Longboat Key Homes with Boatable Water Water Frontage

Welcome to Longboat Key, Florida—a picturesque barrier island that perfectly blends the charm of a tranquil beach town with the sophistication of upscale living. Nestled between the vibrant cities of Sarasota and Bradenton, Longboat Key boasts pristine white-sand beaches, lush tropical landscapes, and a relaxed coastal lifestyle that makes it a sought-after destination for homebuyers and vacationers alike.

One of the most enticing features of Longboat Key is its stunning waterfront properties, offering homes with boatable water frontage. Imagine waking up to panoramic views of shimmering waters, where the gentle lapping of waves sets the tone for your day. These homes provide direct access to the Gulf of Mexico and Sarasota Bay, making it a boater's paradise. Whether you're an avid sailor or enjoy leisurely afternoons on a kayak, living in a waterfront home here means endless opportunities for adventure and relaxation.

As you explore the real estate options available, you'll find a diverse range of architectural styles—from luxurious modern estates to charming coastal cottages. Each property is designed to maximize the beauty of the surrounding environment, with spacious outdoor living areas, private docks, and breathtaking views.

In addition to its stunning homes, Longboat Key offers a vibrant community atmosphere, complete with boutique shops, fine dining, and recreational activities. With a focus on preserving its natural beauty, the island is also home to numerous parks and nature preserves, ensuring that you can enjoy the best of Florida's outdoor lifestyle.

Discover the allure of Longboat Key—where your dream waterfront home awaits!

Newest Longboat Key Homes with Boatable Water Water Frontage

521 Forest Way, Longboat Key — N/A $599,900

Discover your ultimate island escape in this beautifully updated, fully furnished, and pet-friendly 2-bedroom, 2.5-bathroom townhome located within the desirable Cedars T...

2 Beds
3 Baths
Cedars East SubDv.
34228 Zip Code

732 Bayport Way, Longboat Key — 732 $1,050,000

Welcome to 732 Bayport Way, a completely remodeled and beautifully furnished coastal retreat offering a rare Gulf view within Bayport Beach & Tennis Club, one of Longboat...

2 Beds
2 Baths
Bayport Bch & Ten SubDv.
34228 Zip Code

691 Tarawitt Drive, Longboat Key $815,000

Situated on an extra large 11,250 sf waterfront lot, with a 2020 dock and seawall, and deeded beach access, this fabulous single family home represents one of the best in...

2 Beds
2 Baths
Longboat Key SubDv.
34228 Zip Code

2020 Harbourside Drive Unit 442, Longboat Key image

2020 Harbourside Drive Unit 442, Longboat Key — M-4 $699,000

Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within t...

2 Beds
2 Baths
Fairway Bay SubDv.
34228 Zip Code

96 Twin Shores Boulevard, Longboat Key image

96 Twin Shores Boulevard, Longboat Key $399,000

Pre-Construction. To be built. Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can...

2 Beds
2 Baths
Twin Shores Mobile Home SubDv.
34228 Zip Code

7094 Longboat Drive E, Longboat Key image

7094 Longboat Drive E, Longboat Key $3,249,000

A rare opportunity to craft a bespoke waterfront estate on the coveted north end of Longboat Key. Situated on over 11,000 square feet, this exceptional vacant homesite of...

Longboat Key SubDv.
34228 Zip Code

765 Saint Judes Drive N, Longboat Key image

765 Saint Judes Drive N, Longboat Key $1,350,000

Virtually Staged. VIRTUALLY EVERYTHING NEW — BOAT IN YOUR BACKYARD, PRIVATE BEACH DOWN THE STREET. This is the Longboat Key lifestyle buyers dream about: boating from you...

4 Beds
2 Baths
Longboat Key SubDv.
34228 Zip Code

2800 Harbourside Drive Drive Unit M-10, Longboat Key image

2800 Harbourside Drive Drive Unit M-10, Longboat Key $289,000 ▲

A 58 ft. x 20 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enj...

Bay Isles SubDv.
34228 Zip Code

795 Marbury Lane, Longboat Key $3,495,000

This stunning coastal home is the epitome of luxurious island living. A waterfront paradise offering dreamy views from multiple rooms. Gorgeous pecky cypress doors open t...

5 Beds
3 Baths
Sleepy Lagoon SubDv.
34228 Zip Code

4370 Chatham Drive Unit 304, Longboat Key image

4370 Chatham Drive Unit 304, Longboat Key — G $425,000 ▼

MAJOR $74,000 PRICE REDUCTION, don't miss this newly priced opportunity. Experience the best of Bay-to-Gulf living in this beautifully furnished condominium located on th...

2 Beds
2 Baths
Longboat Harbour North SubDv.
34228 Zip Code

560 Chipping Lane, Longboat Key $3,999,990

Exceptional waterfront living meets serious Longboat Key boating in this beautifully updated 4300 sf residence in Country Club Shores. Expansive water views, flexible li...

5 Beds
5 Baths
Country Club Shores SubDv.
34228 Zip Code

729 Saint Judes Drive S Unit 2, Longboat Key image

729 Saint Judes Drive S Unit 2, Longboat Key — 729 $525,000 ▼

Beautifully renovated waterfront unit at 729 St. Jude’s Way with gorgeous water views and a boat dock, plus easy access to the Intracoastal Waterway. Renovated from top t...

2 Beds
2 Baths
St Judes Apts SubDv.
34228 Zip Code