach and bay to explore and with the abundant cultural, dining, and shopping amenities of Sarasota, St. Armand’s Circle, and Anna Maria Island nearby, this timeless home delivers the very best of Longboat Key living.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
5055 GULF OF MEXICO DR #331, LONGBOAT KEY, FL 34228
$895,000204 Days on yellowkey MLS ID: A4670624
1 Days Off yellowkey (back on 5/12/2026)
REDUCED by $90,000 (9.1%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $5,337 (2024)Community: Club LongboatSpa: YesCondo
Taxes:$5,337
Middle School: Martha B. King Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to your coastal retreat in paradise — a stunning third-floor waterfront residence in Club Longboat Beach and Tennis, offering expansive Gulf views and one of the largest floor plans in the community. This exceptional 2-bedroom plus 3rd bedroom/study layout perfectly blends elegance, comfort, and functionality, ideal for full-time living or as a refined vacation escape. With 750 feet of pristine Gulf frontage, this home immerses you in the beauty and serenity of coastal living. Beautiful engineered white oak wood floors flow throughout the open, sun-filled living space, which seamlessly extends to your private balcony’s, the perfect spot to enjoy the tranquil sound of the waves and stunning sunsets. The updated kitchen features stone countertops, white cabinetry, and has been opened up to create a larger, more connected floor plan ideal for entertaining. The primary suite is a private sanctuary, boasting a remodeled marble bath with high-end fixtures and a spa-like ambiance. The guest suite provides equal comfort and privacy, featuring a beautifully appointed travertine-floored bathroom. A custom wall of California closets offers exceptional storage and style. The Club Longboat Beach and Tennis community offers amazing amenities, including private beach access with lounge chairs and beach umbrellas, eight professional har-tru tennis courts, pickleball, fitness center, shuffleboard, barbeque area, clubhouse with regular social events, sauna, spa and two heated swimming pools. Club Longboat is a pet-friendly community allowing up to two pets with fees that include exterior maintenance and insurance, cable, water, sewer and trash. Perfect as a full-time residence or an income-producing rental, with one-month minimum leases permitted up to 12 times per year. Only a short drive to many fine restaurants, boutiques, Anna Maria Island, St. Armands Circle and the City of Sarasota. Sarasota is a well-known center for arts and culture including the Asolo Theater, Van Wezel Performing Arts Center and Ringling Museum. Schedule your showing today and make resort style living a reality.
Listing Agent: Ryan Heers (941-726-1703)
3070 GRAND BAY BLVD #644, LONGBOAT KEY, FL 34228
$799,00040 Days on yellowkey MLS ID: A4690677
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1329 Built: 1995Monthly Fee: $83 Tax: $6,324 (2025)Community: Grand Bay 6Condo
Taxes:$6,324
Remarks: Under contract-accepting backup offers. Penthouse-Level Condo at Grand Bay – Longboat Key Experience luxury living in this beautifully appointed penthouse-level residence at Grand Bay, located behind the gates of Bay Isles on Longboat Key. This spacious 2-bedroom, 2-bath condo offers an open and airy floor plan with stunning east-to-west exposure, capturing both sunrise and sunset from dual balconies with sweeping views of Sarasota Bay, the city skyline, and the golf course. As a penthouse-level home, it also features an added ceiling height of one foot, enhancing the sense of space and light throughout. Both bedrooms are en-suite, with the primary suite featuring dual closets (including one walk-in) and luxurious marble vanities in the bath. The home showcases elegant bamboo flooring in the main living area, marble tile in the bathrooms, and plush carpet in the bedrooms. Floor-to-ceiling sliding glass doors at both ends of the unit flood the space with natural light. The chef’s kitchen is equipped with a Sub-Zero refrigerator, Blue Pearl granite countertops, a breakfast bar, and an in-kitchen laundry room. Recent upgrades include a new AC system in 2021 and a water heater in 2020. The residence also comes with two deeded parking spaces and a private garage-level storage locker, and it is offered furnished for immediate enjoyment. Grand Bay’s exceptional amenities include 24-hour guard-gated Bay Isles entry, an additional Grand Bay gated entrance, secure coded lobby access, on-site property management, and a pet-friendly environment. Residents enjoy two resort-style pools, a state-of-the-art fitness center, tennis courts, and membership to the Bay Isles Beach Club. There are no current or pending assessments. Enjoy the perfect blend of luxury, privacy, and convenience in one of Longboat Key’s premier waterfront communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Nicole Hammons-Dovgopolyi (941-966-8000)
448 GULF OF MEXICO DR #A205, LONGBOAT KEY, FL 34228
$599,00038 Days on yellowkey MLS ID: A4690875
REDUCED by $30,000 (4.8%) on 05/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1306 Built: 1970 Tax: $5,089 (2025)Community: Bay HarbourCondo
Taxes:$5,089
Remarks: Set within an intimate 39-residence waterfront enclave, this Bay Harbour retreat captures the essence of refined island living. Framed by swaying palms and 720 feet of shimmering Sarasota Bay frontage, the community feels like a private tropical sanctuary, where beautiful sunrises paint the sky and waterfowl dive gracefully for fish along the shoreline. Boaters will appreciate the ideal marina location, offering a quick, scenic ride to the Gulf of Mexico. The marina is fully equipped with electrical service, fresh water and a fish-cleaning station, while the seawall provides front-row views of dolphins and playful manatees. A kayak launch adds even more ways to enjoy life on the water. Inside, this spacious two-bedroom, two-bath residence spans 1,300-plus square feet of light-filled living with captivating views of Bay Harbour Marina and Sarasota Bay. Both bedrooms feature walk-in closets, and the kitchen blends style and function with wood cabinetry with glass fronts, stainless-steel appliances, solid-surface countertops and tile flooring throughout. The generous primary suite offers an en-suite bath and a peaceful vantage point overlooking the turquoise bay waters. Offered furnished, the home includes an in-unit washer and dryer, covered assigned parking, ample guest parking and elevator access. Bay Harbour’s amenities elevate the experience with a heated pool, grilling area and first-come boat slips accommodating vessels up to 42 feet. Owners may have one pet. Positioned in south Longboat Key, you’re just 15 minutes from downtown Sarasota, home to upscale shopping, acclaimed dining, galleries, theater, opera, ballet and vibrant arts scene. And for everyday indulgence, you can visit or bike to St. Armands Circle, a beloved destination of boutiques, cafés and coastal charm.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Kathleen Wingate (813-731-3332)
1105 GULF OF MEXICO DR #402, LONGBOAT KEY, FL 34228
$995,000288 Days on yellowkey MLS ID: A4661696
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981 Tax: $9,142 (2024)Community: Beachplace IiCondo
Taxes:$9,142
Elementary School: Southside Elementary
High School: Booker High
Middle School: Pine View School
Remarks: Beachplace at Longboat Key: Major price reduction for this Gulf-front luxury and rental-friendly, turnkey furnished investment opportunity! An iconic condominium in the mid-century modern style, Beachplace was constructed under the direction of Tim Siebert, one of the leaders of the Sarasota School of Architecture, and spans 31 acres with a quarter mile of Gulf beachfront. This price reduction makes this an ideal residence or investment opportunity. With a direct Gulf view, and a gentle walk to the beach, this two-bedroom, two-bathroom residence offers serene living; a spacious primary suite with ensuite bath, plus a guest suite, private balcony with stunning sunset views, full kitchen and dining and living spaces, new impact glass windows, all complemented by nearby amenities, including private beach access, a Junior Olympic-sized pool, spa, and a kid's pool. A clubhouse, two fitness facilities, a sauna, tennis, and pickleball courts, and two grilling stations complete the resort lifestyle. Electric Vehicle charging is on-site. The Resort at Longboat Key Club is immediately adjacent and offers championship golf and tennis facilities, a full-service marina nearby, and fine dining for its members and guests. St. Armands Circle shopping, dining, and entertainment is a short drive south, and Sarasota, with its thriving arts and cultural communities, eclectic shopping and dining, and extraordinary architecture, is a brief ride across the bay. Thirty-day minimum rentals are permitted twelve times annually. The buyer or their agent should review the possibility of any special assessments with the condominium manager. All of the information provided is considered reliable, but should also be verified by the buyer or buyer's agent.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Tom Aposporos (941-704-4250)
3040 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$1,899,00025 Days on yellowkey MLS ID: A4692587
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3009 Built: 1995 Tax: $8,653 (2025)Community: Triton CoveSpa: YesSingle Family
Taxes:$8,653
Middle School: Booker Middle
Remarks: Welcome to island living on Longboat Key, one of Sarasota's premier barrier island destinations. In Triton Cove, this coastal residence offers direct Gulf Beach access across the street and a lifestyle designed for boating, seasonal use or year-round living along Florida's Gulf Coast. Enjoy nightly sunsets along Gulf of Mexico Drive or experience world-class dining and shopping on nearby St. Armands Circle. An elevated entry leads to the main living level, where expansive glass defines the open-concept design, connecting the living room, kitchen and dining areas. Positioned within a five-residence enclave, this property offers convenient access to Sarasota dining, shopping and waterfront recreation while supporting a low-maintenance ownership experience. This tri-level single-family home features four bedrooms and 2.5 baths, complemented by a two-car garage with dual 8-foot doors and extensive storage. The ground level includes multiple flexible-use rooms ideal for fitness, storage or organization of beach equipment, kayaks, bicycles and boating gear. A dumbwaiter provides direct access from the garage to the kitchen. Interior features include engineered wood flooring in main living areas and new carpet in bedrooms. The kitchen is designed with wood cabinetry, granite countertops, deep storage drawers, an appliance garage, a rollout pantry wall and stainless steel appliances, including a GE wall oven/microwave combo, an induction cooktop and an LG refrigerator. Additional features include a wet bar with cabinetry and a mirrored wall, an electric fireplace and plantation shutters. The primary suite offers a private setting with dual vanities, a soaking tub, a separate shower, two walk-in closets and a Juliette balcony with partial gulf views. The third level includes a bonus room suitable for media, an office or a private retreat. Outdoor living includes a natural gas-heated pool and spa, an outdoor shower and a private fenced setting. Pool systems including a new motor, filters and heater, and the interior of the pool has been refinished. Recent improvements include a 2024 shingle roof with warranty, zoned HVAC systems installed in 2018 and 2020, and a 2025 water heater. The home includes a monitored alarm system. Triton Cove offers a maintained environment with low monthly HOA fees of $500, including landscape maintenance of common areas, pest control, pool service and exterior lighting. Leasing is permitted up to four times annually with a one-month minimum. Located near Longboat Key Bayfront Park and Longboat Dog Park, residents may enjoy pickleball, tennis, playgrounds and picnic areas. Nearby conveniences include grocery, pharmacy, boat rentals and storage options along Longboat Key, as well as being within reach of Sarasota amenities. Optional membership to the Longboat Key Club provides access to golf, tennis, beach and social amenities, enhancing the gulf-front lifestyle experience on Florida's west coast. Don’t miss out on your private tour of this special coastal home featuring four bedrooms, 3000-plus square feet of air-conditioned living space, a two-car garage, a 30-foot pool and a hot tub on Longboat Key with beach access with low taxes for under $2 million; this is an extraordinary value!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Frank Lambert (941-920-1500)
3060 GRAND BAY BLVD #155, LONGBOAT KEY, FL 34228
$1,145,00067 Days on yellowkey MLS ID: A4685023
REDUCED by $50,000 (4.2%) on 05/11/2026
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2250 Built: 1994 Tax: $14,345 (2025)Community: Grand Bay 1Spa: YesCondo
Taxes:$14,345
Remarks: Framed by sweeping vistas that span the manicured Harbourside golf course, Sarasota Bay, and the distant city skyline, this 3BR/3.5BA residence in Grand Bay offers an exceptional vantage point that captivates from the moment you arrive. Positioned on the fifth floor, the perspective is both expansive and elevated, showcasing breathtaking panoramic views while maintaining a strong visual connection to the surrounding landscape. The living room is thoughtfully designed to highlight this remarkable setting, with a full wall of sliding glass doors opening to a balcony that extends the entire length of the residence. From this elevated perch, corner walls of glass draw the eye outward, creating a dramatic focal point where golf course, bay, and skyline converge in one uninterrupted panorama. High ceilings with crown molding and tile flooring provide a clean, timeless foundation throughout the main living areas. The kitchen offers generous space and functionality, featuring stone countertops, under-cabinet lighting, a center island, stainless steel appliances, a tray ceiling, and an adjacent dining area. Well laid out and highly functional, it also presents an excellent opportunity to personalize finishes and reflect your own design vision. A versatile bonus room with an enclosure feature adds flexibility, ideal for a private office, media room, or additional guest accommodations. The primary suite serves as a comfortable retreat, complete with direct terrace access and serene sunrise views over Sarasota Bay. The spacious bath includes dual vanities, a soaking tub, glass-enclosed shower, and a separate water closet. Additional conveniences include an in-residence laundry room and under-building parking. Residents of Grand Bay enjoy a refined, amenity-rich lifestyle, with access to a clubhouse, two pools and spas, a fitness center with saunas, and Har-Tru tennis courts. Ownership also includes the privileges of Bay Isles, featuring gated entry, scenic walking paths, and membership to the private Bay Isles Beach Club. Large dogs are welcome.
Listing Agent: Bruce Myer (941-376-5311)
604 SPANISH DR N, LONGBOAT KEY, FL 34228
$465,00068 Days on yellowkey MLS ID: A4687282
0 Days Off yellowkey (back on 5/11/2026)
REDUCED by $30,000 (6.1%) on 04/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1357 Built: 1967 Tax: $2,486 (2025)Community: Spanish Main Yacht Club CondoSpa: NoCondo
Taxes:$2,486
Remarks: Longboat Key waterfront lifestyle at its finest is now yours to discover. We are proud to present this stunning, fully renovated waterfront two-bedroom, two-bathroom freestanding villa-arguably a premier location within the Spanish Main Yacht Club. Situated in the middle of the north shore of serene Lake Spanish Main, it provides breathtaking views in every direction. The effortless waterfront views are the star of the show, especially enjoyed from your oversized paver patio-ideally designed for perfect island lounging-but also from nearly every room in the home. The waterfront backyard of this residence is framed by mature Black Olive trees that provide dappled shade while perfectly preserving the bright southern light and glistening water. This "center-of-everything" location is truly unbeatable, offering effortless access to your private deeded beach, the deep-water marina, the community pool, and boat slips. Modern Luxury Meets Coastal Comfort- Inside, a comprehensive renovation features custom tile flooring throughout, immediately setting an elevated, modern tone. The gourmet kitchen is an entertainer's dream, boasting custom cabinetry, designer stone countertops, and new stainless steel appliances centered around a first-class island with updated statement lighting. The open-concept floor plan flows seamlessly from the kitchen into an elegant dining area and a spacious family room, where natural light pours in alongside expansive lake views. Beyond, a sun-drenched Florida room?perfectly suited for an artist's studio and private office?offers southern-facing windows where you can watch the sunlight glisten off the water. Private Retreats-The primary suite is a sanctuary of its own, featuring a walk-in closet, generous proportions, Lake Views and a fully renovated ensuite bath. The guest wing is equally impressive, offering an ample bedroom and a stunningly renovated bathroom with a contemporary walk-in shower. Rounding out this exceptional property are the interior workshop, laundry room, additional storage, outdoor shower and a spacious carport perfectly sized for all your island toys. New Windows installed 2019, 2022 brought a new Roof and AC.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
6810 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$2,250,000214 Days on yellowkey MLS ID: A4669890
1 Days Off yellowkey (back on 5/11/2026)
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2848 Built: 2024Monthly Fee: $83 Tax: $7,410 (2024)Community: LongbeachSpa: YesSingle Family
Taxes:$7,410
Remarks: Significant Price Reduction on this NEW in 2024, dream retreat that is uniquely positioned in the highly sought after “Village” of Longboat Key, a neighborhood known for its quaint charm and vibrant community atmosphere. Featuring 4 bedrooms and 4 and a half baths in open and light filled rooms, a backyard oasis with a pool and outdoor kitchen, high impact windows and doors throughout, 1230 sq ft of porches and balconies and an amazing rooftop top deck with spectacular water views: this is truly the epitome of luxury island living! The stunning chefs kitchen features high end appliances, including a 6 burner gas range, double ovens and a large center island. A perfect open flow into the inviting dining and living area, allows for exceptional entertaining with picturesque views out to the backyard oasis, seamlessly connecting indoor and outdoor spaces. This rare offering of NEW construction in this wonderful neighborhood is hard to come by. It affords its owner peace of mind, whether this is your forever home, your part time vacation retreat or a fabulous investment rental property. The community features multiple restaurants, a couple of Bayfront docks and even a community boat ramp. The gorgeous Gulf of Mexico is within a short walk, bike or golf cart ride away and is one of the nicest beaches on the island. It stretches for miles and is the perfect spot to spend the day before returning to watch the sunset from your rooftop deck. Come savoir the laid back island lifestyle that Longboat Key is known for and make this tranquil coastal retreat your own.
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
531 WEDGE LN, LONGBOAT KEY, FL 34228
$2,499,00058 Days on yellowkey MLS ID: A4687694
2 Days Off yellowkey (back on 5/11/2026)
REDUCED by $100,999 (3.9%) on 05/01/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2751 Built: 1966Monthly Fee: $21 Tax: $10,602 (2025)Community: Country Club Shores Sec 02Spa: NoSingle Family
Taxes:$10,602
Remarks: A seamless blend of refined design and waterfront living defines this beautifully updated canal-front residence in Country Club Shores. Expanded from its original ranch design, the home offers approximately 2,700+ square feet of thoughtfully curated space, featuring four bedrooms, including dual primary suites on both the first and second levels—an ideal layout for guests or multi-generational living. Each bathroom is finished with timeless, elegant details that elevate the home’s overall sense of sophistication. A comprehensive 2018 renovation introduced elevated style and modern functionality, anchored by a stunning chef’s kitchen appointed with Thermador appliances, built-in refrigeration, and a generous island. Just beyond, an expansive butler’s pantry and secondary prep kitchen enhance both convenience and flow, creating an effortless environment for everyday living and entertaining. Natural light fills the interiors, drawing attention to tranquil canal views and soft glimpses of the bay from the den. The upstairs primary suite serves as a private retreat, complete with its own balcony overlooking the water—an inviting setting for quiet mornings and sunset evenings. Outdoors, a private, low-maintenance setting unfolds with a sparkling pool and beautifully updated waterfront features, including a newer dock, seawall, and 24,000 lb boat lift. Additional highlights include hurricane-impact windows and doors, classic plantation shutters, and 2022 air conditioning systems—completing this exceptional offering in one of Longboat Key’s most desirable waterfront communities. Ideally located just moments from St. Armands Circle, with its renowned dining and boutique shopping, this residence offers a lifestyle of effortless coastal sophistication.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Kerry Mccarthy (720-233-7147)
4825 GULF OF MEXICO DR #504, LONGBOAT KEY, FL 34228
$825,00029 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 Agent: Toni Giliberti (941-284-9208)
4835 GULF OF MEXICO DR #106, LONGBOAT KEY, FL 34228
$749,900113 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
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!!!!!
5591 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$900,00038 Days on yellowkey MLS ID: A4690629
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1979 Tax: $3,532 (2025)Community: Sea Club IiiSpa: NoCondo
Taxes:$3,532
Remarks: Experience coastal living at its finest in this beautifully remodeled (2025) Gulf-front, ground-floor end unit at sought-after Sea Club III on Longboat Key. Sea Club III's daily and weekly rental flexibility accommodates those seeking to maximize rental income potential and/or enjoy that perfect personal retreat and getaway. No driving to beach parking lots or crossing streets for amenities required. Enjoy the convenience of direct Gulf beach access with powdery sands, soothing waters and breathtaking sunsets. All just steps from your covered patio. Heated community pool just steps from your front entry. Step inside to find fully furnished and updated interiors (2025). Impact double pane windows and sliders (2025) for added comfort and peace of mind. This condo offers both tranquility and accessibility. Sea Club III is just a short stroll to dining, cafés and parks. Located just minutes from St. Armands Circle and Downtown Sarasota’s dining, shopping and art scene. Convenient to SRQ airport with its ever-increasing direct flights to Sarasota. Do not miss out. This is truly a rare opportunity to own a piece of Old Florida!
Listing is courtesy of: WAGNER REALTY (941-761-3100)
Listing Agent: Gina Uliano (941-920-0276)
2301 GULF OF MEXICO DR #12N and 11N, LONGBOAT KEY, FL 34228
$2,377,000161 Days on yellowkey MLS ID: A4675054
REDUCED by $111,000 (4.5%) on 04/21/2026
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2415 Built: 1970 Tax: $13,538 (2025)Community: Islander Club Of LongboatSpa: NoCondo
Taxes:$13,538
Remarks: Rare Beachfront Opportunity - Two Adjacent Residences at The Islander Club, South Longboat Key Seize a truly rare and unique opportunity to own two adjacent Gulf-front residences in the North Tower of The Islander Club on South Longboat Key. Featuring highly sought-after southwest and northwest exposures, these first-floor walk-out condos live like a maintenance-free beachfront home, with no stairs or elevators and direct access from two private terraces to the Olympic-size beachfront pool and the private white sandy shores of the Gulf of Mexico’s crystal clear aqua waters. Combined, the residences offer 2,500+ square feet of Gulf-front living space, including four beachfront bedrooms and four full bathrooms, two balconies with over 500 square feet of total outdoor frontage, and expansive walls of glass showcasing panoramic Gulf views, brilliant sunshine, gorgeous sunsets, and refreshing cross-breezes. The layout functions as an expansive and seamless beachfront residence with flexible configuration options—combine both units into one refined Gulf-front luxury home, or live in one and rent the other, or tailor and customize the space for personal use or investment potential. Located directly on the beach in South Longboat Key, this one-of-a-kind legacy property is just three miles from St. Armands Circle and minutes from downtown Sarasota’s dining, shopping, and cultural attractions. Two covered parking spaces are included, along with additional guest parking available. The Islander Club features 400 feet of private beachfront, a new fitness and community center, beachfront pool, two Har-Tru tennis courts (soon to be remodeled for pickleball use as well), library, conference room, on-site management, gated access, and a highly advantageous and rare owner-to-owner rental program. Convenient to Publix, CVS, acclaimed restaurants, boutique shopping, and Sarasota’s renowned arts scene. Enjoy breathtaking Gulf sunsets and an unmatched Longboat Key beachfront lifestyle at one of Longboat Key’s most sought-after beachfront addresses.
Listing Agent: Leah George (941-780-0597)
3636 FAIR OAKS PL, LONGBOAT KEY, FL 34228
$3,600,00071 Days on yellowkey MLS ID: A4686948
0 Days Off yellowkey (back on 5/8/2026)
REDUCED by $200,000 (5.3%) on 04/08/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3732 Built: 1990Monthly Fee: $833 Tax: $33,616 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$33,616
Remarks: Under contract-accepting backup offers. PCATTO! PAY CLOSE ATTENTION TO THIS ONE! There is so much to take in, so let’s start with some bullet points: DIRECT BAY BIG,BIG,BIG WATER VIEW. PRIVACY. 5BED/4.5BATH HOME. ELEVATOR. ALL NEW- DOCK WITH 16,000 LB. LIFT, ROOF, SKYLIGHTS, GUTTERS, OPERATIONAL WINDOWS, DOORS, SHUTTERS (FOR BAYFRONT FIXED WINDOWS), TRAVERTINE POOL DECK, GUNITE POOL SURFACE, FENCE, LANDSCAPING, EXTERIOR PAINT. The work is done for you! Landscaped with privacy in mind and positioned in the cul-de-sac as the last home on the direct Bay in lovely Queens Harbour. The outward attraction of this home will immediately drive your desire to explore further. And, once you enter thru the double glass entry, the exhilaration will overtake you. Bay views abound thru the wide-spread wall of glass that encompasses the common living areas of dinette, kitchen, living room, primary bedroom and bonus rooms. Sky-high ceilings and coastal flooring add to the wonder of this show-place and the fixtures that have been added define the finest of taste. Primary, 2nd and 3rd bedrooms, three full baths, as well as all common space (kitchen, dining, dinette, living room, family room), complete the first level of this home and upstairs you will find two more bedrooms, a bath, and flex space- ELEVATOR OR STAIRCASE ACCESSIBLE. The inside will amaze, but let’s be real- outside living is what Longboat Key is all about. Savor the sunrise from your private dock and ease into the day, poolside. Hop in the boat to head out for a sunset ride to your favorite waterfront dining spot and wrap up with a cocktail in the spa as you admire the stars and Sarasota lights across the Bay. Feel like the beach? Great!! You can do that too because with this home you are a part of Bay Isles which includes the private Beach Club and also provides an added sense of security with guarded and double-gated entry to your community.
Listing Agent: Cindy Schatzle (941-587-7556)
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