38 total properties
Did you mean the neighborhood Windermere?
View 6871 HELMSLEY CIRCLE Windermere, FL MLS# O6387593
  • Virtual Tour
1 of 35
$554,000
3

Beds

2.0

Baths

1,772

Sq.Ft.

6871 HELMSLEY CIRCLE

Windermere, FL

Courtesy of SOUTH KEY REALTY LLC
View 7432 LEIGHSIDE DRIVE Windermere, FL MLS# O6383362
  • 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
$554,555
4

Beds

2.0

Baths

1,798

Sq.Ft.

9319 WOODBREEZE BOULEVARD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
The time to sell is now! THE TIME TO SELL IS NOW!
View 11355 ARBORSIDE BEND WAY Windermere, FL MLS# O6377273
$560,000
4

Beds

2.0

Baths

2,044

Sq.Ft.

11355 ARBORSIDE BEND WAY

Windermere, FL

Courtesy of EXP REALTY LLC
View 13712 SUMMERPORT VILLAGE PARKWAY Windermere, FL MLS# S5143431
$444,900
3

Beds

2.1

Baths

1,997

Sq.Ft.

13712 SUMMERPORT VILLAGE PARKWAY

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 13733 BRESSLER ALLEY Windermere, FL MLS# O6379257
$455,000
3

Beds

2.1

Baths

2,002

Sq.Ft.

13733 BRESSLER ALLEY

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 6673 DUNCASTER STREET Windermere, FL MLS# O6378820
  • Virtual Tour
1 of 25
$539,000
3

Beds

2.0

Baths

2,151

Sq.Ft.

6673 DUNCASTER STREET

Windermere, FL

Courtesy of MY REALTY GROUP, LLC.
View 8648 POWDER RIDGE TRAIL Windermere, FL MLS# O6373065
$499,000
3

Beds

2.1

Baths

1,876

Sq.Ft.

8648 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC
View 13366 ABUELA ALLEY Windermere, FL MLS# O6374298
  • Virtual Tour
1 of 35
$430,000
3

Beds

2.1

Baths

1,589

Sq.Ft.

13366 ABUELA ALLEY

Windermere, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 13369 GORGONA ISLE DRIVE Windermere, FL MLS# O6373676
$449,980
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
$465,000
3

Beds

3.0

Baths

1,891

Sq.Ft.

12305 VIA DERNA PLACE

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
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
View 13312 LONGACRE DRIVE Windermere, FL MLS# S5141031
  • Virtual Tour
1 of 35
$534,900
3

Beds

2.0

Baths

2,058

Sq.Ft.

13312 LONGACRE DRIVE

Windermere, FL

Courtesy of LA ROSA REALTY INTERNACIONAL L
View 6310 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6368983
$490,000
3

Beds

2.1

Baths

1,977

Sq.Ft.

6310 GOLDEN DEWDROP TRAIL

Windermere, FL

Courtesy of JOY ESTATE ENTERPRISE INC
View 12333 VIA DERNA PLACE Windermere, FL MLS# O6362685
  • Virtual Tour
1 of 57
$459,000
3

Beds

2.1

Baths

1,919

Sq.Ft.

12333 VIA DERNA PLACE

Windermere, FL

Courtesy of YELLOW ROCK REALTY CORP
View 11636 WATER RUN ALLEY Windermere, FL MLS# S5136888
  • Virtual Tour
1 of 18
$425,000
3

Beds

2.1

Baths

1,584

Sq.Ft.

11636 WATER RUN ALLEY

Windermere, FL

Courtesy of EXP REALTY LLC
View 10624 REAMS ROAD Windermere, FL MLS# O6338130
  • Virtual Tour
1 of 61
$487,000
4

Beds

2.1

Baths

2,092

Sq.Ft.

10624 REAMS ROAD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 11637 Water Run ALLEY Windermere, FL MLS# O6194326
$429,000
3

Beds

2.1

Baths

1,466

Sq.Ft.

11637 Water Run ALLEY

Windermere, FL

Courtesy of LOKATION

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

350

Estimated median home price

$1,112,490
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 1
$300K - 400K 17
$400K - 500K 25
$500K - 600K 36
$600K - 700K 25
$700K - 800K 26
$800K - 900K 23
$900K - 1M 16
$1M - Max 181

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 295
Townhouse 35
Condo 7
Commercial 1
Rental 94
Lots and Land 12
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 5/2/2026)

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 5/2/2026.