104 total properties
Did you mean the neighborhood Windermere?
View 11531 CHARNOCK DRIVE Windermere, FL MLS# O6418034
  • Recently Listed with Virtual Tour
1 of 58
$3,300
4

Beds

2.1

Baths

2,214

Sq.Ft.

11531 CHARNOCK DRIVE

Windermere, FL

View 7454 TATTANT BOULEVARD Windermere, FL MLS# S5152220
$2,695
3

Beds

2.0

Baths

1,708

Sq.Ft.

7454 TATTANT BOULEVARD

Windermere, FL

View 12113 VIA CASELLI LANE Windermere, FL MLS# O6418296
  • Recently Listed with Virtual Tour
1 of 36
$3,000
4

Beds

3.0

Baths

1,736

Sq.Ft.

12113 VIA CASELLI LANE

Windermere, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 5243 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6418570
  • Recently Listed with Virtual Tour
1 of 65
$25,000
4

Beds

5.1

Baths

6,424

Sq.Ft.

5243 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL

View 11820 WATERSTONE LOOP DRIVE Windermere, FL MLS# O6396187
  • Recently Listed with Virtual Tour
1 of 32
$6,990
4

Beds

3.0

Baths

2,817

Sq.Ft.

11820 WATERSTONE LOOP DRIVE

Windermere, FL

View 7468 FAIRGROVE AVENUE Windermere, FL MLS# O6418047
  • Recently Listed with Virtual Tour
1 of 32
$3,000
3

Beds

2.0

Baths

2,182

Sq.Ft.

7468 FAIRGROVE AVENUE

Windermere, FL

View 6344 LAKE SMITH CIRCLE Windermere, FL MLS# O6418148
  • Recently Listed with Virtual Tour
1 of 18
$2,600
3

Beds

2.1

Baths

1,640

Sq.Ft.

6344 LAKE SMITH CIRCLE

Windermere, FL

View 12219 JOSHUA TREE TRAIL Windermere, FL MLS# O6412560
  • Recently Listed with Virtual Tour
1 of 22
$2,950
3

Beds

2.1

Baths

1,829

Sq.Ft.

12219 JOSHUA TREE TRAIL

Windermere, FL

View 7283 PENKRIDGE LANE Windermere, FL MLS# O6417343
  • Recently Listed with Virtual Tour
1 of 15
$2,700
3

Beds

2.1

Baths

1,614

Sq.Ft.

7283 PENKRIDGE LANE

Windermere, FL

View 7329 AUBURNWOOD LANE Windermere, FL MLS# S5151923
  • Recently Listed with Virtual Tour
1 of 25
$3,200
4

Beds

2.1

Baths

2,696

Sq.Ft.

7329 AUBURNWOOD LANE

Windermere, FL

View 12355 LANGSTAFF DRIVE Windermere, FL MLS# S5151954
  • Recently Listed with Virtual Tour
1 of 39
$2,700
3

Beds

2.1

Baths

1,480

Sq.Ft.

12355 LANGSTAFF DRIVE

Windermere, FL

View 6746 DUNCASTER STREET Windermere, FL MLS# O6417108
  • Recently Listed with Virtual Tour
1 of 23
$3,200
4

Beds

2.1

Baths

2,830

Sq.Ft.

6746 DUNCASTER STREET

Windermere, FL

View 4205 BLUE MAJOR DRIVE Windermere, FL MLS# O6417184
  • Recently Listed with Virtual Tour
1 of 18
$2,700
3

Beds

2.0

Baths

1,536

Sq.Ft.

4205 BLUE MAJOR DRIVE

Windermere, FL

View 13809 AMELIA POND DRIVE Windermere, FL MLS# O6410416
  • Recently Listed with Virtual Tour
1 of 25
$3,360
4

Beds

3.1

Baths

2,804

Sq.Ft.

13809 AMELIA POND DRIVE

Windermere, FL

View 8832 DANFORTH DRIVE Windermere, FL MLS# O6417713
$2,650
3

Beds

2.1

Baths

1,480

Sq.Ft.

8832 DANFORTH DRIVE

Windermere, FL

View 11051 CONISTON WAY Windermere, FL MLS# O6416977
  • Recently Listed with Virtual Tour
1 of 58
$13,000
5

Beds

5.1

Baths

5,498

Sq.Ft.

11051 CONISTON WAY

Windermere, FL

View 7735 FAIRGROVE AVENUE Windermere, FL MLS# O6416769
  • Recently Listed with Virtual Tour
1 of 28
$2,800
3

Beds

2.1

Baths

1,523

Sq.Ft.

7735 FAIRGROVE AVENUE

Windermere, FL

Courtesy of SUMMERSIDE REALTY LLC
View 1125 LASCALA DRIVE Windermere, FL MLS# O6409403
  • Recently Listed with Virtual Tour
1 of 33
$3,500
5

Beds

4.1

Baths

2,874

Sq.Ft.

1125 LASCALA DRIVE

Windermere, FL

Courtesy of BHHS FLORIDA REALTY
View 11355 ARBORSIDE BEND WAY Windermere, FL MLS# O6416043
$3,500
4

Beds

2.0

Baths

2,044

Sq.Ft.

11355 ARBORSIDE BEND WAY

Windermere, FL

View 6431 CHATHAM VIEW COURT Windermere, FL MLS# O6416117
  • Recently Listed with Virtual Tour
1 of 48
$5,800
5

Beds

4.1

Baths

3,310

Sq.Ft.

6431 CHATHAM VIEW COURT

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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

369

Estimated median home price

$1,151,000
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 - 500K36
$500K - 600K30
$600K - 700K28
$700K - 800K21
$800K - 900K18
$900K - 1M16
$1M - Max197

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family293
Townhouse51
Condo7
Commercial1
Rental103
Lots and Land17
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 6/20/2026)

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 6/21/2026.