REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Isleworth Homes for Sale in Windermere - 15 homes

Isleworth homes for sale are located in Orange County, Florida. Find Isleworth Homes in Windermere for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Isleworth, Windermere homes.

Location: Isleworth, Windermere

Sort:
  • 5145 LATROBE DR, WINDERMERE, FL 34786

    $3,449,00054 Days on yellowkey   MLS ID: O6382287

    For Sale O6382287 - 5145 LATROBE DR, WINDERMERE, FL 34786 73 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4512
       Built: 1991
    Monthly Fee: $1,224
       Tax: $27,776 (2025)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $22,437 (change assumption)
    Mortgage ($18,898) + Fees ($1,224) + Taxes in 2025 ($2,315)


    Taxes:$27,776

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 5151 LATROBE DR, WINDERMERE, FL 34786

    $4,100,00021 Days on yellowkey   MLS ID: O6392380

    For Sale O6392380 - 5151 LATROBE DR, WINDERMERE, FL 34786 57 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5301
       Built: 2000
    Monthly Fee: $1,224
       Tax: $23,020 (2025)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $25,608 (change assumption)
    Mortgage ($22,465) + Fees ($1,224) + Taxes in 2025 ($1,918)


    Taxes:$23,020

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6117 LOUISE COVE DR, WINDERMERE, FL 34786

    $5,250,00091 Days on yellowkey   MLS ID: O6372197

    For Sale O6372197 - 6117 LOUISE COVE DR, WINDERMERE, FL 34786 58 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5752
       Built: 2002
    Monthly Fee: $1,224
       Tax: $50,728 (2025)
    Community: Isleworth West
    Single Family


    Estimated Monthly Payment: $34,218 (change assumption)
    Mortgage ($28,766) + Fees ($1,224) + Taxes in 2025 ($4,227)


    Taxes:$50,728

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786

    $3,200,000260 Days on yellowkey   MLS ID: O6330108

    For Sale O6330108 - 4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786 44 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3745
       Built: 2006
    Monthly Fee: $1,146
       Tax: $33,607 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,480 (change assumption)
    Mortgage ($17,534) + Fees ($1,146) + Taxes in 2024 ($2,801)


    Taxes:$33,607

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 9648 MCCORMICK PL, WINDERMERE, FL 34786

    $3,800,000196 Days on yellowkey   MLS ID: O6346918

    For Sale O6346918 - 9648 MCCORMICK PL, WINDERMERE, FL 34786 61 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4751
       Built: 1988
    Monthly Fee: $1,224
       Tax: $33,873 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $24,868 (change assumption)
    Mortgage ($20,821) + Fees ($1,224) + Taxes in 2024 ($2,823)


    Taxes:$33,873

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 9731 CHESTNUT RIDGE DR, WINDERMERE, FL 34786

    $3,400,000237 Days on yellowkey   MLS ID: O6336655

    For Sale O6336655 - 9731 CHESTNUT RIDGE DR, WINDERMERE, FL 34786 57 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4877
       Built: 1986
    Monthly Fee: $1,224
       Tax: $19,867 (2024)
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $21,509 (change assumption)
    Mortgage ($18,630) + Fees ($1,224) + Taxes in 2024 ($1,656)


    Taxes:$19,867

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 5525 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786

    $14,250,000326 Days on yellowkey   MLS ID: O6304800

    For Sale O6304800 - 5525 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786 100 photos

    Bed: 5   Bath: 5.5   Gar: 6
    Liv Area Sq Ft: 9511
       Built: 1999
    Monthly Fee: $1,224
       Tax: $37,372 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $82,419 (change assumption)
    Mortgage ($78,080) + Fees ($1,224) + Taxes in 2024 ($3,114)


    Taxes:$37,372

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 9725 CHESTNUT RIDGE DR, WINDERMERE, FL 34786

    $6,950,00098 Days on yellowkey   MLS ID: O6370294

    For Sale O6370294 - 9725 CHESTNUT RIDGE DR, WINDERMERE, FL 34786 57 photos

    Bed: 7   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 8000
       Built: 1999
    Monthly Fee: $1,043
       Tax: $29,046 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $41,545 (change assumption)
    Mortgage ($38,081) + Fees ($1,043) + Taxes in 2024 ($2,421)


    Taxes:$29,046

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 6113 PAYNE STEWART DR, WINDERMERE, FL 34786

    $4,950,00035 Days on yellowkey   MLS ID: O6386548

    1 Days Off yellowkey (back on 4/6/2026)

    For Sale O6386548 - 6113 PAYNE STEWART DR, WINDERMERE, FL 34786 45 photos

    Bed: 3   Bath: 3.5   Gar: 4
    Liv Area Sq Ft: 2983
       Built: 1987
    Monthly Fee: $1,224
       Tax: $25,551 (2024)
    Community: Isleworth
    Villa


    Estimated Monthly Payment: $30,476 (change assumption)
    Mortgage ($27,123) + Fees ($1,224) + Taxes in 2024 ($2,129)


    Taxes:$25,551

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 5074 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786

    $7,595,00086 Days on yellowkey   MLS ID: O6373191

    For Sale O6373191 - 5074 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786 83 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 6937
       Built: 1988
    Monthly Fee: $1,043
       Tax: $21,279 (2024)
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $44,432 (change assumption)
    Mortgage ($41,615) + Fees ($1,043) + Taxes in 2024 ($1,773)


    Taxes:$21,279

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9323 GLADYS GARDEN CT, WINDERMERE, FL 34786

    $12,500,00056 Days on yellowkey   MLS ID: O6381880

    REDUCED by $1,495,000 (10.7%) on 04/03/2026

    For Sale O6381880 - 9323 GLADYS GARDEN CT, WINDERMERE, FL 34786 84 photos

    Bed: 6   Bath: 8.0   Gar: 4
    Liv Area Sq Ft: 9770
       Built: 2026
    Monthly Fee: $1,099
       Tax: $21,279 (2025)
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $71,364 (change assumption)
    Mortgage ($68,491) + Fees ($1,099) + Taxes in 2025 ($1,773)


    Taxes:$21,279

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 5036 LATROBE DR, WINDERMERE, FL 34786

    $4,900,000189 Days on yellowkey   MLS ID: O6346003

    1 Days Off yellowkey (back on 3/28/2026)

    For Sale O6346003 - 5036 LATROBE DR, WINDERMERE, FL 34786 47 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 5548
       Built: 1990
    Monthly Fee: $1,224
       Tax: $17,326 (2024)
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $29,516 (change assumption)
    Mortgage ($26,849) + Fees ($1,224) + Taxes in 2024 ($1,444)


    Taxes:$17,326

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 5001 LATROBE DR, WINDERMERE, FL 34786

    $3,499,99924 Days on yellowkey   MLS ID: O6389183

    For Sale O6389183 - 5001 LATROBE DR, WINDERMERE, FL 34786 78 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 4417
       Built: 1990
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $19,178 (change assumption)
    Mortgage ($19,178)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 5186 VARDON DR, WINDERMERE, FL 34786

    $4,960,000   MLS ID: O6382040

    For Sale O6382040 - 5186 VARDON DR, WINDERMERE, FL 34786 61 photos

    Bed: 4   Bath: 5.0
    Liv Area Sq Ft: 4739
       Built: 1990
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $27,177 (change assumption)
    Mortgage ($27,177)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None


  • 5243 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786

    $5,100,000   MLS ID: O6348067

    For Sale O6348067 - 5243 ISLEWORTH COUNTRY CLUB DR, WINDERMERE, FL 34786 65 photos

    Bed: 4   Bath: 5.5
    Liv Area Sq Ft: 6424
       Built: 1992
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $27,945 (change assumption)
    Mortgage ($27,945)


    Taxes:

    Elementary School: None

    High School: None

    Tax Year:

    Middle School: None




Why Bother Searching Elsewhere for Isleworth Homes for Sale and Other Windermere Real Estate?

Isleworth home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Isleworth. You can use our website to view Multiple Listing Service (MLS) data on Isleworth Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Isleworth. Windermere listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.