Windermere
Housing Market
Median sale price $640,000, down 1.5% year over year, with homes going under contract in about 37 days, 100 homes on the market.
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Housing Market Analyst
Inventory sits at 3.3 months of supply — balanced by the 3-to-6-month balanced benchmark, and 24% of listed homes are already under contract. Prices are down 1.5% versus the prior year, but sellers are still collecting 95.0% of asking. Taken together, the data points to a broadly balanced market where preparation decides who wins.
Who has leverage right now
Leverage scores are derived from the Momentum Score (supply, demand, speed, pricing power, and trend). Right now the data favors sellers.
- Prices — more likely to stabilize than fall sharply. Supply remains below balanced levels even as prices soften; without a meaningful inventory build, further declines tend to be shallow.
- Inventory — building over the tracked window; watch whether that holds through the season.
- Negotiating power — sellers hold the leverage while 24% of inventory sits under contract.
- Mortgage sensitivity — at 5.2× income, this market is highly sensitive to rate moves; rate relief tends to show up in demand here quickly.
Derived from current Windermere data, not a prediction or guarantee. Markets move; talk to an agent before acting on any single reading.
One inventory number hides four different markets
Months of supply = active listings ÷ monthly sales pace, bucketing communities by their recent median. 3–6 months is the balanced band.
Where Windermere is hot — and where it isn't
Each dot is a community (84 shown, sized by sales volume rank). Click any dot to open its full neighborhood guide.
The read on Windermere
The median sale price across Windermere currently stands at $640,000, down 1.5% from a year ago. Buyers are paying a median of $268 per square foot. The typical home goes under contract in about 37 days. Sellers are capturing 95.0% of their original asking price on average.
There are 100 active listings on the market, with 32 more already under contract. At the current sales pace that works out to 3.3 months of supply — a seller-leaning market by the standard six-month benchmark. 426 homes closed here over the trailing 12 months.
Windermere prices sit above the Orange County median by roughly 38%. Zillow's home value index for Orange County stands at $403,786. About 27% of listings county-wide have taken a price cut — a useful gauge of seller flexibility.
Weighing supply, demand, speed, pricing power, and trend together, the Momentum Score for Windermere is 60 of 100 — balanced market territory. This page recalculates every day as new MLS data lands, so the numbers above reflect the market as of September 15, 2026.
Windermere since 2012 — and where it’s heading
A median home here sold for $420,857 in 2012 and $981,693 over the last recorded year — 133% appreciation across 14 years of recorded sales. Cash buyers took 27% of recent sales, down from a 46% peak.
Median sale price · 2012–2026 (7,117 recorded sales)
Days on market by year
Cash buyers · share of sales
Home value trend · Orange County (Zillow ZHVI)
For-sale inventory · county (Zillow)
Daily active vs pending · Orange County (MLS)
Median price · daily recalculation
What’s driving Windermere
Top inbound states: NY, CA, NJ, TX. Movers arriving report ~$66,457 average income. Source: IRS SOI county-to-county migration, 2022-2023
4,204 Citizens policies in force in Orange County — the state-backed insurer of last resort. Budget insurance into any Orange purchase before you fall in love with a house. Source: Citizens Property Insurance, Detail by County, April 2026
4,221 single-family · 8,919 multi-family · 9.1 per 1,000 residents. Future supply pressure starts here. Source: U.S. Census Bureau, Building Permits Survey, 2025
The calls we’re making from today’s data
The sharpest 1-yr median swing among tracked communities. Thin samples can exaggerate swings — verify with a comp analysis before treating it as trend.
The most crowded shelf in the market. Sellers here are competing hardest — which means overpaying in this band is the most avoidable mistake in Windermere right now.
The tightest band — sellers in this range hold the most leverage, and buyers should walk in with financing done and terms clean.
Sellers: price to the last 60 days of comps, not the peak — well-prepared listings are still commanding strong terms. Buyers: get underwritten now so you can move when the right house hits.
Generated from today’s data by Momentum’s analysis engine and reviewed on a rolling basis by our broker team.
How it stacks up across Orange County
| Market | Median | Active | Score | |
|---|---|---|---|---|
| Windermere ← this page | $640K | 100 | 60 | |
| Orlando | $412K | 1,608 | 58 | Open → |
| Winter Garden | $595K | 348 | 62 | Open → |
| Apopka | $406K | 229 | 70 | Open → |
| Winter Park | $459K | 124 | 58 | Open → |
| Ocoee | $475K | 53 | 77 | Open → |
Neighborhoods on the move
| windermere isleWindermere | $1.00M | ▲ 24% |
| WATERSTONEWindermere | $1.52M | ▲ 12% |
| Keenes Pointe Unit 9Windermere | $1.61M | ▲ 9% |
| LAKE SAWYER SOUTH PH 03Windermere | $640K | ▲ 7% |
| summerportWindermere | $570K | ▲ 6% |
| Windermere TownWindermere | $895K | ▼ 29% |
| Windermere TerraceWindermere | $573K | ▼ 12% |
| silver woodsWindermere | $515K | ▼ 11% |
| IsleworthWindermere | $3.85M | ▼ 11% |
| WINDERMERE TRLS PH 1CWindermere | $602K | ▼ 11% |
| KEENES POINTEWindermere | $1.55M | 19 |
| windermere trailsWindermere | $600K | 11 |
| summerportWindermere | $570K | 6 |
| Windermere TownWindermere | $895K | 6 |
| lake burden south ph iWindermere | $430K | 5 |
| summerportWindermere | $570K | 10 days |
| Wickham Park 04 05 06 09 10 11 12 01 WindermereWindermere | $374K | 16 days |
| IsleworthWindermere | $3.85M | 18 days |
| Lake Sawyer South Ph 5Windermere | $622K | 22 days |
| Windermere TerraceWindermere | $573K | 23 days |
Windermere ZIP codes
Most active communities
More on Windermere
Put this data to work
The questions people actually ask
Should I buy a house in Windermere right now?
The data says conditions currently favor neither side decisively in Windermere — the Momentum Score reads 60/100 with 3.3 months of supply. For buyers that means preparation over hesitation: well-priced homes still move fast, but there is more room to negotiate than a year ago. The right timing always depends on your rate, your equity, and how long you plan to stay — not just the market.
Is Windermere becoming more affordable?
Yes, modestly — the median sale price in Windermere is $640,000, down 1.5% versus the prior year, while sellers still capture 95.0% of asking price. Softening prices plus normal-length marketing times mean affordability is improving at the margin, though financing costs matter more than list prices for most monthly payments.
Where are prices falling fastest in Windermere?
Among tracked communities with enough sales to measure, the sharpest 1-year median declines are Windermere Town (-29%); Windermere Terrace (-12%); silver woods (-11%). Note that community-level medians move on small sale counts — a few high- or low-end closings can swing them — so treat these as leads for a comp analysis, not verdicts.
Which Windermere neighborhoods are most competitive?
Measured by speed of sale, the fastest-moving tracked communities right now are summerport (10 days); Wickham Park 04 05 06 09 10 11 12 01 Windermere (16 days); Isleworth (18 days) — homes there go under contract well ahead of the market-wide pace of 37 days.
How does Windermere compare to the rest of Orange County?
Windermere's median of $640,000 runs 38% above the county-wide median of $462,500, and homes here take 37 days to go under contract versus 40 county-wide.
Windermere housing market FAQ
How is the housing market in Windermere right now?
As of September 15, 2026, the Windermere housing market favors sellers: the median sale price is $640,000 (down 1.5% year over year), 100 homes are for sale against 426 sales in the last 12 months, which is 3.3 months of supply, and the typical home goes under contract in about 37 days.
How much is a house in Windermere?
The median home sold for $640,000 in Windermere over the last 12 months, about $268 per square foot; asking prices on the 100 current listings run from well below to well above that, and the community pages linked below show what each neighborhood actually sells for.
Is it a good time to sell a house in Windermere?
By the numbers, sellers in Windermere are getting 95.0% of asking price and going under contract in about 37 days with 3.3 months of supply. Under four months of supply generally favors sellers; over six favors buyers. Whether it is a good time for you depends on what you paid and where you are going next, which is a conversation with an agent, not a chart.
What is the Windermere housing market forecast?
Momentum Realty publishes the recorded trend, not a prediction: Windermere median sale prices are down 1.5% year over year, inventory stands at 3.3 months of supply, and 24% of listings are under contract. The charts on this page update with every MLS refresh, so the direction shows up here before any forecast catches it.
What is the median home price in Windermere?
The median sale price in Windermere is currently $640,000, down 1.5% from a year ago, based on MLS sales data updated September 15, 2026.
Is Windermere a buyer's or seller's market right now?
The data currently favors sellers. Windermere scores 60 of 100 on the Momentum Score, with 3.3 months of housing supply. Conditions change; this page updates daily.
How long do homes take to sell in Windermere?
The typical home in Windermere goes under contract in about 37 days, per current MLS data.
How many homes are for sale in Windermere?
There are approximately 100 active listings in Windermere as of September 15, 2026.
Are home prices in Windermere rising or falling?
Median sale prices are down 1.5% year over year based on a rolling comparison of MLS sales.
Momentum agents use this intelligence every day to price listings and write winning offers across Windermere. Talk through what the numbers mean for your move.
Every number on this page is computed directly from licensed Florida MLS feeds, recorded public sales, Zillow Research, and U.S. Census data — nothing is manually adjusted or estimated by hand. Medians use recorded closed sales; supply figures use live listing counts refreshed twice daily; the Momentum Score methodology is summarized .
Analyst oversight: Jon Brooks — Co-Founder, Momentum Realty · CEO, Momentum Research · Housing Market Analyst · methodology reviewed quarterly · Last data refresh: September 15, 2026 at 7:33 PM ET
Statistics on this page are computed automatically from licensed MLS feeds and public data sources (Zillow Research, U.S. Census Bureau) and summarized without manual review. Figures are estimates based on recent recorded activity, are deemed reliable but not guaranteed, and should be verified with a licensed agent before making decisions. This page does not constitute an appraisal or an automated valuation of any specific property. Momentum Realty is licensed in Florida and Georgia. Equal Housing Opportunity.