WINDSOR HILL
Homes for Sale in WINDERMERE, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
WINDSOR HILL right now
🟢 Buyer-leaning market. 12.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of August 2, 2026. Confidence: Medium (3 active and pending listings, 3 closed sales in 12 months).
🟢 Still climbing. The trailing-12-month median ($1.04M) is up 14.3% from the prior 12 months ($910K). With about 3 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Low (3 and 4 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
WINDSOR HILL market snapshot (as of August 2, 2026): the median sale price is about $1.04M ($320 per sq ft over the trailing 12 months of closed sales), a median 2 days on market for closed sales, and 12.0 months of supply, a buyer-leaning market. The trailing-12-month median is up 14% from the prior 12 months, computed from record-level Stellar MLS closed sales (3 closings in the current window).
WINDSOR HILL is a community of 100 homes in WINDERMERE, Orange County, built between 1980 and 2022 (median 1998), with a median living area of about 3,652 square feet. 84% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of WINDSOR HILL. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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WINDSOR HILLPrice History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($1.04M) IS the median in the snapshot above, and the move from 2025 ($910K) IS the +14.3% one-year change.
Windows contain 0 to 6 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2026. Deemed reliable but not guaranteed.
WINDSOR HILL Market Scorecard
WINDSOR HILL is currently a strong buyer's market. About 12.0 months of supply, a median asking price of $1,499,900, and homes go under contract in about 31 days.
Go deeper: 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.
Housing distress & ownership in WINDSOR HILL, WINDERMERE
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period August 2026 through August 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in WINDSOR HILL
Live MLS inventory for WINDSOR HILL. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 56 daysTop listing
Active · 62 days
Active · 93 daysActive and pending WINDSOR HILL listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2026. Tap any home to ask about it.
WINDSOR HILL on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at WINDSOR HILL
- Pickleball Court(s) · reported on 2 of 3 listings
- Playground · reported on 2 of 3 listings
- Tennis Court(s) · reported on 2 of 3 listings
- Basketball Court · reported on 1 of 3 listings
- Fence Restrictions · reported on 1 of 3 listings
- Park · reported on 1 of 3 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Thornebrooke Elem · Elementary
- Gotha Middle · Middle
- Olympia High · High
Zoned schools reflect the assignments reported on recent WINDSOR HILL listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any WINDSOR HILL address.
The WINDSOR HILL buying strategy.
If we were buying in WINDSOR HILL 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 HILL.
A closer look at the WINDSOR HILL market
At a median of $320 per square foot, WINDSOR HILL prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 12.0 months of supply, a buyer-leaning market and the trailing-12-month median up 14% year over year. Homes that do trade take a median 2 days on market, useful leverage on any listing that has lingered.
The housing stock is 100 homes built between 1980 and 2022, and 84% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in WINDSOR HILL. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in WINDSOR HILL buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 4 factors (6.5). Basis: Recent Direction +14.3% year-over-year; Liquidity & Demand 12.0 months of supply; Owner Commitment 84% owner-occupied; Pricing Power 97.3% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- Mandatory HOA. Confirm current dues
- 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 HILL 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 HILL sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in WINDSOR HILL, 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 HILL home worth?
Get a no-obligation home value based on real comparable sales in WINDSOR HILL, 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 homes for sale in WINDSOR HILL on the map →
Frequently Asked Questions
What is the median home price in WINDSOR HILL?
How long do homes in WINDSOR HILL take to sell?
Is WINDSOR HILL a buyer's or seller's market right now?
How many homes are in WINDSOR HILL?
What share of WINDSOR HILL is owner-occupied?
When were the homes in WINDSOR HILL built?
Do cash buyers compete in WINDSOR HILL?
Who is the best real estate agent for WINDSOR HILL?
How do I find a top WINDERMERE real estate agent who knows WINDSOR HILL?
Can Momentum Realty connect me with an agent for WINDSOR HILL?
Nearby Communities
Explore more neighborhoods near WINDSOR HILL with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (7 streets, ZIP 34786)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2005 (43 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 your area comps.
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