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Windermere Single Family Homes For Sale - 283 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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  • 6840 HELMSLEY CIR, WINDERMERE, FL 34786

    $649,000127 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

    $6,950,00031 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

    $11,900,000120 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

    $889,00032 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

    $4,399,00040 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


  • 11536 CLAYMONT CIR, WINDERMERE, FL 34786

    $1,175,00079 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

    $629,00058 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


  • 1361 WHITNEY ISLES DR, WINDERMERE, FL 34786

    $1,200,000240 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

    $1,299,00091 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


  • 9527 QUEENSBURY CT, WINDERMERE, FL 34786

    $1,499,90024 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

    $1,039,09149 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


  • 5344 WATER CREEK DR, WINDERMERE, FL 34786

    $1,685,00025 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


  • 811 MAIN ST, WINDERMERE, FL 34786

    $649,99921 Days on yellowkey   MLS ID: O6409463

    For Sale O6409463 - 811 MAIN ST, WINDERMERE, FL 34786 33 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1398
       Built: 1985   Tax: $9,419 (2024)
    Community: Windermere Town
    Single Family


    Estimated Monthly Payment: $4,346 (change assumption)
    Mortgage ($3,562) + Taxes in 2024 ($785)


    Taxes:$9,419

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 3328 WAX BERRY CT, WINDERMERE, FL 34786

    $925,000228 Days on yellowkey   MLS ID: O6355868

    For Sale O6355868 - 3328 WAX BERRY CT, WINDERMERE, FL 34786 56 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 1984
    Monthly Fee: $21
       Tax: $10,867 (2024)
    Community: Lake Butler Estates
    Single Family


    Estimated Monthly Payment: $5,995 (change assumption)
    Mortgage ($5,068) + Fees ($21) + Taxes in 2024 ($906)


    Taxes:$10,867

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 1430 GLENWICK DR, WINDERMERE, FL 34786

    $779,90044 Days on yellowkey   MLS ID: O6403052

    4 Days Off yellowkey (back on 5/22/2026)

    For Sale O6403052 - 1430 GLENWICK DR, WINDERMERE, FL 34786 33 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2606
       Built: 2002
    Monthly Fee: $155
       Tax: $6,877 (2025)
    Community: Reserve At Belmere
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,001 (change assumption)
    Mortgage ($4,273) + Fees ($155) + Taxes in 2025 ($573)


    Taxes:$6,877

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1125 KELSO BLVD, WINDERMERE, FL 34786

    $1,425,00036 Days on yellowkey   MLS ID: O6406003

    0 Days Off yellowkey (back on 5/22/2026)

    For Sale O6406003 - 1125 KELSO BLVD, WINDERMERE, FL 34786 61 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3660
       Built: 1992
    Monthly Fee: $63
       Tax: $13,799 (2025)
    Community: Kelso On Lake Butler
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,021 (change assumption)
    Mortgage ($7,808) + Fees ($63) + Taxes in 2025 ($1,150)


    Taxes:$13,799

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9648 WEATHERSTONE CT, WINDERMERE, FL 34786

    $2,500,00054 Days on yellowkey   MLS ID: O6400680

    For Sale O6400680 - 9648 WEATHERSTONE CT, WINDERMERE, FL 34786 64 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


  • 4819 INDIAN DEER RD, WINDERMERE, FL 34786

    $669,90031 Days on yellowkey   MLS ID: O6403960

    1 Days Off yellowkey (back on 5/22/2026)

    For Sale O6403960 - 4819 INDIAN DEER RD, WINDERMERE, FL 34786 30 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3049
       Built: 2005
    Monthly Fee: $131
       Tax: $9,523 (2025)
    Community: Summerport Ph 05
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,595 (change assumption)
    Mortgage ($3,671) + Fees ($131) + Taxes in 2025 ($794)


    Taxes:$9,523

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13519 BICTON LN, WINDERMERE, FL 34786

    $717,000155 Days on yellowkey   MLS ID: O6372084

    For Sale O6372084 - 13519 BICTON LN, WINDERMERE, FL 34786 54 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2594
       Built: 2004
    Monthly Fee: $170
       Tax: $8,456 (2024)
    Community: Lakes/Windermere-Peachtree
    Single Family


    Estimated Monthly Payment: $4,803 (change assumption)
    Mortgage ($3,929) + Fees ($170) + Taxes in 2024 ($705)


    Taxes:$8,456

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 9225 MCDAVID CT, WINDERMERE, FL 34786

    $815,00091 Days on yellowkey   MLS ID: O6390371

    REDUCED by $20,000 (2.4%) on 05/09/2026

    For Sale O6390371 - 9225 MCDAVID CT, WINDERMERE, FL 34786 49 photos

    Bed: 4   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2713
       Built: 1984
    Monthly Fee: $25
       Tax: $5,005 (2025)
    Community: Roberts Landing
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,908 (change assumption)
    Mortgage ($4,466) + Fees ($25) + Taxes in 2025 ($417)


    Taxes:$5,005

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.