Westchester, Longboat Key, Florida, 34228


Extending about 11 miles from end to end and connecting placid Sarasota Bay and the glistening Gulf of Mexico is the idyllic island known as Longboat Key. This fascinating jewel in the Sarasota real estate crown has long been the address to privileged permanent residents as well as the adored retirees in the winter season. Most of these residents own a 2nd or 3rd home but have planning boards with Longboat Key on the radar to invest here, ultimately retire here, or who already live here.

If real estate on Longboat Key is becoming a focus for your families’ relocation plans, discover countless upscale choices with the burgeoning condominium market being the most popular. Take a leisurely Sunday drive and explore the diverse architectures from resort worthy penthouses with sweeping vistas of the Gulf to classic Key West styled residences with private berths for your boat. The vast array of choices will excite the most jaded investor as a natural existence on Longboat Key is within reach of most budgets.


The ability to live on the beach is a dream for most and the Westchester condos for sale, located at 4825 Gulf of Mexico Drive, present an affordable way to live that dream. Built in 1970, this favored Key West designed six story mid-rise complex sits on its own beach and is within steps of its own citrus grove. With brilliant sunsets at twilight surrounding you, there are also amenities galore from its exquisitely maintained landscaping surrounding 2 swimming pools and spa right on the beach, to a clubhouse, bbq picnic area, tennis, elevators, and shuffleboard.

Boasting 72 residences, the condos for sale at Westchester make judicious use of windows to capture the breathtaking vistas of the Gulf as well as generous sized lanais for fresh air viewing. Featuring floor plans of around 1,393 square feet, the residences here are configured with 2 bedrooms and 2 full baths and each comes with its own private carport. Pets are not allowed, but the excellent onsite management team will assist in creating addition rental income if you occupy your condo only part time. Pricing for all this understated luxury runs around $475,000 to the $560,000 range.


Food here means casual and elegant dining venues sprinkled the length of the Key with a few being Harry’s Continental Kitchens, Chart House, The Blue Dolphin Café, and Lazy Lobster. Residents of Westchester will also find enjoyment in local attractions such as the nearby Myakka River State Park in Sarasota or Parker Manatee Aquarium. Not to be outdone, the pleasure boating and distinguished sport fishing community will also show Westchester should be the residential development you are after.

Westchester Condos for Sale

Below are all of the current real estate listings available for sale at Westchester.

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Listing data source: MFRMLS - IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS.