288 total properties
Did you mean the neighborhood Windermere?
View 9508 Windy Ridge Road Windermere, FL MLS# RX11136385
$19,995,000
6

Beds

12.2

Baths

20,865

Sq.Ft.

9508 Windy Ridge Road

Windermere, FL

BeachesMLS
View 11900 LAKE BUTLER BOULEVARD Windermere, FL MLS# O6275556
$18,500,000
7

Beds

8.1

Baths

10,649

Sq.Ft.

11900 LAKE BUTLER BOULEVARD

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 5525 ISLEWORTH COUNTRY CLUB DR Windermere, FL MLS# O6304800
$14,250,000
5

Beds

5.1

Baths

9,511

Sq.Ft.

5525 ISLEWORTH COUNTRY CLUB DR

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 9621 WINDY RIDGE ROAD Windermere, FL MLS# O6333091
  • New Construction with Virtual Tour
1 of 28
$13,650,000
9

Beds

10.6

Baths

20,445

Sq.Ft.

9621 WINDY RIDGE ROAD

Windermere, FL

Courtesy of CITARELLI REALTY GROUP LLC
View 4226 DOWNEAST LANE Windermere, FL MLS# O6355233
  • Virtual Tour
1 of 16
$11,800,000
5

Beds

3.0

Baths

5,316

Sq.Ft.

4226 DOWNEAST LANE

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 4226 DOWNEAST LANE Windermere, FL MLS# O6367852
  • Virtual Tour
1 of 15
$11,800,000
Studio

Beds

0.0

Baths

4226 DOWNEAST LANE

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 6149 GROSVENOR SHORE DR Windermere, FL MLS# O6356355
$9,999,000
6

Beds

6.2

Baths

6,783

Sq.Ft.

6149 GROSVENOR SHORE DR

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 6507 ROSELLA COURT Windermere, FL MLS# O6353035
  • Virtual Tour
1 of 92
$7,750,000
7

Beds

7.1

Baths

10,485

Sq.Ft.

6507 ROSELLA COURT

Windermere, FL

Courtesy of DEANNA MARIE SECHREST
View 5074 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6373191
$7,595,000
5

Beds

6.1

Baths

6,937

Sq.Ft.

5074 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of MEMARPOURI REALTY LLC
View 9725 CHESTNUT RIDGE DRIVE Windermere, FL MLS# O6370294
  • Recently Listed with Virtual Tour
1 of 55
$6,950,000
7

Beds

5.2

Baths

8,000

Sq.Ft.

9725 CHESTNUT RIDGE DRIVE

Windermere, FL

Courtesy of DOUGLAS ELLIMAN
View 9259 TIBET POINTE CIR Windermere, FL MLS# O6312645
  • Virtual Tour
1 of 70
$6,800,000
5

Beds

5.1

Baths

6,257

Sq.Ft.

9259 TIBET POINTE CIR

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 9639 WESTOVER ROBERTS ROAD Windermere, FL MLS# O6341883
$6,395,000
5

Beds

8.1

Baths

11,861

Sq.Ft.

9639 WESTOVER ROBERTS ROAD

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 12264 MONTALCINO CIRCLE Windermere, FL MLS# O6325454
$5,860,000
4

Beds

4.3

Baths

7,872

Sq.Ft.

12264 MONTALCINO CIRCLE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 9721 CARILLON PARK DRIVE Windermere, FL MLS# O6336879
$5,489,000
6

Beds

7.2

Baths

8,305

Sq.Ft.

9721 CARILLON PARK DRIVE

Windermere, FL

Courtesy of DOUGLAS ELLIMAN
View 6117 LOUISE COVE DRIVE Windermere, FL MLS# O6372197
  • Recently Listed with Virtual Tour
1 of 58
$5,400,000
4

Beds

4.1

Baths

5,752

Sq.Ft.

6117 LOUISE COVE DRIVE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 5243 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6348067
$5,325,000
4

Beds

5.1

Baths

6,424

Sq.Ft.

5243 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 9733 CARILLON PARK DRIVE Windermere, FL MLS# O6355029
$5,250,000
5

Beds

6.1

Baths

7,600

Sq.Ft.

9733 CARILLON PARK DRIVE

Windermere, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 1003 DOWN RESERVE COURT Windermere, FL MLS# O6353952
  • New Construction
1 of 72
$4,999,999
6

Beds

6.2

Baths

6,816

Sq.Ft.

1003 DOWN RESERVE COURT

Windermere, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 11618 VINCI DRIVE Windermere, FL MLS# O6359990
  • Recently Listed with Virtual Tour
1 of 64
$4,950,000
5

Beds

5.2

Baths

6,188

Sq.Ft.

11618 VINCI DRIVE

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 9575 WESTOVER ROBERTS ROAD Windermere, FL MLS# O6357873
$4,925,000
7

Beds

8.0

Baths

8,931

Sq.Ft.

9575 WESTOVER ROBERTS ROAD

Windermere, FL

Courtesy of STOCKWORTH 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

281

Estimated median home price

$1,045,000
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 1
$300K - 400K 20
$400K - 500K 22
$500K - 600K 19
$600K - 700K 28
$700K - 800K 19
$800K - 900K 15
$900K - 1M 13
$1M - Max 144

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 224
Townhouse 34
Condo 8
Commercial 1
Rental 110
Lots and Land 14
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 1/16/2026)

Information deemed reliable but not guaranteed.

Copyright 2026 BeachesMLS, Inc. All rights reserved.

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed.

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.

Data is updated as of 1/21/2026.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

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.

Data is updated as of 1/21/2026.

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 1/21/2026.