281 total properties
Did you mean the neighborhood Windermere?
View 5138 FAIRWAY OAKS DR Windermere, FL MLS# O6401757
$4,999,500
4

Beds

5.0

Baths

4,330

Sq.Ft.

5138 FAIRWAY OAKS DR

Windermere, FL

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 9721 CARILLON PARK DRIVE Windermere, FL MLS# O6336879
$4,778,000
6

Beds

7.2

Baths

8,305

Sq.Ft.

9721 CARILLON PARK DRIVE

Windermere, FL

Courtesy of DOUGLAS ELLIMAN
The time to sell is now! THE TIME TO SELL IS NOW!
View 9575 WESTOVER ROBERTS ROAD Windermere, FL MLS# O6357873
$4,750,000
7

Beds

8.0

Baths

8,931

Sq.Ft.

9575 WESTOVER ROBERTS ROAD

Windermere, FL

View WINDY RIDGE ROAD Windermere, FL MLS# O6439342
$4,750,000
0.0

Baths

WINDY RIDGE ROAD

Windermere, FL

View 12540 PARK AVENUE Windermere, FL MLS# O6381869
  • Virtual Tour
1 of 58
$4,500,000
5

Beds

5.1

Baths

7,740

Sq.Ft.

12540 PARK AVENUE

Windermere, FL

View 6719 VALHALLA WAY Windermere, FL MLS# O6428554
$4,495,000
5

Beds

5.2

Baths

6,159

Sq.Ft.

6719 VALHALLA WAY

Windermere, FL

Courtesy of CELEBRITY GLOBAL REALTY LLC
View 12418 PARK AVENUE Windermere, FL MLS# O6370377
  • Virtual Tour
1 of 26
$4,395,000
0.0

Baths

12418 PARK AVENUE

Windermere, FL

Courtesy of JULIAN PROPERTIES, INC.
View 5186 VARDON DRIVE Windermere, FL MLS# O6443681
  • Recently Listed with Virtual Tour
1 of 52
$4,395,000
6

Beds

6.0

Baths

4,739

Sq.Ft.

5186 VARDON DRIVE

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
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 WINDY RIDGE ROAD Windermere, FL MLS# O6439500
$4,250,000
0.0

Baths

WINDY RIDGE ROAD

Windermere, FL

View 9144 ISLEWORTH GARDENS DRIVE Windermere, FL MLS# O6397842
$4,100,000
3

Beds

3.2

Baths

5,004

Sq.Ft.

9144 ISLEWORTH GARDENS DRIVE

Windermere, FL

View 6120 GREATWATER DRIVE Windermere, FL MLS# O6445244
  • Recently Listed with Virtual Tour
1 of 74
$3,999,000
5

Beds

4.2

Baths

5,580

Sq.Ft.

6120 GREATWATER DRIVE

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 4201 ISABELLA CIRCLE Windermere, FL MLS# O6430081
$3,990,000
6

Beds

7.0

Baths

6,896

Sq.Ft.

4201 ISABELLA CIRCLE

Windermere, FL

View 11002 LAKE BUTLER BOULEVARD Windermere, FL MLS# O6284922
$3,950,000
5

Beds

6.2

Baths

6,248

Sq.Ft.

11002 LAKE BUTLER BOULEVARD

Windermere, FL

Courtesy of SERENDIPITY REALTY LLC
View 4906 AVIVA GARDEN COURT Windermere, FL MLS# O6446042
  • Recently Listed with Virtual Tour
1 of 100
$3,850,000
4

Beds

3.3

Baths

6,605

Sq.Ft.

4906 AVIVA GARDEN COURT

Windermere, FL

Courtesy of THE SIMON SIMAAN GROUP
View 9648 MCCORMICK PLACE Windermere, FL MLS# O6346918
$3,800,000
3

Beds

3.1

Baths

4,751

Sq.Ft.

9648 MCCORMICK PLACE

Windermere, FL

View 5151 LATROBE DR Windermere, FL MLS# O6392380
  • Virtual Tour
1 of 57
$3,800,000
4

Beds

4.1

Baths

5,301

Sq.Ft.

5151 LATROBE DR

Windermere, FL

View 9960 6TH STREET Windermere, FL MLS# O6412077
$3,750,000
5

Beds

5.1

Baths

6,182

Sq.Ft.

9960 6TH STREET

Windermere, FL

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

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

$999,500
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 - 100K0
$100K - 200K1
$200K - 300K3
$300K - 400K27
$400K - 500K26
$500K - 600K25
$600K - 700K31
$700K - 800K20
$800K - 900K9
$900K - 1M14
$1M - Max154

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family237
Townhouse42
Condo10
Commercial1
Rental88
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 10/5/2026)

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 10/5/2026.