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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

471

# of Listings

2

Avg # of Bedrooms

$1,103

Avg. $ / Sq.Ft.

$2,045,402

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

471 Properties Found. Page 25 of 32.

GORGEOUS COMPLETELY REMODELED Villa with Lake Views in Spanish Main Yacht Club!!
Welcome to effortless coastal living in this beautifully remodeled 3-bedroom, 2-bath villa located in the highly sought-after Spanish Main Yacht Club. Rarely available, this 1,516 sq ft STANDALONE villa offers a larger footprint than most in the community and includes a true third bedroom with serene LAKE VIEWS.
The recent remodel brings a fresh, modern feel, complemented by an open-concept floor plan, elegant tile flooring throughout, and abundant natural light. Enjoy peace of mind with NEW IMPACT WINDOWS AND DOORS, NEW WATER HEATER, a NEWER ROOF (2023)AND NEWER A/C system (March 2024).
Spanish Main Yacht Club offers a maintenance-free, pet-friendly community with resort-style amenities, including a large waterfront pool overlooking the marina, a 40-slip deep-water marina with no bridges to Sarasota Bay and the Gulf, and deeded beach access just steps away. Shopping, dining, and the charm of St. Armands Circle are all minutes from your door.
While this is an active 55+ community, ownership is open to all ages, with full-time residency beginning at 50.
"Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. Sarasota SRQ Airport's soaring success added 30 flights in 2024 and 2025, significant passenger growth, a new $72M runway and terminal, and ranks No. 1 best resort airport in the country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. This home in the master-planned community of the Spanish Main Yacht Club could be your destination of choice. Features include a spectacular pool and spa, kayak launch, marina, outdoor grills, and lush tropical landscaping. There is a shell path for walking along to a deeded beach access to enjoy the sand and world-class sunsets. There is also on-site management and maintenance staff making where home and away share the same address. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide's list of Top 12 Destinations for 2025."
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Schedule your private showing today.

LONGBOAT KEY

563 SPANISH DRIVE S

2 Beds

2 Baths

1,516 Sq.Ft.

$615,000

MLS#: A4682513

An easy access slip with the views to along with the superb amenity package, Slip B-13 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 100 x 28, and a usable beam of 25 feet and a long and extra wide finger pier. This location provides close proximity to the hospitality room and Pool. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis and golf facilities, fitness center, with spa and beach access. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 80 feet. Beam dependant on the vessel type and measure. Membership in the Longboat Key Club is required

LONGBOAT KEY

2600 HARBOURSIDE DRIVE B-13

None Beds

None Baths

1.0 acres

$600,000

MLS#: A4666677

104 ft. x 29.5 ft. Boat Slip at Longboat Key Moorings Marina. This is a 104 ft. long T-dock/face dock ready to accommodate a large yacht; ample electrical service outlets. O-13 is 49.5 feet, and O-14 is 54.5 ft, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes restaurant, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle o St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. Longest vessel permitted at the dock is 99 feet, usable beam is 25 feet. Vessel must be approved prior to entering the marina. A photo and boat specs must be provided to the Association.

LONGBOAT KEY

2600 HARBOURSIDE DRIVE O-13/14

None Beds

None Baths

N/A

$600,000

MLS#: A4661181

Price reduced

Peek-a-boo Gulf views from back deck in this open concept 2-Bedroom, 2-Bathroom Condo at Club Longboat Beach & Tennis Resort. This Longboat Key Retreat offers an expansive 1,484 SqFt of thoughtfully designed living space and combines comfort, convenience. There are 2 balconies one off the living room and the second off the master bedroom. Watch a game of tennis and enjoy the salt air as you unwind with your favorite drink. This is a well maintained residence and some upgrades include: (new HVAC 2025, hot water heater, stainless fridge), this home offers a welcoming, move-in ready atmosphere and provides a sanctuary where you can enjoy both peaceful living and the energy of Longboat Key's vibrant community. Longboat Key is renowned for its pristine beaches, relaxed atmosphere, and upscale lifestyle. With easy access to fine dining, shopping, cultural attractions, and outdoor recreation, it’s the ideal location for those seeking a laid-back coastal lifestyle, while still being close to the excitement of Sarasota. Whether you’re taking a morning stroll on the beach or enjoying the world-class amenities nearby, Longboat Key offers a unique blend of tranquility and activity. Club Longboat Beach & Tennis is more than just a place to live – it’s a destination where every day feels like a vacation. The resort has an expansive calendar full of activities outdoors and the clubhouse has gatherings and various events. Enjoy direct access to the beautiful white sands of Longboat Key Beach, perfect for sunbathing, swimming, and watersports. The community offers resort-style amenities, including meticulously maintained tennis courts, a fitness center, a heated pool (one of which is private for adults only), and 24-hour security. Whether you’re looking to relax poolside or stay active with tennis or fitness, there’s something for everyone. Don’t miss out on the opportunity to own your slice of paradise.

LONGBOAT KEY

5055 GULF OF MEXICO DRIVE 435

2 Beds

2 Baths

1,484 Sq.Ft.

$600,000

MLS#: A4671314

This inviting residence at the Islander Club of Longboat Key offers a peaceful retreat with beautiful views of the landscaped grounds. Spanning 1,235 sq ft, the home features two bedrooms, two full bathrooms, and an open floor plan that provides a comfortable space for both living and entertaining. The spacious kitchen and dining area offer plenty of room for cooking and gathering, with ample cabinetry and an open flow that makes the space perfect for hosting. The 38-foot private balcony, accessible from both the living room and bedrooms, offers a tranquil spot to enjoy the coastal breeze and the surrounding scenery. The primary suite serves as a peaceful retreat with an en-suite bathroom and a walk-in closet, while the guest bedroom, located next to the second full bathroom, ensures comfort and privacy. Additional features include a private covered parking space and secure storage. Situated in the heart of Longboat Key, this residence is conveniently located near waterfront dining, shopping, golf, and a short drive to St. Armands Circle and downtown Sarasota. The Islander Club offers a range of resort-style amenities, including 800 feet of private beach frontage, two Har-Tru tennis courts, a renovated community room with a full kitchen, billiards, table tennis, a library, fitness center and a heated pool. This is a wonderful opportunity to enjoy Longboat Key living in a residence that provides both comfort and ample space.

LONGBOAT KEY

2301 GULF OF MEXICO DRIVE 25N

2 Beds

2 Baths

1,235 Sq.Ft.

$599,000

MLS#: A4667153

#A4679458

LONGBOAT KEY

4720 GULF OF MEXICO DRIVE Villa 2

2 Beds

2 Baths

912 Sq.Ft.

$599,000

MLS#: A4679458

Discover relaxed coastal living in this beautifully renovated two-bedroom, two-bath bayfront condominium positioned to capture stunning sunrise views over the water. With an open floor plan and expansive bay views from the great room, this residence blends comfort, style and the best of waterfront living. The updated interior features porcelain tile flooring throughout, a bright and airy living space, and a bayfront lanai where you can start your mornings watching the sun rise over the water. The kitchen is equipped with new appliances, and the home also includes in-unit laundry for everyday convenience. Recent improvements provide peace of mind, including a new air-conditioning system, new water heater and hurricane-rated doors. The spacious primary suite offers a private en-suite bath, while the guest suite enjoys direct access to the second bath, creating an ideal layout for family and friends. The condominium is nicely furnished, making it move-in ready. Residents enjoy a full range of resort-style amenities, including private beach access, community pool, tennis courts, pickleball courts, boat docks accommodating vessels up to 28 feet, a clubhouse, organized social activities, bike storage, kayak storage and launch, and on-site maintenance. The well-maintained association has completed numerous recent upgrades, such as new roof, hurricane-rated carports, new docks, freshly painted buildings, and newly re-surfaced tennis and pickleball courts, ensuring long-term value and appeal. You'll also appreciate the association's pet-friendly policy. Association fees include building and flood insurance, cable, water, sewer, trash, escrow reserves, and comprehensive grounds and building maintenance, offering low-maintenance ownership. In a desirable mid-key location, this property is ideal for enjoying the best of island life with exceptional boating, kayaking, and easy access to the bay and Gulf. Whether you’re looking for a full-time residence, seasonal retreat or investment opportunity, this bayfront condominium delivers the ultimate Florida waterfront lifestyle.

LONGBOAT KEY

4234 GULF OF MEXICO DRIVE J1

2 Beds

2 Baths

1,150 Sq.Ft.

$599,000

MLS#: A4685764

Price reduced

Exceptional full Bay views, private beach access and kayak launch, and incredible value! This 2BR/2BA retreat at Pelican Harbour & Beach Club delivers the quintessential Longboat Key lifestyle. From its 2nd-floor vantage point, enjoy peaceful sunrises over the Bay and the tranquil fountain view from your screened lanai, surrounded by lush tropical landscaping. Then, end your day with spectacular Gulf sunsets and leisurely beach walks from your private beach access. The updated kitchen gleams with new 2025 solid quartz countertops, stainless Samsung appliances, a tile backsplash, and a breakfast bar island—perfect for entertaining. Open living and dining areas flow seamlessly toward the water, creating a bright, inviting space ideal for relaxing or hosting friends. The spacious owner’s suite opens to the lanai and features a 2023-renovated ensuite bath with stone countertops, dual sinks, porcelain tile flooring, a glass shower, and custom closets. The guest suite offers another beautifully updated bath and generous storage. Additional highlights include hurricane-rated windows and doors, in-unit laundry, a 2023 roof, 2024 exterior paint, and a hurricane-rated carport conveniently located just outside your door. This unit is currently rented, and tenants will vacate or stay so you can continue to earn rental income immediately! Ideally situated mid-island, Pelican Harbour & Beach Club offers outstanding amenities: Bay and beach access, first-come dock slips, a heated resort-style pool, two newly resurfaced tennis/pickleball courts, a clubhouse with social activities, kayak storage and launch, bike storage, and ample owner storage. This pet-friendly, rental-friendly community welcomes large dogs and seasonal visitors and perfectly combines luxury, flexibility, and coastal charm—just minutes from Bayfront Park, the new St. Regis Resort, St. Armands Circle, and downtown Sarasota’s vibrant restaurants, culture, and shopping.

LONGBOAT KEY

4234 GULF OF MEXICO DRIVE E2

2 Beds

2 Baths

1,150 Sq.Ft.

$598,000

MLS#: A4667654

Price reduced

#A4667631

LONGBOAT KEY

4540 GULF OF MEXICO DRIVE 204

2 Beds

2 Baths

1,312 Sq.Ft.

$595,000

MLS#: A4667631

Price reduced

$100,000 PRICE REDUCTION! Refined coastal renovation, waterfront location, deeded beach, pet-friendly, pickleball, tennis, kayaking, boating, and the best of casual island living. Enjoy the larger D1 plan, offering owners more square footage in this open concept two-bedroom, two-bath condominium in Longboat Key's Pelican Harbour & Beach Club. Plus this unit comes totally turnkey furnished and is move-in ready. The Association's amenities include private beach, tennis and pickleball courts, heated resort-style pool, clubhouse, bike storage, kayak launch, and owner boat docks. The condominium features include hurricane windows and doors, contemporary-style fireplace, new flooring, custom cabinetry, stainless appliances, crown molding, plantation shutters, tankless water heater, new air conditioner, and designer ceiling fans. Spacious primary suite boasts a private bath with custom walk-in shower, built-in closets, and water views. The guest suite, split from the primary, offers friends and family alike private space and a convenient adjoining bath with a custom walk-in shower, as well. There is plenty of closet space and storage throughout, and an in-unit laundry with matching front-load HE washer and dryer. In addition, with the D1 plan being larger than other Pelican Harbour two-bedroom condominiums, owners will appreciate the larger spaces for gathering and hosting. Association provides on-site maintenance; landscaping; building property, wind, flood and liability insurances; roofs; exterior painting; cable; water; sewer; trash; and more. Pelican Harbour also has fully funded reserves and has installed new roofs, new hurricane-rated carports, upgraded pickleball and tennis courts, and offers owner boat docks with electric and water. Pelican's private beach is only steps away and offers stunning sunset and Gulf views with miles of turquoise waters and crystal sands. You'll also appreciate the convenient mid-island location close to Bayfront Park, grocery, restaurants, shopping, places of worship, and easy access to St. Armands, Sarasota and Anna Maria. Gorgeous coastal renovation, larger D1 floor plan, fantastic mid-island location, pet-friendly and one of the best amenity packages on the island. Enjoy Pelican Harbour and Beach Club. Schedule your private showing today.

LONGBOAT KEY

4234 GULF OF MEXICO DRIVE D1

2 Beds

2 Baths

1,248 Sq.Ft.

$595,000

MLS#: A4673543

Welcome to your tropical retreat on Longboat Key! This newly renovated 2-bedroom, 2-bath ground-floor LARGER END unit, with additional windows blends light coastal charm with modern comfort in a sought-after Gulf-to-Bay community. Thoughtful upgrades include neutral tile flooring throughout (no carpet), crown molding, upgraded baseboards, fresh interior paint, impact-rated PGT windows and sliders, and in-unit laundry with full-size machines. Offered TURNKEY furnished—this is truly the best of Gulf-to-Bay living.

The bright, open kitchen features granite countertops, solid wood cabinetry, new stainless-steel appliances, and a breakfast bar that flows seamlessly into the living and dining areas—ideal for both entertaining and everyday living. The spacious primary suite offers a large closet & updated ensuite bath. Need extra space for an additional guest bedroom or office? As a bonus, the master also has a sliding panel that when closed creates a spare room with its own private barn door entrance. A split-bedroom floor plan ensures privacy, with the guest suite tucked behind a frosted glass door and featuring its own bath and linen closet, effectively offering 2 master suites! A private exterior storage room and peaceful garden-view patio complete the picture.

Located on the bayside of this intimate Gulf-to-Bay community, you will enjoy deeded beach access, a clubhouse, fitness center, heated pool, kayak launch, fishing pier, and tennis/pickleball courts. Spend your mornings kayaking Sarasota Bay and your evenings enjoying sunsets on the private Gulf beach—complete with complimentary beach chairs.

Banyan Bay is a friendly, boutique community of just 44 residences, offering covered parking and a rare pet-friendly policy with no size or breed restrictions. The community has passed its milestone inspection and is certified for another 10 years, providing added peace of mind. Rental-friendly (up to 4 leases per year, 1-month minimum), this property is ideal as a full-time residence, vacation getaway, or income-producing investment.
Conveniently located near shops, dining, parks, Anna Maria Island, St. Armands Circle, and downtown Sarasota.

LONGBOAT KEY

5260 GULF OF MEXICO DRIVE 401

2 Beds

2 Baths

1,173 Sq.Ft.

$595,000

MLS#: A4675930

Welcome to this beautifully updated top floor corner furnished residence with Gulf and Bay views that is move in ready. Coming furnished with an open kitchen floor plan and an enclosed lanai overlooking the pool and Sarasota Bay. Large plank ceramic tiles throughout and ceiling fans in every room, hurricane impact glass windows in the kitchen and living area and a washer/dryer has been added. All tv's within the residence stay. The Longboat Harbour community is located mid-Longboat Key with amenities to enjoy including a large clubhouse where many activities occur, with a catering kitchen and dance floor, art studio, billiard and card rooms, and a fully equipped fitness center. In addition, the community has four heated swimming pools, putting green, tennis and pickleball courts, kayak storage, boat slips available for a minimal annual fee for up to a 34’ boat, mini golf, a scenic waterfront promenade along the harbor and canal, and access to a private gated Beach Club on the Gulf side with bathrooms, showers and beach items. The building has just completed a new roof installed. There is additional storage withing the building for each residence as well as a storage closet on the enclosed lanai.

LONGBOAT KEY

4440 EXETER DRIVE 301

2 Beds

2 Baths

1,376 Sq.Ft.

$595,000

MLS#: A4684917

Discover the irresistible charm of historic Longbeach Village and seize a rare opportunity to build your dream island home on Longboat Key. Welcome to the lowest priced vacant single-family parcel available on Longboat Key, an exceptional chance to design a custom residence just off the coast of Sarasota. This desired corner lot in the heart of the village offers flexible design possibilities, including optional rear alley access in addition to two street frontages, giving you potential entry on up to three sides of the property. Positioned within this golf-cart-friendly community, the homesite provides effortless access to everything that makes Longbeach Village so beloved. Enjoy the dazzling white sands and shimmering turquoise waters of the Gulf of Mexico just moments from your door, along with the serene beauty of Sarasota Bay at opposite end of Broadway, both only about a block away. Here, sunrise and sunset become part of your daily routine. Residents of the village enjoy numerous waterfront conveniences, including multiple neighborhood kayak launch points, two fishing piers, a community boat ramp and a variety of dining, shopping and fitness options within minutes of home. With no mandatory HOA, you can store your boat, golf cart, or other island toys beneath a beautiful new elevated home and fully embrace the relaxed coastal lifestyle. This exceptional piece of island real estate invites you to bring your vision to life. Start planning your dream home or private vacation retreat today and experience the unmatched charm of Longbeach Village for yourself.

LONGBOAT KEY

641 BROADWAY STREET

None Beds

None Baths

0.14 acres

$595,000

MLS#: A4672996

Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? And could you even imagine you could have it for $615,000?! With one owner for the last 29 years, this is your unique opportunity to purchase this fully renovated beachfront walkout 1 bedroom, 1 bath condo in the beach to bay island community of Covert II - and hang onto it like these owners have! With this fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!

LONGBOAT KEY

5231 GULF OF MEXICO DRIVE 104

1 Beds

1 Baths

720 Sq.Ft.

$595,000

MLS#: A4676730

#A4662713

LONGBOAT KEY

528 FOREST WAY

2 Beds

2 Baths

1,440 Sq.Ft.

$595,000

MLS#: A4662713

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