Westchester
Homes for Sale in Clearwater, FL

This is an established Pinellas neighborhood of 246 homes with a mid-century core, where a typical house runs around 1,782 square feet and the age of the stock means renovation status matters more than any single price point.

Stellar MLS sales records identify 20 homes in Westchester that have changed hands since 2004, built between 1956 and 1964 (median 1959), with a median living area of about 1,551 sq ft and a typical 3-bedroom, 2-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

County records show 20 qualified sales in Westchester across 2024–2025 (15 in 2024, 5 in 2025), median $430,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Westchester is too small for its own price trend, so here is the market around it.

In ZIP 33756, 258 homes are on the market and 14% are under contract — a slower corner of Clearwater.

Across Pinellas County, 6,628 homes are active and 1,729 pending (21% under contract).

In ZIP 33756 (Clearwater), 534 homes closed in the last 12 months at a median of $355K ($257/sq ft), down 1.9% year over year, with a median 45 days on market. Right now 124 active and 24 pending listings put supply at about 4.7 months — a balanced market. See the live ZIP 33756 housing market and the Pinellas County market.

ZIP and county figures describe the wider market, not Westchester specifically. Momentum Research analysis of MLS records.

A year-built range from 1900 to 2021 is unusually wide, and it signals a neighborhood that has been added to and rebuilt over time rather than delivered all at once. The median build year of 1960 means most of what you'll tour is genuinely mid-century — roofs, systems, and layouts should be evaluated on their update history, not assumed from the asking price.

At a median of about 1,782 living square feet, these are moderate-sized homes rather than large ones. That footprint suits buyers who want single-story practicality over sprawl, and it keeps carrying and maintenance scope contained relative to newer, larger construction elsewhere in the county.

In a neighborhood where value hinges on condition and update history rather than a clean price band, the work is in reading each house accurately. We help sellers position against genuinely comparable work and help buyers separate a solid renovation from cosmetic cover, so nobody overpays for age or underestimates a needed system replacement.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.