Windermere Downs
Homes for Sale in Windermere, FL
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
Price here is driven by the home itself, not a uniform product. With a build range spanning 1973 to 2023 and a median year built of 1988, you are looking at a community where original, lightly updated, and fully rebuilt homes sit side by side. The median sits at $825,000 on roughly $278 per square foot against a median of about 2,731 living square feet, but condition and level of renovation move individual homes well off that midpoint.
The current posture favors sellers of well-prepared homes. A median of 7 days on market signals that correctly priced, presentable listings move fast. For buyers, that means little room to deliberate on the best homes and a real need to have financing and inspection logistics ready before you tour. The closings window is thin, so treat any single comp with caution and lean on the broader pattern.
Figures in this note are as of July 13, 2026. The live market numbers elsewhere on this page update nightly and are newer.
The 60-Second Overview
Windermere Downs 1St Add is a small, established pocket of about 80 homes in Windermere, Orange County, where a wide age range means the real variable is how much a given home has been updated. A homestead share near 88% points to an owner-occupied, low-turnover street rather than an investor-driven one.
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 Windermere Downs is best for.
Best for
- Buyers targeting a mid-$800s budget who want more living space than a compact new build offers
- Long-hold owner-occupants comfortable in a low-turnover, established pocket
- Buyers open to a renovation or a recent rebuild and willing to price each home on its own condition
Probably not for
- Buyers needing a tight budget ceiling well under the median
- Investors chasing quick turnover in a heavily owner-occupied community
- Buyers who want uniform, standardized product and cannot underwrite home-by-home condition differences
The market around Windermere Downs
Windermere Downs is too small for its own price trend, so here is the market around it.
In ZIP 34786, 282 homes are on the market and 26% are under contract — a steady corner of Windermere.
Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).
ZIP and county figures describe the wider market, not Windermere Downs specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in Windermere Downs 1St Add, 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 October 2026 through October 2026. Deemed reliable but not guaranteed.
The Windermere Downs buying strategy.
If we were buying in Windermere Downs 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 Windermere Downs.
Age spread, condition-driven pricing
The story of this community is the gap between its oldest and newest homes. With construction dates running from 1973 through 2023 and the midpoint at 1988, no two sales are truly comparable on paper. A 1970s-era home in original condition and a recent rebuild can share a street and command very different numbers, which is why the $825,000 median tells you the center of gravity but not much about any one house.
At roughly 2,731 median living square feet and about $278 per square foot, homes here are substantial rather than compact. Buyers should underwrite each property on its own renovation level, systems age, and lot. Sellers should recognize that presentation and documented updates are what separate the fast, strong sales from the ones that sit.
The location and the amenities are priced into every listing in Windermere Downs. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A community this small with this much age variation rewards local reading over broad averages. We help sellers position a home against the right comps given its condition, and we help buyers move with speed and discipline when a 7-day median leaves little margin for hesitation.
Windermere Downs in 15 seconds.
Tools for a Windermere Downs 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 Windermere Downs sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windermere Downs, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Windermere Downs home worth?
Get a no-obligation home value based on real comparable sales in Windermere Downs, 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 Windermere Downs on the map →
Frequently Asked Questions
How many homes are in Windermere Downs?
What share of Windermere Downs is owner-occupied?
When were the homes in Windermere Downs built?
Who is the best real estate agent for Windermere Downs?
How do I find a top Windermere real estate agent who knows Windermere Downs?
Can Momentum Realty connect me with an agent for Windermere Downs?
Should you buy in Windermere Downs?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Windermere Downs with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 26, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (4 streets, ZIP 34786)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2006 (36 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 Windermere Downs 1St Add fits the bigger picture — live prices, inventory, and Momentum Scores: