38 total properties
Did you mean the neighborhood Windermere?
View 6552 HELMSLEY CIRCLE Windermere, FL MLS# O6392752
$469,000
4

Beds

3.0

Baths

1,980

Sq.Ft.

6552 HELMSLEY CIRCLE

Windermere, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 12305 VIA DERNA PLACE Windermere, FL MLS# O6374964
$465,000
3

Beds

3.0

Baths

1,891

Sq.Ft.

12305 VIA DERNA PLACE

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 12353 VIA DERNA PLACE Windermere, FL MLS# O6392401
$465,000
3

Beds

2.1

Baths

1,974

Sq.Ft.

12353 VIA DERNA PLACE

Windermere, FL

Courtesy of AUTHENTIC REAL ESTATE TEAM
The time to sell is now! THE TIME TO SELL IS NOW!
View 7327 MILLSTONE STREET Windermere, FL MLS# O6397203
$459,000
3

Beds

2.1

Baths

1,531

Sq.Ft.

7327 MILLSTONE STREET

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 12333 VIA DERNA PLACE Windermere, FL MLS# O6362685
$458,000
3

Beds

2.1

Baths

1,919

Sq.Ft.

12333 VIA DERNA PLACE

Windermere, FL

Courtesy of YELLOW ROCK REALTY CORP
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 11401 EVESHAM DRIVE Windermere, FL MLS# O6386678
$455,000
3

Beds

2.1

Baths

1,847

Sq.Ft.

11401 EVESHAM DRIVE

Windermere, FL

Courtesy of LPT REALTY, LLC
View 5849 SOTER LANE Windermere, FL MLS# O6388590
  • Virtual Tour
1 of 31
$449,900
3

Beds

2.1

Baths

2,001

Sq.Ft.

5849 SOTER LANE

Windermere, FL

Courtesy of ORLANDO HOME DEALER LLC
View 7644 RIPPLEPOINTE WAY Windermere, FL MLS# O6395582
$445,000
3

Beds

2.1

Baths

1,881

Sq.Ft.

7644 RIPPLEPOINTE WAY

Windermere, FL

Courtesy of HOMEVEST REALTY
View 7560 BENTONSHIRE AVENUE Windermere, FL MLS# O6405384
$445,000
4

Beds

3.1

Baths

1,905

Sq.Ft.

7560 BENTONSHIRE AVENUE

Windermere, FL

Courtesy of SOLD BY SIX 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 7612 FAIRGROVE AVENUE Windermere, FL MLS# S5149402
  • Recently Listed with Virtual Tour
1 of 33
$440,000
3

Beds

2.1

Baths

1,742

Sq.Ft.

7612 FAIRGROVE AVENUE

Windermere, FL

Courtesy of FLORIDA FANTASY REAL ESTATE INC
View 13366 ABUELA ALLEY Windermere, FL MLS# O6374298
$430,000
3

Beds

2.1

Baths

1,589

Sq.Ft.

13366 ABUELA ALLEY

Windermere, FL

Courtesy of BAHIA INTERNATIONAL REALTY
View 8866 HERENCIA ALY Windermere, FL MLS# O6407518
  • Recently Listed with Virtual Tour
1 of 31
$430,000
3

Beds

2.1

Baths

1,577

Sq.Ft.

8866 HERENCIA ALY

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
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
View 9055 LEGADO DRIVE Windermere, FL MLS# O6403350
  • Virtual Tour
1 of 22
$425,000
3

Beds

2.1

Baths

1,584

Sq.Ft.

9055 LEGADO DRIVE

Windermere, FL

Courtesy of PREFERRED REAL ESTATE BROKERS
View 12405 CRUXBURY DRIVE Windermere, FL MLS# O6394966
$415,000
2

Beds

2.1

Baths

1,429

Sq.Ft.

12405 CRUXBURY DRIVE

Windermere, FL

Courtesy of HOMEVEST REALTY
View 12930 VENNETTA WAY Windermere, FL MLS# O6301208
$414,900
3

Beds

2.1

Baths

1,644

Sq.Ft.

12930 VENNETTA WAY

Windermere, FL

Courtesy of FLORIDA IN MOTION REALTY INC
View 7249 SHADEVIEW ALLEY Windermere, FL MLS# S5146580
$410,000
3

Beds

2.1

Baths

1,569

Sq.Ft.

7249 SHADEVIEW ALLEY

Windermere, FL

Courtesy of REMAX PREMIER PROPERTIES
View 11686 WATER RUN ALY Windermere, FL MLS# O6390542
$409,900
3

Beds

2.1

Baths

1,584

Sq.Ft.

11686 WATER RUN ALY

Windermere, FL

Courtesy of IRM INVEST., REAL EST.& MGMT.

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

341

Estimated median home price

$1,130,000
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

PriceCount
$0 - 100K0
$100K - 200K0
$200K - 300K1
$300K - 400K16
$400K - 500K25
$500K - 600K33
$600K - 700K22
$700K - 800K25
$800K - 900K20
$900K - 1M16
$1M - Max183

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family287
Townhouse36
Condo5
Commercial1
Rental91
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 5/17/2026)

Information deemed reliable but not guaranteed.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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 5/17/2026.