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Windermere Homes For Sale & Real Estate - 314 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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  • 11536 CLAYMONT CIR, WINDERMERE, FL 34786

    $1,175,00066 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

    $629,00045 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

    $649,99494 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

    $1,200,000227 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

    $1,299,00078 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

    $1,750,000118 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


  • 13730 CALERA ALY, WINDERMERE, FL 34786

    $465,0007 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

    $1,499,90011 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

    $1,039,09136 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

    $2,888,88825 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

    $1,685,00012 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


  • 7612 FAIRGROVE AVE, WINDERMERE, FL 34786

    $440,00025 Days on yellowkey   MLS ID: S5149402

    For Sale S5149402 - 7612 FAIRGROVE AVE, WINDERMERE, FL 34786 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1742
       Built: 2016
    Monthly Fee: $347
       Tax: $6,515 (2025)
    Community: Windermere Sound Ph 2
    Townhouse


    Estimated Monthly Payment: $3,301 (change assumption)
    Mortgage ($2,411) + Fees ($347) + Taxes in 2025 ($543)


    Taxes:$6,515

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11419 CAMDEN PARK DR, WINDERMERE, FL 34786

    $1,295,00068 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

    $599,0008 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


  • 811 MAIN ST, WINDERMERE, FL 34786

    $649,9998 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


  • 8411 WOBURN CT, WINDERMERE, FL 34786

    $1,200,00066 Days on yellowkey   MLS ID: O6391980

    REDUCED by $50,000 (4.0%) on 05/12/2026

    For Sale O6391980 - 8411 WOBURN CT, WINDERMERE, FL 34786 41 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2582
       Built: 1999
    Monthly Fee: $222
       Tax: $12,964 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,877 (change assumption)
    Mortgage ($6,575) + Fees ($222) + Taxes in 2025 ($1,080)


    Taxes:$12,964

    Elementary School: Windermere Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 3328 WAX BERRY CT, WINDERMERE, FL 34786

    $925,000215 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


  • 13842 ORANGE CREST DR, WINDERMERE, FL 34786

    $739,88830 Days on yellowkey   MLS ID: O6402132

    REDUCED by $10,000 (1.3%) on 05/22/2026

    For Sale O6402132 - 13842 ORANGE CREST DR, WINDERMERE, FL 34786 48 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2620
       Built: 2003
    Monthly Fee: $116
       Tax: $9,561 (2026)
    Community: Eden Isle
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,967 (change assumption)
    Mortgage ($4,054) + Fees ($116) + Taxes in 2026 ($797)


    Taxes:$9,561

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2026

    Middle School: Bridgewater Middle


  • 7249 SHADEVIEW ALY, WINDERMERE, FL 34786

    $407,00065 Days on yellowkey   MLS ID: S5146580

    REDUCED by $3,000 (0.7%) on 05/20/2026

    For Sale S5146580 - 7249 SHADEVIEW ALY, WINDERMERE, FL 34786 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1569
       Built: 2016
    Monthly Fee: $332
       Tax: $5,983 (2025)
    Community: Ashlin Park Ph 2
    Townhouse


    Estimated Monthly Payment: $3,061 (change assumption)
    Mortgage ($2,230) + Fees ($332) + Taxes in 2025 ($499)


    Taxes:$5,983

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786

    $3,450,000124 Days on yellowkey   MLS ID: O6377244

    REDUCED by $25,000 (0.7%) on 05/07/2026

    For Sale O6377244 - 10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786 100 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 5273
       Built: 1986
    Monthly Fee: $103
       Tax: $28,092 (2025)
    Community: Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,348 (change assumption)
    Mortgage ($18,904) + Fees ($103) + Taxes in 2025 ($2,341)


    Taxes:$28,092

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha 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.