147 Homes
Windermere, FL homes on Orchard for more than 60 days
In the last 30 days, Windermere home prices were down 10.5% compared to last year. The median price of a home was $850,000. View Windermere Market Insights
1 / 3
Price Drop
$1,139,000
$1,202,310
OLYMPUS EXECUTIVE REALTY INC • MLS G5101495 • Status: Active
1 / 62
Price Drop
$1,639,985
$1,649,985
NOBSKA REAL ESTATE LLC • MLS O6338904 • Status: Active
1 / 63
Price Drop
$765,000
$799,000
WRA BUSINESS & REAL ESTATE • MLS O6338823 • Status: Active
1 / 30
$3,200,000
EPIQUE REALTY, INC. • MLS TB8421056 • Status: Active
1 / 44
Price Drop
$775,000
$795,000
HOMEVEST REALTY • MLS O6328443 • Status: Active
1 / 55
Price Drop
$2,399,000
$2,425,000
UPSIDE REAL ESTATE INC • MLS O6290296 • Status: Active
1 / 46
Price Drop
$2,000,000
$2,150,000
NOVA REAL ESTATE SERVICES INC • MLS O6271044 • Status: Active
1 / 34
Price Drop
$659,000
$675,000
SERHANT • MLS O6337094 • Status: Active
1 / 51
$3,950,000
REVEL REALTY LLC • MLS O6312690 • Status: Active
1 / 59
Price Drop
$1,660,000
$1,750,000
COLDWELL BANKER RESIDENTIAL RE • MLS O6333319 • Status: Active
1 / 39
Price Drop
$875,000
$899,900
THE WILKINS WAY LLC • MLS O6325415 • Status: Active
1 / 42
Price Drop
$575,000
$585,000
REDFIN CORPORATION • MLS O6315831 • Status: Active
1 / 60
Price Drop
$1,250,000
$1,380,500
KELLER WILLIAMS CLASSIC • MLS O6288931 • Status: Active
1 / 36
Price Drop
$627,500
$635,000
COMPASS FLORIDA LLC • MLS O6336925 • Status: Active
1 / 49
Price Drop
$1,389,000
$1,448,000
ALIGN REAL ESTATE LLC • MLS O6336789 • Status: Active
1 / 49
Price Drop
$934,900
$954,900
COLDWELL BANKER RESIDENTIAL RE • MLS O6334881 • Status: Active
1 / 42
Price Drop
$649,900
$664,900
CORE REAL ESTATE GROUP • MLS O6330497 • Status: Active
1 / 70
Price Drop
$850,000
$869,000
CENTURY 21 CARIOTI • MLS O6327172 • Status: Active
1 / 18
Price Drop
$1,299,000
$1,375,000
ALL REAL ESTATE & INVESTMENTS • MLS O6328889 • Status: Active
1 / 44
Price Drop
$749,900
$754,900
US SQUARE REAL ESTATE • MLS O6321333 • Status: Active
1 / 21
Price Drop
$397,499
$399,999
PREFERRED REAL ESTATE BROKERS • MLS O6311347 • Status: Active
1 / 90
Price Drop
$6,799,000
$7,250,000
THE SIMON SIMAAN GROUP • MLS O6315165 • Status: Active
1 / 100
Back On Market
$2,650,000
MAXIM REALTY ORLANDO • MLS S5129274 • Status: Active
1 / 70
$6,800,000
SOUTHERN REALTY GROUP LLC • MLS O6312645 • Status: Active
1 / 54
Price Drop
$1,295,000
$1,325,000
KEENE'S POINTE REALTY • MLS O6333065 • Status: Active
1 / 53
$2,300,000
COMPASS FLORIDA LLC • MLS O6273288 • Status: Active
1 / 42
$2,799,000
SOUTHERN REALTY GROUP LLC • MLS O6288273 • Status: Active
1 / 1
Price Drop
$2,850,000
$2,995,000
KELLER WILLIAMS ELITE PARTNERS III REALTY • MLS O6305503 • Status: Active
1 / 51
Price Drop
$1,080,000
$1,110,000
KELLER WILLIAMS ELITE PARTNERS III REALTY • MLS O6333377 • Status: Active
1 / 53
Price Drop
$650,000
$660,000
THE SIMON SIMAAN GROUP • MLS O6330995 • Status: Active
1 / 100
$3,250,000
THE SIMON SIMAAN GROUP • MLS O6324115 • Status: Active
1 / 100
Price Drop
$3,500,000
$3,650,000
THE SIMON SIMAAN GROUP • MLS O6296796 • Status: Active
1 / 13
$2,200,000
COMPASS FLORIDA LLC • MLS O6322270 • Status: Active
1 / 16
Price Drop
$850,000
$875,000
FATHOM REALTY FL LLC • MLS O6327464 • Status: Active
1 / 93
Price Drop
$4,399,999
$4,500,000
JACK KELLER INC • MLS TB8382641 • Status: Active
1 / 81
$5,489,000
EXP REALTY LLC • MLS O6336879 • Status: Active
Viewing 1-36 of 147 homes
Windermere Market Trends
All Home Types
In the last 30 days, homes for sale in Windermere, FL sold for a median price of $850,000, down 10.5% compared to the same period last year. The median price per square foot was $295.41, down 1.3% year-over-year. There were 31 homes sold, down from 53 last year.
Median Sale Price
$850,000
-10.5% year-over-year
Median Price per Sq. Ft.
$295.41
-1.3% year-over-year
Number of Homes Sold
31
-41.5% 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 $850,000, down 10.5% 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 243 homes for sale in Windermere as of October 27, 2025. There were 68 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 22. 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 10/28/2025, 10:35PM. 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.