Westchester of Countryside market snapshot (as of June 25, 2026): the median sale price is about $651K ($264 per sq ft), a buyer-leaning market (limited data). Based on 8 recent closings in live Stellar MLS data.
Westchester of Countryside is an established single-family neighborhood in the Countryside area of Clearwater, in Pinellas County, off Countryside Boulevard near State Road 580 and Countryside Mall (neighborhood real estate guides, 2026). It is a defined subdivision rather than a sprawling master plan, known for larger homes on mature, wooded lots.
Listing and neighborhood guides describe homes built mainly in 1976 to 1977, generally in the range of roughly 2,900 to 3,200 square feet with about four to five bedrooms, a larger footprint than much of the surrounding 1970s and 1980s Countryside stock (neighborhood real estate guides, 2026). Confirm the exact year built, size, bedroom count, and lot for any specific home.
Because this is a single-family neighborhood of mid-1970s homes, the money is made or lost on the house and the lot, not the address alone. The drivers are the roof, the systems, the kitchen and bath updates a home of this vintage usually needs, the lot and trees, and the inland flood and insurance picture, all of which have to be read by address and from the current listing.
The pitch is a quiet, mature inland address with Countryside Boulevard, Countryside Mall, State Road 580, and the US 19 corridor close, plus easy reach to Safety Harbor, Dunedin, and Tampa over the bridges. The work is the diligence: read the condition and updates, quote the insurance, and check the flood zone by address before you buy the trees.
