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 3Rd Add in Clearwater, FL since 2014, the most recent in July 2026. 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).
What sets price in Windsor Park Add is condition, not location premium. With a median build year of 1970 and homes stretching back to 1922 and forward to 2022, this is a wide-spread market where a renovated house and a tired original sit on the same street at very different numbers. The median living area of roughly 1,691 square feet points to modest, right-sized homes rather than sprawl, so the spread you see is driven mostly by what has been done to the house.
The posture here is settled rather than churning. A homestead share of about 73% tells you most of these homes are held long-term, which tends to keep inventory tight and turnover slow. For a buyer that means patience and a willingness to move when the right updated home appears; for a seller it means the condition of your home is the lever you control, and pricing to the actual work done matters more than chasing a neighbor's headline number.
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
Windsor Park Add is a small, established Clearwater pocket of 137 homes in Pinellas County, with a housing stock centered on the 1970s but ranging from century-old cottages to recent builds. The mix rewards buyers who can read condition and renovation quality rather than square footage alone.
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 (2 in 2024, 2 in 2025), median $475,000 — 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 who want a compact, established home and are willing to wait for the right updated listing
- Renovation-minded buyers looking to buy on condition and add value through updates
- Long-hold owners who value a stable, low-turnover pocket over a fast-moving market
Probably not for
- Buyers who need a large floor plan well above the ~1,691-square-foot median
- Buyers wanting uniform, new-construction consistency across a subdivision
- Buyers on a tight timeline who cannot absorb inspection surprises or renovation costs
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.
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.
A century of housing stock on one map
The year-built range from 1922 to 2022 is the single most important fact about this community. You are not shopping one era of construction; you are shopping a full spectrum, from prewar cottages to homes finished within the last few years. That means inspection discipline matters here — roof, systems, and prior permit history will vary enormously house to house, and two listings a block apart can carry completely different maintenance realities.
With a median living area near 1,691 square feet, most homes here are compact and practical rather than oversized. The value question is almost always about condition and updates: an original 1970 house and a rebuilt or newer one occupy the same neighborhood but not the same price tier. Bring a contractor's eye, and treat the median price as a midpoint of a wide, condition-driven range rather than a going rate.
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 137-home community where turnover is slow and roughly 73% of homes are held as homestead, listings are scarce and condition is everything. We track what actually trades, help you separate a genuinely updated home from a cosmetic flip, and price your sale to the work done rather than to a neighbor's asking number. That local read is what keeps you from overpaying on a buy or underpricing on a sale.
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
| Live listings | Stellar MLS, refreshed twice daily (last: September 19, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2014 (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.
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
Explore more neighborhoods near Windsor Park with Momentum Realty’s local guides.
Windsor Park 3Rd Add Market Scorecard
Windsor Park 3Rd Add is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 33755 ZIP is $342,659, about 15.2% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.