
Condos for Sale in Windward Bay
Experience Windward Bay - a boater-friendly community that's packed with amenities and boat slip access.
Condominiums & villas
900 - 1,900
$400s - $900s
Bayfront with deeded beach access
Condominiums for Sale in Windward Bay
Home Type
Price Range
Bedrooms
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.
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 in Windward Bay

Beach Access
Yes
Private Beach
No
Boat Slips
Yes
Marina Nearby
No
Beach Club Access
No
Clubhouse
Yes
Community Pool
Yes
Fitness Center
Yes
Walking Paths
Yes
Golf Nearby
No
Tennis
Yes
Lifestyle Activities
No
Pickleball
Yes
Maintenance Included
Yes
Gated
No
55+ Community
No
Visual Tour of Windward Bay


Nearby Neighborhoods in Longboat Key
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.
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.
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.
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.


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












