34 total properties
Did you mean the neighborhood Windermere?
View 11401 EVESHAM DRIVE Windermere, FL MLS# O6410182
  • Recently Listed with Virtual Tour
1 of 47
$440,000
3

Beds

2.1

Baths

1,847

Sq.Ft.

11401 EVESHAM DRIVE

Windermere, FL

Courtesy of DENIZ REALTY PARTNERS LLC
View 7867 BERKSHIRE OAK ALLEY Windermere, FL MLS# S5149947
  • Recently Listed with Virtual Tour
1 of 39
$539,000
4

Beds

2.1

Baths

2,221

Sq.Ft.

7867 BERKSHIRE OAK ALLEY

Windermere, FL

Courtesy of MULTI CHOICE REALTY LLC
View 5225 LEMON TWIST LANE Windermere, FL MLS# O6406747
$499,900
3

Beds

2.0

Baths

1,700

Sq.Ft.

5225 LEMON TWIST LANE

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
The time to sell is now! THE TIME TO SELL IS NOW!
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 1661 ROBERTS LANDING ROAD Windermere, FL MLS# O6407725
  • Recently Listed with Virtual Tour
1 of 16
$549,900
Studio

Beds

0.0

Baths

1661 ROBERTS LANDING ROAD

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
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 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 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 11486 MISTY OAK ALLEY Windermere, FL MLS# S5148331
$549,000
3

Beds

2.1

Baths

1,950

Sq.Ft.

11486 MISTY OAK ALLEY

Windermere, FL

Courtesy of CENTURY 21 CARIOTI
View 6820 THORNHILL CIRCLE Windermere, FL MLS# V4948591
$520,000
3

Beds

2.1

Baths

1,725

Sq.Ft.

6820 THORNHILL CIRCLE

Windermere, FL

Courtesy of LIFESTYLE INTERNATIONAL REALTY
View 7137 BEEK STREET Windermere, FL MLS# O6398814
  • Virtual Tour
1 of 33
$550,000
3

Beds

2.0

Baths

1,910

Sq.Ft.

7137 BEEK STREET

Windermere, FL

Courtesy of EXP REALTY LLC
View 7327 MILLSTONE STREET Windermere, FL MLS# O6397203
  • Virtual Tour
1 of 42
OPEN HOUSE: Sunday 5/24 12:00 PM - 3:00 PM
$459,000
3

Beds

2.1

Baths

1,531

Sq.Ft.

7327 MILLSTONE STREET

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 7644 RIPPLEPOINTE WAY Windermere, FL MLS# O6395582
$435,000
3

Beds

2.1

Baths

1,881

Sq.Ft.

7644 RIPPLEPOINTE WAY

Windermere, FL

Courtesy of HOMEVEST REALTY
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 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
View 12863 HOLDENBURY LANE Windermere, FL MLS# O6393781
$539,000
3

Beds

2.0

Baths

2,148

Sq.Ft.

12863 HOLDENBURY LANE

Windermere, FL

Courtesy of LPT REALTY, LLC
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 12761 HOLDENBURY LANE Windermere, FL MLS# O6392337
$529,900
4

Beds

2.0

Baths

2,380

Sq.Ft.

12761 HOLDENBURY LANE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 13755 BRAVANTE ALLEY Windermere, FL MLS# O6389321
$489,999
3

Beds

2.1

Baths

1,996

Sq.Ft.

13755 BRAVANTE ALLEY

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
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

334

Estimated median home price

$1,197,000
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 - 400K18
$400K - 500K24
$500K - 600K31
$600K - 700K20
$700K - 800K21
$800K - 900K18
$900K - 1M16
$1M - Max185

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family279
Townhouse36
Condo6
Commercial1
Rental93
Lots and Land12
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 5/24/2026)

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 5/24/2026.