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Windermere Single Family Homes For Sale - 265 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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  • 7180 BEEK ST, WINDERMERE, FL 34786

    $780,00070 Days on yellowkey   MLS ID: O6393213

    For Sale O6393213 - 7180 BEEK ST, WINDERMERE, FL 34786 33 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3648
       Built: 2013
    Monthly Fee: $124
       Tax: $11,023 (2025)
    Community: Windermere Terrace
    Single Family


    Estimated Monthly Payment: $5,316 (change assumption)
    Mortgage ($4,274) + Fees ($124) + Taxes in 2025 ($919)


    Taxes:$11,023

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 6615 HELMSLEY CIR, WINDERMERE, FL 34786

    $690,00019 Days on yellowkey   MLS ID: O6406997

    0 Days Off yellowkey (back on 5/26/2026)

    For Sale O6406997 - 6615 HELMSLEY CIR, WINDERMERE, FL 34786 38 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3390
       Built: 2011
    Monthly Fee: $99
       Tax: $605 (2025)
    Community: Preston Square
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,930 (change assumption)
    Mortgage ($3,781) + Fees ($99) + Taxes in 2025 ($50)


    Taxes:$605

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 6840 HELMSLEY CIR, WINDERMERE, FL 34786

    $649,000116 Days on yellowkey   MLS ID: S5142930

    1 Days Off yellowkey (back on 5/14/2026)

    REDUCED by $40,000 (5.8%) on 05/07/2026

    For Sale S5142930 - 6840 HELMSLEY CIR, WINDERMERE, FL 34786 76 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2847
       Built: 2009
    Monthly Fee: $129
       Tax: $5,044 (2024)
    Community: Preston Square
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,105 (change assumption)
    Mortgage ($3,556) + Fees ($129) + Taxes in 2024 ($420)


    Taxes:$5,044

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6462 DEACON CIR, WINDERMERE, FL 34786

    $6,950,00020 Days on yellowkey   MLS ID: O6407107

    For Sale O6407107 - 6462 DEACON CIR, WINDERMERE, FL 34786 46 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 7178
       Built: 1997
    Monthly Fee: $1,224
       Tax: $108,011 (2025)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $48,306 (change assumption)
    Mortgage ($38,081) + Fees ($1,224) + Taxes in 2025 ($9,001)


    Taxes:$108,011

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 9323 GLADYS GARDEN CT, WINDERMERE, FL 34786

    $11,900,000109 Days on yellowkey   MLS ID: O6381880

    REDUCED by $600,000 (4.8%) on 05/26/2026

    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
    Spa: No

    Single Family


    Estimated Monthly Payment: $68,076 (change assumption)
    Mortgage ($65,204) + 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


  • 111 MAIN ST, WINDERMERE, FL 34786

    $889,00021 Days on yellowkey   MLS ID: O6407060

    2 Days Off yellowkey (back on 5/26/2026)

    For Sale O6407060 - 111 MAIN ST, WINDERMERE, FL 34786 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2272
       Built: 1984   Tax: $9,734 (2025)
    Community: Windermere Town
    Single Family


    Estimated Monthly Payment: $5,682 (change assumption)
    Mortgage ($4,871) + Taxes in 2025 ($811)


    Taxes:$9,734

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6120 GREATWATER DR, WINDERMERE, FL 34786

    $4,399,00029 Days on yellowkey   MLS ID: O6404574

    For Sale O6404574 - 6120 GREATWATER DR, WINDERMERE, FL 34786 92 photos

    Bed: 5   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 5580
       Built: 1999
    Monthly Fee: $298
       Tax: $32,016 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,070 (change assumption)
    Mortgage ($24,104) + Fees ($298) + Taxes in 2025 ($2,668)


    Taxes:$32,016

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5500 W LAKE BUTLER RD, WINDERMERE, FL 34786

    $4,700,00015 Days on yellowkey   MLS ID: O6408637

    For Sale O6408637 - 5500 W LAKE BUTLER RD, WINDERMERE, FL 34786 96 photos

    Bed: 8   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 7000
       Built: 1997   Tax: $17,387 (2025)
    Community: West Lake Butler Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $27,202 (change assumption)
    Mortgage ($25,753) + Taxes in 2025 ($1,449)


    Taxes:$17,387

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11536 CLAYMONT CIR, WINDERMERE, FL 34786

    $1,175,00068 Days on yellowkey   MLS ID: O6392958

    REDUCED by $75,000 (6.0%) on 05/26/2026

    For Sale O6392958 - 11536 CLAYMONT CIR, WINDERMERE, FL 34786 68 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2882
       Built: 2002
    Monthly Fee: $298
       Tax: $8,766 (2025)
    Community: Keenes Pointe Ut 04 Sec 31 48 82
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,467 (change assumption)
    Mortgage ($6,438) + Fees ($298) + Taxes in 2025 ($731)


    Taxes:$8,766

    Elementary School: Windermere Elem

    High School: Winter Park High

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9011 CHAPMAN OAK CT, WINDERMERE, FL 34786

    $629,00047 Days on yellowkey   MLS ID: S5148031

    REDUCED by $20,000 (3.1%) on 05/26/2026

    For Sale S5148031 - 9011 CHAPMAN OAK CT, WINDERMERE, FL 34786 30 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2050
       Built: 1987
    Monthly Fee: $31
       Tax: $8,592 (2025)
    Community: Silver Woods Ph 05
    Single Family


    Estimated Monthly Payment: $4,194 (change assumption)
    Mortgage ($3,446) + Fees ($31) + Taxes in 2025 ($716)


    Taxes:$8,592

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13013 OVERSTREET RD, WINDERMERE, FL 34786

    $649,99496 Days on yellowkey   MLS ID: O6380917

    REDUCED by $15,000 (2.3%) on 05/12/2026

    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: $3,906 (change assumption)
    Mortgage ($3,562) + 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


  • 1361 WHITNEY ISLES DR, WINDERMERE, FL 34786

    $1,200,000229 Days on yellowkey   MLS ID: O6352069

    For Sale O6352069 - 1361 WHITNEY ISLES DR, WINDERMERE, FL 34786 49 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2787
       Built: 2006
    Monthly Fee: $136
       Tax: $6,975 (2024)
    Community: Whitney Isles/Belmere Ph 02
    Single Family


    Estimated Monthly Payment: $7,292 (change assumption)
    Mortgage ($6,575) + Fees ($136) + Taxes in 2024 ($581)


    Taxes:$6,975

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 1849 WATERMERE LN, WINDERMERE, FL 34786

    $1,299,00080 Days on yellowkey   MLS ID: O6389840

    0 Days Off yellowkey (back on 5/25/2026)

    REDUCED by $26,000 (2.0%) on 05/04/2026

    For Sale O6389840 - 1849 WATERMERE LN, WINDERMERE, FL 34786 31 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3934
       Built: 2005
    Monthly Fee: $267
       Tax: $8,439 (2024)
    Community: Windermere Grande
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,088 (change assumption)
    Mortgage ($7,118) + Fees ($267) + Taxes in 2024 ($703)


    Taxes:$8,439

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 3013 SEIGNEURY DR, WINDERMERE, FL 34786

    $1,750,000120 Days on yellowkey   MLS ID: O6377087

    REDUCED by $100,000 (5.4%) on 05/25/2026

    For Sale O6377087 - 3013 SEIGNEURY DR, WINDERMERE, FL 34786 62 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 5130
       Built: 2002
    Monthly Fee: $250
       Tax: $24,337 (2024)
    Community: Harbor Isle
    Single Family


    Estimated Monthly Payment: $11,867 (change assumption)
    Mortgage ($9,589) + Fees ($250) + Taxes in 2024 ($2,028)


    Taxes:$24,337

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 9527 QUEENSBURY CT, WINDERMERE, FL 34786

    $1,499,90013 Days on yellowkey   MLS ID: O6408997

    For Sale O6408997 - 9527 QUEENSBURY CT, WINDERMERE, FL 34786 78 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 5378
       Built: 1998
    Monthly Fee: $101
       Tax: $20,104 (2025)
    Community: Windsor Hill
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,995 (change assumption)
    Mortgage ($8,218) + Fees ($101) + Taxes in 2025 ($1,675)


    Taxes:$20,104

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 14353 CREST PALM AVE, WINDERMERE, FL 34786

    $1,039,09138 Days on yellowkey   MLS ID: G5111542

    For Sale G5111542 - 14353 CREST PALM AVE, WINDERMERE, FL 34786 32 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $245
       Tax: $1,309 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,048 (change assumption)
    Mortgage ($5,694) + Fees ($245) + Taxes in 2025 ($109)


    Taxes:$1,309

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 5061 SAWYER COVE WAY, WINDERMERE, FL 34786

    $2,888,88827 Days on yellowkey   MLS ID: O6403804

    For Sale O6403804 - 5061 SAWYER COVE WAY, WINDERMERE, FL 34786 77 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3888
       Built: 2020
    Monthly Fee: $253
       Tax: $22,337 (2025)
    Community: Sawyer Sound
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $17,944 (change assumption)
    Mortgage ($15,829) + Fees ($253) + Taxes in 2025 ($1,861)


    Taxes:$22,337

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5344 WATER CREEK DR, WINDERMERE, FL 34786

    $1,685,00014 Days on yellowkey   MLS ID: O6408495

    0 Days Off yellowkey (back on 5/24/2026)

    For Sale O6408495 - 5344 WATER CREEK DR, WINDERMERE, FL 34786 67 photos

    Bed: 5   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 3924
       Built: 2004   Tax: $13,028 (2025)
    Community: Lake Davis Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,318 (change assumption)
    Mortgage ($9,233) + Taxes in 2025 ($1,086)


    Taxes:$13,028

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11419 CAMDEN PARK DR, WINDERMERE, FL 34786

    $1,295,00070 Days on yellowkey   MLS ID: O6392667

    0 Days Off yellowkey (back on 5/24/2026)

    For Sale O6392667 - 11419 CAMDEN PARK DR, WINDERMERE, FL 34786 25 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3686
       Built: 2005
    Monthly Fee: $283
       Tax: $7,583 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,011 (change assumption)
    Mortgage ($7,096) + Fees ($283) + Taxes in 2025 ($632)


    Taxes:$7,583

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13732 SUMMER HARBOR CT, WINDERMERE, FL 34786

    $599,00010 Days on yellowkey   MLS ID: O6410454

    For Sale O6410454 - 13732 SUMMER HARBOR CT, WINDERMERE, FL 34786 20 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2236
       Built: 2015
    Monthly Fee: $90
       Tax: $5,074 (2025)
    Community: Summerport Trail Ph 2
    Single Family


    Estimated Monthly Payment: $3,795 (change assumption)
    Mortgage ($3,282) + Fees ($90) + Taxes in 2025 ($423)


    Taxes:$5,074

    Elementary School: Keene Crossing Elementary

    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.