326 listings available right now — swipe to find your perfect match.
Updated daily ·
326
Active Listings
$1,878,809
Avg. Price
$295,000
Starting From
$30,000,000
Up To
The median home price in Windermere is $999,999, with listings ranging from $295,000 to $30,000,000. Buyers can expect to pay around $421/sqft on average. Homes typically spend 95 days on market.
Price Distribution
34 Windermere homes dropped price in the last 30 days · average drop -3.4%.
5067 Sawyer Cove Way
$2,490,000 → $2,224,900 · 2026-05-15
5538 W Lake Butler Rd
$3,495,000 → $3,195,000 · 2026-05-15
5413 Walsh Pond Ct
$875,000 → $800,000 · 2026-05-08
5106 Tildens Grove Blvd
$1,700,000 → $1,600,000 · 2026-05-14
11419 Camden Park Dr
$1,375,000 → $1,295,000 · 2026-05-17
6840 Helmsley Cir
$689,000 → $649,000 · 2026-05-07
And 28 more — sorted by largest drop first.
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Start SwipingWindermere listings average 4.3 bedrooms, 4.2 bathrooms, and 3,740 square feet. The average year built is 2004. Single Family homes are the most common property type, making up 87% of available inventory.
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Start Swiping in WindermereRight now there are 326 homes for sale across Windermere. Asking prices run from $295,000 to $30,000,000, landing on a $999,999 median, averaging $421 per square foot. The dominant property type is single family (87% of inventory). Townhouse (11%) and Condo (2%) round out the mix.
The average home here has 4.3 bedrooms, 4.2 bathrooms, 3,740 square feet. Average year built: 2004. Homes typically go under contract after 95 days on market.
Lakeside Village, Lake Butler, Keenes Pointe, Lakes of Windermere are among the most-listed neighborhoods in Windermere. Each has its own character and price point — worth exploring whether you're optimizing for walkability, schools, views, or square footage.
Rather than scrolling endless grids, you can swipe Windermere homes on HomeSwipr one at a time. The more you swipe, the better it gets at surfacing homes you'd actually tour.
There are 326 homes for sale in Windermere, FL right now, with prices ranging from $295,000 to $30,000,000. Inventory is refreshed daily from live listing feeds.
The median home price in Windermere is $999,999, with an average of $1,878,809. Prices span $295,000 to $30,000,000 across 326 current listings.
The average price per square foot in Windermere is $421 based on current listings. Per-sqft varies meaningfully by neighborhood and property type within the city.
Single Family homes dominate Windermere inventory at 87% of listings. Townhouse (11%) and Condo (2%) round out the mix.
A typical Windermere listing offers 4.3 bedrooms, 4.2 bathrooms, and 3,740 square feet, with an average year built of 2004.
Active inventory in Windermere is concentrated in Lakeside Village, Lake Butler, Keenes Pointe, Lakes of Windermere. Each neighborhood differs on price and property type, so comparing across them usually surfaces more range than a single one.
Windermere homes have been on the market an average of 95 days. Newer listings (under 7 days) typically indicate fresh inventory worth early attention.
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