One of the most popular communities provided by {{page_data.agentName}}

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

467

# of Listings

2

Avg # of Bedrooms

$1,151

Avg. $ / Sq.Ft.

$2,117,301

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

467 Properties Found. Page 25 of 32.

#A4666980

LONGBOAT KEY

3320 GULF OF MEXICO DRIVE 207-C

2 Beds

2 Baths

1,187 Sq.Ft.

$599,999

MLS#: A4666980

Discover the ideal blend of comfort, convenience and coastal charm in this beautifully furnished townhouse in Fairway Bay, a sought-after, gated community within Bay Isles on Longboat Key. Enjoy easy access to the gorgeous Gulf beach of Longboat Key via a private beach club, and an abundance of activities, including biking, recreation, pickleball and tennis, ideal for those who embrace an active lifestyle. The main level of this townhome offers an open, eat-in kitchen with a breakfast bar that flows effortlessly into the inviting living room, complete with a wood-burning fireplace and large sliding doors leading to a screened lanai with stairs to the outdoors. A convenient half bath completes this level, making it ideal for entertaining. Upstairs, the primary suite features a spacious walk-in closet and a private en-suite bath with double sinks. A second bedroom, also with its full en-suite bath, provides comfort and privacy for guests. The laundry is conveniently on this upper level. On the garage level, you’ll find a large storage room and a bonus space, offering endless possibilities such as a home gym, hobby area or even a space for guests. Fairway Bay homeowners have access to the on-site clubhouse, where there are social activities, a community gym and Har-Tru tennis courts for residents only. Fairway Bay is in Bay Isles, where you have 24/7 gated security and deeded access to the beautiful and private Bay Isles Beach Club. Here you can enjoy gated parking, restrooms, beach chair and umbrella storage, an ice machine, refrigerator and microwave, the ideal place for barbecues, picnics, and sunset gatherings with family and friends. Furniture is included, making this an effortless move-in opportunity to start enjoying the Longboat Key lifestyle from day one. This home is in proximity to Longboat Key Club where you have 45 holes of golf, a world-class tennis center, pickleball courts and five private restaurants accessible to you with additional membership. It’s rare to find a home in Bay Isles offering this level of lifestyle, amenities and value. Don’t miss this opportunity to live your best life on Longboat Key and start making memories of a lifetime today.

LONGBOAT KEY

1912 HARBOURSIDE DRIVE 602

2 Beds

2 Baths

1,590 Sq.Ft.

$599,900

MLS#: A4668394

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

New on site 4 days ago

This perfect slice of paradise offers Spectacular Bay Views for Beautiful Sunrises from your Spacious Lanai or Primary Bedroom and Deeded Beach Access for Breath Taking Sunsets. To top it off you have an assigned, deep water slip for your boating needs with no bridges to the intercoastal. This beautiful 2 bedroom, 2 bath, 1,284 sqft Condo is a first floor unit, above the garage level. Split Floor Plan delivers separation from your Primary Bedroom Suite and your Guestroom. Bright white walls and updated ceilings with recessed lights add to the bright airy feel. Open concept Living Room and Dining Room combination. Plantation shutters, impact windows. Tastefully decorated and furnished with exclusions. Complex offers park like grounds, a beautiful Heated Pool and Tennis/Pickleball courts for when you are done boating or enjoying the views. Assigned Garage Level Storage Closet and Parking Space. Convenient mid key location, less than a mile from Publix and CVS, and a short ride to the shops and restaurants of St Armand’s and Downtown Sarasota.

LONGBOAT KEY

3540 GULF OF MEXICO DRIVE 102

2 Beds

2 Baths

1,284 Sq.Ft.

$599,000

MLS#: A4685789

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 fully furnished 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 with 90 days notice 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 tennis/pickleball courts, a clubhouse, kayak storage and launch, 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

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

Price reduced

#A4667631

LONGBOAT KEY

4540 GULF OF MEXICO DRIVE 204

2 Beds

2 Baths

1,312 Sq.Ft.

$595,000

MLS#: A4667631

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

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

#TB8460267

LONGBOAT KEY

713 SAINT JUDES DRIVE S 2

2 Beds

2 Baths

1,215 Sq.Ft.

$595,000

MLS#: TB8460267

Price reduced

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

A fabulous opportunity to build your dream home on the lowest priced single family vacant lot in all of Longboat Key! Enjoy deeded beach access just across Gulf of Mexico Drive. Surrounded by multi million dollar homes and with walking or biking distance to multiple restaurants, shopping, Cedars Tennis club, and the tree lined splendor of Joan Durante Park, this is where your island living dream begins.

LONGBOAT KEY

620 COMPANION WAY

None Beds

None Baths

0.19 acres

$589,000

MLS#: A4680278

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