Windsor Woods
Homes for Sale in Clearwater, FL

Windsor Woods is a small, established Clearwater community of just under 100 homes spanning nearly five decades of construction, where roughly 87% of owners carry a homestead exemption — a sign of a settled, owner-occupied street rather than a rental-heavy one.

Stellar MLS sales records identify 48 homes in Windsor Woods that have changed hands since 2004, built between 1978 and 2005 (median 1980), with a median living area of about 2,011 sq ft and a typical 3-bedroom, 2-bath layout; 98% 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 4 qualified sales in Windsor Woods across 2024–2025 (3 in 2024, 1 in 2025), median $615,000 — 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.

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

In ZIP 33755, 163 homes are on the market and 23% are under contract — a steady corner of Clearwater.

Across Pinellas County, 6,539 homes are active and 1,627 pending (20% under contract).

In ZIP 33755 (Clearwater), 513 homes closed in the last 12 months at a median of $280K ($242/sq ft), down 4.7% year over year, with a median 52 days on market. Right now 64 active and 23 pending listings put supply at about 3.5 months — a balanced market. See the live ZIP 33755 housing market and the Pinellas County market.

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

The wide year-built range here — 1958 to 2004 — matters more than most buyers expect. Roof age, systems, and the depth of any renovation will swing what a home is worth far more than square footage alone. With a median build year around 1979, plenty of these homes are candidates for updating, and buyers should budget for inspections and price the work honestly rather than assume the median tells them what they will pay.

The generous median footprint of about 2,155 square feet means there is usually structure to work with, which favors buyers willing to modernize an original home and sellers who have already done the work. Because inventory is limited and closings are infrequent, the market can look quiet on the surface while a well-prepared listing still moves; the right pricing read is everything.

In a 98-home community with few recent sales, the number that gets published is almost never the number that fits your specific house. We price and negotiate off condition, systems, and the handful of genuinely comparable closings rather than a blanket neighborhood figure — and we will tell you plainly when a home needs work the asking price does not reflect.

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