Windsor Park
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 12 closed sales in Windsor Park 2Nd Add in Clearwater, FL since 2013, the most recent in March 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 Park Add is a small, established pocket of Clearwater — 57 homes built between 1962 and 1988, with the middle of the pack dating to 1968. At a median of roughly 1,785 square feet, these are mid-century-era single-family homes, and in a subdivision this age condition is the price story. Two homes of similar footprint can trade well apart depending on roof, systems, and whether the kitchen and baths have been touched. There is no single price band here; expect a wide spread driven by updates, not square footage.
The other number that matters is the homestead share: about 83% of these homes are owner-occupied on homestead. That points to a tightly held, low-churn street where inventory is thin and turnover is slow. For a seller, a well-maintained or updated home has scarcity working in its favor. For a buyer, patience matters — you may wait for the right listing rather than choose from many, and you should underwrite the cost of bringing an older home current.
Nearby homes for sale
No active listings inside Windsor ParkHomes 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
A compact enclave of 57 mid-century-era homes in Clearwater's Pinellas County, held largely by owner-occupants, where the difference between a dated and an updated house is the whole ballgame on price.
Stellar MLS sales records identify 88 homes in Windsor Park that have changed hands since 2004, built between 1962 and 1988 (median 1966), with a median living area of about 1,453 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 4 qualified sales in Windsor Park across 2024–2025 (3 in 2024, 1 in 2025), median $480,000 — 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 Park is best for.
Best for
- Buyers targeting an established Clearwater location who will renovate an older home to their taste
- Long-hold owner-occupants who value a stable, low-turnover street over inventory selection
- Buyers with a renovation budget who want to buy on condition and build equity through updates
Probably not for
- Buyers who need newer construction and modern systems out of the box
- Shoppers who want many active listings to compare at once
- Buyers with no contingency budget for the maintenance older homes typically require
The market around Windsor Park
Windsor Park 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 Park specifically. Momentum Research analysis of MLS records.
Windsor Park Add by the numbers
From county property records and closed MLS sales for the Windsor Park Add subdivision: 12 homes on record; built 1964–1988; typical size about 1,570 heated sq ft; 2 bedrooms is the median. Housing mix: single-family 100%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2014 | 1 | $147,500 |
| 2017 | 3 | $226,500 |
| 2019 | 2 | $280,000 |
| 2021 | 1 | $320,000 |
| 2024 | 1 | $429,000 |
| 2025 | 1 | $427,000 |
Newest recorded sale: $427,000 on 2025-03-21.
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 Park buying strategy.
If we were buying in Windsor Park 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 Park.
An older, owner-held Clearwater pocket
With a build window of 1962 to 1988 and a median year built of 1968, this is a neighborhood where you buy the bones and the location, then judge each house on what has been done to it since. Median living area sits near 1,785 square feet — enough room to work with, but the meaningful variable is mechanical and cosmetic condition. Roof age, plumbing and electrical updates, window replacement, and kitchen/bath renovation will separate one asking price from another far more than layout will.
The 82.5% homestead share tells you this is a place people stay. That stability keeps supply limited, so listings can be worth acting on when they appear rather than waiting for a comparable that may not come soon. Buyers should budget for inspection findings typical of homes of this vintage; sellers who have already handled the big-ticket systems should document that work, because it is exactly what commands the top of this market.
The location and the amenities are priced into every listing in Windsor Park. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a 57-home neighborhood with thin turnover, comps are scarce and condition-adjusted pricing is everything. We read each home on its actual systems and updates rather than a blanket price-per-foot, and we know how to position an updated home against a dated one — on either side of the deal.
Windsor Park 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 Park 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 Park sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windsor Park, 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 Park home worth?
Get a no-obligation home value based on real comparable sales in Windsor Park, 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 Park?
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 2013 (12 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.
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See how Windsor Park Add fits the bigger picture — live prices, inventory, and Momentum Scores:
Schools serving nearby communities
We do not have a confirmed school assignment for Windsor Park. 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 Park
Where is Windsor Park?
Windsor Park is a community in Clearwater, Pinellas County, Florida, ZIP 33755.
How many homes are in Windsor Park?
County property records list 12 homes in Windsor Park, built between 1964 and 1988; the typical home is about 1,570 heated square feet.
What do homes in Windsor Park sell for?
Windsor Park has no MLS sales in the last 12 months. The most recent year with recorded sales on file is 2025 (1 sale, median $427,000). For context, ZIP 33755 has 160 homes on the market with 19% under contract.
Are there homes for sale in Windsor Park right now?
No active listings inside Windsor Park 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 Park have an HOA or CDD?
No HOA is on record for Windsor Park 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
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