Windermere
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56 Homes

Windermere, FL homes on Orchard for less than 30 days

In the last 30 days, Windermere home prices were down 7.2% compared to last year. The median price of a home was $900,000. View Windermere Market Insights

1 / 36
Windermere
6864 Helmsley Cir
6864 Helmsley Cir
  • 3 beds
  • 2 baths
  • 1,609 sqft
$485,000
1 / 51
Windermere
8337 Vivaro Isle Way
8337 Vivaro Isle Way
  • 5 beds
  • 4 baths
  • 3,294 sqft
$850,000
1 / 63
Windermere
101 Lee St
101 Lee St
  • 5 beds
  • 4 baths
  • 4,186 sqft
$1,650,000
1 / 61
Windermere
1250 Belfiore Way
1250 Belfiore Way
  • 5 beds
  • 4.5 baths
  • 4,175 sqft
$1,225,000
1 / 30
Windermere
10600 Reams Rd
10600 Reams Rd
  • 3 beds
  • 2.5 baths
  • 1,845 sqft
$500,000
1 / 40
Price Drop
Windermere
13775 Bressler Aly
13775 Bressler Aly
  • 3 beds
  • 2.5 baths
  • 2,001 sqft
$460,000
$470,000
1 / 69
Windermere
13448 Bellaria Cir
13448 Bellaria Cir
  • 6 beds
  • 7 baths
  • 6,308 sqft
$3,250,000
1 / 51
Windermere
4926 Indian Deer Rd
4926 Indian Deer Rd
  • 5 beds
  • 4.5 baths
  • 3,849 sqft
$960,000
1 / 63
Windermere
1703 Roberts Landing Rd
1703 Roberts Landing Rd
  • 4 beds
  • 4.5 baths
  • 3,288 sqft
$1,680,000
1 / 46
Windermere
13943 Eden Isle Blvd
13943 Eden Isle Blvd
  • 4 beds
  • 2 baths
  • 2,420 sqft
$625,000
1 / 89
Windermere
6102 S Hampshire Ct
6102 S Hampshire Ct
  • 4 beds
  • 5.5 baths
  • 4,810 sqft
$2,650,000
1 / 37
Price Drop
Windermere
6134 Keenes Pointe Dr
6134 Keenes Pointe Dr
  • 4 beds
  • 3.5 baths
  • 4,440 sqft
$2,395,000
$2,445,000
1 / 73
Windermere
9826 Laurel Valley Dr
9826 Laurel Valley Dr
  • 5 beds
  • 5 baths
  • 7,491 sqft
$5,900,000
1 / 69
Price Drop
Windermere
3130 Butler Bay Dr N
3130 Butler Bay Dr N
  • 4 beds
  • 5 baths
  • 4,490 sqft
$1,725,000
$1,775,000
1 / 3
Windermere
2 Chase Rd
2 Chase Rd
  • 4 beds
  • 4.5 baths
  • 3,889 sqft
$3,200,000
1 / 82
Windermere
12880 Holdenbury Ln
12880 Holdenbury Ln
  • 4 beds
  • 3 baths
  • 3,103 sqft
$725,000
1 / 63
Windermere
7545 Lake Albert Dr
7545 Lake Albert Dr
  • 4 beds
  • 4 baths
  • 3,425 sqft
$1,100,000
1 / 28
Windermere
8168 Boat Hook Loop #107
8168 Boat Hook Loop #107
  • 3 beds
  • 2 baths
  • 1,455 sqft
$339,000
1 / 18
Windermere
7628 Billingham St
7628 Billingham St
  • 3 beds
  • 2.5 baths
  • 1,480 sqft
$410,000
1 / 83
Price Drop
Windermere
13048 Lake Roper Ct
13048 Lake Roper Ct
  • 5 beds
  • 3.5 baths
  • 4,130 sqft
$1,999,000
$2,100,000
12
Viewing 37-56 of 56 homes

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 $900,000, down 7.2% 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 238 homes for sale in Windermere as of October 11, 2025. There were 69 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.