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Windermere Homes For Sale & Real Estate - 330 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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  • 9011 PINNACLE CIR, WINDERMERE, FL 34786

    $2,250,00057 Days on yellowkey   MLS ID: O6400872

    For Sale O6400872 - 9011 PINNACLE CIR, WINDERMERE, FL 34786 53 photos

    Bed: 5   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 6546
       Built: 2002
    Monthly Fee: $172
       Tax: $23,090 (2025)
    Community: Lake Down Crest
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,425 (change assumption)
    Mortgage ($12,328) + Fees ($172) + Taxes in 2025 ($1,924)


    Taxes:$23,090

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 5825 OXFORD MOOR BLVD, WINDERMERE, FL 34786

    $1,500,00061 Days on yellowkey   MLS ID: O6399697

    1 Days Off yellowkey (back on 5/15/2026)

    For Sale O6399697 - 5825 OXFORD MOOR BLVD, WINDERMERE, FL 34786 57 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4319
       Built: 2002
    Monthly Fee: $183
       Tax: $16,530 (2025)
    Community: Oxford Moor
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,779 (change assumption)
    Mortgage ($8,219) + Fees ($183) + Taxes in 2025 ($1,378)


    Taxes:$16,530

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 2219 RIDGEWIND WAY, WINDERMERE, FL 34786

    $1,299,00058 Days on yellowkey   MLS ID: O6400508

    1 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $50,000 (3.7%) on 05/04/2026

    For Sale O6400508 - 2219 RIDGEWIND WAY, WINDERMERE, FL 34786 45 photos

    Bed: 6   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3364
       Built: 1997
    Monthly Fee: $218
       Tax: $10,027 (2024)
    Community: Estates At Windermere
    Single Family


    Estimated Monthly Payment: $8,171 (change assumption)
    Mortgage ($7,118) + Fees ($218) + Taxes in 2024 ($836)


    Taxes:$10,027

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 212 W 1ST AVE, WINDERMERE, FL 34786

    $3,900,00050 Days on yellowkey   MLS ID: S5148430

    INCREASED by $2,300,000 (143.8%) on 05/13/2026

    For Sale S5148430 - 212 W 1ST AVE, WINDERMERE, FL 34786 11 photos

    Bed: 5   Bath: 5.0   Gar: 2
    Liv Area Sq Ft: 3800
       Built: 2026   Tax: $12,463 (2025)
    Community: Windermere Town
    Spa: No

    Single Family


    Estimated Monthly Payment: $22,408 (change assumption)
    Mortgage ($21,369) + Taxes in 2025 ($1,039)


    Taxes:$12,463

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 14368 DESERT HAVEN ST #4106, WINDERMERE, FL 34786

    $360,00071 Days on yellowkey   MLS ID: O6396784

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

    For Sale O6396784 - 14368 DESERT HAVEN ST #4106, WINDERMERE, FL 34786 27 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1840
       Built: 2013
    Monthly Fee: $541
       Tax: $3,885 (2025)
    Community: Oasis Cove Ii/Lakeside Village #Xi
    Spa: No

    Condo


    Estimated Monthly Payment: $2,837 (change assumption)
    Mortgage ($1,973) + Fees ($541) + Taxes in 2025 ($324)


    Taxes:$3,885

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2127 LILYPAD LN, WINDERMERE, FL 34786

    $1,250,00046 Days on yellowkey   MLS ID: O6403899

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

    For Sale O6403899 - 2127 LILYPAD LN, WINDERMERE, FL 34786 60 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3349
       Built: 1989
    Monthly Fee: $122
       Tax: $10,870 (2025)
    Community: Willows At Lake Rhea Ph 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,877 (change assumption)
    Mortgage ($6,849) + Fees ($122) + Taxes in 2025 ($906)


    Taxes:$10,870

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 81 OAKDALE ST, WINDERMERE, FL 34786

    $2,300,000211 Days on yellowkey   MLS ID: S5138567

    For Sale S5138567 - 81 OAKDALE ST, WINDERMERE, FL 34786 87 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4284
       Built: 2001   Tax: $24,940 (2025)
    Community: Davis Shores
    Single Family


    Estimated Monthly Payment: $14,681 (change assumption)
    Mortgage ($12,602) + Taxes in 2025 ($2,078)


    Taxes:$24,940

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 8866 HERENCIA ALY, WINDERMERE, FL 34786

    $430,00034 Days on yellowkey   MLS ID: O6407518

    For Sale O6407518 - 8866 HERENCIA ALY, WINDERMERE, FL 34786 31 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1577
       Built: 2021
    Monthly Fee: $240
       Tax: $5,532 (2025)
    Community: Legado 95/47 Lot 100
    Townhouse


    Estimated Monthly Payment: $3,057 (change assumption)
    Mortgage ($2,356) + Fees ($240) + Taxes in 2025 ($461)


    Taxes:$5,532

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 606 E 6TH AVE, WINDERMERE, FL 34786

    $2,350,00090 Days on yellowkey   MLS ID: O6390327

    2 Days Off yellowkey (back on 5/13/2026)

    For Sale O6390327 - 606 E 6TH AVE, WINDERMERE, FL 34786 42 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4471
       Built: 2016   Tax: $25,043 (2025)
    Community: Diamondhead
    Single Family


    Estimated Monthly Payment: $14,963 (change assumption)
    Mortgage ($12,876) + Taxes in 2025 ($2,087)


    Taxes:$25,043

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 7503 LAKE ALBERT DR, WINDERMERE, FL 34786

    $1,650,00039 Days on yellowkey   MLS ID: S5149564

    3 Days Off yellowkey (back on 5/11/2026)

    For Sale S5149564 - 7503 LAKE ALBERT DR, WINDERMERE, FL 34786 77 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4329
       Built: 2015
    Monthly Fee: $180
       Tax: $17,734 (2025)
    Community: Lake Burden South Phase 1
    Single Family


    Estimated Monthly Payment: $10,699 (change assumption)
    Mortgage ($9,041) + Fees ($180) + Taxes in 2025 ($1,478)


    Taxes:$17,734

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 5603 MARLEON DR, WINDERMERE, FL 34786

    $27,000,00036 Days on yellowkey   MLS ID: O6404938

    For Sale O6404938 - 5603 MARLEON DR, WINDERMERE, FL 34786 92 photos

    Bed: 7   Bath: 9.0   Gar: 10
    Liv Area Sq Ft: 22108
       Built: 2008   Tax: $138,635 (2025)
    Community: Na
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $159,494 (change assumption)
    Mortgage ($147,942) + Taxes in 2025 ($11,553)


    Taxes:$138,635

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5421 TILDENS GROVE BLVD, WINDERMERE, FL 34786

    $1,999,90046 Days on yellowkey   MLS ID: O6402594

    For Sale O6402594 - 5421 TILDENS GROVE BLVD, WINDERMERE, FL 34786 66 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5922
       Built: 2005
    Monthly Fee: $317
       Tax: $17,783 (2025)
    Community: Tildens Grove
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,757 (change assumption)
    Mortgage ($10,958) + Fees ($317) + Taxes in 2025 ($1,482)


    Taxes:$17,783

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12333 VIA DERNA PL, WINDERMERE, FL 34786

    $458,000202 Days on yellowkey   MLS ID: O6362685

    REDUCED by $1,000 (0.2%) on 05/11/2026

    For Sale O6362685 - 12333 VIA DERNA PL, WINDERMERE, FL 34786 57 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1919
       Built: 2014
    Monthly Fee: $316
       Tax: $6,305 (2024)
    Community: Carrington
    Townhouse


    Estimated Monthly Payment: $3,351 (change assumption)
    Mortgage ($2,510) + Fees ($316) + Taxes in 2024 ($525)


    Taxes:$6,305

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11686 WATER RUN ALY, WINDERMERE, FL 34786

    $409,90095 Days on yellowkey   MLS ID: O6390542

    REDUCED by $2,000 (0.5%) on 04/20/2026

    For Sale O6390542 - 11686 WATER RUN ALY, WINDERMERE, FL 34786 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1584
       Built: 2017
    Monthly Fee: $332
       Tax: $6,025 (2025)
    Community: Ashlin Park Ph 2
    Spa: No

    Townhouse


    Estimated Monthly Payment: $3,080 (change assumption)
    Mortgage ($2,246) + Fees ($332) + Taxes in 2025 ($502)


    Taxes:$6,025

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 13733 BRESSLER ALY, WINDERMERE, FL 34786

    $455,000130 Days on yellowkey   MLS ID: O6379257

    1 Days Off yellowkey (back on 5/11/2026)

    REDUCED by $9,999 (2.2%) on 04/20/2026

    For Sale O6379257 - 13733 BRESSLER ALY, WINDERMERE, FL 34786 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2002
       Built: 2019
    Monthly Fee: $185
       Tax: $7,023 (2024)
    Community: Vineyards/Horizons West Ph 4
    Townhouse


    Estimated Monthly Payment: $3,263 (change assumption)
    Mortgage ($2,493) + Fees ($185) + Taxes in 2024 ($585)


    Taxes:$7,023

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 9575 WESTOVER ROBERTS RD, WINDERMERE, FL 34786

    $4,850,000217 Days on yellowkey   MLS ID: O6357873

    REDUCED by $75,000 (1.5%) on 05/11/2026

    For Sale O6357873 - 9575 WESTOVER ROBERTS RD, WINDERMERE, FL 34786 95 photos

    Bed: 7   Bath: 8.0   Gar: 6
    Liv Area Sq Ft: 8931
       Built: 2008   Tax: $30,908 (2024)
    Community: Gotha Town
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $29,150 (change assumption)
    Mortgage ($26,575) + Taxes in 2024 ($2,576)


    Taxes:$30,908

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 8552 POWDER RIDGE TRL, WINDERMERE, FL 34786

    $680,000111 Days on yellowkey   MLS ID: S5144276

    For Sale S5144276 - 8552 POWDER RIDGE TRL, WINDERMERE, FL 34786 30 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2612
       Built: 2016
    Monthly Fee: $82
       Tax: $8,150 (2024)
    Community: Windermere Trls Ph 3B
    Single Family


    Estimated Monthly Payment: $4,487 (change assumption)
    Mortgage ($3,726) + Fees ($82) + Taxes in 2024 ($679)


    Taxes:$8,150

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5413 WALSH POND CT, WINDERMERE, FL 34786

    $800,00084 Days on yellowkey   MLS ID: O6391919

    REDUCED by $75,000 (8.6%) on 05/09/2026

    For Sale O6391919 - 5413 WALSH POND CT, WINDERMERE, FL 34786 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3124
       Built: 2006
    Monthly Fee: $130
       Tax: $10,646 (2025)
    Community: Edens Hammock
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,401 (change assumption)
    Mortgage ($4,383) + Fees ($130) + Taxes in 2025 ($887)


    Taxes:$10,646

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11472 PARK AVE NE, WINDERMERE, FL 34786

    $1,125,000154 Days on yellowkey   MLS ID: G5105731

    5 Days Off yellowkey (back on 4/28/2026)

    For Sale G5105731 - 11472 PARK AVE NE, WINDERMERE, FL 34786 67 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3166
       Built: 1985
    Monthly Fee: $21
       Tax: $5,774 (2025)
    Community: Windermere
    Single Family


    Estimated Monthly Payment: $6,666 (change assumption)
    Mortgage ($6,164) + Fees ($21) + Taxes in 2025 ($481)


    Taxes:$5,774

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Gotha Middle


  • 6606 SAWYER SHORES LN, WINDERMERE, FL 34786

    $2,500,000110 Days on yellowkey   MLS ID: O6386058

    For Sale O6386058 - 6606 SAWYER SHORES LN, WINDERMERE, FL 34786 19 photos

    Bed: 5   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 5516
       Built: 2025   Tax: $3,720 (2024)
    Community: Sawyer Shores Sub
    Single Family


    Estimated Monthly Payment: $14,008 (change assumption)
    Mortgage ($13,698) + Taxes in 2024 ($310)


    Taxes:$3,720

    Elementary School: None

    High School: None

    Tax Year: 2024

    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.