Windermere
Homes for Sale in Windermere, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Over the 12 months ending 2026-09-03, 4 recorded sales closed at a median of $1,287,500, $426 per square foot, a median 54 days on market, sellers accepting 78% of original asking (-47% versus the prior year). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $21,470 ($20,800 with the full homestead exemption).
Windermere sits in Orange County on the chain of lakes west of Orlando, and price here is driven far more by the specific lot and structure than by any neighborhood average. Waterfront versus interior, gated enclave versus older lakeside street, original build versus renovated — those distinctions move the number more than anything, which is why a single median tells you very little about what a given address should trade for.
Because value is so condition- and location-specific, both sides need to underwrite the individual home rather than lean on a headline figure. For buyers, that means scrutinizing what you're actually paying for beyond the acreage and water access. For sellers, it means the pricing conversation starts with an honest read of your home's condition and position, not a comp pulled from a very different property down the road.
Windermere right now
🔴 Off the recent peak. The trailing-12-month median ($1.29M) is down 47.1% from the prior 12 months ($2.43M). With about 2 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 September 3. Confidence: Low (4 and 4 sales in the two windows).
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Updated September 3, 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
Windermere market snapshot (as of September 3, 2026): the median sale price is about $1.29M ($426 per sq ft over the trailing 12 months of closed sales), and a median 55 days on market for closed sales. The trailing-12-month median is down 47% from the prior 12 months, computed from record-level Stellar MLS closed sales (4 closings in the current window).
Windermere is a lake-oriented community west of Orlando where the spread between properties is wide, so the story is always the individual home and its relationship to the water, the lot, and its finish level rather than a tidy town-wide number.
Who Windermere is best for.
Best for
- Buyers prioritizing lake access and larger lots who are prepared to pay for water frontage and evaluate each property individually
- Buyers with the budget and patience to compare distinct property types and do full diligence on condition and association terms
- Buyers who value an established, lake-oriented setting near the west side of the Orlando metro
Probably not for
- Buyers who want a standardized, easily comparable product with a predictable price-per-foot
- Buyers looking for a quick, low-diligence purchase off a headline market figure
- Buyers who don't want to pay a premium for water access or acreage
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 3 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($1.29M) IS the median in the snapshot above, and the move from 2025 ($2.43M) IS the -47.1% one-year change.
Windows contain 0 to 7 sales each (4 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 2004 through 2026. Deemed reliable but not guaranteed.
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.
24% of homes for sale in ZIP 34786 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-08-30).
The Windermere buying strategy.
If we were buying in Windermere 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.
Why the lot writes the price
The defining feature of Windermere is its setting on the Butler Chain of Lakes, and that geography fragments the market into very different products. A direct-waterfront parcel with a dock, an interior lot in a gated community, and an older home on a quiet street near town all live under the same name and behave like separate markets. Buyers should expect to compare properties on their merits, not on price-per-square-foot shortcuts.
Condition and vintage matter just as much as position. Windermere carries both established, mature-lot homes and newer construction, and the gap between an updated home and one needing work can be substantial. Do the diligence on the structure, the water access, and any association obligations before you anchor on a number.
The location and the amenities are priced into every listing in Windermere. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a market this driven by the specific lot, water access, and condition, the value of a broker is in reading one property against genuinely comparable ones instead of a town-wide average that hides more than it reveals. We'll walk the lot, weigh the water access and the finish level honestly, and tell you when a listing is priced for a home it isn't — on either side of the deal.
Windermere 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 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 sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windermere, 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 home worth?
Get a no-obligation home value based on real comparable sales in Windermere, 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 on the map →
Frequently Asked Questions
What is the median home price in Windermere?
How long do homes in Windermere take to sell?
Who is the best real estate agent for Windermere?
How do I find a top Windermere real estate agent who knows Windermere?
Can Momentum Realty connect me with an agent for Windermere?
Should you buy in Windermere?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 3, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-08-30 |
| Historical depth | Closed-sale records back to 2004 (103 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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