311 total properties
Did you mean the neighborhood Windermere?
View 5243 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6348067
$5,100,000
4

Beds

5.1

Baths

6,424

Sq.Ft.

5243 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 1009 DOWN RESERVE COURT Windermere, FL MLS# O6346638
  • Recently Listed with Virtual Tour
1 of 73
$5,000,000
5

Beds

6.2

Baths

7,940

Sq.Ft.

1009 DOWN RESERVE COURT

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
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
The time to sell is now! THE TIME TO SELL IS NOW!
View 5070 DOWN POINT LANE Windermere, FL MLS# O6385276
  • Recently Listed with Virtual Tour
1 of 57
$4,995,000
6

Beds

6.1

Baths

7,349

Sq.Ft.

5070 DOWN POINT LANE

Windermere, FL

Courtesy of EXP REALTY LLC
View 5186 VARDON DRIVE Windermere, FL MLS# O6382040
  • Virtual Tour
1 of 61
$4,960,000
4

Beds

5.0

Baths

4,739

Sq.Ft.

5186 VARDON DRIVE

Windermere, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 11618 VINCI DRIVE Windermere, FL MLS# O6359990
  • 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 6113 PAYNE STEWART DRIVE Windermere, FL MLS# O6386548
  • Recently Listed with Virtual Tour
1 of 45
$4,950,000
3

Beds

3.1

Baths

2,983

Sq.Ft.

6113 PAYNE STEWART DRIVE

Windermere, FL

Courtesy of IRWIN REALTY GROUP 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
View 5036 LATROBE DRIVE Windermere, FL MLS# O6346003
$4,900,000
5

Beds

4.1

Baths

5,548

Sq.Ft.

5036 LATROBE DRIVE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 12540 PARK AVENUE Windermere, FL MLS# O6381869
  • Virtual Tour
1 of 58
$4,599,000
5

Beds

5.1

Baths

7,740

Sq.Ft.

12540 PARK AVENUE

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 3026 PORTO LAGO COURT Windermere, FL MLS# O6381606
  • Recently Listed with Virtual Tour
1 of 89
$4,500,000
5

Beds

7.2

Baths

8,714

Sq.Ft.

3026 PORTO LAGO COURT

Windermere, FL

Courtesy of SERHANT
View 6109 ORTA COURT Windermere, FL MLS# O6374125
$4,495,000
5

Beds

5.2

Baths

5,895

Sq.Ft.

6109 ORTA COURT

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 12418 PARK AVENUE Windermere, FL MLS# O6370377
  • Virtual Tour
1 of 26
$4,395,000
Studio

Beds

0.0

Baths

12418 PARK AVENUE

Windermere, FL

Courtesy of JULIAN PROPERTIES, INC.
View 1821 WINDERMERE ROAD Windermere, FL MLS# O6339740
  • New Construction with Virtual Tour
1 of 19
$4,276,160
5

Beds

6.1

Baths

6,401

Sq.Ft.

1821 WINDERMERE ROAD

Windermere, FL

Courtesy of ORLANDO TBI REALTY LLC
View 6208 WINTER GARDEN VINELAND ROAD Windermere, FL MLS# O6382642
  • Recently Listed with Virtual Tour
1 of 78
$4,150,000
6

Beds

7.1

Baths

5,441

Sq.Ft.

6208 WINTER GARDEN VINELAND ROAD

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 11002 LAKE BUTLER BOULEVARD Windermere, FL MLS# O6284922
  • Virtual Tour
1 of 62
OPEN HOUSE: Saturday 3/14 11:00 AM - 4:00 PM
$3,999,999
5

Beds

6.2

Baths

6,248

Sq.Ft.

11002 LAKE BUTLER BOULEVARD

Windermere, FL

Courtesy of SERENDIPITY REALTY LLC
View 11010 SCHOONER WAY Windermere, FL MLS# O6381886
  • Recently Listed with Virtual Tour
1 of 43
$3,999,000
Studio

Beds

0.0

Baths

11010 SCHOONER WAY

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 801 W 2ND AVENUE Windermere, FL MLS# O6375693
1 of 44
OPEN HOUSE: Saturday 3/14 12:00 PM - 2:00 PM
$3,995,000
5

Beds

6.1

Baths

5,639

Sq.Ft.

801 W 2ND AVENUE

Windermere, FL

Courtesy of PREMIER SOTHEBY'S INTL. REALTY
View 12132 MONTALCINO CIRCLE Windermere, FL MLS# O6319854
$3,950,000
6

Beds

7.0

Baths

5,709

Sq.Ft.

12132 MONTALCINO CIRCLE

Windermere, FL

Courtesy of BELLA VIEW REALTY LLC
View 9648 MCCORMICK PLACE Windermere, FL MLS# O6346918
  • Virtual Tour
1 of 61
$3,800,000
3

Beds

3.1

Baths

4,751

Sq.Ft.

9648 MCCORMICK PLACE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC

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

311

Estimated median home price

$1,030,000
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 0
$300K - 400K 17
$400K - 500K 25
$500K - 600K 29
$600K - 700K 24
$700K - 800K 27
$800K - 900K 19
$900K - 1M 13
$1M - Max 157

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 257
Townhouse 37
Condo 3
Commercial 1
Rental 102
Lots and Land 13
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 3/11/2026)

Information deemed reliable but not guaranteed.

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 3/11/2026.

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 3/11/2026.