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Windermere Single Family Homes For Sale - 257 homes

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

Location: Windermere

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  • 17514 BLACK RAIL ST, WINDERMERE, FL 34786

    $725,00087 Days on yellowkey   MLS ID: O6376756

    0 Days Off yellowkey (back on 4/21/2026)

    For Sale O6376756 - 17514 BLACK RAIL ST, WINDERMERE, FL 34786 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2373
       Built: 2014
    Monthly Fee: $167
       Tax: $8,578 (2025)
    Community: Enclave
    Single Family


    Estimated Monthly Payment: $4,854 (change assumption)
    Mortgage ($3,973) + Fees ($167) + Taxes in 2025 ($715)


    Taxes:$8,578

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13243 CHARFIELD ST, WINDERMERE, FL 34786

    $699,00055 Days on yellowkey   MLS ID: O6385405

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6385405 - 13243 CHARFIELD ST, WINDERMERE, FL 34786 39 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2794
       Built: 2010
    Monthly Fee: $81
       Tax: $6,403 (2024)
    Community: Lake Sawyer South Ph 02
    Single Family


    Estimated Monthly Payment: $4,445 (change assumption)
    Mortgage ($3,830) + Fees ($81) + Taxes in 2024 ($534)


    Taxes:$6,403

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13013 OVERSTREET RD, WINDERMERE, FL 34786

    $669,99455 Days on yellowkey   MLS ID: O6380917

    REDUCED by $10,000 (1.5%) on 04/21/2026

    For Sale O6380917 - 13013 OVERSTREET RD, WINDERMERE, FL 34786 47 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2053
       Built: 2009
    Monthly Fee: $82
       Tax: $3,146 (2024)
    Community: Lakes/Windermere
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,015 (change assumption)
    Mortgage ($3,671) + Fees ($82) + Taxes in 2024 ($262)


    Taxes:$3,146

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 9648 WEATHERSTONE CT, WINDERMERE, FL 34786

    $2,500,0002 Days on yellowkey   MLS ID: O6400680

    For Sale O6400680 - 9648 WEATHERSTONE CT, WINDERMERE, FL 34786 65 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4482
       Built: 2000
    Monthly Fee: $227
       Tax: $20,450 (2025)
    Community: Weatherstone On Lake Olivia
    Spa: No

    Single Family


    Estimated Monthly Payment: $15,629 (change assumption)
    Mortgage ($13,698) + Fees ($227) + Taxes in 2025 ($1,704)


    Taxes:$20,450

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 13312 LONGACRE DR, WINDERMERE, FL 34786

    $534,900106 Days on yellowkey   MLS ID: S5141031

    REDUCED by $9,000 (1.7%) on 04/06/2026

    For Sale S5141031 - 13312 LONGACRE DR, WINDERMERE, FL 34786 35 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2058
       Built: 2013
    Monthly Fee: $120
       Tax: $7,533 (2024)
    Community: Windermere Terrace
    Single Family


    Estimated Monthly Payment: $3,679 (change assumption)
    Mortgage ($2,931) + Fees ($120) + Taxes in 2024 ($628)


    Taxes:$7,533

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 12761 HOLDENBURY LN, WINDERMERE, FL 34786

    $539,90033 Days on yellowkey   MLS ID: O6392337

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6392337 - 12761 HOLDENBURY LN, WINDERMERE, FL 34786 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2380
       Built: 2002
    Monthly Fee: $82
       Tax: $3,561 (2025)
    Community: Lakes/Windermere Ph 01 49 108
    Single Family


    Estimated Monthly Payment: $3,337 (change assumption)
    Mortgage ($2,958) + Fees ($82) + Taxes in 2025 ($297)


    Taxes:$3,561

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11922 ANGLE POND AVE, WINDERMERE, FL 34786

    $760,000278 Days on yellowkey   MLS ID: O6328443

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6328443 - 11922 ANGLE POND AVE, WINDERMERE, FL 34786 45 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3382
       Built: 2013
    Monthly Fee: $81
       Tax: $8,155 (2024)
    Community: Windermere Trls Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,925 (change assumption)
    Mortgage ($4,164) + Fees ($81) + Taxes in 2024 ($680)


    Taxes:$8,155

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 5186 VARDON DR, WINDERMERE, FL 34786

    $6,980,00067 Days on yellowkey   MLS ID: O6382040

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

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4739
       Built: 1990
    Monthly Fee: $985
       Tax: $32,002 (2025)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $41,897 (change assumption)
    Mortgage ($38,246) + Fees ($985) + Taxes in 2025 ($2,667)


    Taxes:$32,002

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 9713 ENDICOTT CT, WINDERMERE, FL 34786

    $5,250,0005 Days on yellowkey   MLS ID: O6393891

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6393891 - 9713 ENDICOTT CT, WINDERMERE, FL 34786 100 photos

    Bed: 6   Bath: 7.0   Gar: 6
    Liv Area Sq Ft: 7818
       Built: 2007
    Monthly Fee: $313
       Tax: $66,793 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $34,646 (change assumption)
    Mortgage ($28,766) + Fees ($313) + Taxes in 2025 ($5,566)


    Taxes:$66,793

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 4 CHASE RD, WINDERMERE, FL 34786

    $875,00061 Days on yellowkey   MLS ID: O6384257

    REDUCED by $25,000 (2.8%) on 04/20/2026

    For Sale O6384257 - 4 CHASE RD, WINDERMERE, FL 34786 47 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 2386
       Built: 1971   Tax: $7,637 (2024)
    Community: Windermere Town
    Single Family


    Estimated Monthly Payment: $5,431 (change assumption)
    Mortgage ($4,794) + Taxes in 2024 ($636)


    Taxes:$7,637

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6638 BRIDGEWATER VILLAGE RD, WINDERMERE, FL 34786

    $664,90093 Days on yellowkey   MLS ID: O6374429

    1 Days Off yellowkey (back on 4/21/2026)

    For Sale O6374429 - 6638 BRIDGEWATER VILLAGE RD, WINDERMERE, FL 34786 40 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2908
       Built: 2013
    Monthly Fee: $223
       Tax: $8,467 (2024)
    Community: Vineyards/Horizons West Ph 1B
    Single Family


    Estimated Monthly Payment: $4,572 (change assumption)
    Mortgage ($3,643) + Fees ($223) + Taxes in 2024 ($706)


    Taxes:$8,467

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 8742 PEACHTREE PARK CT, WINDERMERE, FL 34786

    $574,000369 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

    $4,690,0002 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

    $13,550,0002 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

    $1,999,9992 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


  • 6799 HELMSLEY CIR, WINDERMERE, FL 34786

    $658,000156 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

    $1,475,000788 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

    $585,000208 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


  • 12411 MONTALCINO CIR, WINDERMERE, FL 34786

    $1,550,0005 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

    $3,299,0006 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




Why Bother Searching Elsewhere for Windermere Single Family Homes for Sale?

Windermere home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Windermere . You can use our website to view Multiple Listing Service (MLS) data on Windermere single family homes. 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 single family home 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.