Westchester
Discover the Westchester - a classic Gulf-side community that offers a well-rounded set of amenities and a simple beachside experience.
Condominiums
1,300 - 1,500
$600s - $1M
Classic and simple beachfront living
About Westchester
The Westchester is a classic beachside community with 72 residences near the middle of Longboat Key. Nearly every home looks straight out at the water. The plans are simple and consistent, two bedrooms and two baths at about 1,400 square feet, with elevators, covered parking, and storage.
Amenities here are designed around relaxing or connecting with your neighbors. They include two heated pools, a tennis/pickleball court, a shuffleboard court, and a clubhouse. Down on the sand is a private beach for reading, napping, or watching the Gulf change colors.
Shops and restaurants sit minutes away in both directions along Gulf of Mexico Drive. Anna Maria Island makes an easy day trip north, and St. Armands Circle and downtown Sarasota are a comfortable drive south.
Condos for Sale in Westchester
Home Type
Price Range
Bedrooms
Some IDX listings have been excluded from this website
Can’t find your ideal home in Westchester? View more beachfront condos in Longboat Key, Florida.
Amenities in Westchester
Beach Access
Yes
Private Beach
Yes
Boat Slips
No
Marina Nearby
No
Beach Club Access
No
Clubhouse
Yes
Community Pool
Yes
Fitness Center
No
Walking Paths
No
Golf Nearby
No
Tennis
Yes
Lifestyle Activities
No
Pickleball
Yes
Maintenance Included
Yes
Gated
No
55+ Community
No
Visual Tour of Westchester
Nearby Communities in Longboat Key
Infinity is a boutique Gulf-front condominium of just 11 residences. Known for its coastal contemporary architecture and private-elevator entries, Infinity also includes a heated beachfront pool and spa, sun deck with direct beach access, clubhouse with catering kitchen, fitness center, and tennis/pickleball courts - all behind a gated entry.
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.
Windward Bay is a boater-friendly community of condos and villas on Sarasota Bay. Deep-water boat slips line the seawall and are available to rent, and there is a fishing pier and kayak storage. On land, there are two heated pools, a clubhouse, tennis courts, and walking paths along the water. Ownership also carries deeded beach access to the Gulf.
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.
