0 Homes
Windermere, FL homes for sale under $250,000
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Windermere Market Trends
All Home Types
In the last 30 days, homes for sale in Windermere, FL sold for a median price of $940,000, down 6% compared to the same period last year. The median price per square foot was $299.45, down 5.2% year-over-year. There were 49 homes sold, up from 48 last year.
Median Sale Price
$940,000
-6% year-over-year
Median Price per Sq. Ft.
$299.45
-5.2% year-over-year
Number of Homes Sold
49
+2.1% year-over-year
Frequently Asked Questions
What is the median home sale price in Windermere, FL?
In the last 30 days, the median home sale price in Windermere was $940,000, down 6% compared to the same period last year. The "median" price is the middle price - half of the homes here were sold for less, the other half for more.
How many homes are for sale in Windermere, FL?
There were 230 homes for sale in Windermere as of September 23, 2025. There were 60 new listings within the last 30 days as well. The more homes on the market, the more choices buyers have.
How up-to-date are Orchard's new listings in Windermere, FL?
The new homes and houses for sale on Orchard's listings pages are updated hundreds of times each day, with listings in Windermere last seen updated at . New listings can appear every day, but many listings first appear on the market mid-week.
How much competition is there to buy a home in Windermere, FL?
In the last 30 days, the median number of days a home in Windermere remained on the market (DOM) was 56. In areas with a low DOM, homes are sold quickly and the competition is fierce; in areas with higher DOMs, you may have more options and more time to make an offer.
Home Buying Resources
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Based on information submitted to the MLS GRID as of 9/24/2025, 10:54PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.