319 total properties
Did you mean the neighborhood Windermere?
View 13525 GORGONA ISLE DRIVE Windermere, FL MLS# O6377789
$1,120,000
6

Beds

4.1

Baths

4,625

Sq.Ft.

13525 GORGONA ISLE DRIVE

Windermere, FL

Courtesy of COLDWELL BANKER REALTY
View 6533 CARTMEL LANE Windermere, FL MLS# O6381498
  • Virtual Tour
1 of 37
$1,298,000
4

Beds

3.1

Baths

3,751

Sq.Ft.

6533 CARTMEL LANE

Windermere, FL

Courtesy of THE AGENCY FL
View 9940 GROSVENOR POINTE CIRCLE Windermere, FL MLS# O6380812
$3,195,000
5

Beds

5.2

Baths

5,071

Sq.Ft.

9940 GROSVENOR POINTE CIRCLE

Windermere, FL

Courtesy of DOUGLAS ELLIMAN
The time to sell is now! THE TIME TO SELL IS NOW!
View 13609 ANCILLA BOULEVARD Windermere, FL MLS# O6381542
$749,999
4

Beds

3.1

Baths

3,360

Sq.Ft.

13609 ANCILLA BOULEVARD

Windermere, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 13712 SUMMERPORT VILLAGE PARKWAY Windermere, FL MLS# S5143431
$444,900
3

Beds

2.1

Baths

1,997

Sq.Ft.

13712 SUMMERPORT VILLAGE PARKWAY

Windermere, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 9257 OUTLOOK ROCK TRAIL Windermere, FL MLS# S5143447
$899,990
5

Beds

4.1

Baths

3,619

Sq.Ft.

9257 OUTLOOK ROCK TRAIL

Windermere, FL

Courtesy of PRIMUS CRE GROUP
View 13302 ROSKIN LANE Windermere, FL MLS# O6380701
  • Virtual Tour
1 of 46
$899,900
4

Beds

3.1

Baths

3,424

Sq.Ft.

13302 ROSKIN LANE

Windermere, FL

Courtesy of RATIO REAL ESTATE, LLC
View 5837 CAYMUS LOOP Windermere, FL MLS# O6380732
  • Virtual Tour
1 of 36
$1,349,000
4

Beds

3.0

Baths

2,937

Sq.Ft.

5837 CAYMUS LOOP

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 7123 CALM COVE COURT Windermere, FL MLS# O6380782
$814,000
4

Beds

3.1

Baths

3,044

Sq.Ft.

7123 CALM COVE COURT

Windermere, FL

Courtesy of RE/MAX PRIME PROPERTIES
View 13733 BRESSLER ALLEY Windermere, FL MLS# O6379257
    1 of 32
    OPEN HOUSE: Sunday 4/19 1:00 PM - 4:00 PM
    $464,999
    3

    Beds

    2.1

    Baths

    2,002

    Sq.Ft.

    13733 BRESSLER ALLEY

    Windermere, FL

    Courtesy of CORCORAN PREMIER REALTY
    View 8767 IRON MOUNTAIN TRAIL Windermere, FL MLS# O6379681
    $870,000
    5

    Beds

    3.1

    Baths

    3,724

    Sq.Ft.

    8767 IRON MOUNTAIN TRAIL

    Windermere, FL

    Courtesy of KARDOSH REALTY
    View 58 MAIN STREET Windermere, FL MLS# O6370886
    • Virtual Tour
    1 of 52
    $3,725,000
    5

    Beds

    4.0

    Baths

    4,875

    Sq.Ft.

    58 MAIN STREET

    Windermere, FL

    Courtesy of LPT REALTY, LLC
    View 6673 DUNCASTER STREET Windermere, FL MLS# O6378820
    $539,000
    3

    Beds

    2.0

    Baths

    2,151

    Sq.Ft.

    6673 DUNCASTER STREET

    Windermere, FL

    Courtesy of MY REALTY GROUP, LLC.
    View 6001 CAYMUS LOOP Windermere, FL MLS# O6379564
    • Virtual Tour
    1 of 44
    $1,599,000
    5

    Beds

    5.0

    Baths

    3,520

    Sq.Ft.

    6001 CAYMUS LOOP

    Windermere, FL

    Courtesy of QUATTRO R E SOLUTIONS LLC
    View 13734 LAKE CAWOOD DRIVE Windermere, FL MLS# G5107723
    $1,390,000
    4

    Beds

    3.1

    Baths

    4,437

    Sq.Ft.

    13734 LAKE CAWOOD DRIVE

    Windermere, FL

    Courtesy of CHARLES RUTENBERG REALTY ORLANDO
    View 6840 HELMSLEY CIRCLE Windermere, FL MLS# S5142930
    $719,999
    4

    Beds

    4.0

    Baths

    2,847

    Sq.Ft.

    6840 HELMSLEY CIRCLE

    Windermere, FL

    Courtesy of IAD FLORIDA LLC
    View 3013 SEIGNEURY DRIVE Windermere, FL MLS# O6377087
    $1,890,000
    4

    Beds

    3.2

    Baths

    5,130

    Sq.Ft.

    3013 SEIGNEURY DRIVE

    Windermere, FL

    Courtesy of STOCKWORTH REALTY GROUP
    View 6382 GOLDEN DEWDROP TRAIL Windermere, FL MLS# O6379533
    $595,000
    3

    Beds

    2.1

    Baths

    2,139

    Sq.Ft.

    6382 GOLDEN DEWDROP TRAIL

    Windermere, FL

    Courtesy of CORCORAN PREMIER REALTY
    View 1134 KELSO BOULEVARD Windermere, FL MLS# O6378782
    $1,590,000
    2

    Beds

    2.0

    Baths

    2,044

    Sq.Ft.

    1134 KELSO BOULEVARD

    Windermere, FL

    Courtesy of REALTY AND COMPANY INT., LLC
    View 2931 SUNBITTERN COURT Windermere, FL MLS# O6378100
    $1,199,000
    4

    Beds

    3.0

    Baths

    4,018

    Sq.Ft.

    2931 SUNBITTERN COURT

    Windermere, FL

    Courtesy of REVEL 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

    354

    Estimated median home price

    $999,999
    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 - 200K0
    $200K - 300K1
    $300K - 400K18
    $400K - 500K26
    $500K - 600K36
    $600K - 700K31
    $700K - 800K26
    $800K - 900K21
    $900K - 1M21
    $1M - Max174

    Homes for Sale by Type in Windermere, FL

    Property TypeCount
    Single Family295
    Townhouse37
    Condo7
    Commercial1
    Rental103
    Lots and Land14
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home0
    Farms0

    (Data as of 4/15/2026)

    Information deemed reliable but not guaranteed.

    The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

    The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

    Data is updated as of 4/15/2026.

    The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

    The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties 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 4/15/2026.