Location: Longboat Key
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
1918 HARBOURSIDE DR #902, LONGBOAT KEY, FL 34228
$1,299,000118 Days on yellowkey MLS ID: A4680710
2 Days Off yellowkey (back on 5/12/2026)
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,598
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. 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)
3040 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$1,899,00036 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
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 Agent: Frank Lambert (941-920-1500)
531 WEDGE LN, LONGBOAT KEY, FL 34228
$2,499,00069 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)
562 RANGER LN, LONGBOAT KEY, FL 34228
$3,499,900173 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
Tax Year: 2024
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)
775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228
$2,195,000110 Days on yellowkey MLS ID: A4683021
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2122 Built: 1984 Tax: $17,930 (2025)Community: Beaches Of Longboat KeyCondo
Taxes:$17,930
Remarks: Behind the gates of the Longboat Key Club, this exceptional residence at The Beaches captures sweeping, unobstructed views of the Gulf of Mexico and its pristine shoreline, where vivid sunsets paint the horizon each evening. Perched on the eighth floor, this coveted Star floor plan is ideally positioned as a spacious end residence, offering 2,122 square feet of thoughtfully designed living space with 3 bedrooms and 3 full baths. Walls of glass frame panoramic water vistas and invite natural light to pour into the main living areas. Newly installed impact-rated sliders enhance both storm protection and seamless indoor-outdoor living, while oak engineered hardwood flooring flows beautifully through the living room, dining area, and kitchen, creating a warm yet sophisticated coastal aesthetic. The generous layout provides an effortless blend of comfort and refinement, with well-proportioned bedrooms and baths designed to accommodate both everyday living and gracious entertaining. The Beaches is recognized as one of the premier beachfront addresses within the Longboat Key Club, offering direct access to the sugar-white sands and turquoise waters of the Gulf. Residents enjoy an elevated level of service and amenities, including a 24-hour concierge, resort-style pool, fitness center, tennis courts, and impeccably maintained grounds. Ideally located on the southern end of Longboat Key, this gated community affords convenient access to the fine dining and boutiques of St. Armands Circle, the vibrant arts and culture of downtown Sarasota, and the exclusive offerings of the Longboat Key Club. This is a rare opportunity to secure a front-row seat to the Gulf and embrace the effortless elegance of Florida’s most sought-after coastal lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
1281 GULF OF MEXICO DR #708, LONGBOAT KEY, FL 34228
$3,275,000151 Days on yellowkey MLS ID: A4677632
Bed: 3 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 3273 Built: 1999 Tax: $26,304 (2024)Community: Water Club At Longboat KeySpa: NoCondo
Taxes:$26,304
High School: Sarasota High
Remarks: Welcome to an extraordinary corner residence at The Water Club where timeless elegance meets effortless coastal living on Longboat Key. Offering 3,275 square feet of beautifully designed interior space, this 3-bedroom, 4.5-bath condominium captures sweeping unobstructed expansive views of the Gulf of Mexico, glowing sunsets, Sarasota Bay, and the city skyline from nearly every room. Floor-to-ceiling windows and expansive sightlines fill the home with natural light, creating a serene and sophisticated atmosphere throughout. Designed with refined craftsmanship, the residence showcases custom woodworking, hardwood floors, and soaring 10-foot ceilings that enhance the sense of scale and luxury. The thoughtfully designed layout provides generous living and entertaining spaces while maintaining privacy for guests. The home is in true move-in condition and has been thoughtfully updated with all-new appliances in 2025, blending modern convenience with classic finishes. Enjoy the exclusivity of private elevator access directly to the residence, along with full concierge services that elevate everyday living. The building offers an impressive collection of resort-style amenities, including a Gulf-front swimming pool overlooking pristine white sand beaches, a fully equipped fitness studio, an elegant library, a grand ballroom for entertaining, and a game room for relaxation and recreation, a premier parking space, and as well as climate controlled storage units. This exceptional property delivers the best of beachfront living with luxury, privacy, and breathtaking views all within one of Longboat Key’s most desirable addresses. A rare opportunity to own a refined coastal retreat where every detail has been carefully considered and every day feels like a getaway.
Listing Agent: Kim Ogilvie (941-951-6660)
2055 GULF OF MEXICO DR #G2-213, LONGBOAT KEY, FL 34228
$622,00090 Days on yellowkey MLS ID: TB8485915
REDUCED by $3,000 (0.5%) on 05/03/2026
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 1094 Built: 1974 Tax: $5,426 (2025)Community: Seaplace ICondo
Taxes:$5,426
Remarks: NO expense spared and everything replaced! Gulf and greenbelt views await from your top floor Seaplace condo! Completely remodeled. This gorgeous gulf-facing oversized one bedroom, 1.5 bath end unit with vaulted ceilings features 1,094 square feet of living space and spacious lanai adding an additional 112 square feet with custom 95% UV blocking solar shades. The convenient second floor location provides quick access to the beach, which is only 178 yards from your front door. Enjoy beautiful sunsets with a glass of wine, while taking in the peaceful greenbelt and gulf views from your screened-in lanai complete with high quality Polywood outdoor furniture and Modern Forms WIFI enabled ceiling fan. The spectacular remodel includes new hurricane impact sliding glass doors and bedroom window, new front door and casement window, HVAC unit replaced in 2022, LG Thin Q stacked washer and dryer, ceiling fans in bedroom and living room, Nest programable WIFI thermostat, all new plumbing and plumbing fixtures, all electrical replaced including electrical outlets, new switches and LED recessed lighting throughout. The new porcelain plank "driftwood look" floor tiles throughout the condo and into the Lanai compliment the coastal, beachy vibe of the Cypress Pecky Wood and shiplap accent walls. The gourmet kitchen was completely redesigned with an open concept and includes Kraftmaid soft close wood cabinetry and drawers, GE Cafe appliances suite with convection oven, warming drawer and conduction cooktop, floating shelves and Cambria Quartz counters. The popcorn ceilings were removed and re-plastered with smooth texture throughout. Both bathrooms have new vanities with Cararra marble counters, tile accent walls, including Calcatta Gold Marble Penny tile in half bath and redesigned primary bath. The bedroom features custom open concept built-in closets with soft close drawers and doors. Custom woven wood shades in living room and black out shades in bedroom. Other features include all new solid core interior doors, expansive storage closet under the stairs, owner's locker in common area, dedicated bike storage room adjacent to condo and one assigned parking space. Situated on 42 acres of manicured resort grounds and amenities, Seaplace is one of Longboat Key's most desirable communities. Enjoy two Olympic sized swimming pools, spas, one mile of trails along the shore and throughout the complex, 3 tennis courts, remodeled club house, fitness center, barbecue islands and parklike grounds. Whether you are looking for a vacation get-away, second home, investment property or permanent residence, this is the one! Seaplace is a gated community with a 24-hour guarded gate. Situated only one complex North of the famed St. Regis Luxury Hotel and Residences. This lovely condo is sold completed outfitted, fully-furnished with high quality furnishings from Pottery Barn, Restoration Hardware and comes complete with two fairly new Schwinn bicycles. Must see to appreciate. Owner has a real estate license in CA.
Listing is courtesy of: CONTINENTAL REAL ESTATE GROUP (877-996-5728)
Listing Agent: Derek Eisenberg
2120 HARBOURSIDE DR #623, LONGBOAT KEY, FL 34228
$1,095,00079 Days on yellowkey MLS ID: A4686721
REDUCED by $130,000 (10.6%) on 04/28/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988Monthly Fee: $137 Tax: $11,079 (2025)Community: Fairway Bay AtriumSpa: YesCondo
Taxes:$11,079
Remarks: Step into coastal elegance in this fully renovated three-bedroom, two-bathroom Fairway Bay residence, where every detail has been thoughtfully reimagined. A charming private lanai and seating area welcome you before entering the unit, setting the tone for relaxed waterfront living. Inside, an open-concept layout seamlessly blends the kitchen, dining, and living spaces, creating a bright, airy environment perfect for both entertaining and everyday comfort. The gourmet kitchen is outfitted with GE Profile appliances, custom soft-close cabinetry, and ample storage, offering both style and functionality. The primary suite is a serene retreat featuring a spacious walk-in closet, additional storage, and a beautifully updated en-suite bath with a large walk-in shower. From both the living room and the primary suite, step onto the expansive north-facing balcony to take in the tranquil Sarasota Bay views, where you can enjoy the morning sunrise and the soft glow of the evening sky. The second bedroom is generously proportioned and easily accommodates a king-size bed, creating a luxurious space for guests. The third bedroom is also spacious, complete with a custom built-in, ideal for a guest room, home office, or flexible living area. A thoughtfully designed guest bath ensures privacy and convenience for family or visitors. This unit also includes the ease and security of one covered parking space beneath the building. Fairway Bay residents enjoy an exceptional suite of amenities including two heated pools, a spa, a clubhouse, a fitness center, tennis and pickleball courts, and private beach access on Longboat Key. With the shops, dining, and vibrant lifestyle of St. Armands Circle just minutes away, this residence combines the best of convenience and refined waterfront living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1065 GULF OF MEXICO DR #201, LONGBOAT KEY, FL 34228
$629,000229 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)
1000 LONGBOAT CLUB RD #204, LONGBOAT KEY, FL 34228
$949,000208 Days on yellowkey MLS ID: A4671838
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972 Tax: $6,901 (2024)Community: Privateer SouthCondo
Taxes:$6,901
Remarks: Sublime Gulfside Retreat at Privateer South — 1000 Longboat Club Rd #204 Experience the pinnacle of effortless beachfront living behind the prestigious gates of the Longboat Key Club. This immaculate, fully remodeled 2-bedroom/2-bath residence at Privateer South is offered turnkey furnished, presenting an immediate sanctuary of modern coastal style. Meticulously renovated with longevity in mind, the home is enveloped in impact-rated windows and sliders, ensuring quiet comfort, energy efficiency, and ultimate peace of mind. An inviting entry flows into a radiant, open-concept great room where living and dining zones transition seamlessly to the outdoors. Step onto your private covered balcony to take in unobstructed, panoramic views of the Gulf of Mexico— the ultimate backdrop for sunrise coffee, golden-hour cocktails, and the soothing sounds of the surf. Inside, cohesive coastal flooring and a sophisticated neutral palette provide an elegant canvas for personal style, accented by designer lighting and polished hardware. The renovated kitchen is a sleek culinary workspace featuring custom cabinetry, lustrous stone countertops, and premium stainless-steel appliances. The thoughtful split-bedroom layout guarantees privacy for owners and guests alike. The serene primary suite is a true retreat, offering extensive custom built-out wardrobes and a spa-inspired en-suite bath with a frameless walk-in shower. The oversized guest bedroom is equally impressive, boasting its own generous custom walk-in closet and adjacency to a second, well-appointed full bath. This residence is designed for a true "lock-and-leave" lifestyle, complete with abundant interior storage, an assigned covered parking space, and an additional dedicated storage locker. Privateer South provides an unrivaled resort experience on a pristine stretch of sugar-sand beach. Enjoy a Gulf-front heated pool and spa, tennis and pickleball courts, a modern fitness center, a vibrant clubhouse, on-site management, and 24-hour gated security, all framed by lush tropical landscaping. Comprehensive association services handle practically everything, supporting a stress-free ownership experience. Minutes beyond the shoreline lie world-class amenities: championship golf, a full-service marina, and fine dining at the Longboat Key Club (membership optional), the chic boutiques of St. Armands Circle, and the cultural vibrancy of downtown Sarasota. A rare blend of thoughtful renovation, storm-ready construction, and amenity-rich Gulfside living, Privateer South #204 is more than a condo—it’s an endless getaway.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Mike Griffin (941-586-6402)
2600 HARBOURSIDE DR #B-08, LONGBOAT KEY, FL 34228
$425,00044 Days on yellowkey MLS ID: A4691499
Bed: Bath: 0.0 Monthly Fee: $574 Tax: $4,370 (2025)Community: Longboat Key MooringsDock-Rackominium
Taxes:$4,370
Remarks: A 85 ft. x 28 ft. Boat Slip at Longboat Key Moorings Marina; extra long finger pier, wide beam, and extra wide finger pier. This is a Yacht Club slip. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. Buyer must join the Longboat Key Club on or before the closing date. Longest vessel this slip will accommodate is 80 feet LOA, with the beam depends on the make of the vessel. All vessels must be approved by the BOD prior to entering the Marina. A current photo and specs of the vessel must be submitted for review.
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
2600 HARBOURSIDE DR #B-06, LONGBOAT KEY, FL 34228
$425,00044 Days on yellowkey MLS ID: A4691498
Bed: Bath: 0.0 Built: 1985Monthly Fee: $574 Tax: $4,193 (2025)Community: Bay IslesDock-Rackominium
Taxes:$4,193
1975 GULF OF MEXICO DR #G4-206, LONGBOAT KEY, FL 34228
$449,000279 Days on yellowkey MLS ID: A4663933
0 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1977Monthly Fee: $1,438 Tax: $3,420 (2024)Community: Seaplace IiiSpa: YesCondo
Taxes:$3,420
Remarks: Gated Gulf-front community • Two heated pools & tennis courts • Beach access within minutes Experience coastal living at Seaplace, a gated Gulf-front community on the southern end of Longboat Key. This two-bedroom, two-bath residence (Unit G4-206) features an open-concept layout and a screened lanai overlooking lush tropical landscaping and community green space. Recent improvements include hurricane-rated impact windows and lanai enclosure, providing peace of mind and energy efficiency while enhancing natural light and sound protection. Inside, durable flooring and a neutral color palette create a bright, relaxed atmosphere. The kitchen offers ample cabinetry, and a breakfast bar that opens to the main living area. The primary suite includes a walk-in closet and private bath, while the guest bedroom and full hall bath provide comfortable separation for visitors. A full-size washer and dryer inside the unit adds convenience and functionality. Residents of Seaplace enjoy approximately ½ mile of Gulf beach frontage and an array of resort-style amenities across 42 acres of manicured grounds. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, walking paths, a clubhouse with fitness center, sauna, and library, a playground, and community grilling areas. The on-site management and 24-hour staffed gatehouse provide security and peace of mind in this established coastal community. The quarterly association fee of $4,315 covers exterior maintenance, building insurance, water, sewer, cable, and amenities. Service animals permitted per association rules; no pets otherwise. Seasonal and annual rentals are allowed with a two-month minimum. Seaplace’s location combines tranquility with access to shopping, dining, and cultural attractions. Publix (0.8 mi) and Bayfront Park (1.6 mi) are nearby for groceries, recreation, and pickleball. Enjoy dining at Harry’s Continental Kitchens (1.3 mi), Euphemia Haye (1.1 mi), or The Shore Restaurant (1.9 mi), and explore boutique shopping at St. Armands Circle (3.8 mi). Longboat Key Club Golf & Tennis (2.7 mi) and Downtown Sarasota (6.5 mi) offer golf, marinas, and cultural venues including the Ringling Museum and Selby Gardens. Seaplace residents enjoy direct beach access for sunset walks along the Gulf, tropical courtyards, and a private coastal setting minutes from everything. Whether a seasonal retreat or year-round home, Unit G4-206 blends location, comfort, and quality within a secure, Gulf-front environment on Longboat Key. Includes hurricane-rated windows and lanai enclosure, in-unit laundry, screened lanai, and access to pools, tennis, clubhouse, and Gulf-front amenities. A 3D virtual tour and floor plan viewer are available within the listing for additional detail.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
2185 GULF OF MEXICO DR #223, LONGBOAT KEY, FL 34228
$2,300,00091 Days on yellowkey MLS ID: A4685872
2 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2445 Built: 1996 Tax: $12,693 (2025)Community: Villa Di LanciaSpa: NoCondo
Taxes:$12,693
Remarks: Experience refined coastal living at Villa Di Lancia, one of Longboat Key’s favorite Gulf-front communities. This expansive three-bedroom, three-bath residence offers 2,445 Square Feet of living space paired with breathtaking Gulf and pool views and exclusive private beach access. Designed for both comfort and sophistication, the residence showcases an open floor plan enhanced by elegant crown molding throughout, rich wood doors with gold hardware, and seamless indoor-outdoor living. Sliding glass doors invite natural light while opening to a spacious private balcony—perfect for enjoying sunsets over the Gulf of Mexico and tranquil coastal breezes. The well-appointed kitchen blends functionality with timeless style, featuring granite countertops, solid white cabinetry, built-in appliances, center island with storage, pantry, and a charming breakfast/dinette area. A separate dining space flows effortlessly into the living area, creating an ideal setting for entertaining. The luxurious primary suite serves as a private retreat with balcony access, sweeping Gulf views, a spacious walk-in closet, and a spa-inspired bath complete with Jacuzzi tub, glass-enclosed shower, dual vanities, and additional storage. A guest suite with en-suite bath ensures privacy for visitors, while the third bedroom-perfect as a den or office-features French door entry and built-in workspace. Residents of Villa Di Lancia enjoy an exceptional resort-style lifestyle with guarded security, heated Gulf-side pool and spa, private deeded beach access, Har-Tru tennis courts, fitness center, and community gathering spaces. A strong, well-managed condo association with healthy reserves is a benchmark of the community. Additional conveniences include garage parking, a deeded storage unit, and beautifully maintained grounds within a gated beachfront enclave.
2165 GULF OF MEXICO DR #115, LONGBOAT KEY, FL 34228
$2,350,000102 Days on yellowkey MLS ID: A4684194
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2485 Built: 1996 Tax: $12,382 (2025)Community: Villa Di Lancia Ph 1Condo
Taxes:$12,382
Remarks: Experience and enjoy breathtaking, unobstructed Gulf views from this exceptional “walk-down” corner 3-bedroom 3-bath residence in the prestigious Villa Di Lancia community on South Longboat Key. Fully updated and spanning 2,485 sq. ft., this residence feels like its own private beachfront home. Upon entering from the semi-private elevator lobby, you are welcomed into an open and light-filled floor plan with soaring 10-foot ceilings and expansive walls of glass. As one of the most desirable corner residences in the community, this residence showcases panoramic Gulf views from nearly every room, which can be enjoyed by an additional wall of windows that flood the interior with natural light. The expansive great room connects to a nearly 500 sq. ft. covered terrace — your front-row seat to spectacular sunsets over turquoise waters! The terrace also has a private staircase allowing direct access to the beach and Gulf-front pool and spa, creating a rare and seamless indoor-outdoor lifestyle. The updated eat-in kitchen features a serving bar, walk-in pantry, full laundry room, and generous storage. The split floor plan allows owners and guests alike to enjoy quiet privacy. The primary suite is a true retreat, complete with direct Gulf views, private terrace access, spacious closets, and a large en-suite bath. The guest wing includes a second en-suite bedroom, as well as a third bedroom or a convenient and flexible den space with an adjacent bath. Villa Di Lancia is an exclusive boutique community with only 38 residences with resort-style amenities. Relax by the heated Gulf-front pool and spa, or enjoy friendly competition on the Har-Tru tennis and pickleball courts, as well as a state-of-the-art fitness center and steam room. Resort-style living has been effortlessly achieved throughout the community, including the newly updated clubhouse, social room and kitchen, on-site management, 24-hour manned gate, EV charging station, secure under-building parking, guest parking, and a private storage room. This welcoming community is both pet-friendly and impeccably maintained. Ideally located on the southern end of Longboat Key, residents enjoy proximity to fine and casual dining, golf, marinas, shopping, St. Armands Circle, and Sarasota’s cultural attractions. Residences here are rarely available. This is a rare opportunity to own a luxurious beachfront sanctuary and experience refined coastal living at its finest. This residence feels like a beautiful private home on the beach!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
3010 GRAND BAY BLVD #493, LONGBOAT KEY, FL 34228
$1,879,000243 Days on yellowkey MLS ID: A4668143
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2550 Built: 1999 Tax: $16,976 (2025)Community: Grand Bay 4Spa: YesCondo
Taxes:$16,976
Remarks: One or more photo(s) has been virtually staged. Perched just one floor below the penthouse in the sought-after Grand Bay IV community on Longboat Key, this 2,550-sq.-ft. Cayman floor plan offers an exceptional opportunity to enjoy the Grand Bay lifestyle immediately—while still allowing a future owner to complete their personal renovation plans once the building’s elevator modernization is finished. The furniture rental will extend for up to one year, giving the buyer time to enjoy the residence while preparing for future customization or construction. With ideal north–south exposure, this residence captures breathtaking sunrises over Sarasota Bay and stunning Gulf sunsets from two expansive terraces. Walls of glass and abundant natural light enhance the open-concept layout, which includes 2 bedrooms, 2.5 baths, and a den that can easily be reconfigured to include a walk-in closet for a 3rd bedroom. The primary suite opens directly to the Bayfront terrace, the second bedroom offers an en-suite bath and private Gulf-view balcony, and the den, kitchen, and third bedroom share access to a second terrace for effortless indoor-outdoor living. Two prime, side-by-side parking spaces on the upper main level sit conveniently next to the elevator, leading to a private elevator foyer. Residents of Grand Bay enjoy world-class amenities including 24-hour security, a clubhouse with library and game room, fitness center, tennis and pickleball courts, two heated pools and a spa, and deeded access to the exclusive Bay Isles Beach Club.
569 ROUNTREE DR, LONGBOAT KEY, FL 34228
$2,890,000216 Days on yellowkey MLS ID: A4670192
0 Days Off yellowkey (back on 4/22/2026)
Bed: 3 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 2756 Built: 2024Monthly Fee: $167 Tax: $15,281 (2024)Community: Longboat Key EstatesSpa: NoSingle Family
Taxes:$15,281
Elementary School: Pine View School
Remarks: Under contract-accepting backup offers. STUNNING New Construction WATERFRONT Home in LONGBOAT KEY ESTATES!!! Experience the pinnacle of coastal luxury in this new modern waterfront residence, perfectly positioned in one of Longboat Key’s most prestigious neighborhoods. Completed at the end of 2024, this architectural masterpiece offers direct Sarasota Bay access and a DEEDED BEACH ACCESS just steps away—the rare opportunity to enjoy both boating and beachside living in one extraordinary setting. Built to today’s highest standards, this all-block concrete home is designed for peace of mind with hurricane impact windows and doors, and engineered to withstand the toughest conditions while exuding timeless sophistication. Clean architectural lines, expansive glass, and a balanced façade define its striking contemporary profile, with an impressive entry that introduces the home’s elegant yet minimalist aesthetic. Inside, a spacious open concept living area seamlessly blends modern design with coastal comfort. The great room centers around a sleek gas fireplace framed by custom built-ins, while floor-to-ceiling sliding doors flood the space with natural light and open to the waterfront terrace. The gourmet kitchen is a showpiece in itself, featuring a massive quartz island with seating for five, custom dark cabinetry, glass subway tile backsplash, and top-tier Italian stainless-steel appliances, including double wall ovens and a gas cooktop. Designer lighting adds a bold splash of color, balancing style and warmth for effortless entertaining. Step outside to a covered deck that extends the main living area, complete with a full summer kitchen, wood-paneled ceiling, and multiple fans for year-round comfort. The third floor rooftop terrace delivers panoramic 360 degree views of the bay and beach—perfect for enjoying unforgettable Florida sunsets. The home offers three luxurious ensuite bedrooms, each with spa like bathrooms and designer finishes. The primary suite is a private sanctuary overlooking the water, featuring a large walk-in closet and a lavish bath with soaking tub, dual vanities, and an oversized walk-in shower. A private mother-in-law suite includes its own bedroom, bath, and full kitchen, providing ideal accommodations for guests or extended family. The backyard oasis is anchored by a sparkling lap pool surrounded by modern pavers and lush tropical landscaping. A brand-new seawall and dock provide deep water access to Sarasota Bay with no fixed bridges to the Gulf, making it a boater’s dream. The four car garage and in-home elevator add both convenience and functionality to this exceptional property. Located in the heart of Longboat Key, just steps from Bayfront Park and minutes from Saint Armands Circle and downtown Sarasota, this home delivers an unparalleled lifestyle. Enjoy world class dining, boutique shopping, championship golf, and some of the most beautiful beaches on Florida’s Gulf Coast—all at your doorstep. DO NOT WAIT ON THIS AMAZING OPPORTUNITY!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Jay Travis, Pa (941-812-7277)
524 KETCH LN, LONGBOAT KEY, FL 34228
$1,650,000253 Days on yellowkey MLS ID: A4666645
2 Days Off yellowkey (back on 4/22/2026)
REDUCED by $149,000 (8.3%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2028 Built: 1968Monthly Fee: $8 Tax: $11,988 (2024)Community: Country Club ShoresSpa: NoSingle Family
Taxes:$11,988
Remarks: Under contract-accepting backup offers. Discover the quintessential Longboat Key lifestyle in this classic masonry beach home located just “3” properties in from Sarasota Bay. Boasting 110 feet of canal frontage, your own private dock, a 7,500 lb. boatlift to complement this classic waterfront treasure it offers direct access for boating, fishing, and kayaking, with frequent visits from playful manatees and dolphins right in your backyard canal. The thoughtfully designed 2,000+ square foot split floor plan provides exceptional privacy with 3 bedrooms and 2 baths, ensuring guest suites are comfortably separated from the primary living spaces. The “secret” closet delivers a private office space for when you need to work or plan your next boat trip down the ICW. At the heart of the home, an expansive great room and dining area showcases a wine captain, wet bar, and large refreshment cooler—perfect for hosting unforgettable gatherings while enjoying views of the shimmering enclosed pool and water views of your canal beyond. The chef's kitchen is a culinary masterpiece featuring high-end stainless-steel appliances, built-in ovens, microwave, trash compactor, custom cherrywood cabinetry, separate pantry, and elegant stone countertops with a "chef's prep" island. The layout seamlessly flows into the family room, where glass sliders invite refreshing bay breezes and open to an entertainer's dream: an enclosed lanai, expansive paver patio, and sparkling pool surrounded by multiple seating areas and serene tropical vegetation. Move-in ready with a new HVAC system and generator, this home has been meticulously maintained with numerous upgrades. Please see the attached “Sellers’ Improvement” feature sheet too many to mention…Offered turnkey furnished, it's perfect as either a primary residence or investment property with substantial seasonal rental income potential. The versatile, expansive lot provides endless possibilities to create your ideal waterfront retreat. Situated in the exclusive & sought after neighborhood of Country Club Shores, this property offers an enviable lifestyle just steps from world-class amenities. Directly across the street, you'll find championship golf and tennis at the prestigious Resort at Longboat Key Club, along with sugar-sand beaches and fine dining venues that define the resort experience. The location provides the perfect balance of tranquility and convenience—just minutes to St. Armands Circle, where upscale shopping, eclectic art galleries, and acclaimed restaurants await. Beyond these attractions, Longboat Key offers an array of recreational and cultural experiences, all easily accessible from your doorstep. As a Country Club Shores resident, you'll enjoy exclusive private beach access for only $100 in annual HOA dues—an exceptional value that enhances the already remarkable lifestyle this address provides. Whether you're seeking a year-round sanctuary or a seasonal escape with strong investment potential, this is a rare opportunity to embrace the coveted Longboat Key lifestyle. Schedule your private showing today and discover why this barrier island paradise is one of Florida's most treasured destinations. Come live the dream today & just move right in, it’s all here waiting for you !
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Kathy Callahan (941-900-8088)
2425 GULF OF MEXICO DR #8C, LONGBOAT KEY, FL 34228
$1,550,00056 Days on yellowkey MLS ID: A4688797
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $17,374 (2025)Community: Sea Gate ClubCondo
Taxes:$17,374
Remarks: Welcome to the prestigious Sea Gate community on world renowned Longboat Key! With direct views of the Gulf of Mexico from every room and situated perfectly on the 8th floor, this stunning 2-bedroom, 2-bathroom residence offers just under 1500 square feet of refined coastal living on pristine white shores, endless turquoise waters and vibrant sunsets that create a truly extraordinary backdrop that is postcard worthy! This beautifully appointed residence has been meticulously maintained by the owners and showcases expansive glass sliders that flood the home with natural light, seamlessly connecting the indoor living spaces to a private balcony and your front-row seat to one of Florida’s most coveted coastlines.Thoughtfully enhanced for both comfort and style, the residence features fresh interior paint, a new HVAC system and Hot Water Tank and some new kitchen appliances, delivering a modern and move-in-ready experience. The addition of an in-unit washer and dryer provides a rare and highly desirable level of convenience within the building. The spacious layout offers an effortless flow between the living, dining and kitchen areas for both everyday living and entertaining.The primary suite serves as a peaceful retreat, complete with generous proportions, ample storage and a calming ambiance inspired by the surrounding Gulf views, walk- in closet and ensuite. A well-appointed guest bedroom boasts a private balcony and large closet, while the guest bath provides comfort and privacy for visitors. Residents of Sea Gate enjoy an intimate, resort-style lifestyle with direct beach access, a beachfront pool, tennis courts, a fitness center, and beautifully maintained grounds, all within a private, boutique community setting. Additionally, Sea Gate offers covered parking, ample guest parking and a large storage unit! The building has undergone major capital improvements in recent years, including impact-rated windows (2021), a full exterior restucco and repaint (2022), a new roof (2023) and upgrades to the pool, spa, sundeck and elevator doors. Residents enjoy resort-style amenities including a Gulf front pool and hot tub, fitness center, clay tennis court, library, and a social room with catering kitchen. Shaded tiki huts, outdoor showers, and climate-controlled storage for bikes, kayaks, and paddleboards complete the experience of true beachfront living. All fully paid for by current owners, totaling over $100K/unit. Ideally located near daily shopping, Longboat Key offers a lifestyle defined by elegance and ease, with world-class golf, waterfront dining, boating, and the upscale shops and restaurants of St. Armands Circle just moments away, along with the cultural attractions of Sarasota. With monthly rentals allowed, a unit of this stature could rent for 10k a month in season offering potential income. Option to be sold turnkey furnished as well. Don't hesitate, this unit is a beaut and easy to show!
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Melissa Killion (941-248-6840)
1085 GULF OF MEXICO DR #205, LONGBOAT KEY, FL 34228
$999,000123 Days on yellowkey MLS ID: A4681713
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1819 Built: 1981 Tax: $8,830 (2025)Community: Beachplace IiiSpa: YesCondo
Taxes:$8,830
Remarks: Spacious 3-Bedroom End-Unit Residence in Sought-After Beachplace Welcome to this beautifully maintained three-bedroom, two-bath end-unit condominium offering exceptional natural light, generous living spaces, and serene views in one of South Longboat Key’s most desirable beachfront communities. The open living and dining areas are thoughtfully designed for comfort and entertaining, featuring expansive sliders and windows that flood the space with sunlight and create seamless indoor-outdoor flow. A spacious living room opens to a south-facing screened lanai—perfect for enjoying morning light, golf course views, and gentle coastal breezes. The kitchen is bright and functional, offering ample cabinetry, full appliance package, and convenient in-unit laundry tucked neatly into a dedicated closet. Adjacent dining space provides flexibility for everyday living or hosting guests. The primary suite is generously sized and enjoys tranquil views, abundant natural light, and direct access to the lanai. Two additional bedrooms are versatility for guests, family, or a home office, all thoughtfully laid out to maximize privacy and comfort. Being an end unit, this residence benefits from additional windows and enhanced light throughout, creating an airy, welcoming atmosphere. Neutral finishes and tasteful furnishings allow for immediate enjoyment while offering an excellent canvas for personalization. Residents of Beachplace enjoy resort-style amenities, including a heated pool with lap lanes, spa, tennis courts, a fully equipped clubhouse with gathering spaces, on-site management, and private deeded beach access complete with lounge chairs and umbrellas. The community’s prime location places you moments from St. Armands Circle, Longboat Key Club, and downtown Sarasota’s dining, shopping, and cultural attractions. This well-cared-for residence presents an outstanding opportunity—whether as a primary home, vacation retreat, or income-producing investment in a premier Gulf-front community.
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