Longboat Key Homes with Sailboat Water Water Extras

Welcome to Longboat Key, a stunning barrier island located in Florida. This picturesque city is known for its pristine beaches, world-class dining, and luxurious waterfront properties.

If you're a sailing enthusiast looking for your dream home, Longboat Key offers an array of exquisite properties with sailboat water extras. Imagine waking up to the gentle sound of waves lapping against the shore and setting sail right from your backyard. Whether you're an experienced sailor or looking to start a new maritime adventure, Longboat Key provides the perfect setting for waterfront living.

From elegant estates to modern condos, homes with sailboat water extras are a coveted feature in this coastal paradise. Enjoy breathtaking sunsets, panoramic water views, and easy access to the Gulf of Mexico for all your boating excursions.

Longboat Key is not just a place to live; it's a lifestyle. Indulge in upscale amenities, championship golf courses, and a vibrant community that celebrates the coastal way of life. With its proximity to Sarasota and its cultural attractions, Longboat Key offers the perfect blend of relaxation and sophistication.

Come experience the magic of Longboat Key and find your slice of paradise with homes featuring sailboat water extras. Live where every day feels like a vacation and make your waterfront living dreams a reality in this exclusive coastal enclave.

Newest Longboat Key Homes with Sailboat Water Water Extras

65 Lighthouse Point Drive, Longboat Key image

65 Lighthouse Point Drive, Longboat Key $6,995,000

Some homes are simply built differently. Conceived as a grand private waterfront estate, this remarkable residence within the exclusive gated enclave of Lighthouse Point ...

4 Beds
5 Baths
Lighthouse Point SubDv.
34228 Zip Code

5310 Gulf Of Mexico Drive Unit 16, Longboat Key image

5310 Gulf Of Mexico Drive Unit 16, Longboat Key $689,000

Turnkey-Furnished Longboat Key Condo with Dock Access & Rental Potential. Discover effortless coastal living in this beautifully furnished turnkey condo on desirable Long...

2 Beds
2 Baths
Longboat Key SubDv.
34228 Zip Code

448 Gulf Of Mexico Drive Unit A104, Longboat Key image

448 Gulf Of Mexico Drive Unit A104, Longboat Key — A $725,000

Location! Location! Location! Awesome, Spectacular Bay views from the kitchen, dining room, living room and primary bedroom! One Bridge to the Gulf! No wait list boat sli...

2 Beds
2 Baths
Bay Harbour Apts SubDv.
34228 Zip Code

4340 Falmouth Drive Unit 104, Longboat Key image

4340 Falmouth Drive Unit 104, Longboat Key — D $499,900

Welcome to your slice of paradise on beautiful Longboat Key. Priced to sell and offered fully furnished, this beautifully maintained two-bedroom condominium is truly move...

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

2600 Harbourside Drive Unit P-05, Longboat Key image

2600 Harbourside Drive Unit P-05, Longboat Key $200,000

Nestled in a beautifully protected marina on the exclusive Longboat Key, this premium 48x20-foot wet slip accommodates vessels up to 43 feet and provides a true vacation ...

Longboat Key Moorings SubDv.
34228 Zip Code

2800 Harbourside Drive Unit D-16, Longboat Key image

2800 Harbourside Drive Unit D-16, Longboat Key $425,000

Easy access and docking at this 75 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina on D-dock. Located on the West side of the marina. Ample turning radius between ...

Longboat Key Moorings SubDv.
34228 Zip Code

711 Old Compass Road, Longboat Key image

711 Old Compass Road, Longboat Key $6,495,000 ▼

This spectacular waterfront pool home was just completed in 2026 and built with uncompromising craftsmanship and every attention to detail. A West Indies-inspired residen...

4 Beds
6 Baths
Emerald Harbor SubDv.
34228 Zip Code

2600 Harbourside Drive Unit B-16, Longboat Key image

2600 Harbourside Drive Unit B-16, Longboat Key $500,000

An easy access slip with the views to along with the superb amenity package, Slip B-16 at Longboat Key Club Moorings Marina provides one of the most desired locations as ...

Longboat Key Moorings SubDv.
34228 Zip Code

1600 Harbor Sound Drive, Longboat Key image

1600 Harbor Sound Drive, Longboat Key $3,995,000

Discover the rare opportunity to create a legacy waterfront estate in the prestigious Harbor Section of Bay Isles, one of Longboat Key's most coveted boating communities....

Bay Isles SubDv.
34228 Zip Code

71 Twin Shores Boulevard, Longboat Key image

71 Twin Shores Boulevard, Longboat Key $395,000

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

657 Halyard Lane, Longboat Key $4,300,000

Experience timeless coastal luxury in this exceptional custom estate, perfectly positioned in the prestigious Country Club Shores on the sought-after south end of Longboa...

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

2600 Harbourside Drive Unit R-13, Longboat Key image

2600 Harbourside Drive Unit R-13, Longboat Key $400,000

Stunning Sarasota Bay Views! An easy access slip with the views to go along with the superb amenity package, Slip R-13 at Longboat Key Club Moorings Marina provides one o...

Longboat Key Moorings SubDv.
34228 Zip Code