284 total properties
Did you mean the neighborhood Windermere?
View 5237 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6427447
$3,600,000
5

Beds

5.0

Baths

5,972

Sq.Ft.

5237 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 3986 ISABELLA CIRCLE Windermere, FL MLS# O6432946
  • Adult Community with Virtual Tour
1 of 29
$3,599,000
5

Beds

5.2

Baths

5,342

Sq.Ft.

3986 ISABELLA CIRCLE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 9310 ISLEWORTH GARDENS DRIVE Windermere, FL MLS# O6442366
  • Recently Listed with Virtual Tour
1 of 51
$3,595,000
3

Beds

3.2

Baths

4,333

Sq.Ft.

9310 ISLEWORTH GARDENS DRIVE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 4302 ISABELLA CIR Windermere, FL MLS# O6436735
  • Virtual Tour
1 of 90
$3,580,000
5

Beds

6.1

Baths

5,362

Sq.Ft.

4302 ISABELLA CIR

Windermere, FL

Courtesy of JC FLORIDA REALTY LLC
View 5524 WORSHAM COURT Windermere, FL MLS# O6430755
$3,500,000
4

Beds

6.0

Baths

7,669

Sq.Ft.

5524 WORSHAM COURT

Windermere, FL

Courtesy of ATLIS REALTY GROUP LLC
View 9679 WESTOVER ROBERTS RD Windermere, FL MLS# S5154885
$3,400,000
6

Beds

6.1

Baths

5,666

Sq.Ft.

9679 WESTOVER ROBERTS RD

Windermere, FL

Courtesy of TONYDAVIDSHOMES.COM, LLC
View 515 W 2ND AVENUE Windermere, FL MLS# O6439554
  • Virtual Tour
1 of 74
$3,300,000
4

Beds

5.1

Baths

3,966

Sq.Ft.

515 W 2ND AVENUE

Windermere, FL

Courtesy of VINTAGE REALTY GROUP LLC
View 4243 ISABELLA CIRCLE Windermere, FL MLS# O6439995
$3,290,000
5

Beds

5.2

Baths

5,502

Sq.Ft.

4243 ISABELLA CIRCLE

Windermere, FL

Courtesy of JOHN SILVA REALTY & ASSOCIATES
View 6126 PAYNE STEWART DRIVE Windermere, FL MLS# O6444116
  • Recently Listed with Virtual Tour
1 of 38
$3,250,000
3

Beds

3.1

Baths

2,848

Sq.Ft.

6126 PAYNE STEWART DRIVE

Windermere, FL

Courtesy of IRWIN REALTY GROUP LLC
View 4819 ALEXANDRA GARDEN COURT Windermere, FL MLS# O6330108
$3,200,000
4

Beds

4.1

Baths

3,745

Sq.Ft.

4819 ALEXANDRA GARDEN COURT

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 5050 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6438618
$3,189,000
4

Beds

4.1

Baths

3,365

Sq.Ft.

5050 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 1815 WINDERMERE ROAD Windermere, FL MLS# O6447555
  • New Construction with Virtual Tour
1 of 97
$3,150,000
4

Beds

4.1

Baths

4,290

Sq.Ft.

1815 WINDERMERE ROAD

Windermere, FL

Courtesy of BALDWIN PARK REALTY LLC
View 12102 MONTALCINO CIRCLE Windermere, FL MLS# O6428441
$3,100,000
4

Beds

4.1

Baths

4,296

Sq.Ft.

12102 MONTALCINO CIRCLE

Windermere, FL

Courtesy of EXP REALTY LLC
View 12624 PARK AVENUE Windermere, FL MLS# O6429787
$3,100,000
0.0

Baths

12624 PARK AVENUE

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 11539 LAKE BUTLER BOULEVARD Windermere, FL MLS# O6416913
$3,000,000
5

Beds

5.0

Baths

5,018

Sq.Ft.

11539 LAKE BUTLER BOULEVARD

Windermere, FL

Courtesy of VINTAGE REALTY GROUP LLC
View 7720 FICQUETTE ROAD Windermere, FL MLS# O6426088
$2,999,996
6

Beds

4.1

Baths

4,282

Sq.Ft.

7720 FICQUETTE ROAD

Windermere, FL

Courtesy of REVEL REALTY LLC
View 13101 BELLARIA CIRCLE Windermere, FL MLS# O6434168
  • Recently Listed with Virtual Tour
1 of 70
$2,995,000
6

Beds

7.2

Baths

7,321

Sq.Ft.

13101 BELLARIA CIRCLE

Windermere, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 7545 FICQUETTE ROAD Windermere, FL MLS# S5074124
$2,950,000
0.0

Baths

7545 FICQUETTE ROAD

Windermere, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 6130 GROSVENOR SHORE DRIVE Windermere, FL MLS# O6361099
$2,950,000
4

Beds

4.1

Baths

4,676

Sq.Ft.

6130 GROSVENOR SHORE DRIVE

Windermere, FL

Courtesy of DOUGLAS ELLIMAN
View 4301 DOWN POINT LANE Windermere, FL MLS# O6439832
$2,950,000
5

Beds

4.0

Baths

7,153

Sq.Ft.

4301 DOWN POINT LANE

Windermere, FL

Courtesy of MARIANI REALTY GROUP

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

310

Estimated median home price

$1,032,500
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 - 100K1
$100K - 200K0
$200K - 300K3
$300K - 400K28
$400K - 500K26
$500K - 600K24
$600K - 700K29
$700K - 800K20
$800K - 900K9
$900K - 1M14
$1M - Max156

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family236
Townhouse42
Condo11
Commercial1
Rental91
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 10/8/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective 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 10/9/2026.