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Windermere Homes For Sale & Real Estate - 328 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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  • 7560 BENTONSHIRE AVE, WINDERMERE, FL 34786

    $445,00039 Days on yellowkey   MLS ID: O6405384

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

    For Sale O6405384 - 7560 BENTONSHIRE AVE, WINDERMERE, FL 34786 45 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1905
       Built: 2009
    Monthly Fee: $185
       Tax: $6,652 (2025)
    Community: Wickham Park 04 05 06 09 10 11 12 01
    Townhouse


    Estimated Monthly Payment: $3,178 (change assumption)
    Mortgage ($2,438) + Fees ($185) + Taxes in 2025 ($554)


    Taxes:$6,652

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11536 CLAYMONT CIR, WINDERMERE, FL 34786

    $1,175,00080 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

    $629,00059 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

    $1,200,000241 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

    $1,299,00092 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


  • 13730 CALERA ALY, WINDERMERE, FL 34786

    $465,00021 Days on yellowkey   MLS ID: O6410129

    For Sale O6410129 - 13730 CALERA ALY, WINDERMERE, FL 34786 58 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2091
       Built: 2017
    Monthly Fee: $439
       Tax: $7,593 (2025)
    Community: Vineyards/Horizons West Ph 2B
    Townhouse


    Estimated Monthly Payment: $3,620 (change assumption)
    Mortgage ($2,548) + Fees ($439) + Taxes in 2025 ($633)


    Taxes:$7,593

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9527 QUEENSBURY CT, WINDERMERE, FL 34786

    $1,499,90025 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

    $1,039,09150 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

    $1,685,00026 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

    $649,99922 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

    $925,000229 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


  • 8180 BOAT HOOK LOOP #109, WINDERMERE, FL 34786

    $299,50025 Days on yellowkey   MLS ID: S5150297

    For Sale S5150297 - 8180 BOAT HOOK LOOP #109, WINDERMERE, FL 34786 19 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1161
       Built: 2006
    Monthly Fee: $485
       Tax: $4,173 (2025)
    Community: Lakeside/Lks
    Condo


    Estimated Monthly Payment: $2,474 (change assumption)
    Mortgage ($1,641) + Fees ($485) + Taxes in 2025 ($348)


    Taxes:$4,173

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1430 GLENWICK DR, WINDERMERE, FL 34786

    $779,90045 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


  • 5849 SOTER LN, WINDERMERE, FL 34786

    $445,90096 Days on yellowkey   MLS ID: O6388590

    REDUCED by $4,000 (0.9%) on 05/22/2026

    For Sale O6388590 - 5849 SOTER LN, WINDERMERE, FL 34786 31 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2001
       Built: 2019
    Monthly Fee: $171
       Tax: $6,775 (2024)
    Community: Vineyards/Horizons West Ph 4
    Townhouse


    Estimated Monthly Payment: $3,179 (change assumption)
    Mortgage ($2,443) + Fees ($171) + Taxes in 2024 ($565)


    Taxes:$6,775

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 1125 KELSO BLVD, WINDERMERE, FL 34786

    $1,425,00037 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

    $2,500,00055 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

    $669,90032 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


  • 14005 SPARKLING COVE LN, WINDERMERE, FL 34786

    $375,00024 Days on yellowkey   MLS ID: O6409827

    For Sale O6409827 - 14005 SPARKLING COVE LN, WINDERMERE, FL 34786 56 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1647
       Built: 2007
    Monthly Fee: $539
       Tax: $1,943 (2025)
    Community: Oasis Cove 1 At Lakeside Village Condo Ph 1
    Townhouse


    Estimated Monthly Payment: $2,756 (change assumption)
    Mortgage ($2,055) + Fees ($539) + Taxes in 2025 ($162)


    Taxes:$1,943

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 13519 BICTON LN, WINDERMERE, FL 34786

    $717,000156 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

    $815,00092 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 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.