102 total properties
Did you mean the neighborhood Windermere?
View 11602 BLACK RAIL STREET Windermere, FL MLS# O6450642
  • Recently Listed with Virtual Tour
1 of 40
$3,000
3

Beds

2.1

Baths

2,139

Sq.Ft.

11602 BLACK RAIL STREET

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 12844 WOODMERE CLOSE DRIVE Windermere, FL MLS# O6451398
$2,950
3

Beds

2.1

Baths

2,214

Sq.Ft.

12844 WOODMERE CLOSE DRIVE

Windermere, FL

Courtesy of UNIONE REALTY INC
View 7481 FAIRGROVE AVENUE Windermere, FL MLS# O6452140
  • Recently Listed with Virtual Tour
1 of 42
$3,990
5

Beds

4.1

Baths

2,961

Sq.Ft.

7481 FAIRGROVE AVENUE

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 1361 WHITNEY ISLES DRIVE Windermere, FL MLS# O6449234
  • Recently Listed with Virtual Tour
1 of 49
$5,000
4

Beds

4.0

Baths

2,787

Sq.Ft.

1361 WHITNEY ISLES DRIVE

Windermere, FL

Courtesy of ALVES AND HOWELL REALTY
View 8341 LOOKOUT POINTE DRIVE Windermere, FL MLS# O6451627
  • Recently Listed with Virtual Tour
1 of 41
$2,995
3

Beds

2.1

Baths

2,152

Sq.Ft.

8341 LOOKOUT POINTE DRIVE

Windermere, FL

Courtesy of LAKEFIELD REALTY GROUP LLC
View 4813 RIVER GEM AVENUE Windermere, FL MLS# O6451560
  • Recently Listed with Virtual Tour
1 of 30
$2,750
3

Beds

2.0

Baths

2,085

Sq.Ft.

4813 RIVER GEM AVENUE

Windermere, FL

Courtesy of INTOP REALTY LLC
View 11630 WATER RUN ALLEY Windermere, FL MLS# R4912207
  • Recently Listed with Virtual Tour
1 of 33
$2,600
3

Beds

2.1

Baths

1,584

Sq.Ft.

11630 WATER RUN ALLEY

Windermere, FL

Courtesy of BHM PROPERTIES II, LLC
View 4715 INDIAN DEER ROAD Windermere, FL MLS# O6450159
  • Recently Listed with Virtual Tour
1 of 48
$3,250
5

Beds

2.1

Baths

2,863

Sq.Ft.

4715 INDIAN DEER ROAD

Windermere, FL

Courtesy of LPT REALTY, LLC
View 14304 DESERT HAVEN STREET 3902 Windermere, FL MLS# O6449161
$2,800
3

Beds

2.1

Baths

2,067

Sq.Ft.

14304 DESERT HAVEN STREET 3902

Windermere, FL

Courtesy of EXP REALTY LLC
View 7722 FAIRGROVE AVENUE Windermere, FL MLS# O6450211
  • Recently Listed with Virtual Tour
1 of 35
$2,499
3

Beds

2.1

Baths

1,644

Sq.Ft.

7722 FAIRGROVE AVENUE

Windermere, FL

Courtesy of WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC
View 2936 MIDSUMMER DRIVE Windermere, FL MLS# O6450390
  • Recently Listed with Virtual Tour
1 of 68
$33,500
4

Beds

6.0

Baths

6,592

Sq.Ft.

2936 MIDSUMMER DRIVE

Windermere, FL

Courtesy of REVEL REALTY LLC
View 7719 MASLIN STREET Windermere, FL MLS# R4912174
  • Recently Listed with Virtual Tour
1 of 23
$2,600
3

Beds

2.1

Baths

1,545

Sq.Ft.

7719 MASLIN STREET

Windermere, FL

Courtesy of SIMS REALTY LLC
View 13466 ZORI LANE Windermere, FL MLS# O6450627
  • Recently Listed with Virtual Tour
1 of 37
$4,500
4

Beds

3.0

Baths

2,813

Sq.Ft.

13466 ZORI LANE

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 6826 DUNCASTER STREET Windermere, FL MLS# O6450172
  • Recently Listed with Virtual Tour
1 of 25
$2,800
3

Beds

2.1

Baths

2,230

Sq.Ft.

6826 DUNCASTER STREET

Windermere, FL

Courtesy of SUNSTAR REALTY FL INC
View 13706 BECKMAN DRIVE Windermere, FL MLS# O6448176
  • Recently Listed with Virtual Tour
1 of 36
$2,700
3

Beds

2.1

Baths

1,912

Sq.Ft.

13706 BECKMAN DRIVE

Windermere, FL

Courtesy of SUNNY 365 REALTY GROUP
View 11945 WATER RUN ALLEY Windermere, FL MLS# O6449994
  • Recently Listed
1 of 38
$2,850
3

Beds

2.1

Baths

1,724

Sq.Ft.

11945 WATER RUN ALLEY

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 11649 WATER RUN ALLEY Windermere, FL MLS# O6449420
  • Recently Listed with Virtual Tour
1 of 20
$2,800
3

Beds

2.1

Baths

1,584

Sq.Ft.

11649 WATER RUN ALLEY

Windermere, FL

Courtesy of LEGENDS REALTY
View 11812 WATER RUN ALLEY Windermere, FL MLS# O6444415
  • Recently Listed with Virtual Tour
1 of 26
$3,500
3

Beds

2.1

Baths

1,569

Sq.Ft.

11812 WATER RUN ALLEY

Windermere, FL

Courtesy of BR2US REALTY CORP
View 8128 JAILENE DRIVE Windermere, FL MLS# O6449154
$2,799
4

Beds

3.0

Baths

2,214

Sq.Ft.

8128 JAILENE DRIVE

Windermere, FL

Courtesy of PREMIUM PROPERTIES R.E SERVICE
View 11654 WATER RUN ALLEY Windermere, FL MLS# R4912153
  • Recently Listed with Virtual Tour
1 of 15
$2,650
3

Beds

2.1

Baths

1,712

Sq.Ft.

11654 WATER RUN ALLEY

Windermere, FL

Courtesy of BHM PROPERTIES II, 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

310

Estimated median home price

$1,082,000
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 - 100K1
$100K - 200K0
$200K - 300K4
$300K - 400K27
$400K - 500K22
$500K - 600K28
$600K - 700K34
$700K - 800K14
$800K - 900K7
$900K - 1M12
$1M - Max161

Homes for Sale by Type in Windermere, FL

Property TypeCount
Single Family236
Townhouse41
Condo11
Commercial1
Rental102
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 10/26/2026)

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 10/26/2026.