Windsor Woods
Homes for Sale in Clearwater, FL
All 1,157 homes for sale in Clearwater, FL · median $299,000 · 138 homes for sale in 33755 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, the MLS records 14 closed sales in Windsor Woods Ii in Clearwater, FL since 2004, the most recent in April 2025. Across Clearwater as a whole, 1,358 homes closed in the last 12 months at a median of $312,500, 50 median days on market, with 415 homes for sale today. At that median and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $6,060 ($5,250 with the full homestead exemption).
Windsor Woods II sits in Clearwater, in the heart of Pinellas County, and pricing here is going to be driven by the individual home more than by any neighborhood-wide number. Without a current median or spread in front of me, I'd treat condition, updates, and lot position as the levers that move value in this pocket rather than assuming a floor or ceiling.
For a buyer, that means underwriting each listing on its own merits and not anchoring to a rumored range. For a seller, it means presentation and honest condition disclosure will do more for your outcome than chasing a headline figure. Come to the table with real comps, not aspirations.
Nearby homes for sale
No active listings inside Windsor WoodsHomes for Sale in Clearwater, FL right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Windsor Woods II is a defined residential community within Clearwater, giving buyers the pull of a central Pinellas County location without the anonymity of a larger, sprawling subdivision.
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 3 qualified sales in Windsor Woods across 2024–2025 (2 in 2024, 1 in 2025), median $720,000 — 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.
Who Windsor Woods is best for.
Best for
- Buyers prioritizing a central Pinellas County location over new-construction polish
- Buyers willing to underwrite each home on its own condition and updates
- Owner-occupants planning to hold rather than flip on a short timeline
Probably not for
- Buyers who need a predictable, published price band before touring
- Buyers wanting resort-style community amenities and heavy HOA programming
- Investors chasing a quick, low-effort turnaround
The market around Windsor Woods
Windsor Woods is too small for its own price trend, so here is the market around it.
In ZIP 33755, 160 homes are on the market and 19% are under contract — a steady corner of Clearwater.
Across Pinellas County, 6,628 homes are active and 1,729 pending (21% 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.
Windsor Woods by the numbers
From county property records and closed MLS sales for the Windsor Woods subdivision: 12 homes on record; built 1987–1995; typical size about 2,165 heated sq ft; 3 bedrooms is the median. Housing mix: single-family 100%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2020 | 1 | $408,000 |
| 2021 | 2 | $435,000 |
| 2022 | 1 | $529,900 |
| 2023 | 2 | $582,500 |
| 2024 | 2 | $847,500 |
| 2025 | 1 | $577,500 |
Newest recorded sale: $577,500 on 2025-04-30.
Recorded data as of 2026-09-12; counts cover addresses tagged to this subdivision in the public record, not every parcel. Not an appraisal.
The Windsor Woods buying strategy.
If we were buying in Windsor Woods today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Windsor Woods.
The location and the amenities are priced into every listing in Windsor Woods. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small Clearwater community like Windsor Woods II, the difference between a fair deal and a mistake is knowing how each home compares to the last few that actually closed nearby. We work the Pinellas market on the ground, we read condition honestly, and we'll tell you when a listing isn't worth what it's asking.
Windsor Woods in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Windsor Woods buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Windsor Woods sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windsor Woods, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Windsor Woods home worth?
Get a no-obligation home value based on real comparable sales in Windsor Woods, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Clearwater →
Should you buy in Windsor Woods?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2004 (14 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Windsor Woods fits the bigger picture — live prices, inventory, and Momentum Scores:
Schools serving nearby communities
We do not have a confirmed school assignment for Windsor Woods. These are the public schools most often assigned to other communities in ZIP 33755; zones change and vary by address, so confirm with the district before you buy.
- Clearwater High · Public · FLDOE grade A (assigned to 3 nearby communities)
- Skycrest Elementary · Public · FLDOE grade A (assigned to 2 nearby communities)
- Clearwater High School · High · FLDOE grade A (assigned to 2 nearby communities)
Assignments from district data for neighboring communities; grades are official Florida Department of Education school grades (2025-26).
Common questions about Windsor Woods
Where is Windsor Woods?
Windsor Woods is a community in Clearwater, Pinellas County, Florida, ZIP 33755.
How many homes are in Windsor Woods?
County property records list 12 homes in Windsor Woods, built between 1987 and 1995; the typical home is about 2,165 heated square feet.
What do homes in Windsor Woods sell for?
Windsor Woods has no MLS sales in the last 12 months. The most recent year with recorded sales on file is 2025 (1 sale, median $577,500). For context, ZIP 33755 has 160 homes on the market with 19% under contract.
Are there homes for sale in Windsor Woods right now?
No active listings inside Windsor Woods at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Windsor Woods have an HOA or CDD?
No HOA is on record for Windsor Woods in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Windsor Woods with Momentum Realty’s local guides.