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Windermere Single Family Homes For Sale in Windermere - 68 homes

Windermere single family homes for sale are located in Orange County, Florida. Find Windermere single family homes in Windermere for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your search for Windermere, Windermere single family houses.

Location: Windermere, Windermere

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  • 9257 OUTLOOK ROCK TRL, WINDERMERE, FL 34786

    $879,999113 Days on yellowkey   MLS ID: S5143447

    REDUCED by $19,991 (2.2%) on 05/28/2026

    For Sale S5143447 - 9257 OUTLOOK ROCK TRL, WINDERMERE, FL 34786 56 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3619
       Built: 2017   Tax: $488 (2024)
    Community: Windermere Trls Ph 4B
    Single Family


    Estimated Monthly Payment: $4,862 (change assumption)
    Mortgage ($4,822) + Taxes in 2024 ($41)


    Taxes:$488

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 8360 VIVARO ISLE WAY, WINDERMERE, FL 34786

    $690,0006 Days on yellowkey   MLS ID: S5150324

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

    For Sale S5150324 - 8360 VIVARO ISLE WAY, WINDERMERE, FL 34786 11 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2224
       Built: 2019
    Monthly Fee: $299
       Tax: $9,812 (2025)
    Community: Windermere Isle - Phase 2
    Single Family


    Estimated Monthly Payment: $4,897 (change assumption)
    Mortgage ($3,781) + Fees ($299) + Taxes in 2025 ($818)


    Taxes:$9,812

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6673 DUNCASTER ST, WINDERMERE, FL 34786

    $530,000113 Days on yellowkey   MLS ID: O6378820

    REDUCED by $9,000 (1.7%) on 05/27/2026

    For Sale O6378820 - 6673 DUNCASTER ST, WINDERMERE, FL 34786 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2151
       Built: 2005   Tax: $3,351 (2024)
    Community: Lakes/Windermere Ph 02A
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,183 (change assumption)
    Mortgage ($2,904) + Taxes in 2024 ($279)


    Taxes:$3,351

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 14383 CREST PALM AVE, WINDERMERE, FL 34786

    $1,166,990128 Days on yellowkey   MLS ID: G5107222

    16 Days Off yellowkey (back on 5/27/2026)

    For Sale G5107222 - 14383 CREST PALM AVE, WINDERMERE, FL 34786 51 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3550
       Built: 2026
    Monthly Fee: $245
       Tax: $2,489 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,847 (change assumption)
    Mortgage ($6,394) + Fees ($245) + Taxes in 2025 ($207)


    Taxes:$2,489

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 7180 BEEK ST, WINDERMERE, FL 34786

    $780,00069 Days on yellowkey   MLS ID: O6393213

    For Sale O6393213 - 7180 BEEK ST, WINDERMERE, FL 34786 33 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3648
       Built: 2013
    Monthly Fee: $124
       Tax: $11,023 (2025)
    Community: Windermere Terrace
    Single Family


    Estimated Monthly Payment: $5,316 (change assumption)
    Mortgage ($4,274) + Fees ($124) + Taxes in 2025 ($919)


    Taxes:$11,023

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 111 MAIN ST, WINDERMERE, FL 34786

    $889,00020 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


  • 13013 OVERSTREET RD, WINDERMERE, FL 34786

    $649,99495 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


  • 1849 WATERMERE LN, WINDERMERE, FL 34786

    $1,299,00079 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


  • 14353 CREST PALM AVE, WINDERMERE, FL 34786

    $1,039,09137 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


  • 811 MAIN ST, WINDERMERE, FL 34786

    $649,9999 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


  • 13519 BICTON LN, WINDERMERE, FL 34786

    $717,000143 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


  • 12718 WINDERMERE ISLES PL, WINDERMERE, FL 34786

    $1,490,00046 Days on yellowkey   MLS ID: O6399958

    For Sale O6399958 - 12718 WINDERMERE ISLES PL, WINDERMERE, FL 34786 57 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3487
       Built: 1997
    Monthly Fee: $130
       Tax: $6,661 (2025)
    Community: Isles Windermere
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,849 (change assumption)
    Mortgage ($8,164) + Fees ($130) + Taxes in 2025 ($555)


    Taxes:$6,661

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6442 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786

    $575,000142 Days on yellowkey   MLS ID: G5106279

    REDUCED by $10,000 (1.7%) on 05/20/2026

    SHORT SALE G5106279 - 6442 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2139
       Built: 2012
    Monthly Fee: $125
       Tax: $7,649 (2024)
    Community: Windermere Lndgs Ph 02
    Single Family


    Estimated Monthly Payment: $3,913 (change assumption)
    Mortgage ($3,151) + Fees ($125) + Taxes in 2024 ($637)


    Taxes:$7,649

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 105 PINE STREET, WINDERMERE, FL 34786

    $2,500,00025 Days on yellowkey   MLS ID: O6405163

    3 Days Off yellowkey (back on 5/19/2026)

    For Sale O6405163 - 105 PINE STREET, WINDERMERE, FL 34786 73 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5696
       Built: 2015   Tax: $16,804 (2025)
    Community: Windermere
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $15,099 (change assumption)
    Mortgage ($13,698) + Taxes in 2025 ($1,400)


    Taxes:$16,804

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 6897 NORTHWICH DR, WINDERMERE, FL 34786

    $574,90040 Days on yellowkey   MLS ID: O6400673

    0 Days Off yellowkey (back on 5/18/2026)

    REDUCED by $5,000 (0.9%) on 05/13/2026

    For Sale O6400673 - 6897 NORTHWICH DR, WINDERMERE, FL 34786 31 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2229
       Built: 2003
    Monthly Fee: $82
       Tax: $7,925 (2025)
    Community: Lakes Windermere Ph 01 49 108
    Single Family


    Estimated Monthly Payment: $3,892 (change assumption)
    Mortgage ($3,150) + Fees ($82) + Taxes in 2025 ($660)


    Taxes:$7,925

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12533 CRAGSIDE LN, WINDERMERE, FL 34786

    $575,00024 Days on yellowkey   MLS ID: O6405628

    For Sale O6405628 - 12533 CRAGSIDE LN, WINDERMERE, FL 34786 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2151
       Built: 2004
    Monthly Fee: $82
       Tax: $8,484 (2025)
    Community: Lakes Windermere Ph 01 49 108
    Single Family


    Estimated Monthly Payment: $3,940 (change assumption)
    Mortgage ($3,151) + Fees ($82) + Taxes in 2025 ($707)


    Taxes:$8,484

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 14341 CREST PALM AVE, WINDERMERE, FL 34786

    $1,130,64316 Days on yellowkey   MLS ID: G5112469

    For Sale G5112469 - 14341 CREST PALM AVE, WINDERMERE, FL 34786 1 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3153
       Built: 2026
    Monthly Fee: $245
       Tax: $1,309 (2025)
    Community: Palms At Windermere
    Single Family


    Estimated Monthly Payment: $6,549 (change assumption)
    Mortgage ($6,195) + 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


  • 12863 HOLDENBURY LN, WINDERMERE, FL 34786

    $539,00068 Days on yellowkey   MLS ID: O6393781

    For Sale O6393781 - 12863 HOLDENBURY LN, WINDERMERE, FL 34786 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 2006
    Monthly Fee: $82
       Tax: $7,361 (2024)
    Community: Lakes Of Windermere
    Single Family


    Estimated Monthly Payment: $3,649 (change assumption)
    Mortgage ($2,953) + Fees ($82) + Taxes in 2024 ($613)


    Taxes:$7,361

    Elementary School: Sunset Park Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 505 JENNIFER LN, WINDERMERE, FL 34786

    $2,199,00094 Days on yellowkey   MLS ID: O6384643

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

    REDUCED by $51,000 (2.3%) on 04/28/2026

    For Sale O6384643 - 505 JENNIFER LN, WINDERMERE, FL 34786 95 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3525
       Built: 1989
    Monthly Fee: $333
       Tax: $7,624 (2024)
    Community: Windermere Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,017 (change assumption)
    Mortgage ($12,049) + Fees ($333) + Taxes in 2024 ($635)


    Taxes:$7,624

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 2219 RIDGEWIND WAY, WINDERMERE, FL 34786

    $1,299,00043 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




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.