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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

436

# of Listings

2

Avg # of Bedrooms

$1,120

Avg. $ / Sq.Ft.

$2,015,938

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

436 Properties Found. Page 18 of 30.

#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

Step into a bright, inviting coastal retreat just moments from the sand at Beachplace on Longboat Key. This beautifully furnished first-floor residence in Building 3 offers true walk-down convenience from the private wraparound terrace—an effortless way to enjoy the Gulf-front lifestyle. Designed for comfort and ease, the interior features porcelain tile flooring throughout, plus new impact windows and walls of sliders installed in 2021–2022, creating a light-filled setting that feels connected to the outdoors.
The spacious living and dining area is framed by floor-to-ceiling glass, opening directly to the screened lanai with views of the community’s lush landscaping, pool deck, and the Gulf’s sparkling waters. The updated eat-in kitchen includes all-white appliances, LED lighting, Corian countertops, and a convenient breakfast bar pass-through—ideal for casual meals or entertaining.
The private primary suite features wood-grain tile flooring, French-door terrace access, a large closet, and an en-suite bath. A split floor plan ensures comfort for guests, with the second bedroom tucked away for privacy and located next to a well-appointed full bath. Additional conveniences include Turnkey Furnishings and one coveted under-building covered parking space plus an additional assigned outdoor space, a rare benefit in this sought-after Gulf-front community.
Residents of Beachplace enjoy resort-style amenities that enhance the coastal lifestyle. A wonderful Gulf-front community, Beachplace offers 24-hour guard-gated entry, an on-site management team, a stylish clubhouse, fitness center, tennis courts, pickleball, and an expansive Gulf-front deck with heated swimming pool and spa. Walking paths, lush gardens, and direct beach access create a tranquil environment for relaxation.
Perfectly located on the south end of Longboat Key, this residence places you minutes from world-class shopping and dining at St. Armands Circle, renowned golf and tennis clubs, marinas, the cultural venues of downtown Sarasota, and the exceptional beaches that make this area one of Florida’s most desirable coastal destinations.
Whether you're searching for a seasonal escape or a full-time beachfront home, this Beachplace residence delivers impressive value, thoughtful updates, and a premier location along Longboat Key’s pristine shoreline.

LONGBOAT KEY

1125 GULF OF MEXICO DRIVE 101

2 Beds

2 Baths

1,172 Sq.Ft.

$849,000

MLS#: A4672544

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

Discover coastal living at its finest in this beautifully positioned 2-bedroom, 2-bath condominium on one of Longboat Key’s most sought-after stretches. This residence offers spectacular, breathtaking views from both private lanais—perfect for enjoying sunrise coffee or evening sunsets over the water.

Inside, the layout is bright and inviting, with seamless indoor-outdoor flow that maximizes the scenery from multiple vantage points. Whether you’re looking for a full-time residence or a serene getaway, this condo delivers both comfort and location.

The community is elevating its appeal with exciting enhancements, including upcoming clubhouse renovations featuring a boutique fitness center, newly refreshed landscaping, and a hot tub addition to the pool deck—creating a true resort-style atmosphere with two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan FURNISHED 5th floor panoramic view, master en-suite unit awaits YOU!

Enjoy the best of island living with pristine beaches, nearby dining, and a relaxed yet refined lifestyle—all just moments from your door.
R&R IS THE PACE, LBK IS THE PLACE!!!!

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 504

2 Beds

2 Baths

1,393 Sq.Ft.

$825,000

MLS#: A4689724

#TB8439776

LONGBOAT KEY

766 SAINT JUDES DRIVE N

None Beds

None Baths

0.15 acres

$799,000

MLS#: TB8439776

Experience breathtaking beach and Gulf views from this spacious, turnkey-furnished two-bedroom, two-bath residence in Cedars West. Beautifully updated with no detail overlooked, this exceptional property features elegant stone countertops, quality appliances, and a relaxed coastal ambiance that makes it highly sought after. Offering over 1,270 square feet of air-conditioned living space, the residence includes a large walkout screened lanai where you can enjoy gentle Gulf breezes and spectacular sunsets over the tranquil waters of the Gulf of Mexico. The thoughtfully designed layout provides abundant storage throughout, including generous closets in both bedrooms as well as a dedicated owner’s closet. Just steps from the unit, the pristine beach is a renowned nesting ground for sea turtles, offering the unique opportunity to watch dolphins and manatees pass by while relaxing on one of Florida’s most beautiful beaches. Cedars West residents enjoy a wide range of resort-style amenities, including a large heated and cooled swimming pool, two tennis courts, BBQ grilling areas, and convenient kayak and bike racks. Owners also have the option to generate rental income by taking advantage of Cedars West’s rare two-week minimum rental policy on Longboat Key. Don’t miss this incredible opportunity to experience the ultimate beachfront lifestyle.

LONGBOAT KEY

5655 GULF OF MEXICO DRIVE D107

2 Beds

2 Baths

1,274 Sq.Ft.

$799,000

MLS#: TB8483958

Penthouse-Level Condo at Grand Bay – Longboat Key Experience luxury living in this beautifully appointed penthouse-level residence at Grand Bay, located behind the gates of Bay Isles on Longboat Key. This spacious 2-bedroom, 2-bath condo offers an open and airy floor plan with stunning east-to-west exposure, capturing both sunrise and sunset from dual balconies with sweeping views of Sarasota Bay, the city skyline, and the golf course. As a penthouse-level home, it also features an added ceiling height of one foot, enhancing the sense of space and light throughout. Both bedrooms are en-suite, with the primary suite featuring dual closets (including one walk-in) and luxurious marble vanities in the bath. The home showcases elegant bamboo flooring in the main living area, marble tile in the bathrooms, and plush carpet in the bedrooms. Floor-to-ceiling sliding glass doors at both ends of the unit flood the space with natural light. The chef’s kitchen is equipped with a Sub-Zero refrigerator, Blue Pearl granite countertops, a breakfast bar, and an in-kitchen laundry room. Recent upgrades include a new AC system in 2021 and a water heater in 2020. The residence also comes with two deeded parking spaces and a private garage-level storage locker, and it is offered furnished for immediate enjoyment. Grand Bay’s exceptional amenities include 24-hour guard-gated Bay Isles entry, an additional Grand Bay gated entrance, secure coded lobby access, on-site property management, and a pet-friendly environment. Residents enjoy two resort-style pools, a state-of-the-art fitness center, tennis courts, and membership to the Bay Isles Beach Club. There are no current or pending assessments. Enjoy the perfect blend of luxury, privacy, and convenience in one of Longboat Key’s premier waterfront communities.

LONGBOAT KEY

3070 GRAND BAY BOULEVARD 644

2 Beds

2 Baths

1,329 Sq.Ft.

$799,000

MLS#: A4690677

Price reduced

#A4679944

LONGBOAT KEY

4750 GULF OF MEXICO DRIVE Villa 8

3 Beds

2 Baths

1,504 Sq.Ft.

$799,000

MLS#: A4679944

Experience the best of Gulf-front living and gorgeous views in this move-in-ready, two-bedroom, two-bath waterfront condominium, perfectly positioned in an elevated community just steps from the beach. This home is in impeccable condition and is designed for relaxation, with a seamless blend of comfort, style and convenience. It's being sold turnkey with lovely furnishings. The kitchen features new Samsung stainless steel appliances, plenty of counter space, and a comfortable sitting area. An open floor plan with a large living room, remote-controlled sunshades and three-panel impact sliding glass doors opens to an inviting screened lanai with a tropical ceiling fan, blurring the lines between indoor and outdoor living. There are ceiling fans in every room. The primary suite offers a large bath with a separate water closet and a huge walk-in closet. There are also impact sliders leading out to the lanai with a view of the Gulf. The guest suite is spacious with lots of closet space. The laundry is neatly tucked away and features Bosch machines. If you love the beach and enjoy stunning sunsets, Cedars West is really the perfect place to live. This location is walking distance to our local restaurants (Lo-Key, Harry's and Hugos), convenience shopping and all the amenities you’ll need to enjoy life here on Longboat Key. This community has tennis, a heated pool, BBQ area, bike racks, and kayak storage. Cedars East, just across the street, offers tennis membership with a world-class facility. This financially sound community offers peace of mind with a new roof and no assessments planned. With a liberal rental policy allowing up to 26 rentals/year, this property presents an exceptional investment opportunity while still offering the flexibility to enjoy your own beach getaway. There is a locking owner's closet in the unit. You have to see this home to really appreciate how special it is.

LONGBOAT KEY

5655 GULF OF MEXICO DRIVE A107

2 Beds

2 Baths

1,274 Sq.Ft.

$799,000

MLS#: A4687549

Completely reimagined with an uncompromising eye for detail, this furnished, southeast-facing 3-bedroom residence in The Atrium of Fairway Bay offers refined living with sweeping views across the lagoon, mangroves, open bay, and Sarasota skyline beyond. Thoughtfully remodeled with no expense spared, the flexible layout feels both elegant and exceptionally functional. Rich wood floors run throughout the main living areas, grounding the residence in warmth and sophistication while complementing the shimmering water and city views beyond the glass. A curated mix of tile, wood, stone, and carefully selected colors creates a distinctive ambiance throughout. In the living room, a full wall of sliders opens to a covered terrace that invites the outdoors in and captures the tranquil beauty of the surrounding vistas. Recessed lighting, 8-inch crown molding, plantation shutters, custom-built cabinetry, and a dry bar with wine fridge elevate the space with both style and purpose. The kitchen is beautifully tailored for daily living and entertaining alike, featuring a large custom island with cooktop, granite counters, tile backsplash, tray ceiling, Bosch stainless steel appliances, a built-in desk, and an oversized custom pantry that adds rare storage and convenience. The primary suite is a spacious retreat, highlighted by a dramatic corner wall of floor-to-ceiling glass and slider access to the terrace. Its bath is generously sized and beautifully finished with dual vanities, warm wood accents, and a glass walk-in shower with built-in bench. Two additional bedrooms provide flexibility for guests, a home office, or den, complemented by a beautifully updated full bath. Additional features include an in-residence laundry room and a top-tier AC system equipped with ultraviolet germicidal UV light and an Ecobee smart programmable thermostat. Located behind the gates of Bay Isles, The Atrium of Fairway Bay offers a relaxed, amenity-rich lifestyle with two community pools, tennis courts, fitness facilities, beautifully landscaped bayfront walking paths, kayak access, and deeded Gulf beach access through the Bay Isles Beach Club. Residents also enjoy 24-hour gated security, with optional access to Longboat Key Golf & Tennis Country Club memberships and deepwater slips.

LONGBOAT KEY

2110 HARBOURSIDE DRIVE 536

3 Beds

2 Baths

2,031 Sq.Ft.

$799,000

MLS#: A4685244

Turnkey furnished and positioned just steps from the Gulf’s sandy shoreline, this first-floor residence at Beach Castle on Longboat Key offers a compelling combination of coastal living and proven rental potential. With flexible daily or weekly rental allowances, this two-bedroom retreat presents an exceptional opportunity for personal use, income generation, or both.
The light-filled interior features an open layout designed for ease and comfort, where the kitchen, dining, and living areas flow together naturally. Oversized tile flooring, updated impact glass, and sliding doors enhance both durability and livability, while the kitchen is well-appointed with granite countertops, solid wood cabinetry, stainless steel appliances, and built-in shelving—creating a functional space for everyday living or hosting.
Floor-to-ceiling sliders lead to a private patio and screened lanai, offering a seamless transition to the outdoors and placing you just moments from the beach. The split-bedroom plan provides added privacy, with the primary suite enjoying direct access to the outdoor space, while the guest bedroom is comfortably sized with its own en-suite bath.
Set within the boutique Beach Castle community, residents enjoy a unique beach-to-bay lifestyle with deeded Gulf access, a heated swimming pool and spa, grilling areas, and a fishing pier with day dock on Sarasota Bay. Lush landscaping and well-maintained grounds create a relaxed, resort-style setting that enhances both owner enjoyment and guest appeal.
Located on the desirable north end of Longboat Key, this property is just minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic biking and walking paths. A short drive south brings you to the Longboat Key Club, St. Armands Circle’s dining and boutiques, and downtown Sarasota’s renowned cultural venues, waterfront parks, and year-round events.
With strong rental history, immediate beach access, and a turnkey presentation, this Beach Castle residence offers a rare opportunity to enjoy the best of Longboat Key—whether as an investment, a private getaway, or a combination of both.

LONGBOAT KEY

5311 GULF OF MEXICO DRIVE 5

2 Beds

2 Baths

1,110 Sq.Ft.

$799,000

MLS#: A4691314

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