Windermere Town
Homes for Sale in Windermere, FL
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 3 closed sales in windermere town rep in Windermere, FL since 2017, the most recent in February 2026. Across Windermere as a whole, 440 homes closed in the last 12 months at a median of $640,000, 40 median days on market, with 126 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $10,670 ($10,000 with the full homestead exemption).
With only 43 homes active in the Stellar MLS feed for this Windermere segment, pricing here is set home-by-home rather than by a tight comparable set. The build spread - from 1927 up through 2024, with a median year built of 1979 - means condition and age do more to explain any given asking price than location alone.
A median living area of 2,749 square feet points to larger-format homes rather than starter product, and a 62.2% homestead share suggests a market weighted toward owner-occupants rather than transient or investor-heavy ownership. For sellers, that supports a straightforward, condition-first pricing conversation; for buyers, it means each listing has to be evaluated on its own age and updates rather than assumed to track a neighborhood norm.
The 60-Second Overview
This is a small, mixed-vintage slice of Windermere in Orange County - homes here span nearly a century of construction, with a median year built of 1979 and a median size of 2,749 square feet, and no community amenities are identified from current MLS listings.
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 Town is best for.
Best for
- Buyers seeking a larger living footprint (median near 2,749 square feet) rather than a compact or starter layout
- Buyers comfortable evaluating construction age case-by-case, given a build range stretching from 1927 to 2024
- Sellers or buyers prioritizing owner-occupied surroundings, reflected in the 62.2% homestead share
Probably not for
- Buyers who want a packaged set of community amenities, since none are identified from current MLS listings
- Buyers who need a tightly uniform architectural style, given the near century-long build spread
- Buyers expecting a large active inventory to compare against, since only 43 homes make up this dataset
The market around Windermere Town
Windermere Town is too small for its own price trend, so here is the market around it.
In ZIP 34786, 336 homes are on the market and 26% are under contract — a steady corner of Windermere.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
ZIP and county figures describe the wider market, not Windermere Town specifically. Momentum Research analysis of MLS records.
windermere town rep by the numbers
From county property records and closed MLS sales for the windermere town rep subdivision: 8 homes on record; built 1954–2025; typical size about 2,914 heated sq ft; 3.5 bedrooms is the median. Housing mix: single-family 100%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2015 | 1 | $400,000 |
| 2017 | 1 | $347,500 |
| 2019 | 1 | $910,000 |
| 2020 | 2 | $805,000 |
| 2021 | 1 | $700,000 |
| 2026 | 1 | $2,075,000 |
Newest recorded sale: $2,075,000 on 2026-02-09.
Recorded data as of 2026-09-12; counts cover addresses tagged to this subdivision in the public record, not every parcel. Not an appraisal.
Housing distress & ownership in WINDERMERE TOWN REP, 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 September 2026 through September 2026. Deemed reliable but not guaranteed.
The Windermere Town buying strategy.
If we were buying in Windermere Town 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 Town.
A market defined by age spread, not uniformity
Forty-three homes is a small enough pool that this cannot be treated like a cookie-cutter subdivision. The 1927-to-2024 build range means original construction, mid-century homes, and new builds are all competing in the same dataset, and a median year built of 1979 lands roughly in the middle of that span rather than at either extreme.
The 2,749-square-foot median points to homes built for more living space than an entry-level footprint, which tends to draw buyers looking to settle in rather than churn through a starter purchase - a read reinforced by the 62.2% homestead share. No community amenities are identified from current MLS listings, so buyers evaluating lifestyle draws should look at what's within reach of the immediate area rather than assume an on-site amenity package.
The location and the amenities are priced into every listing in Windermere Town. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a pool this small - 43 homes spanning nearly a century of construction - pricing and comparables require case-by-case judgment rather than a formula. We walk each listing's age, condition, and size against what's actually active in the feed, so you're not pricing a 1930s home off a 2020s comp or vice versa.
Windermere Town 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 Windermere Town 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 Town sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windermere Town, 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 Town home worth?
Get a no-obligation home value based on real comparable sales in Windermere Town, 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 Town on the map →
Should you buy in Windermere Town?
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 2017 (3 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.
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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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The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.