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Windermere Homes For Sale & Real Estate - 301 homes

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

Location: Windermere

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  • 8742 PEACHTREE PARK CT, WINDERMERE, FL 34786

    $574,000370 Days on yellowkey   MLS ID: O6301023

    1 Days Off yellowkey (back on 7/10/2025)

    For Sale O6301023 - 8742 PEACHTREE PARK CT, WINDERMERE, FL 34786 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1709
       Built: 2016
    Monthly Fee: $216
       Tax: $7,209 (2024)
    Community: Peachtree Park
    Single Family


    Estimated Monthly Payment: $3,962 (change assumption)
    Mortgage ($3,145) + Fees ($216) + Taxes in 2024 ($601)


    Taxes:$7,209

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 4906 AVIVA GARDEN CT, WINDERMERE, FL 34786

    $4,690,0003 Days on yellowkey   MLS ID: O6400218

    For Sale O6400218 - 4906 AVIVA GARDEN CT, WINDERMERE, FL 34786 27 photos

    Bed: 3   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 6236
       Built: 2016
    Monthly Fee: $1,146
       Tax: $48,425 (2025)
    Community: Gardens/Isleworth Un #2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $30,879 (change assumption)
    Mortgage ($25,698) + Fees ($1,146) + Taxes in 2025 ($4,035)


    Taxes:$48,425

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9621 WINDY RIDGE RD, WINDERMERE, FL 34786

    $13,550,0003 Days on yellowkey   MLS ID: O6400740

    For Sale O6400740 - 9621 WINDY RIDGE RD, WINDERMERE, FL 34786 28 photos

    Bed: 9   Bath: 13.0   Gar: 8
    Liv Area Sq Ft: 20445
       Built: 2025   Tax: $13,931 (2025)
    Community: Windsor Hill
    Single Family


    Estimated Monthly Payment: $75,406 (change assumption)
    Mortgage ($74,245) + Taxes in 2025 ($1,161)


    Taxes:$13,931

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6036 GREATWATER DR, WINDERMERE, FL 34786

    $1,999,9993 Days on yellowkey   MLS ID: O6400277

    For Sale O6400277 - 6036 GREATWATER DR, WINDERMERE, FL 34786 47 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4013
       Built: 2001
    Monthly Fee: $298
       Tax: $15,493 (2024)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,548 (change assumption)
    Mortgage ($10,959) + Fees ($298) + Taxes in 2024 ($1,291)


    Taxes:$15,493

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 14236 OASIS COVE BLVD, WINDERMERE, FL 34786

    $379,90023 Days on yellowkey   MLS ID: O6395058

    REDUCED by $4,400 (1.1%) on 04/12/2026

    For Sale O6395058 - 14236 OASIS COVE BLVD, WINDERMERE, FL 34786 70 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1512
       Built: 2011
    Monthly Fee: $541
       Tax: $3,995 (2025)
    Community: Oasis Cove At Lakeside Village
    Townhouse


    Estimated Monthly Payment: $2,956 (change assumption)
    Mortgage ($2,082) + Fees ($541) + Taxes in 2025 ($333)


    Taxes:$3,995

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 6799 HELMSLEY CIR, WINDERMERE, FL 34786

    $658,000157 Days on yellowkey   MLS ID: O6361417

    3 Days Off yellowkey (back on 4/20/2026)

    REDUCED by $12,000 (1.8%) on 04/08/2026

    For Sale O6361417 - 6799 HELMSLEY CIR, WINDERMERE, FL 34786 69 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2615
       Built: 2011
    Monthly Fee: $129
       Tax: $9,339 (2024)
    Community: Preston Square
    Single Family


    Estimated Monthly Payment: $4,513 (change assumption)
    Mortgage ($3,605) + Fees ($129) + Taxes in 2024 ($778)


    Taxes:$9,339

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 6443 CARTMEL LN, WINDERMERE, FL 34786

    $1,475,000789 Days on yellowkey   MLS ID: O6179128

    For Sale O6179128 - 6443 CARTMEL LN, WINDERMERE, FL 34786 31 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4257
       Built: 2004
    Monthly Fee: $520
       Tax: $14,632 (2023)
    Community: Reserve At Lake Butler Sound Unit 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,821 (change assumption)
    Mortgage ($8,082) + Fees ($520) + Taxes in 2023 ($1,219)


    Taxes:$14,632

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2023

    Middle School: Bridgewater Middle


  • 13430 HOPKINTON CT, WINDERMERE, FL 34786

    $585,000209 Days on yellowkey   MLS ID: O6346406

    For Sale O6346406 - 13430 HOPKINTON CT, WINDERMERE, FL 34786 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1732
       Built: 2005
    Monthly Fee: $167
       Tax: $7,277 (2024)
    Community: Lakes/Windermere-Peachtree
    Single Family


    Estimated Monthly Payment: $3,979 (change assumption)
    Mortgage ($3,205) + Fees ($167) + Taxes in 2024 ($606)


    Taxes:$7,277

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13712 SUMMERPORT VILLAGE PKWY, WINDERMERE, FL 34786

    $444,90073 Days on yellowkey   MLS ID: S5143431

    For Sale S5143431 - 13712 SUMMERPORT VILLAGE PKWY, WINDERMERE, FL 34786 64 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1997
       Built: 2019
    Monthly Fee: $171
       Tax: $5,448 (2025)
    Community: Vineyards/Horizons West Ph 4
    Townhouse


    Estimated Monthly Payment: $3,063 (change assumption)
    Mortgage ($2,438) + Fees ($171) + Taxes in 2025 ($454)


    Taxes:$5,448

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12411 MONTALCINO CIR, WINDERMERE, FL 34786

    $1,550,0006 Days on yellowkey   MLS ID: O6400067

    For Sale O6400067 - 12411 MONTALCINO CIR, WINDERMERE, FL 34786 65 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3399
       Built: 2011
    Monthly Fee: $150
       Tax: $11,027 (2025)
    Community: Casa Del Lago
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,562 (change assumption)
    Mortgage ($8,493) + Fees ($150) + Taxes in 2025 ($919)


    Taxes:$11,027

    Elementary School: Sunset Park Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 4029 ISABELLA CIR, WINDERMERE, FL 34786

    $3,299,0007 Days on yellowkey   MLS ID: O6400064

    For Sale O6400064 - 4029 ISABELLA CIR, WINDERMERE, FL 34786 98 photos

    Bed: 6   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 7217
       Built: 2018
    Monthly Fee: $480
       Tax: $30,300 (2025)
    Community: Casabella
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,081 (change assumption)
    Mortgage ($18,076) + Fees ($480) + Taxes in 2025 ($2,525)


    Taxes:$30,300

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 7137 BEEK ST, WINDERMERE, FL 34786

    $550,0007 Days on yellowkey   MLS ID: O6398814

    0 Days Off yellowkey (back on 4/20/2026)

    For Sale O6398814 - 7137 BEEK ST, WINDERMERE, FL 34786 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1910
       Built: 2013
    Monthly Fee: $120
       Tax: $7,932 (2025)
    Community: Windermere Terrace
    Single Family


    Estimated Monthly Payment: $3,795 (change assumption)
    Mortgage ($3,014) + Fees ($120) + Taxes in 2025 ($661)


    Taxes:$7,932

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 713 MAIN ST, WINDERMERE, FL 34786

    $2,235,000126 Days on yellowkey   MLS ID: O6368185

    For Sale O6368185 - 713 MAIN ST, WINDERMERE, FL 34786 82 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 5031
       Built: 2013   Tax: $9,559 (2025)
    Community: Windermere
    Spa: No

    Single Family


    Estimated Monthly Payment: $13,043 (change assumption)
    Mortgage ($12,246) + Taxes in 2025 ($797)


    Taxes:$9,559

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 3130 BUTLER BAY DR N, WINDERMERE, FL 34786

    $1,725,00020 Days on yellowkey   MLS ID: O6395307

    For Sale O6395307 - 3130 BUTLER BAY DR N, WINDERMERE, FL 34786 51 photos

    Bed: 5   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 4490
       Built: 1985
    Monthly Fee: $199
       Tax: $21,502 (2025)
    Community: Butler Bay
    Single Family


    Estimated Monthly Payment: $11,443 (change assumption)
    Mortgage ($9,452) + Fees ($199) + Taxes in 2025 ($1,792)


    Taxes:$21,502

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11686 WATER RUN ALY, WINDERMERE, FL 34786

    $409,90041 Days on yellowkey   MLS ID: O6390542

    REDUCED by $2,000 (0.5%) on 04/20/2026

    For Sale O6390542 - 11686 WATER RUN ALY, WINDERMERE, FL 34786 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1584
       Built: 2017
    Monthly Fee: $332
       Tax: $6,025 (2025)
    Community: Ashlin Park Ph 2
    Spa: No

    Townhouse


    Estimated Monthly Payment: $3,080 (change assumption)
    Mortgage ($2,246) + Fees ($332) + Taxes in 2025 ($502)


    Taxes:$6,025

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 8411 WOBURN CT, WINDERMERE, FL 34786

    $1,250,00028 Days on yellowkey   MLS ID: O6391980

    REDUCED by $10,000 (0.8%) on 04/20/2026

    For Sale O6391980 - 8411 WOBURN CT, WINDERMERE, FL 34786 41 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2582
       Built: 1999
    Monthly Fee: $222
       Tax: $12,964 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,151 (change assumption)
    Mortgage ($6,849) + Fees ($222) + Taxes in 2025 ($1,080)


    Taxes:$12,964

    Elementary School: Windermere Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 13622 DARCHANCE RD, WINDERMERE, FL 34786

    $629,90033 Days on yellowkey   MLS ID: S5146266

    REDUCED by $19,100 (2.9%) on 04/20/2026

    For Sale S5146266 - 13622 DARCHANCE RD, WINDERMERE, FL 34786 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2147
       Built: 2007
    Monthly Fee: $81
       Tax: $5,403 (2025)
    Community: Enclave/Berkshire Park B G H I
    Single Family


    Estimated Monthly Payment: $3,983 (change assumption)
    Mortgage ($3,451) + Fees ($81) + Taxes in 2025 ($450)


    Taxes:$5,403

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4200 DOWN POINT LN, WINDERMERE, FL 34786

    $9,900,00069 Days on yellowkey   MLS ID: O6382393

    2 Days Off yellowkey (back on 2/23/2026)

    For Sale O6382393 - 4200 DOWN POINT LN, WINDERMERE, FL 34786 63 photos

    Bed: 6   Bath: 8.0   Gar: 4
    Liv Area Sq Ft: 14435
       Built: 2001   Tax: $82,719 (2025)
    Community: Down Point Sub
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $61,139 (change assumption)
    Mortgage ($54,245) + Taxes in 2025 ($6,893)


    Taxes:$82,719

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 1420 DINGENS AVE, WINDERMERE, FL 34786

    $1,600,00084 Days on yellowkey   MLS ID: O6376538

    2 Days Off yellowkey (back on 4/20/2026)

    For Sale O6376538 - 1420 DINGENS AVE, WINDERMERE, FL 34786 41 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4072
       Built: 2018   Tax: $13,393 (2025)
    Community: Gotha
    Single Family


    Estimated Monthly Payment: $9,883 (change assumption)
    Mortgage ($8,767) + Taxes in 2025 ($1,116)


    Taxes:$13,393

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 13733 BRESSLER ALY, WINDERMERE, FL 34786

    $455,00076 Days on yellowkey   MLS ID: O6379257

    REDUCED by $9,999 (2.2%) on 04/20/2026

    For Sale O6379257 - 13733 BRESSLER ALY, WINDERMERE, FL 34786 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2002
       Built: 2019
    Monthly Fee: $185
       Tax: $7,023 (2024)
    Community: Vineyards/Horizons West Ph 4
    Townhouse


    Estimated Monthly Payment: $3,263 (change assumption)
    Mortgage ($2,493) + Fees ($185) + Taxes in 2024 ($585)


    Taxes:$7,023

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle




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

Windermere 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 Windermere . You can use our website to view Multiple Listing Service (MLS) data on Windermere 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 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.