Refine Search
Map
Sort by
2055 Gulf Of Mexico Drive Unit G2-213, Longboat Key
$595,000
1 Beds ⋅ 2 Baths ⋅ TB8554048 MLS ⋅ G2 BLDG.
Gulf and greenbelt views from a completely remodeled, gulf-facing Seaplace end unit. This oversized 1 bedroom, 1.5 bath top-floor (second-floor) condo offers 1,094 sq ft plus a 112 sq ft screened lanai with custom 95% UV-blocking solar shades. Vaulted ceilings, an open layout and 178 yards from the front door to the sand. The remodel is comprehensive: new hurricane-impact sliding glass doors and bedroom window, new front door and casement window, HVAC replaced in 2022, all-new plumbing and fixtures and full electrical updates including outlets, switches and LED recessed lighting. Porcelain plank driftwood-look tile runs through the living areas and onto the lanai. Cypress pecky wood and shiplap accent walls, smooth plastered ceilings (popcorn removed), Nest programmable Wi-Fi thermostat, ceiling fans in the living room and bedroom and an LG ThinQ stacked washer and dryer. The open gourmet kitchen features KraftMaid soft-close wood cabinetry, floating shelves, Cambria quartz counters and a GE Cafe appliance suite with convection oven, warming drawer and induction cooktop. Both baths have new vanities with Carrara marble counters and tile accent walls, including Calacatta Gold marble penny tile in the half bath and a redesigned primary bath. The bedroom has custom open-concept built-in closets with soft-close drawers and doors, plus blackout shades; the living room has custom woven wood shades. Additional features include all-new solid-core interior doors, storage under the stairs, an owner's locker, dedicated bike storage adjacent to the unit, one assigned parking space and a screened lanai with quality outdoor furniture and a Wi-Fi-enabled ceiling fan. Seaplace sits on 42 acres of gated, guarded resort grounds with two Olympic-size pools, spas, about a mile of trails, three tennis courts, remodeled clubhouse, fitness center, barbecue islands and park-like grounds. One complex north of the St. Regis. Sold fully furnished and outfitted. Ideal as a vacation home, second home, investment or full-time residence. Owner has a real estate license in CA.

2055 Gulf Of Mexico Drive Unit G2-213, Longboat Key
4800 Gulf Of Mexico Drive Unit PH 3, Longboat Key
$795,000
2 Beds ⋅ 2 Baths ⋅ A4704564 MLS ⋅ Windward Bay BLDG.
Welcome to your Longboat Key PENTHOUSE, where unobstructed PANORAMIC WATER VIEWS from every room create a breathtaking backdrop from the moment you walk through the door. Recently renovated from top to bottom and offered TURNKEY FURNISHED, this residence is ready to enjoy from day one. The BRAND-NEW KITCHEN showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, opening seamlessly to the bright and airy living space. Both bathrooms have been completely updated with modern finishes and quartz countertops, creating a fresh, cohesive feel throughout the home. Other thoughtful updates throughout include luxury vinyl flooring throughout, fresh carpeting in the bedrooms, beautifully remodeled, IMPACT WINDOWS, generous storage, and the convenience of an in-unit washer and dryer. Located in the pet-friendly waterfront community of Windward Bay, residents enjoy an impressive collection of amenities including boat slips, two swimming pools, a fitness center, sauna, tennis and pickleball courts, and three beach access points. NO upcoming special assessments, FULLY FUNDED reserves, and a PASSED Milestone. Perfectly positioned on Longboat Key, this penthouse offers the relaxed island lifestyle while keeping you conveniently connected to the dining, shopping, beaches, and entertainment of Longboat Key, St Armands, and Anna Maria Island. Whether you're searching for a full-time residence or your own Florida getaway, this turnkey waterfront penthouse is ready to welcome you home.

4800 Gulf Of Mexico Drive Unit PH 3, Longboat Key
2350 Harbour Oaks Drive, Longboat Key
$950,000
3 Beds ⋅ 3 Baths ⋅ A4699679 MLS
Move right in and start enjoying the Longboat Key lifestyle! Perfectly positioned behind the gates of highly sought after Bay Isles, this beautifully renovated residence combines elegant updates, low-maintenance living, and one of the area's most desirable resort-style communities. Every major improvement has already been completed, allowing you to simply unpack and begin enjoying paradise. The thoughtfully redesigned kitchen is the heart of the home, featuring all-new appliances, a wine refrigerator, custom all-wood cabinetry with convenient pull-out shelving, and an open design that flows effortlessly into the spacious living and dining areas. New tile flooring extends throughout the kitchen, living room, and primary suite, while new carpet creates warm, inviting guest bedrooms. The impressive list of recent upgrades provides exceptional peace of mind, including a new tile roof with hurricane-rated skylights, hurricane-impact windows and doors, new HVAC system with UV air purification lights, tankless water heater, water softener, new garage door opener, fresh interior paint throughout, and beautiful plantation shutters installed throughout the home. One of the home's most outstanding features is the enormous private screened lanai, creating an exceptional outdoor living space rarely found in this price range. Complete with an awning for covered grilling and tranquil pond views, this oversized outdoor retreat is perfect for morning coffee, afternoon relaxation, entertaining friends, or enjoying Florida's spectacular sunsets. A charming garden patio, accessible from both the guest bedroom and laundry room brings in the Florida sunlight and a place to grow tropical plants or a private herb garden. Ownership in Bay Isles includes exclusive access to the private Bay Isles Beach Club, where residents enjoy deeded Gulf-front beach access complete with gated parking, pavilions, picnic facilities, grills, restrooms, and miles of Longboat Key's world-famous white sand beaches. Flood insurance is conveniently included within the HOA fees, providing additional value and peace of mind. Just minutes away, the Longboat Key Moorings Marina offers deep-water boating accommodations, waterfront dining, and one of the Gulf Coast's premier marinas. Residents also have the opportunity to apply for membership at the renowned Longboat Key Club, featuring championship golf, world-class tennis and pickleball, resort pools, spa facilities, fitness centers, private beach amenities, and exceptional waterfront dining. Beyond the gates, enjoy the sophisticated coastal lifestyle that makes Longboat Key one of Florida's most sought-after destinations. Discover award-winning restaurants, waterfront dining, boutique shopping, art galleries, and charming cafés throughout Longboat Key, while nearby St. Armands Circle and Lido Key offer additional upscale shopping, fine dining, entertainment, and beach experiences just a short drive away. Downtown Sarasota's vibrant arts, theater, and cultural attractions are also conveniently close. Whether you're searching for a year-round residence, seasonal retreat, or luxurious lock-and-leave home, this extensively updated Bay Isles residence offers an exceptional combination of quality, comfort, location, and resort-style amenities that is truly difficult to match.

2350 Harbour Oaks Drive, Longboat Key
578 Spanish Drive S, Longboat Key
$499,000
2 Beds ⋅ 2 Baths ⋅ A4698065 MLS
Welcome to 578 Spanish Drive S, a completely renovated 2 bedroom, 2 bathroom villa in Spanish Main Yacht Club on Longboat Key. Renovated completely with thoughtful attention to detail, this move-in ready residence showcases high-quality modern finishes while providing access & amenities to one of Longboat Key's established waterfront communities with a deepwater marina and deeded beach access. The redesigned interior features an open kitchen centered around a quartz waterfall edge island, soft close cabinetry, with all new stainless-steel appliances, including a wine refrigerator and a refrigerator with a built-in craft ice maker. Luxury vinyl plank flooring extends throughout the home, complemented by a smart thermostat for everyday convenience. Every room reflects the comprehensive renovation, and the home is further enhanced by a 2012 tile roof, new PGT hurricane impact windows, and sliding glass doors that open to a private paver patio overlooking a wooded landscaped setting. Spanish Main Yacht Club offers private deeded beach access to the Gulf of Mexico, a heated community pool, clubhouse, shuffleboard courts, and a pet-friendly environment. The community’s deepwater marina offers approximately 40 boat slips available for lease, accommodating vessels up to 40 feet with water and electric service, while providing direct boating access from Sarasota Bay to the Gulf of Mexico. Residents also enjoy opportunities for fishing, kayaking, paddleboarding, and other waterfront recreation. Located near Publix, St. Armands Circle, downtown Sarasota, shopping, dining, cultural attractions, botanical gardens, Anna Maria Island, and Sarasota-Bradenton International Airport, this extensively renovated villa offers an exceptional combination of updated interior finishes, outdoor living, boating amenities, and convenient access to the best of Longboat Key and the surrounding Sarasota area. Please see attached document for the full list of renovations & upgrades and full walkthrough video and virtual walkthrough. Not required to be 55 to purchase.

578 Spanish Drive S, Longboat Key
524 Spanish Drive S Unit 125, Longboat Key
$569,000
2 Beds ⋅ 2 Baths ⋅ A4698047 MLS
If you are looking for a tastefully upgraded Longboat Key beach house, this is it! Relax in your completely renovated coastal-contemporary, stand-alone villa, with its front pond view, private rear patio and large yard space. The uncrowded, 11-mile Longboat Key beach is directly across Gulf of Mexico Drive via Spanish Main's private deeded access. Your spacious, light-filled home welcomes you with a charming entrance foyer, open living-dining room with built-in cabinets and a large kitchen-family room area with sliding doors to the rear yard. Your bright kitchen has an island, new appliances, quartz counters, and wood cabinets with lots of storage space. Important additional benefits include a new electric hot water tank, new hurricane rated doors and rear sliders, tile roof replaced in 2017, flat roof in 2024, impact windows in 2020 and 2024, and A/C in 2022. The primary bedroom has a walk-in closet and an en suite bath with a new walk-in shower and vanity. The guest bedroom has a view of the pond and double closets. The guest bathroom has a skylight and a new walk-in shower, vanity, linen and medicine cabinets. If you want to move right in or rent it, the attractive turn-key furnishings are negotiable. Outside, there is a large side storage area for bicycles and beach toys. The front porch offers a tranquil area to relax and view the large pond with its ducks, jumping fish, and pretty night lights. Walk, bike or drive to the heated community pool, patio area, and clubhouse adjacent to the deep water marina and kayak launch. If you are a boat person, slips can be rented, as available, for an extremely reasonable cost and there is easy access to Sarasota bay and the Intracoastal Waterway with no fixed bridges. Spanish Main Yacht Club is an over-55 community, conveniently located near several restaurants, Durante Park, community tennis, pickle-ball, dog park, fitness activities and St. Armands Circle shops and restaurants. Let me show you the lifestyle that this beautiful, unique villa has to offer.

524 Spanish Drive S Unit 125, Longboat Key
100 Sands Point Road Unit 303, Longboat Key
$915,000
3 Beds ⋅ 2 Baths ⋅ A4696825 MLS ⋅ Sands Point BLDG.
Don’t miss this rare opportunity to call Sands Point home – an iconic beachfront community widely regarded as the crown jewel of Longboat Key. Nestled on the island’s coveted southernmost tip, this move-in-ready residence offers breathtaking sunsets and an unparalleled coastal lifestyle. Offered at an attractive value, this coastal escape presents a rare opportunity for the new owner to add their own finishing touches and create a truly personalized retreat. Welcome to your slice of paradise, where every day feels like a five-star coastal retreat, nestled inside the gates of the Longboat Key Club. Gracefully framed by towering palms, the curved waterfront drive creates a memorable sense of arrival, setting the tone for this one-of-a-kind mid-century modern residence where coastal elegance and timeless design converge. This spacious 1941 square feet, with its open floor plan feels more like a home than a condo. Step inside this bright third floor residence and discover a two bedroom, an office staged as a 3rd. bedroom and two baths, set in a split plan for privacy. Thoughtfully designed with warm custom cabinetry, elegant stone-inspired surfaces, and contemporary stainless appliances, this kitchen combines timeless craftsmanship with effortless coastal living. Floor-to-ceiling expanses of glass span the living area, offering a panoramic garden view and bathing the room in sunshine. The oversized layout provides endless possibilities for entertaining, gathering or simply enjoying the peaceful surroundings. Community amenities abound – enjoy the private beach with tiki’s, lounge chairs, pool, spa, library, community room w/ kitchen, marina access, bicycle storage, kayak launch, and additional owner’s storage space. Within walking distance to the well-renowned St Armands Circle for shopping and dining experiences. The pristine white sandy beach and gentle turquoise waters are calling your name. Schedule your private showing today and discover the lifestyle you deserve.

100 Sands Point Road Unit 303, Longboat Key
3527 Fair Oaks Lane, Longboat Key
$2,300,000
4 Beds ⋅ 5 Baths ⋅ A4694532 MLS
Experience refined coastal luxury in this impeccably renovated 4,154-square-foot golf course estate, ideally positioned within the exclusive Queens Harbour enclave of gated Bay Isles on Longboat Key. This extraordinary two-story residence offers 4 bedrooms, 4.5 bathrooms, and an elegant open floor plan thoughtfully curated with exquisite finishes and designer details throughout. Extensive recent enhancements include a newer roof (2021), new panoramic pool cage with picture-frame screening (2025), new hurricane Armor Screen shutters protecting every opening (2025), and a custom two-person Pneumatic Vacuum elevator, along with numerous additional upgrades and improvements. Dramatic two-story windows fill the expansive great room and chef’s kitchen with natural light while showcasing breathtaking views of the sparkling pool, serene lake, lush landscaping, majestic oak trees, and the manicured fairway. Designed for both everyday living and entertaining, the gourmet kitchen is a culinary masterpiece, complete with a large gas range, dual ovens, solid wood cabinetry, abundant counter space, and a charming breakfast nook framed by bay windows overlooking the pool and golf course. The luxurious first-floor owner’s retreat offers Brazilian cherry wood flooring, vaulted ceilings, French doors opening to the lanai, dual walk-in closets, and a spa-inspired bathroom. Two additional guest bedrooms on the main level are connected by a beautifully appointed Jack-and-Jill bathroom. Outdoor living is equally exceptional, with an oversized pool and spa set within a spacious private lanai designed for relaxation and entertaining while enjoying tranquil sunsets over the lake and golf course. Residents of Queens Harbour enjoy maintenance-free living, a private community pool, and exclusive access to the Bay Isles Beach Club with deeded Gulf beach access. Ideally located near the Longboat Key Club Harbourside golf course, tennis facilities, and the Moorings Yacht Club, this residence embodies the finest in Longboat Key luxury living.

3527 Fair Oaks Lane, Longboat Key
581 Rountree Drive, Longboat Key
$2,500,000
O6400352 MLS
BREAKING NEWS: LUXURY WATERFRONT LIVING • LONGBOAT KEY, FLORIDA! A Rare Opportunity to Build Your Dream Home Between Two Brand-New Mansions!! Discover an exceptional build-ready waterfront lot in Longboat Key Estates, featuring 100 feet of deep-water canal frontage and 117 feet of depth with direct boating access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico. Well-known John Cannon Custom Homes offers a selection of distinctive home plans designed to complement this extraordinary setting. Enjoy sunrise over the Bay and spectacular Gulf sunsets, plus PRIVATE DEEDED BEACH ACCESS with a charming Tiki Hut directly across Gulf of Mexico Drive. Just minutes from Sarasota’s world-class dining, shopping, arts and culture, championship golf, marinas, and Gulf beaches. Bayfront Park is also next door with pickleball, tennis, kayaking, fitness, and more. Boating. Beach. Bay. Gulf. Sarasota. An extraordinary location for an extraordinary home!! Longboat Key Estates is one of the only communities on Longboat Key with underground utilities! Sellers are MOTIVATED!

581 Rountree Drive, Longboat Key
1915 Harbour Links Circle Unit 6, Longboat Key
$1,950,000
3 Beds ⋅ 4 Baths ⋅ A4688148 MLS ⋅ 1915 BLDG.
PRIVATE HEATED SALTWATER POOL | DEEDED BAY ISLES GULF BEACH ACCESS | FULLY FURNISHED & TURNKEY | LONGBOAT KEY VILLA Enjoy the best of Longboat Key living in this beautifully furnished 3-bedroom, 3.5-bath villa in gated Bay Isles. Offering 2,476 sq. ft. and the spacious feel of a single-family home, this maintenance-free residence is move-in ready and designed for effortless Florida living. The private screened lanai features a heated saltwater pool and spa, creating your own outdoor retreat for relaxing and entertaining. Inside, soaring ceilings, abundant natural light, generous living spaces and a first-floor primary suite provide comfort and privacy. Two additional en-suite bedrooms are ideal accommodations for family and guests, while the attached 2-car garage adds convenience and storage. Enjoy exclusive Bay Isles Beach Club access with deeded Gulf beach access, plus an optional Longboat Key Club membership for golf, tennis, pickleball, fitness, marina and dining. Conveniently located near St. Armands Circle, Sarasota, boating, shopping and world-class beaches. Private pool. Deeded beach access. Fully furnished. Single-family-home feel. Turnkey Longboat Key living. Schedule your private showing today!

1915 Harbour Links Circle Unit 6, Longboat Key
1065 Gulf Of Mexico Drive Unit 305, Longboat Key
$1,199,000
3 Beds ⋅ 2 Baths ⋅ A4681609 MLS ⋅ 10 BLDG.
One or more photo(s) has been virtually staged. 3 BEDROOM CORNER/ END RESIDENCE! SOUTHWEST GULF VIEW! 2 OWNED PARKING SPACES- ONE COVERED! EXCELLENT RENTAL POTENTIAL! A vivid palette of white perfected with the backdrop of Gulf waters kissed by brilliant hues amid spanning skies as the sun sets on yet another perfect day. Yours to be experienced daily, from the bright inside or out on the patios, of this corner home spread over more than 1,800 square feet. Well-positioned at the southwest corner of Building 10 to take full advantage of what it means to be the fortunate owner of a beachfront Longboat Key retreat. Clean, crisp and white, this home is move-in ready, OR it is fresh and primed for you to begin the design of your dreams. Finding 3 bedrooms, 2 baths, and 2 owned parking spaces (one under-building and one outside steps to the building entry) on the beach at this reasonable price point is a FIND in this zip code, so closely consider the opportunity at hand. Beachplace is a sprawling community of 31 acres and full of amenities including, but not limited to, deeded beach access, junior Olympic size pool, kiddie pool, spa, clubhouse, fitness, tennis, pickleball, guarded/ gated entry, community grilling, fun gaming area with ping pong, cornhole, seasonal community activity calendar, etc. Truly a special place to call home or an absolute escape to refresh, restore, relax, release and renew the wellbeing of mind, body and spirit.

1065 Gulf Of Mexico Drive Unit 305, Longboat Key
4500 Gulf Of Mexico Drive Unit 206, Longboat Key
$769,000
2 Beds ⋅ 2 Baths ⋅ A4671822 MLS ⋅ G-Building BLDG.
"One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” This residence is now available for public and private showings. Restricted access resulted in only three private showings in six months. Buyer's have a rare chance to discover a home that’s been under the radar. (Do not let the days on the market fool you. Snowbirds were unable to view this listing the entire "season"). The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”

4500 Gulf Of Mexico Drive Unit 206, Longboat Key
1065 Gulf Of Mexico Drive Unit 201, Longboat Key
$599,000
2 Beds ⋅ 2 Baths ⋅ A4669086 MLS ⋅ Building 10 BLDG.
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.

1065 Gulf Of Mexico Drive Unit 201, Longboat Key
2425 Gulf Of Mexico Drive Unit 14B, Longboat Key
$1,699,000
2 Beds ⋅ 2 Baths ⋅ A4654664 MLS ⋅ Sea Gate BLDG.
BREATHTAKING WATER VIEWS FROM EVERY ROOM! Enjoy nightly sunsets from your private balcony in this beautifully updated 14th-floor condominium. This highly sought-after two-bedroom, two-bath split floorplan offers the perfect blend of privacy and open living. Each bedroom is positioned on opposite sides of the unit, creating an ideal layout for guests or remote work. Recent upgrades include Hurricane Impact Windows (2021), new flooring in both bedrooms (2021), updated bathrooms, fresh paint (2021), and an A/C system replaced in 2015. The convenience of an in-unit washer and dryer, a dedicated parking space, and ample guest parking add to the comfort of this coastal retreat. The beach and heated pool are just steps from your building, creating a true resort-style experience. Enjoy premium amenities such as a tennis court, air-conditioned bike room, kayak/paddleboard storage, clubhouse with kitchen, library/meeting space, and a fully equipped fitness center. Located within walking distance to Publix, CVS, places of worship, banks, the public library, and Town Hall. Just minutes to St. Armands Circle, where you'll find world-class dining and shopping. Immerse yourself in Sarasota’s rich cultural scene with easy access to the Sarasota Opera, Ballet, Ringling Museum, Selby Gardens, and numerous art galleries and theaters. This is your chance to live the Gulf Coast lifestyle—don’t miss it!

2425 Gulf Of Mexico Drive Unit 14B, Longboat Key

How much is your home worth?

Get instant property value now!