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Long Boat Key

One of the most popular communities provided by The Graf Group of Coldwell Banker

Long Boat Key

About Long Boat Key

Longboat Key, Florida, is a tranquil paradise that offers the perfect blend of luxurious living and natural beauty. Nestled between the sparkling waters of the Gulf of Mexico and Sarasota Bay, residents enjoy stunning beaches, picturesque sunsets, and a laid-back, island lifestyle. The community is renowned for its upscale amenities, including gourmet dining, boutique shopping, and world-class golf courses, all while maintaining a quaint, small-town charm. With year-round warm weather, ample outdoor recreational activities, and a strong sense of community, Longboat Key is an ideal place for both relaxation and adventure, making it a highly desirable destination for those seeking a serene coastal retreat.

One of the most popular communities provided by The Graf Group of Coldwell Banker

427

# of Listings

2

Avg # of Bedrooms

$1,135

Avg. $ / Sq.Ft.

$2,024,401

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

427 Properties Found. Page 17 of 29.

Price reduced

TURNKEY Furnished Portobello condo with Deeded Beach Access! TWO Balconies with Sunsets AND Sunrises included! Enjoy Beach and Bayou water access! Rarely available end unit with two balconies and lots of privacy and natural lighting. The front open balcony has unobstructed Gulf views whilst the rear balcony is glassed in with sliders/screens and faces the Bayou. This 4th Floor condo has elevator access, 1 owners storage locker, ample in unit storage and 1 assigned parking space. Condo fee includes Water, Sewer, Trash, Cable/Internet, Pest Control, on site Maintenance and Exterior Insurance. Well established social community with Community Pool, Clubhouse, Tennis Courts, Kayak storage/launch, Fishing Pier, BBQ area and ELEVATED mature landscaping. This spacious floorplan is one of the larger floorpans in the community providing you with list and bright spaces, tons of closet space and even a bonus study/den area to use as you please! Stacked Washer/Dryer located near the hallway 2nd Bathroom which has been renovated. Beautifully upgraded Kitchen with high quality cabinetry and 4 storage closets for all your pantry, cleaning and large cooking items. The Primary Bedroom has the most wonderful private bayou water views! Attached en suite full bathroom with lots of counter space. Secondary bedroom has its own separate balcony entrance. This community is located a short drive away from Publix, CVS, banks, Post office, nail salons and Golfing! New development nearby is bringing more shopping and dining! Don't miss this opportunity to own in the sough after Portobello community!

LONGBOAT KEY

3240 GULF OF MEXICO DRIVE B402

2 Beds

2 Baths

1,505 Sq.Ft.

$895,000

MLS#: A4686024

Gulfside Condo on north Longboat Key with direct beach access: This 2-bedroom, with bonus room, second floor condo offers the island lifestyle you've been searching for—a waterfront community, stunning sunset views from the lanai, and steps to the beach. Located in Longbeach Condo community on Longboat Key, this turnkey furnished, coastal Florida condo features 2 bedrooms, 2 bathrooms,and a bonus room currently used as a den. The comfortable floorplan features a bonus room for bunks, an office, or a reading room, a wide galley kitchen with Corian counters and tossed marble tile backsplash, in-unit washer/dryer, tile floors throughout, and a private balcony with views of the Gulf. At 19.5 foot base flood elevation, this unit was well above the storm surge of previous hurricanes.
Longboat Key Living means beach access, world-class golf courses, world class tennis and waterfront dining just minutes away. The Longbeach Condo community offers 9.2 acres of gulf front, beach property, amenities like heated pool, club house, open parking, private beach access, kayak storage and private tennis. You're 15 minutes to St. Armands Circle shopping, 20 minutes to downtown Sarasota, and close to world-class fishing charters from Cortez Fishing Village. This barrier island property is perfect for full-time Florida living, a vacation home, a snowbird retreat or investment rental property. Rental history/projections available. The location puts you near Coquina Beach, Marina Jack, and easy access to Sarasota-Bradenton International Airport. Nationally ranked medical facilities located within minutes and all LBK first responders are EMTs!

LONGBOAT KEY

7105 GULF OF MEXICO DRIVE 21

2 Beds

2 Baths

1,170 Sq.Ft.

$895,000

MLS#: A4665082

#A4674248

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 202

2 Beds

2 Baths

1,393 Sq.Ft.

$890,000

MLS#: A4674248

Experience elevated coastal living in this beautifully renovated two-bedroom, two-bath golf-front condominium, ideally situated behind the gates of the prestigious Longboat Key Club in the sought-after community of Privateer South on Longboat Key. Thoughtfully redesigned with a refined coastal aesthetic, this residence showcases a seamless blend of modern elegance and relaxed waterfront living. From the moment you enter, you are welcomed by an open-concept layout filled with natural light, enhanced by expansive windows and tranquil golf course views. The fully updated kitchen features sleek cabinetry, premium finishes, and a clean, contemporary design that flows effortlessly into the spacious living and dining areas—ideal for entertaining guests or enjoying quiet evenings at home. Every detail has been carefully curated to provide both style and functionality. The primary suite offers a serene retreat, complete with a beautifully appointed en-suite bath and generous closet space, while the guest bedroom and bath provide comfort and privacy for visitors. Both bathrooms have been tastefully renovated with modern fixtures and finishes, creating a spa-like atmosphere throughout the home. Residents of Privateer South enjoy a true resort-style lifestyle with an impressive array of amenities. Relax by the sparkling beachfront pool overlooking the Gulf of Mexico, maintain your wellness routine in the fully equipped fitness center, or gather with neighbors in the inviting social room. On-site management ensures ease of ownership and peace of mind. Perfectly positioned between the Gulf and Sarasota Bay, this exceptional property offers convenient access to world-class dining, shopping, and cultural attractions, all while being tucked away in a secure, gated enclave. Whether you are seeking a full-time residence or a luxurious seasonal retreat, this golf-front condominium delivers the very best of Longboat Key living.

LONGBOAT KEY

1000 LONGBOAT CLUB ROAD 304

2 Beds

2 Baths

1,409 Sq.Ft.

$874,500

MLS#: A4689434

Embrace the island life style within the gates of Longboat Key's premier resort community of Bay Isles. You'll love this spacious townhome-style condo in Fairway Bay. Designed with soaring ceilings and large windows to allow maximum light and expansive views of the neighborhood’s tropical foliage, this beautifully and thoughtfully renovated home offers lots of space for gatherings with friends or family. The main living area opens effortlessly to a screened porch through sliding doors, creating a bright and airy space perfect for entertaining. The open floorplan, cozy fireplace, freshly painted interiors, fully updated kitchen and bathrooms, two bedrooms, and abundant storage make this home as functional as it is inviting. Downstairs, a flexible bonus space off the oversized 2-car garage offers endless possibilities. This bonus area includes a spacious living room, a flex space (currently set up as a 3rd bedroom), a full bath, and laundry room – perfect for guests, hobbies, or working from home. Just a few steps away, enjoy one of the community’s pools and hot tubs, or explore all the amenities this vibrant neighborhood offers – another heated pool and hot tub, miles of manicured paths, a clubhouse, fitness center, tennis/pickleball courts, and 24-hour gated security. Plus, gain deeded access to the Bay Isles Beach Club, a private, gated Gulf-side retreat with a covered pavilion, parking, restrooms, grills, a beach volleyball court, and sunsets that will take your breath away. This home truly lives like a retreat. Just 10 miles from Anna Maria Island to the North, South 4 miles to St. Armands Circle, and another 4 to Downtown Sarasota, with plenty of shopping, dining, and entertainment options. Your tropical beach getaway is ready and waiting – come make it yours!

LONGBOAT KEY

1912 HARBOURSIDE DRIVE 604

3 Beds

3 Baths

1,316 Sq.Ft.

$850,000

MLS#: A4683819

Price reduced

Presenting the perfect waterfront island getaway! Uniquely situated on an extra large 11,250 sf lot on a canal with easy access to the intracoastal waterway, making a day out on the water an easy escape. This completely remodeled home offers a new kitchen with all new appliances and is done up in seaside hues; Beautiful new wood look tile flooring flows seamlessly from room to room; New water resistant Enduroboard surrounds the living area lower walls and creates an extra added artistic detail to this already charmingly decorated home. Used primarily as a beach escape (with deeded beach access) for this Florida owner, it also presents a great opportunity for monthly rental income. In only a short walk or bike ride down the street, you have access to multiple restaurants, shopping, 12 miles of bike paths and the beautiful nature trails of Joan Durante Park. Just a short drive off island and over the bridge is world famous St. Armands Circle and just beyond that, the culture rich city of downtown Sarasota. This is truly what laid back island life on Longboat Key is all about. Make an appointment to see this home today and start enjoying your piece of island paradise.

LONGBOAT KEY

691 TARAWITT DRIVE

2 Beds

2 Baths

1,500 Sq.Ft.

$850,000

MLS#: A4678131

The best-priced homesite in The Preserve on Longboat Key—an exceptional opportunity to create your custom dream home in one of the island’s most picturesque neighborhoods. Nestled in the charming north village, this property offers both privacy and convenience. Walk to local favorites like Shore LBK, Mar Vista, and Whitney’s, enjoy the water with the neighborhood boat dock and ramp, or take your golf cart to the beach for unforgettable Gulf sunsets. Enjoy the Longboat Key lifestyle—where pristine beaches, vibrant dining, and a welcoming community define everyday living. From here, you’re only a short drive to the St. Regis Longboat Key Resort, the boutiques and dining of St. Armands Circle, the island charm of Anna Maria and the world-renowned IMG Sports Academy. Whether as a full-time residence or vacation retreat, this lot provides the perfect canvas to bring your vision to life in paradise. Don’t miss the rare chance to own the best value in The Preserve.

LONGBOAT KEY

610 HIBISCUS WAY

None Beds

None Baths

0.17 acres

$850,000

MLS#: A4667206

Welcome to a true hidden gem of tropical paradise at Bayport Beach and Tennis Club on Longboat Key. Designed by renowned architect Tim Seibert, this one-of-a-kind community spans 27 lush, tropical acres and offers an unmatched coastal lifestyle with 1,200 feet of pristine private beach, where chairs and umbrellas are ready for you to enjoy endless days along the Gulf.

As you arrive, you’re immediately surrounded by beautifully maintained grounds and the relaxed, resort-style atmosphere that makes this community so special. Stepping inside this spacious 2 bedroom, 2 bathroom furnished residence, you’re welcomed by a light and airy interior with terracotta-look tile flooring flowing throughout the main living areas, setting a warm coastal tone.

The kitchen has been thoughtfully renovated with all new cabinetry, under-cabinet lighting, quartz countertops, a modern backsplash, and stainless steel appliances, creating a clean and functional space that opens seamlessly into the living and dining areas. The expansive living room is both inviting and impressive, designed to feel like a single-family home, with stunning Sarasota Bay views that instantly capture your attention. Shutter doors provide privacy while leading into a sunroom, offering a flexible space to relax and take in the scenery.

The owner’s suite is a true retreat, complete with a dedicated office nook perfectly positioned to enjoy peaceful water views. The ensuite bathroom features dual quartz-topped vanities and a walk-in closet, combining comfort and convenience. A split bedroom floorplan ensures privacy, with the guest bedroom offering its own walk-in closet and easy access to the updated guest bathroom. An in-unit laundry area adds to the everyday ease of living.

Step outside onto your expansive private deck, where breathtaking views of Sarasota Bay create the perfect backdrop for morning coffee, evening wine, or entertaining guests while surrounded by nature.

Bayport Beach and Tennis Club offers an incredible array of amenities, including a Junior-Olympic heated pool, four Har-Tru tennis courts, a fitness center, fishing pier, kayak storage + launch, and an active clubhouse filled with social events. Scenic walking trails wind through the property, where you’ll often spot local wildlife such as osprey, herons, ibis, and egrets, enhancing the serene, natural setting.

Just moments away, Bayfront Park offers pickleball courts, green space, and stunning bay views, while St. Armands Circle provides exceptional shopping and dining. A short drive over the iconic Ringling Bridge brings you into vibrant downtown Sarasota, known for its world-class arts scene, including theaters, museums, galleries, and waterfront dining.

From private beach access to unmatched amenities and breathtaking bay views, this residence offers the perfect blend of comfort, nature, and coastal elegance in one of Longboat Key’s most sought-after communities.

LONGBOAT KEY

815 BAYPORT WAY 815

2 Beds

2 Baths

1,601 Sq.Ft.

$850,000

MLS#: A4689278

Experience contemporary coastal living in this fully renovated, turnkey-furnished unit ideally located in the heart of Longboat Key! Nestled between 1,200 feet of private, powder-soft beach on the Gulf and a serene fishing pier on Sarasota Bay, this residence offers the perfect blend of island tranquility and luxury!Step inside to discover a meticulously cared for interior space updated with elegant flooring, a sleek kitchen, spa-inspired bathrooms, high-end appliances, tankless water heater, designer lighting, and custom furnishings throughout featuing a neutral yet distinctive décor, creating a relaxed coastal ambiance. Added conveniences include a full-size stacked washer and dryer in a discreet laundry closet, and a private under-building carport with a secure storage closet.Located within the architecturally significant Bayport Beach & Tennis Club, the community spans across 27 lush Gulf-to-Bay acres. Residents enjoy a wealth of resort-style amenities including: A private Gulf-front beach with chaise lounges and umbrellas, on site nature trails, lakes with fountains, a bayside fishing pier with kayak launch, heated Junior Olympic-sized pool, Har-Tru tennis courts, bocce ball, and a fitness center!

LONGBOAT KEY

750 BAYPORT WAY 750

2 Beds

2 Baths

1,370 Sq.Ft.

$850,000

MLS#: A4651083

#A4642701

LONGBOAT KEY

4835 GULF OF MEXICO DRIVE 302B

2 Beds

2 Baths

1,393 Sq.Ft.

$849,900

MLS#: A4642701

Sought after mid-key cottage home with DEEDED BEACH ACCESS on the barrier island of Longboat Key. Entering the home, you are greeted by terrazzo floors, wood beam ceilings and a tile accented gas fireplace in the large living room. An additional room overlooking screened in pool can be used as an office, exercise room or extra space for guests. Newly renovated kitchen with wood cabinets, quartz countertops, new sink and fixtures. Bathrooms have been completely renovated with beautiful walk-in tiled showers. A built-in bookcase in the living room adds charm with plantation shutters, accent lighting and ceiling fans throughout.

Completely restored home by licensed general contractor and professionally mitigated after hurricane Helene flood damage. The house shares a driveway and deeded beach access with 5920 Gulf of Mexico Drive making it a perfect guest house or family compound when purchased together. Another possibility is to use one as as a rental for an ongoing revenue stream. The property is being sold As-Is (use FAR-BAR-ASIS-7.

LONGBOAT KEY

5924 GULF OF MEXICO DRIVE

2 Beds

2 Baths

1,359 Sq.Ft.

$849,500

MLS#: A4651805

Price reduced

Motivated Seller—Priced to Sell! Enjoy sweeping Sarasota Bay views from this refreshed 3-bedroom, 2-bath end-unit condo in the highly sought-after Pelican Harbour & Beach Club on Longboat Key. This light-filled second-floor residence offers over 1,600 sq ft of coastal living with panoramic water views from the living room, primary suite, and private screened balcony.
The spacious floor plan includes a bright living area, tranquil dining space, and a serene owner’s suite with lanai access and a beautifully renovated ensuite bath. Recent improvements include new carpet, recessed lighting, interior paint, mounted TVs, and a new AC (2025), water heater (2024) and roof (2023). Additional conveniences include in-unit laundry and covered parking and private Beach Access directly across the street.
Pelican Harbour provides resort-style amenities: 200 ft of private deeded beach with new lounge chairs, heated pool and clubhouse, marina with boat slips (up to 28 ft) and kayak launch, plus tennis and pickleball courts. Pet-friendly community allowing up to two pets (dog/cat combinations permitted). Professionally managed with new roofs and hurricane-rated carports.
Ideally located mid-key, just minutes to St. Armands Circle, Bayfront Park, and the new St. Regis Resort. Perfect as a full-time residence, seasonal retreat, or investment property—this bayside condo offers an unbeatable combination of location, amenities, and motivated-seller value.

LONGBOAT KEY

4234 GULF OF MEXICO DRIVE G2

3 Beds

2 Baths

1,636 Sq.Ft.

$849,000

MLS#: A4653045

This stunning 2 bed/2 bath residence comes turnkey furnished offering a full view of the Longboat Key Islandside Golf Course and partial views of the Gulf, Sarasota Bay, and the Sarasota city skyline through Hurricane Impact Sliders installed in 2024. The kitchen has been opened up to the living/dining area providing a beautiful view over the golf course greens while owners are creating culinary delights in the kitchen. There is a breakfast bar, a laundry closet, pantry, and plenty of solid wood cabinet space for storage. The primary suite pampers owners with access to the southeast-facing terrace along with a spacious primary bath offering dual vanities, an updated tile shower, and abundant closet space. The split floor plan allows for maximum privacy for both the primary and the ensuite guest bedroom. Other highlights include ceramic tile flooring throughout, stone counters, a coveted underbuilding parking space and an excellent rental policy of 1 month minimum 12 X per year. Beachplace offers a 24-hour manned guard gate, heated swimming pool & spa, tennis courts, dedicated pickleball courts, fitness center, clubhouse, on-site management, and miles of pristine beach to relax, enjoy and explore. Conveniently located on the south end of Longboat Key just minutes from the fine dining and shopping on St. Armands Circle and a short drive over the bridge to the cultural hub of downtown Sarasota.

LONGBOAT KEY

1065 GULF OF MEXICO DRIVE 402

2 Beds

2 Baths

1,392 Sq.Ft.

$845,000

MLS#: A4666641

Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The pool area is currently undergoing a transforamtion and will include a new spa, a tiki hut and new landscaping when complete. Also important: The Westchester has completed its Milestone Inspection and all assessments have been paid in full.

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 105

2 Beds

2 Baths

1,393 Sq.Ft.

$839,900

MLS#: A4667044

Turnkey furnished and direct Gulf-front, this exceptional ground-floor residence at Turtle Crawl Inn on Longboat Key offers both effortless beachfront living and remarkable, documented rental performance. Residence T-101 has averaged a yearly gross rental income of approximately $90,000 over the past three years, making it a compelling opportunity for investors, seasonal owners, or those seeking a flexible coastal retreat with established returns.

Positioned directly on the sand, this rare walk-out Gulf-front residence features a private patio just steps from the turquoise waters of the Gulf of Mexico—ideal for enjoying sunset views over the shoreline. The professionally designed interior blends coastal comfort with modern updates, featuring imported contemporary porcelain flooring from Italy throughout the open layout.

The kitchen offers updated cabinetry, stone countertops, white appliances, and a seamless connection to the living and dining areas—perfect for relaxed beachside living or hosting guests. Impact windows with plantation shutters and impact glass sliders enhance peace of mind while filling the space with natural light. The spacious bedroom accommodates guests comfortably, while the completely updated bathroom (2021) showcases clean, timeless finishes.

Step outside to the travertine-tiled Gulf-front patio, your private vantage point overlooking the beach, dunes, and horizon—an amenity highly valued by renters and owners alike.

Turtle Crawl Inn is known for its laid-back resort atmosphere and strong rental appeal, offering a heated swimming pool, beachside cabanas, gas grilling stations, picnic areas, fishing opportunities, a putting green, shuffleboard courts, and deeded beach access. Flexible rental options make this community especially attractive for income-focused ownership.

Located on the desirable mid-island stretch of Longboat Key, the property is minutes from waterfront dining, marinas, Bayfront Park, Joan M. Durante Park, and boating access. Anna Maria Island lies just to the north, while St. Armands Circle and downtown Sarasota’s shopping, dining, and cultural attractions are a short drive south.

Whether you’re seeking a high-performing income property, a personal beachfront escape, or a blend of both, this Gulf-front residence delivers proven rental history, prime location, and direct beach access—a rare combination on Longboat Key.

LONGBOAT KEY

4235 GULF OF MEXICO DRIVE T101

1 Beds

1 Baths

720 Sq.Ft.

$825,000

MLS#: A4673158

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