210 total properties
Did you mean the neighborhood Windermere?
View 17526 BLACK RAIL STREET Windermere, FL MLS# O6433513
  • Virtual Tour
1 of 95
OPEN HOUSE: Saturday 10/31 12:00 PM - 3:00 PM
$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 4282 MCKINNON ROAD Windermere, FL MLS# O6432910
$1,845,000
6

Beds

6.0

Baths

5,869

Sq.Ft.

4282 MCKINNON ROAD

Windermere, FL

Courtesy of COMPASS FLORIDA LLC
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

Courtesy of NOVA REAL ESTATE SERVICES INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 8241 TIBET BUTLER DRIVE Windermere, FL MLS# O6431500
$1,699,000
4

Beds

3.1

Baths

3,680

Sq.Ft.

8241 TIBET BUTLER DRIVE

Windermere, FL

Courtesy of GOLFPARK PROPERTIES
View 212 W 1ST AVENUE Windermere, FL MLS# S5155372
  • Virtual Tour
1 of 20
$1,488,000
4

Beds

2.0

Baths

2,627

Sq.Ft.

212 W 1ST AVENUE

Windermere, FL

Courtesy of HOME WISE REALTY GROUP, INC.
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
$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
$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
$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
$510,000
4

Beds

2.1

Baths

2,074

Sq.Ft.

11938 SILVERLAKE PARK DRIVE

Windermere, FL

Courtesy of BEYCOME OF FLORIDA LLC
View 7752 RIGBY STREET Windermere, FL MLS# O6422269
  • Virtual Tour
1 of 23
$385,000
3

Beds

2.1

Baths

1,335

Sq.Ft.

7752 RIGBY STREET

Windermere, FL

Courtesy of ATLIS REALTY GROUP LLC
View 12749 GARRIDAN AVENUE Windermere, FL MLS# O6430484
$610,000
4

Beds

4.1

Baths

2,192

Sq.Ft.

12749 GARRIDAN AVENUE

Windermere, FL

Courtesy of JR CERQUEIRA REALTY CORP
View 12744 LANGSTAFF DRIVE Windermere, FL MLS# S5154691
  • Virtual Tour
1 of 33
OPEN HOUSE: Saturday 10/31 1:00 PM - 5:00 PM
$394,900
3

Beds

2.1

Baths

1,369

Sq.Ft.

12744 LANGSTAFF DRIVE

Windermere, FL

Courtesy of MY REALTY GROUP, LLC.
View 14213 CREST PALM AVENUE Windermere, FL MLS# G5115749
$1,204,990
6

Beds

4.1

Baths

4,564

Sq.Ft.

14213 CREST PALM AVENUE

Windermere, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 8001 Enchantment Drive 1001 Windermere, FL MLS# B26057366
$395,000
4

Beds

3.1

Baths

1,792

Sq.Ft.

8001 Enchantment Drive 1001

Windermere, FL

View 13231 ROXBORO ROAD Windermere, FL MLS# O6427997
    1 of 42
    OPEN HOUSE: Sunday 11/1 12:30 PM - 4:30 PM
    $579,000
    3

    Beds

    2.0

    Baths

    1,706

    Sq.Ft.

    13231 ROXBORO ROAD

    Windermere, FL

    Courtesy of LA ROSA REALTY KISSIMMEE
    View 8386 IRON MOUNTAIN TRAIL Windermere, FL MLS# S5154426
    $438,000
    4

    Beds

    2.1

    Baths

    1,631

    Sq.Ft.

    8386 IRON MOUNTAIN TRAIL

    Windermere, FL

    Courtesy of MY REALTY GROUP, LLC.
    View 6208 TALARIA DRIVE Windermere, FL MLS# O6427527
    $750,000
    5

    Beds

    4.0

    Baths

    3,373

    Sq.Ft.

    6208 TALARIA DRIVE

    Windermere, FL

    Courtesy of OLYMPUS EXECUTIVE REALTY INC
    View 12417 MONTALCINO CIRCLE Windermere, FL MLS# O6425494
    $1,495,000
    4

    Beds

    3.1

    Baths

    3,166

    Sq.Ft.

    12417 MONTALCINO CIRCLE

    Windermere, FL

    Courtesy of LA ROSA REALTY 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

    $1,097,500
    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 - 100K1
    $100K - 200K0
    $200K - 300K4
    $300K - 400K27
    $400K - 500K23
    $500K - 600K28
    $600K - 700K30
    $700K - 800K14
    $800K - 900K8
    $900K - 1M12
    $1M - Max163

    Homes for Sale by Type in Windermere, FL

    Property TypeCount
    Single Family235
    Townhouse40
    Condo12
    Commercial1
    Rental106
    Lots and Land22
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home0
    Farms0

    (Data as of 10/31/2026)

    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 11/1/2026.