38 total properties
Did you mean the neighborhood Windermere?
View 7432 LEIGHSIDE DRIVE Windermere, FL MLS# O6383362
  • Recently Listed with Virtual Tour
1 of 36
$475,000
4

Beds

2.1

Baths

1,898

Sq.Ft.

7432 LEIGHSIDE DRIVE

Windermere, FL

Courtesy of METROPOLITAN R.E SOLUTIONS INC
View 9319 WOODBREEZE BOULEVARD Windermere, FL MLS# O6384930
  • Recently Listed
1 of 41
$574,995
4

Beds

2.0

Baths

1,798

Sq.Ft.

9319 WOODBREEZE BOULEVARD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 7125 BEEK STREET Windermere, FL MLS# O6382948
  • Virtual Tour
1 of 48
$559,000
3

Beds

2.0

Baths

1,753

Sq.Ft.

7125 BEEK STREET

Windermere, FL

Courtesy of SUNNY 365 REALTY GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 11355 ARBORSIDE BEND WAY Windermere, FL MLS# O6377273
  • Recently Listed with Virtual Tour
1 of 32
$600,000
4

Beds

2.0

Baths

2,044

Sq.Ft.

11355 ARBORSIDE BEND WAY

Windermere, FL

Courtesy of EXP REALTY LLC
View 11408 CENTER LAKE DRIVE Windermere, FL MLS# O6381662
  • Recently Listed with Virtual Tour
1 of 39
$460,000
3

Beds

2.1

Baths

1,910

Sq.Ft.

11408 CENTER LAKE DRIVE

Windermere, FL

Courtesy of METROPOLITAN R.E SOLUTIONS INC
View 13733 BRESSLER ALLEY Windermere, FL MLS# O6379257
  • Recently Listed
1 of 32
$469,999
3

Beds

2.1

Baths

2,002

Sq.Ft.

13733 BRESSLER ALLEY

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 6382 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6379533
  • Recently Listed with Virtual Tour
1 of 56
$595,000
3

Beds

2.1

Baths

2,139

Sq.Ft.

6382 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 5463 GEMGOLD COURT Windermere, FL MLS# O6375567
  • Virtual Tour
1 of 42
$599,000
4

Beds

3.0

Baths

2,246

Sq.Ft.

5463 GEMGOLD COURT

Windermere, FL

Courtesy of INFINITY REALTY GROUP LLC
View 8650 ABBOTSBURY DRIVE Windermere, FL MLS# O6376488
  • Virtual Tour
1 of 47
$575,000
4

Beds

3.1

Baths

2,628

Sq.Ft.

8650 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of THE AGENCY FL
View 7451 FAIRGROVE AVENUE Windermere, FL MLS# O6375170
  • Virtual Tour
1 of 46
$580,000
3

Beds

2.0

Baths

2,092

Sq.Ft.

7451 FAIRGROVE AVENUE

Windermere, FL

Courtesy of TALENT REALTY SOLUTIONS
View 8648 POWDER RIDGE TRAIL Windermere, FL MLS# O6373065
$528,000
3

Beds

2.1

Baths

1,876

Sq.Ft.

8648 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of FLORIDA CONNEXION PROPERTIES
View 7885 BERKSHIRE OAK ALLEY Windermere, FL MLS# O6374875
$579,000
4

Beds

2.1

Baths

2,214

Sq.Ft.

7885 BERKSHIRE OAK ALLEY

Windermere, FL

Courtesy of U S GLORY REALTY
View 8632 ABBOTSBURY DRIVE Windermere, FL MLS# O6374937
  • Virtual Tour
1 of 43
$614,999
4

Beds

3.1

Baths

2,720

Sq.Ft.

8632 ABBOTSBURY DRIVE

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
View 13369 GORGONA ISLE DRIVE Windermere, FL MLS# O6373676
$459,900
3

Beds

2.1

Baths

1,767

Sq.Ft.

13369 GORGONA ISLE DRIVE

Windermere, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 12305 VIA DERNA PLACE Windermere, FL MLS# O6374964
  • Virtual Tour
1 of 24
$470,000
3

Beds

3.0

Baths

1,891

Sq.Ft.

12305 VIA DERNA PLACE

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 11675 SNAIL KITE WAY Windermere, FL MLS# O6373317
$596,400
3

Beds

2.1

Baths

2,139

Sq.Ft.

11675 SNAIL KITE WAY

Windermere, FL

Courtesy of ORLANDO PROPERTY ADVISORS
View 13850 AMELIA POND DRIVE Windermere, FL MLS# O6371503
$599,000
4

Beds

3.0

Baths

2,428

Sq.Ft.

13850 AMELIA POND DRIVE

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 6718 ROMNEY LANE Windermere, FL MLS# O6371234
  • Virtual Tour
1 of 56
$555,000
4

Beds

2.1

Baths

2,460

Sq.Ft.

6718 ROMNEY LANE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 6442 GOLDEN DEWDROP TRAIL Windermere, FL MLS# G5106279
$585,000
3

Beds

2.1

Baths

2,139

Sq.Ft.

6442 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of EMPIRE NETWORK REALTY
View 8225 BRYCE CANYON AVENUE Windermere, FL MLS# O6371960
$560,000
4

Beds

2.1

Baths

1,840

Sq.Ft.

8225 BRYCE CANYON AVENUE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

About Windermere

"Among the lakes" is the phrase that the town of Windermere has chosen for its description, and aptly so.  Almost completely surrounded by water, Windermere is a lovely small town that will always be limited in population growth by available land.  Lake Butler is the largest body of water in the region, which is often referred to as the "Butler chain of lakes."  Situated in southeast Orange County, the residential villages and homes throughout the lake area are as beautiful as the backdrop of scenery they enjoy.  Some multi-million dollar lakefront mansions combine with more modest but often luxurious homes in a variety of architectural styles.  The Islesworth Golf & Country Club in Windermere rivals the lush fairways of highly acclaimed Bay Hill for sheer bayside splendor.  Also located in this small town is a fully accredited independent school for students in pre-kindergarten through eighth grade called Buena Vista Academy.  While the residents of Windermere can enjoy the exclusive resort setting and serenity of their community, the first-rate cultural, educational, and healthcare advantages of Orlando remain close to home. 

Listings in Windermere, FL

299

Estimated median home price

$1,037,000
Windermere FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Windermere, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Windermere, FL.

Homes for Sale by Price in Windermere, FL

Price Count
$0 - 100K 0
$100K - 200K 0
$200K - 300K 0
$300K - 400K 19
$400K - 500K 22
$500K - 600K 27
$600K - 700K 25
$700K - 800K 24
$800K - 900K 20
$900K - 1M 10
$1M - Max 152

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 246
Townhouse 32
Condo 7
Commercial 1
Rental 103
Lots and Land 13
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 2/24/2026)

Information deemed reliable but not guaranteed.

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 2/25/2026.