View 4 CHASE ROAD Windermere, FL MLS# O6384257
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$900,000
3

Beds

2.0

Baths

2,386

Sq.Ft.

4 CHASE ROAD

Windermere, FL

Courtesy of REAL BROKER, LLC
View 9323 GLADYS GARDEN COURT Windermere, FL MLS# O6381880
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$13,995,000
6

Beds

6.4

Baths

9,770

Sq.Ft.

9323 GLADYS GARDEN COURT

Windermere, FL

Courtesy of CORCORAN PREMIER REALTY
View 11355 ARBORSIDE BEND WAY Windermere, FL MLS# O6377273
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$600,000
4

Beds

2.0

Baths

2,044

Sq.Ft.

11355 ARBORSIDE BEND WAY

Windermere, FL

Courtesy of EXP REALTY LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 5186 VARDON DRIVE Windermere, FL MLS# O6382040
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1 of 61
$5,680,000
6

Beds

6.0

Baths

5,376

Sq.Ft.

5186 VARDON DRIVE

Windermere, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 5745 EMERINGTON CRESCENT Orlando, FL MLS# O6382015
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1 of 100
$4,590,000
7

Beds

7.1

Baths

7,881

Sq.Ft.

5745 EMERINGTON CRESCENT

Orlando, FL

Courtesy of EXP REALTY LLC
View 6533 CARTMEL LANE Windermere, FL MLS# O6381498
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$1,298,000
4

Beds

3.1

Baths

3,751

Sq.Ft.

6533 CARTMEL LANE

Windermere, FL

Courtesy of THE AGENCY FL
View 5727 EMERINGTON CRESCENT Orlando, FL MLS# O6380297
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$4,500,000
5

Beds

5.1

Baths

7,621

Sq.Ft.

5727 EMERINGTON CRESCENT

Orlando, FL

Courtesy of PROPERTY INVESTMENT BROKERS
View 6248 LOUISE COVE DR Windermere, FL MLS# O6378223
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1 of 71
$2,850,000
5

Beds

5.1

Baths

6,253

Sq.Ft.

6248 LOUISE COVE DR

Windermere, FL

Courtesy of ISLEWORTH REALTY LLC
View 5938 MASTERS BOULEVARD Orlando, FL MLS# OM717835
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$999,950
Studio

Beds

0.0

Baths

5938 MASTERS BOULEVARD

Orlando, FL

Courtesy of SUNCOAST MANSIONS LLC
View 9111 MID PINES COURT Orlando, FL MLS# O6377235
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1 of 67
$2,400,000
5

Beds

4.1

Baths

5,315

Sq.Ft.

9111 MID PINES COURT

Orlando, FL

Courtesy of THE AGENCY FL
View 5145 LATROBE DRIVE Windermere, FL MLS# O6382287
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1 of 73
$3,499,000
4

Beds

4.1

Baths

4,512

Sq.Ft.

5145 LATROBE DRIVE

Windermere, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 9426 PALM TREE DRIVE Windermere, FL MLS# O6373158
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1 of 29
$650,000
4

Beds

2.0

Baths

2,063

Sq.Ft.

9426 PALM TREE DRIVE

Windermere, FL

Courtesy of IRON VALLEY REAL ESTATE CENTRAL FLORIDA
View 5074 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6373191
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    1 of 83
    $7,595,000
    5

    Beds

    6.1

    Baths

    6,937

    Sq.Ft.

    5074 ISLEWORTH COUNTRY CLUB DRIVE

    Windermere, FL

    Courtesy of MEMARPOURI REALTY LLC
    View 6117 LOUISE COVE DRIVE Windermere, FL MLS# O6372197
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    1 of 58
    $5,400,000
    4

    Beds

    4.1

    Baths

    5,752

    Sq.Ft.

    6117 LOUISE COVE DRIVE

    Windermere, FL

    Courtesy of ISLEWORTH REALTY LLC
    View 5509 EMERSON POINTE WAY Orlando, FL MLS# O6369643
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    1 of 68
    $1,790,000
    6

    Beds

    5.0

    Baths

    4,296

    Sq.Ft.

    5509 EMERSON POINTE WAY

    Orlando, FL

    Courtesy of CROWN REALTY INT-L LLC
    View 5050 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL MLS# O6372348
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    1 of 40
    $3,690,000
    4

    Beds

    4.1

    Baths

    3,365

    Sq.Ft.

    5050 ISLEWORTH COUNTRY CLUB DRIVE

    Windermere, FL

    Courtesy of COMPASS FLORIDA LLC
    View 9725 CHESTNUT RIDGE DRIVE Windermere, FL MLS# O6370294
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    1 of 57
    $6,950,000
    7

    Beds

    5.2

    Baths

    8,000

    Sq.Ft.

    9725 CHESTNUT RIDGE DRIVE

    Windermere, FL

    Courtesy of DOUGLAS ELLIMAN
    View 109 E 12TH AVENUE Windermere, FL MLS# O6368253
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    1 of 73
    $1,219,000
    4

    Beds

    3.1

    Baths

    2,791

    Sq.Ft.

    109 E 12TH AVENUE

    Windermere, FL

    Courtesy of THE AGENCY FL
    View 9107 IVEY HILL COURT Orlando, FL MLS# O6365241
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    1 of 48
    $879,000
    4

    Beds

    3.0

    Baths

    3,055

    Sq.Ft.

    9107 IVEY HILL COURT

    Orlando, FL

    Courtesy of FOLIO REALTY LLC
    View 9179 DOLLANGER COURT Orlando, FL MLS# O6362340
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    1 of 42
    $750,000
    4

    Beds

    3.0

    Baths

    2,544

    Sq.Ft.

    9179 DOLLANGER COURT

    Orlando, FL

    Courtesy of EXP REALTY LLC

    About Isleworth

    Listings in Isleworth, Windermere, FL

    48

    Estimated median home price

    $1,632,500
    Isleworth, Windermere Real Estate

    Search Isleworth, Florida Real Estate Listings & New Homes for Sale in Isleworth, FL. Find Isleworth Houses, Townhouses, Condos, & Properties for Sale at Weichert.com

    Homes for Sale by Price in Isleworth, Windermere, FL

    PriceCount
    $0 - 100K0
    $100K - 200K0
    $200K - 300K0
    $300K - 400K0
    $400K - 500K1
    $500K - 600K1
    $600K - 700K6
    $700K - 800K3
    $800K - 900K3
    $900K - 1M2
    $1M - Max32

    Homes for Sale by Type in Isleworth, Windermere, FL

    Property TypeCount
    Single Family44
    Townhouse0
    Condo0
    Commercial0
    Rental6
    Lots and Land4
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home0
    Farms0

    (Data as of 2/17/2026)

    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 2/21/2026.

    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 2/21/2026.