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Windermere Homes For Sale & Real Estate - 311 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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  • 4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786

    $3,200,000358 Days on yellowkey   MLS ID: O6330108

    For Sale O6330108 - 4819 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786 44 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3745
       Built: 2006
    Monthly Fee: $1,146
       Tax: $33,607 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,480 (change assumption)
    Mortgage ($17,534) + Fees ($1,146) + Taxes in 2024 ($2,801)


    Taxes:$33,607

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 13836 BLUEBIRD POND RD, WINDERMERE, FL 34786

    $675,00080 Days on yellowkey   MLS ID: TB8502779

    1 Days Off yellowkey (back on 7/1/2026)

    REDUCED by $23,000 (3.3%) on 06/04/2026

    For Sale TB8502779 - 13836 BLUEBIRD POND RD, WINDERMERE, FL 34786 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2108
       Built: 2004
    Monthly Fee: $100
       Tax: $3,052 (2025)
    Community: Summerport
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,053 (change assumption)
    Mortgage ($3,699) + Fees ($100) + Taxes in 2025 ($254)


    Taxes:$3,052

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11015 HAWKSHEAD CT, WINDERMERE, FL 34786

    $1,489,99958 Days on yellowkey   MLS ID: O6405977

    REDUCED by $10,000 (0.7%) on 07/01/2026

    For Sale O6405977 - 11015 HAWKSHEAD CT, WINDERMERE, FL 34786 42 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3868
       Built: 2004
    Monthly Fee: $640
       Tax: $18,824 (2025)
    Community: Reserve At Lake Butler Sound
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,373 (change assumption)
    Mortgage ($8,164) + Fees ($640) + Taxes in 2025 ($1,569)


    Taxes:$18,824

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6379 SWANSON ST, WINDERMERE, FL 34786

    $1,099,00086 Days on yellowkey   MLS ID: O6400522

    1 Days Off yellowkey (back on 7/1/2026)

    REDUCED by $20,000 (1.8%) on 06/25/2026

    For Sale O6400522 - 6379 SWANSON ST, WINDERMERE, FL 34786 35 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3804
       Built: 2014
    Monthly Fee: $167
       Tax: $10,769 (2025)
    Community: Enclave
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,086 (change assumption)
    Mortgage ($6,022) + Fees ($167) + Taxes in 2025 ($897)


    Taxes:$10,769

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 516 JENNIFER LN, WINDERMERE, FL 34786

    $1,295,00022 Days on yellowkey   MLS ID: O6419731

    0 Days Off yellowkey (back on 6/29/2026)

    For Sale O6419731 - 516 JENNIFER LN, WINDERMERE, FL 34786 71 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3021
       Built: 1982
    Monthly Fee: $333
       Tax: $6,252 (2025)
    Community: Windermere Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,950 (change assumption)
    Mortgage ($7,096) + Fees ($333) + Taxes in 2025 ($521)


    Taxes:$6,252

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 11861 VERMILLION AVE, WINDERMERE, FL 34786

    $475,00045 Days on yellowkey   MLS ID: O6410430

    For Sale O6410430 - 11861 VERMILLION AVE, WINDERMERE, FL 34786 98 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1600
       Built: 2015
    Monthly Fee: $363
       Tax: $6,340 (2025)
    Community: Windermere Trls Prcl 3
    Townhouse


    Estimated Monthly Payment: $3,494 (change assumption)
    Mortgage ($2,603) + Fees ($363) + Taxes in 2025 ($528)


    Taxes:$6,340

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11617 CAMDEN PARK DR, WINDERMERE, FL 34786

    $1,375,00070 Days on yellowkey   MLS ID: O6405409

    REDUCED by $22,000 (1.6%) on 06/18/2026

    For Sale O6405409 - 11617 CAMDEN PARK DR, WINDERMERE, FL 34786 64 photos

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3463
       Built: 2005
    Monthly Fee: $283
       Tax: $7,189 (2025)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $8,416 (change assumption)
    Mortgage ($7,534) + Fees ($283) + Taxes in 2025 ($599)


    Taxes:$7,189

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1408 LAKE WHITNEY DRIVE, WINDERMERE, FL 34786

    $2,650,00025 Days on yellowkey   MLS ID: O6418721

    For Sale O6418721 - 1408 LAKE WHITNEY DRIVE, WINDERMERE, FL 34786 80 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5433
       Built: 2003
    Monthly Fee: $271
       Tax: $24,189 (2025)
    Community: Reserve At Belmere Ph 02 48 144
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,807 (change assumption)
    Mortgage ($14,520) + Fees ($271) + Taxes in 2025 ($2,016)


    Taxes:$24,189

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13424 HOPKINTON CT, WINDERMERE, FL 34786

    $549,99922 Days on yellowkey   MLS ID: O6419100

    For Sale O6419100 - 13424 HOPKINTON CT, WINDERMERE, FL 34786 8 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2190
       Built: 2005
    Monthly Fee: $169
       Tax: $7,268 (2025)
    Community: Lakes Of Windermere-Peachtree
    Single Family


    Estimated Monthly Payment: $3,788 (change assumption)
    Mortgage ($3,014) + Fees ($169) + Taxes in 2025 ($606)


    Taxes:$7,268

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11636 WATER RUN ALY, WINDERMERE, FL 34786

    $408,000273 Days on yellowkey   MLS ID: S5136888

    3 Days Off yellowkey (back on 6/30/2026)

    REDUCED by $17,000 (4.0%) on 05/06/2026

    For Sale S5136888 - 11636 WATER RUN ALY, WINDERMERE, FL 34786 18 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1584
       Built: 2017
    Monthly Fee: $332
       Tax: $5,634 (2024)
    Community: Ashlin Park Ph 2
    Townhouse


    Estimated Monthly Payment: $3,037 (change assumption)
    Mortgage ($2,236) + Fees ($332) + Taxes in 2024 ($469)


    Taxes:$5,634

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12305 VIA DERNA PL, WINDERMERE, FL 34786

    $450,000178 Days on yellowkey   MLS ID: O6374964

    REDUCED by $15,000 (3.2%) on 06/30/2026

    For Sale O6374964 - 12305 VIA DERNA PL, WINDERMERE, FL 34786 24 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1891
       Built: 2014
    Monthly Fee: $316
       Tax: $5,016 (2025)
    Community: Carrington
    Townhouse


    Estimated Monthly Payment: $3,200 (change assumption)
    Mortgage ($2,466) + Fees ($316) + Taxes in 2025 ($418)


    Taxes:$5,016

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 9316 GLADYS GARDEN CT, WINDERMERE, FL 34786

    $6,500,00018 Days on yellowkey   MLS ID: O6420326

    For Sale O6420326 - 9316 GLADYS GARDEN CT, WINDERMERE, FL 34786 73 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5471
       Built: 2026
    Monthly Fee: $2,370
       Tax: $9,424 (2025)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $38,771 (change assumption)
    Mortgage ($35,616) + Fees ($2,370) + Taxes in 2025 ($785)


    Taxes:$9,424

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 9011 CHAPMAN OAK CT, WINDERMERE, FL 34786

    $599,00092 Days on yellowkey   MLS ID: S5148031

    REDUCED by $30,000 (4.8%) on 06/29/2026

    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: $4,029 (change assumption)
    Mortgage ($3,282) + Fees ($31) + Taxes in 2025 ($716)


    Taxes:$8,592

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9725 CHESTNUT RIDGE DR, WINDERMERE, FL 34786

    $6,000,000196 Days on yellowkey   MLS ID: O6370294

    REDUCED by $150,000 (2.4%) on 05/01/2026

    For Sale O6370294 - 9725 CHESTNUT RIDGE DR, WINDERMERE, FL 34786 64 photos

    Bed: 7   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 8000
       Built: 1999
    Monthly Fee: $1,043
       Tax: $29,046 (2024)
    Community: Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $36,339 (change assumption)
    Mortgage ($32,876) + Fees ($1,043) + Taxes in 2024 ($2,421)


    Taxes:$29,046

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 13755 BRAVANTE ALY, WINDERMERE, FL 34786

    $465,000121 Days on yellowkey   MLS ID: O6389321

    REDUCED by $15,000 (3.1%) on 06/29/2026

    For Sale O6389321 - 13755 BRAVANTE ALY, WINDERMERE, FL 34786 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1996
       Built: 2017
    Monthly Fee: $254
       Tax: $5,646 (2025)
    Community: Vineyards/Horizons West Ph 2B
    Townhouse


    Estimated Monthly Payment: $3,272 (change assumption)
    Mortgage ($2,548) + Fees ($254) + Taxes in 2025 ($471)


    Taxes:$5,646

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13366 ABUELA ALY, WINDERMERE, FL 34786

    $415,000183 Days on yellowkey   MLS ID: O6374298

    REDUCED by $15,000 (3.5%) on 06/29/2026

    For Sale O6374298 - 13366 ABUELA ALY, WINDERMERE, FL 34786 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1589
       Built: 2020
    Monthly Fee: $240
       Tax: $6,237 (2024)
    Community: Legado
    Townhouse


    Estimated Monthly Payment: $3,034 (change assumption)
    Mortgage ($2,274) + Fees ($240) + Taxes in 2024 ($520)


    Taxes:$6,237

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 1554 LAKE RHEA DR, WINDERMERE, FL 34786

    $1,350,00070 Days on yellowkey   MLS ID: O6406297

    REDUCED by $50,000 (3.6%) on 05/29/2026

    For Sale O6406297 - 1554 LAKE RHEA DR, WINDERMERE, FL 34786 59 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3427
       Built: 2004
    Monthly Fee: $241
       Tax: $9,102 (2025)
    Community: Reserve At Belmere
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,397 (change assumption)
    Mortgage ($7,397) + Fees ($241) + Taxes in 2025 ($759)


    Taxes:$9,102

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 11401 EVESHAM DR, WINDERMERE, FL 34786

    $425,00056 Days on yellowkey   MLS ID: O6410182

    0 Days Off yellowkey (back on 6/29/2026)

    REDUCED by $10,000 (2.3%) on 06/15/2026

    For Sale O6410182 - 11401 EVESHAM DR, WINDERMERE, FL 34786 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1847
       Built: 2008
    Monthly Fee: $315
       Tax: $3,077 (2024)
    Community: Preston Square
    Townhouse


    Estimated Monthly Payment: $2,900 (change assumption)
    Mortgage ($2,329) + Fees ($315) + Taxes in 2024 ($256)


    Taxes:$3,077

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 9110 PALM TREE DR, WINDERMERE, FL 34786

    $650,00035 Days on yellowkey   MLS ID: O6414631

    REDUCED by $25,000 (3.7%) on 06/29/2026

    For Sale O6414631 - 9110 PALM TREE DR, WINDERMERE, FL 34786 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1819
       Built: 1985
    Monthly Fee: $32
       Tax: $8,182 (2025)
    Community: Silver Woods Ph 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,275 (change assumption)
    Mortgage ($3,562) + Fees ($32) + Taxes in 2025 ($682)


    Taxes:$8,182

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 8744 DANFORTH DR, WINDERMERE, FL 34786

    $350,00030 Days on yellowkey   MLS ID: O6414301

    2 Days Off yellowkey (back on 6/29/2026)

    For Sale O6414301 - 8744 DANFORTH DR, WINDERMERE, FL 34786 32 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1375
       Built: 2005
    Monthly Fee: $200
       Tax: $2,938 (2025)
    Community: Lakes Of Windermere - Lake Reams Townhomes
    Townhouse


    Estimated Monthly Payment: $2,363 (change assumption)
    Mortgage ($1,918) + Fees ($200) + Taxes in 2025 ($245)


    Taxes:$2,938

    Elementary School: Keene Crossing Elementary

    High School: West Orange High

    Tax Year: 2025

    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.