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Condos for Sale in Windward Bay

Experience Windward Bay - a boater-friendly community that's packed with amenities and boat slip access.

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Condominiums & villas

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900 - 1,900

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$400s - $900s

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Bayfront with deeded beach access

Condominiums for Sale in Windward Bay

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Home Type

Price Range

Bedrooms

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$769,000

Beds

Baths

2

2

Sq. Ft.

1,523

Neighborhood:

Windward Bay

4500 Gulf Of Mexico Drive Unit 206, Longboat Key, FL 34228

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$599,000

Beds

Baths

2

2

Sq. Ft.

912

Neighborhood:

Windward Bay

4720 Gulf Of Mexico Drive Unit Villa 2, Longboat Key, FL 34228

Some IDX listings have been excluded from this website

Can’t find your ideal home in Windward Bay? Browse additional waterfront condos in Longboat Key, Florida.

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About Windward Bay

Windward Bay sits along Sarasota Bay on the north end of Longboat Key. The community is a mix of low-rise condominiums and a cluster of single-story villas. Homes run from about 900 square feet up to about 1,900, and many look straight out over the water.

Boating is the draw here. Deep-water slips line the seawall, available to rent as they open up, with water and power at the dock. There is a fishing pier with cleaning stations, plus kayak storage and a launch. On land, two heated pools serve the community, and the clubhouse holds a kitchen and a library. Residents also have a fitness room, saunas, two tennis courts, shuffleboard, and half a mile of walking paths along the bay.

Ownership carries deeded access to the Gulf beach, just across the street. A nature preserve backs the southern edge of the property, which keeps that side quiet. Grills, fire pits, and picnic tables are set out along the water. The community welcomes pets. Two are allowed, and one can weigh up to 75 pounds.

Amenities
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Amenities in Windward Bay

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Beach Access

Yes

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Private Beach

No

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Boat Slips

Yes

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Marina Nearby

No

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Beach Club Access

No

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Clubhouse

Yes

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Community Pool

Yes

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Fitness Center

Yes

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Walking Paths

Yes

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Golf Nearby

No

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Tennis

Yes

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Lifestyle Activities

No

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Pickleball

Yes

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Maintenance Included

Yes

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Gated

No

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55+ Community

No

Visual Tour

Visual Tour of Windward Bay

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 Nearby Neighborhoods in Longboat Key

Azario Esplanade Gated Entry

The Westchester is a Gulf-front community near the middle of Longboat Key. Residents share two heated beachside pools, a tennis/pickleball court, a shuffleboard court, a clubhouse, and a private beach. It suits buyers who want simple, classic beachfront living with the sand right out the door.

Azario Park East Sign

Club Longboat is a beachfront condominium community featuring eight tennis courts, two heated pools, a fitness center, and clubhouse. It's perfect for those who want an amenity-rich community with plenty of social activities happening regularly.

A Building in Cresswind Lakewood Ranch

Positano is a very exclusive community right on the Gulf, where just 29 residences share 10 landscaped acres. Amenities include a a beachside clubhouse, fitness facilities, a heated pool and spa, and private garages beneath each building. Residences are expansive with many having private elevators.

Entrance for Sweetwater Village

Sand Cay Beach Resort is a Gulf-front condo community of 60 furnished condos on Longboat Key. It is one of the few communities on the island that allows short vacation rentals, with an in-house rental office and a full-time on-site manager. Amenities include a private beach, heated pool, a tennis and pickleball court, shuffleboard, and beachside grills.

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Homes for Sale

You can also check out all homes for sale in Longboat Key, Florida.  Explore these unforgettable homes before they're gone.

Lynn Brown, REALTOR® (licensed in the state of Florida)

Coldwell Banker Realty

‪(941) 256-3441‬

8334 Market Street, Lakewood Ranch, FL 34202

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Life in Longboat Key is an independent resource and is not affiliated with the official developers of Longboat Key, Florida. We’re here to help you explore, buy in Longboat Key with confidence.​

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