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Homes for Sale Near Chain Of Lakes Middle in Windermere - 15 homes

Chain Of Lakes Middle is an Middle School in Orange County. Find homes for sale close to Chain Of Lakes Middle. Our REALTORS® can assist you in your search for Chain Of Lakes Middle, Windermere nearby homes.

Location: Windermere

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  • 5145 LATROBE DR, WINDERMERE, FL 34786

    $3,449,00055 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


  • 4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786

    $3,200,000261 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

    $3,800,000197 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

    $3,400,000238 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

    $14,250,000327 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


  • 4226 DOWNEAST LN, WINDERMERE, FL 34786

    $10,500,000169 Days on yellowkey   MLS ID: O6355233

    REDUCED by $1,300,000 (11.0%) on 04/08/2026

    For Sale O6355233 - 4226 DOWNEAST LN, WINDERMERE, FL 34786 18 photos

    Bed: 5   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 5316
       Built: 1980   Tax: $10,926 (2024)
    Community: Na
    Single Family


    Estimated Monthly Payment: $58,443 (change assumption)
    Mortgage ($57,533) + Taxes in 2024 ($910)


    Taxes:$10,926

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 9056 WOODBREEZE BLVD, WINDERMERE, FL 34786

    $565,00028 Days on yellowkey   MLS ID: O6390709

    1 Days Off yellowkey (back on 3/17/2026)

    For Sale O6390709 - 9056 WOODBREEZE BLVD, WINDERMERE, FL 34786 31 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2063
       Built: 1988
    Monthly Fee: $31
       Tax: $3,836 (2024)
    Community: Silver Woods Ph 01
    Single Family


    Estimated Monthly Payment: $3,446 (change assumption)
    Mortgage ($3,096) + Fees ($31) + Taxes in 2024 ($320)


    Taxes:$3,836

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 9725 CHESTNUT RIDGE DR, WINDERMERE, FL 34786

    $6,950,00099 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

    $4,950,00036 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


  • 1002 DOWN RESERVE CT, WINDERMERE, FL 34786

    $6,490,00049 Days on yellowkey   MLS ID: O6383597

    0 Days Off yellowkey (back on 4/4/2026)

    For Sale O6383597 - 1002 DOWN RESERVE CT, WINDERMERE, FL 34786 30 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 6706
       Built: 2021
    Monthly Fee: $433
       Tax: $61,838 (2024)
    Community: Rosser Reserve Rep
    Single Family


    Estimated Monthly Payment: $41,147 (change assumption)
    Mortgage ($35,561) + Fees ($433) + Taxes in 2024 ($5,153)


    Taxes:$61,838

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 9323 GLADYS GARDEN CT, WINDERMERE, FL 34786

    $12,500,00057 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


  • 5130 SUN PALM DR, WINDERMERE, FL 34786

    $525,0009 Days on yellowkey   MLS ID: O6390875

    For Sale O6390875 - 5130 SUN PALM DR, WINDERMERE, FL 34786 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1723
       Built: 1987
    Monthly Fee: $30
       Tax: $8,032 (2025)
    Community: Silver Woods Ph 04
    Single Family


    Estimated Monthly Payment: $3,576 (change assumption)
    Mortgage ($2,877) + Fees ($30) + Taxes in 2025 ($669)


    Taxes:$8,032

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 1330 LAKE OLIVIA, WINDERMERE, FL 34786

    $5,500,00016 Days on yellowkey   MLS ID: S5144942

    For Sale S5144942 - 1330 LAKE OLIVIA, WINDERMERE, FL 34786 13 photos

    Bed: 6   Bath: 7.0
    Liv Area Sq Ft: 6442
       Built: 2026
    Monthly Fee: $400
       Tax: $9,870 (2024)
    Community: Lake Olivia Reserve
    Single Family


    Estimated Monthly Payment: $31,359 (change assumption)
    Mortgage ($30,136) + Fees ($400) + Taxes in 2024 ($823)


    Taxes:$9,870

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 5036 LATROBE DR, WINDERMERE, FL 34786

    $4,900,000190 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


  • 505 JENNIFER LN, WINDERMERE, FL 34786

    $2,250,00043 Days on yellowkey   MLS ID: O6384643

    1 Days Off yellowkey (back on 3/27/2026)

    For Sale O6384643 - 505 JENNIFER LN, WINDERMERE, FL 34786 95 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3525
       Built: 1989
    Monthly Fee: $333
       Tax: $7,624 (2024)
    Community: Windermere Oaks
    Single Family


    Estimated Monthly Payment: $13,297 (change assumption)
    Mortgage ($12,328) + Fees ($333) + Taxes in 2024 ($635)


    Taxes:$7,624

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle




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Home, townhome, condo, villa, and other listing sales data closeby Chain Of Lakes Middle is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on homes for sale nearby Chain Of Lakes Middle, Windermere . You can use our website to view Multiple Listing Service (MLS) data on Windermere homes near Chain Of Lakes Middle. 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 listings that are close to Chain Of Lakes Middle.



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.