12 total properties
Did you mean the neighborhood Windermere?
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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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 9826 LAUREL VALLEY DRIVE Windermere, FL MLS# O6345711
$5,900,000
5

Beds

4.2

Baths

7,491

Sq.Ft.

9826 LAUREL VALLEY DRIVE

Windermere, FL

Courtesy of EXP REALTY LLC
View 12540 PARK AVENUE Windermere, FL MLS# O6346858
  • Virtual Tour
1 of 67
$4,650,000
5

Beds

5.1

Baths

7,183

Sq.Ft.

12540 PARK AVENUE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
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 EXP REALTY LLC
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 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 5199 LATROBE DRIVE Windermere, FL MLS# O6315618
  • Virtual Tour
1 of 58
$5,494,000
5

Beds

6.1

Baths

4,665

Sq.Ft.

5199 LATROBE DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER RESIDENTIAL RE
View 225 MAGNOLIA STREET Windermere, FL MLS# O6292745
  • Virtual Tour
1 of 86
$4,899,000
7

Beds

10.1

Baths

5,935

Sq.Ft.

225 MAGNOLIA STREET

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
View 4089 ISABELLA CIRCLE Windermere, FL MLS# O6273887
  • Virtual Tour
1 of 58
$5,000,000
6

Beds

6.2

Baths

6,855

Sq.Ft.

4089 ISABELLA CIRCLE

Windermere, FL

Courtesy of NOVA REAL ESTATE SERVICES INC

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

289

Estimated median home price

$1,075,000
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 25
$400K - 500K 23
$500K - 600K 16
$600K - 700K 21
$700K - 800K 17
$800K - 900K 20
$900K - 1M 17
$1M - Max 150

Homes for Sale by Type in Windermere, FL

Property Type Count
Single Family 229
Townhouse 38
Condo 9
Commercial 1
Rental 112
Lots and Land 12
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 12/27/2025)

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 12/27/2025.