253 total properties
Did you mean the neighborhood Windermere?
View 17526 BLACK RAIL STREET Windermere, FL MLS# O6433513
$1,500,000
5

Beds

4.0

Baths

3,656

Sq.Ft.

17526 BLACK RAIL STREET

Windermere, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 8701 IRON MOUNTAIN TRAIL Windermere, FL MLS# O6433721
$998,999
6

Beds

4.1

Baths

4,507

Sq.Ft.

8701 IRON MOUNTAIN TRAIL

Windermere, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 4282 MCKINNON ROAD Windermere, FL MLS# O6432910
$1,895,000
6

Beds

6.0

Baths

5,869

Sq.Ft.

4282 MCKINNON ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 7467 LAKE ALBERT DRIVE Windermere, FL MLS# O6432932
$1,870,000
6

Beds

6.1

Baths

5,140

Sq.Ft.

7467 LAKE ALBERT DRIVE

Windermere, FL

View 8630 POWDER RIDGE TRAIL Windermere, FL MLS# C7529514
$528,000
3

Beds

2.1

Baths

1,853

Sq.Ft.

8630 POWDER RIDGE TRAIL

Windermere, FL

Courtesy of SUNCOAST CHOICE REALTY
View 8241 TIBET BUTLER DRIVE Windermere, FL MLS# O6431500
$1,740,000
4

Beds

3.1

Baths

3,680

Sq.Ft.

8241 TIBET BUTLER DRIVE

Windermere, FL

View 212 W 1ST AVENUE Windermere, FL MLS# S5155372
  • Virtual Tour
1 of 20
$1,599,000
4

Beds

2.0

Baths

2,627

Sq.Ft.

212 W 1ST AVENUE

Windermere, FL

Courtesy of HOME WISE REALTY GROUP, INC.
View 7668 FAIRGROVE AVENUE Windermere, FL MLS# O6432258
$485,000
4

Beds

2.1

Baths

1,866

Sq.Ft.

7668 FAIRGROVE AVENUE

Windermere, FL

Courtesy of VESTI LLC
View 6679 DUNCASTER STREET Windermere, FL MLS# A4702367
$525,000
3

Beds

2.0

Baths

1,926

Sq.Ft.

6679 DUNCASTER STREET

Windermere, FL

Courtesy of FLATFEE.COM
View 14360 CREST PALM AVENUE Windermere, FL MLS# O6431854
  • Virtual Tour
1 of 54
OPEN HOUSE: Saturday 10/3 12:00 PM - 2:00 PM
$1,270,000
6

Beds

4.1

Baths

4,585

Sq.Ft.

14360 CREST PALM AVENUE

Windermere, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 12303 LANGSTAFF DRIVE Windermere, FL MLS# O6430630
$400,000
3

Beds

2.1

Baths

1,545

Sq.Ft.

12303 LANGSTAFF DRIVE

Windermere, FL

Courtesy of REAL BROKER, LLC
View 7236 PENKRIDGE LANE Windermere, FL MLS# O6429931
    1 of 69
    OPEN HOUSE: Saturday 10/3 11:00 AM - 3:00 PM
    $675,000
    5

    Beds

    4.1

    Baths

    2,963

    Sq.Ft.

    7236 PENKRIDGE LANE

    Windermere, FL

    Courtesy of ATLAS BLUE REALTY INC
    View 11425 BROWNSTONE STREET Windermere, FL MLS# O6430411
    • Virtual Tour
    1 of 35
    OPEN HOUSE: Saturday 10/3 12:00 PM - 2:00 PM
    $410,000
    3

    Beds

    2.1

    Baths

    1,881

    Sq.Ft.

    11425 BROWNSTONE STREET

    Windermere, FL

    Courtesy of REDFIN CORPORATION
    View 11938 SILVERLAKE PARK DRIVE Windermere, FL MLS# O6430196
    $519,900
    4

    Beds

    2.1

    Baths

    2,074

    Sq.Ft.

    11938 SILVERLAKE PARK DRIVE

    Windermere, FL

    View 12749 GARRIDAN AVENUE Windermere, FL MLS# O6430484
    $610,000
    4

    Beds

    4.1

    Baths

    2,192

    Sq.Ft.

    12749 GARRIDAN AVENUE

    Windermere, FL

    View 12676 SALOMON COVE DRIVE Windermere, FL MLS# O6429934
    $1,300,000
    6

    Beds

    4.0

    Baths

    3,667

    Sq.Ft.

    12676 SALOMON COVE DRIVE

    Windermere, FL

    Courtesy of WEBB FLORIDA REALTY LLC
    View 13228 ROSKIN LANE Windermere, FL MLS# O6429810
    • Virtual Tour
    1 of 34
    $637,000
    4

    Beds

    2.0

    Baths

    2,745

    Sq.Ft.

    13228 ROSKIN LANE

    Windermere, FL

    Courtesy of OPENDOOR BROKERAGE LLC
    View 12914 VENNETTA WAY Windermere, FL MLS# O6428484
    $379,900
    3

    Beds

    2.1

    Baths

    1,644

    Sq.Ft.

    12914 VENNETTA WAY

    Windermere, FL

    View 12744 LANGSTAFF DRIVE Windermere, FL MLS# S5154691
    $394,900
    3

    Beds

    2.1

    Baths

    1,369

    Sq.Ft.

    12744 LANGSTAFF DRIVE

    Windermere, FL

    Courtesy of MY REALTY GROUP, LLC.
    View 9904 BRENTFORD COURT Windermere, FL MLS# O6428604
    $2,250,000
    5

    Beds

    4.1

    Baths

    4,504

    Sq.Ft.

    9904 BRENTFORD COURT

    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

    321

    Estimated median home price

    $998,999
    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 - 300K4
    $300K - 400K27
    $400K - 500K27
    $500K - 600K27
    $600K - 700K31
    $700K - 800K20
    $800K - 900K9
    $900K - 1M16
    $1M - Max159

    Homes for Sale by Type in Windermere, FL

    Property TypeCount
    Single Family246
    Townhouse43
    Condo11
    Commercial1
    Rental90
    Lots and Land20
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home0
    Farms0

    (Data as of 10/3/2026)

    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 10/4/2026.