365 total properties
Did you mean the neighborhood Windermere?
View 9725 CHESTNUT RIDGE DRIVE Windermere, FL MLS# O6370294
$6,000,000
7

Beds

5.2

Baths

8,000

Sq.Ft.

9725 CHESTNUT RIDGE DRIVE

Windermere, FL

Courtesy of DOUGLAS ELLIMAN
View 9639 WESTOVER ROBERTS ROAD Windermere, FL MLS# O6341883
$5,900,000
5

Beds

8.1

Baths

11,861

Sq.Ft.

9639 WESTOVER ROBERTS ROAD

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 1330 LAKE OLIVIA Windermere, FL MLS# S5144942
  • New Construction with Virtual Tour
1 of 13
$5,500,000
6

Beds

6.2

Baths

6,442

Sq.Ft.

1330 LAKE OLIVIA

Windermere, FL

Courtesy of EMPIRE NETWORK REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 5138 FAIRWAY OAKS DR Windermere, FL MLS# O6401757
$5,500,000
4

Beds

5.0

Baths

4,330

Sq.Ft.

5138 FAIRWAY OAKS DR

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 12264 MONTALCINO CIRCLE Windermere, FL MLS# O6404587
$5,490,000
4

Beds

4.3

Baths

7,872

Sq.Ft.

12264 MONTALCINO CIRCLE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 5199 LATROBE DR Windermere, FL MLS# O6409961
  • Recently Listed with Virtual Tour
1 of 64
$5,300,000
6

Beds

6.1

Baths

4,665

Sq.Ft.

5199 LATROBE DR

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 6117 LOUISE COVE DRIVE Windermere, FL MLS# O6372197
$5,250,000
4

Beds

4.1

Baths

5,752

Sq.Ft.

6117 LOUISE COVE DRIVE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 9713 ENDICOTT COURT Windermere, FL MLS# O6393891
$5,250,000
6

Beds

6.2

Baths

7,818

Sq.Ft.

9713 ENDICOTT COURT

Windermere, FL

Courtesy of EXP REALTY LLC
View 6142 GROSVENOR SHORE DRIVE Windermere, FL MLS# O6388222
$5,150,000
4

Beds

5.1

Baths

6,950

Sq.Ft.

6142 GROSVENOR SHORE DRIVE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
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 9721 CARILLON PARK DRIVE Windermere, FL MLS# O6336879
$5,000,000
6

Beds

7.2

Baths

8,305

Sq.Ft.

9721 CARILLON PARK DRIVE

Windermere, FL

Courtesy of DOUGLAS ELLIMAN
View 5070 DOWN POINT LANE Windermere, FL MLS# O6385276
$4,995,000
6

Beds

6.1

Baths

7,349

Sq.Ft.

5070 DOWN POINT LANE

Windermere, FL

Courtesy of EXP REALTY LLC
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 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 9575 WESTOVER ROBERTS ROAD Windermere, FL MLS# O6357873
$4,850,000
7

Beds

8.0

Baths

8,931

Sq.Ft.

9575 WESTOVER ROBERTS ROAD

Windermere, FL

Courtesy of STOCKWORTH REALTY GROUP
View 5500 W LAKE BUTLER ROAD Windermere, FL MLS# O6408637
$4,700,000
8

Beds

6.0

Baths

7,000

Sq.Ft.

5500 W LAKE BUTLER ROAD

Windermere, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 1009 DOWN RESERVE COURT Windermere, FL MLS# O6346638
  • New Construction with Virtual Tour
1 of 73
$4,650,000
5

Beds

6.2

Baths

7,940

Sq.Ft.

1009 DOWN RESERVE COURT

Windermere, FL

Courtesy of WEMERT GROUP REALTY LLC
View 4906 AVIVA GARDEN COURT Windermere, FL MLS# O6400218
$4,590,000
3

Beds

4.1

Baths

6,236

Sq.Ft.

4906 AVIVA GARDEN COURT

Windermere, FL

Courtesy of CAMPBELL CUSTOM HOMES INC
View 3026 PORTO LAGO COURT Windermere, FL MLS# O6381606
$4,500,000
5

Beds

7.2

Baths

8,714

Sq.Ft.

3026 PORTO LAGO COURT

Windermere, FL

Courtesy of SERHANT
View 9144 ISLEWORTH GARDENS DRIVE Windermere, FL MLS# O6397842
$4,450,000
3

Beds

3.2

Baths

5,004

Sq.Ft.

9144 ISLEWORTH GARDENS DRIVE

Windermere, FL

Courtesy of MEGAN DOWDY 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

365

Estimated median home price

$1,150,000
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 - 400K22
$400K - 500K30
$500K - 600K32
$600K - 700K30
$700K - 800K19
$800K - 900K20
$900K - 1M16
$1M - Max195

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family298
Townhouse45
Condo6
Commercial1
Rental99
Lots and Land15
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 6/13/2026)

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

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

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.

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 6/14/2026.