313 total properties
Did you mean the neighborhood Windermere?
View 8342 BOYLA COURT Windermere, FL MLS# O6422852
  • New Construction with Virtual Tour
1 of 93
$6,700,000
8

Beds

7.3

Baths

8,133

Sq.Ft.

8342 BOYLA COURT

Windermere, FL

Courtesy of THE SIMON SIMAAN GROUP
View 9921 LAKE LOUISE DRIVE Windermere, FL MLS# O6429164
$6,650,000
5

Beds

5.2

Baths

6,970

Sq.Ft.

9921 LAKE LOUISE DRIVE

Windermere, FL

View 6462 DEACON CIR Windermere, FL MLS# O6407107
  • Virtual Tour
1 of 46
$6,595,000
5

Beds

4.2

Baths

7,178

Sq.Ft.

6462 DEACON CIR

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 9316 GLADYS GARDEN CT Windermere, FL MLS# O6420326
  • New Construction with Virtual Tour
1 of 73
$6,500,000
5

Beds

6.1

Baths

5,471

Sq.Ft.

9316 GLADYS GARDEN CT

Windermere, FL

View 800 W 2ND AVENUE Windermere, FL MLS# O6422976
  • Virtual Tour
1 of 78
$5,999,000
5

Beds

4.1

Baths

5,511

Sq.Ft.

800 W 2ND AVENUE

Windermere, FL

Courtesy of ONE LUXURY INTERNATIONAL LLC
View 9725 CHESTNUT RIDGE DRIVE Windermere, FL MLS# O6370294
$5,975,000
7

Beds

5.2

Baths

8,000

Sq.Ft.

9725 CHESTNUT RIDGE DRIVE

Windermere, FL

Courtesy of DOUGLAS ELLIMAN
View 1330 LAKE OLIVIA Windermere, FL MLS# S5155388
  • 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
View 12264 MONTALCINO CIRCLE Windermere, FL MLS# O6404587
$5,390,000
4

Beds

4.3

Baths

7,872

Sq.Ft.

12264 MONTALCINO CIRCLE

Windermere, FL

View 5199 LATROBE DR Windermere, FL MLS# O6409961
  • Virtual Tour
1 of 64
$5,300,000
6

Beds

6.1

Baths

4,665

Sq.Ft.

5199 LATROBE DR

Windermere, FL

View WINDY RIDGE ROAD Windermere, FL MLS# O6439497
$5,250,000
0.0

Baths

WINDY RIDGE ROAD

Windermere, FL

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
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 9602 MAYWOOD DRIVE Windermere, FL MLS# O6446848
$4,350,000
5

Beds

5.0

Baths

5,305

Sq.Ft.

9602 MAYWOOD DRIVE

Windermere, FL

Courtesy of DIAMOND REAL ESTATE 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

313

Estimated median home price

$1,000,000
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 - 200K1
$200K - 300K3
$300K - 400K27
$400K - 500K26
$500K - 600K25
$600K - 700K32
$700K - 800K20
$800K - 900K9
$900K - 1M14
$1M - Max156

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family240
Townhouse42
Condo10
Commercial1
Rental90
Lots and Land20
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 10/6/2026)

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 10/6/2026.