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Windermere Homes For Sale & Real Estate - 309 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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  • 6241 BLAKEFORD DR, WINDERMERE, FL 34786

    $1,795,0009 Days on yellowkey   MLS ID: O6417788

    For Sale O6417788 - 6241 BLAKEFORD DR, WINDERMERE, FL 34786 59 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3556
       Built: 1999
    Monthly Fee: $298
       Tax: $18,784 (2025)
    Community: Keenes Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $11,699 (change assumption)
    Mortgage ($9,835) + Fees ($298) + Taxes in 2025 ($1,565)


    Taxes:$18,784

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8715 QUIET MEADOWS TRL, WINDERMERE, FL 34786

    $825,00051 Days on yellowkey   MLS ID: O6410762

    0 Days Off yellowkey (back on 6/14/2026)

    REDUCED by $15,000 (1.8%) on 06/04/2026

    For Sale O6410762 - 8715 QUIET MEADOWS TRL, WINDERMERE, FL 34786 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3388
       Built: 2013
    Monthly Fee: $10
       Tax: $11,511 (2025)
    Community: Windermere Trls Ph 1C
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,490 (change assumption)
    Mortgage ($4,520) + Fees ($10) + Taxes in 2025 ($959)


    Taxes:$11,511

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11249 RAPALLO LN, WINDERMERE, FL 34786

    $750,00014 Days on yellowkey   MLS ID: O6421056

    For Sale O6421056 - 11249 RAPALLO LN, WINDERMERE, FL 34786 37 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2366
       Built: 2002
    Monthly Fee: $136
       Tax: $9,355 (2025)
    Community: Belmere Village G2 48 65
    Single Family


    Estimated Monthly Payment: $5,025 (change assumption)
    Mortgage ($4,109) + Fees ($136) + Taxes in 2025 ($780)


    Taxes:$9,355

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 20 OAKDALE ST, WINDERMERE, FL 34786

    $1,499,00014 Days on yellowkey   MLS ID: O6421265

    For Sale O6421265 - 20 OAKDALE ST, WINDERMERE, FL 34786 30 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2188
       Built: 2004   Tax: $21,535 (2025)
    Community: Davis Shores
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,008 (change assumption)
    Mortgage ($8,213) + Taxes in 2025 ($1,795)


    Taxes:$21,535

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 8351 BOWDEN WAY, WINDERMERE, FL 34786

    $1,149,000110 Days on yellowkey   MLS ID: O6393659

    REDUCED by $50,000 (4.2%) on 06/02/2026

    For Sale O6393659 - 8351 BOWDEN WAY, WINDERMERE, FL 34786 71 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2599
       Built: 2001
    Monthly Fee: $283
       Tax: $8,252 (2025)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $7,266 (change assumption)
    Mortgage ($6,296) + Fees ($283) + Taxes in 2025 ($688)


    Taxes:$8,252

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 81 OAKDALE ST, WINDERMERE, FL 34786

    $2,300,000240 Days on yellowkey   MLS ID: S5138567

    11 Days Off yellowkey (back on 6/28/2026)

    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


  • 11446 JASPER KAY TER #103, WINDERMERE, FL 34786

    $330,00013 Days on yellowkey   MLS ID: O6420653

    For Sale O6420653 - 11446 JASPER KAY TER #103, WINDERMERE, FL 34786 32 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1442
       Built: 2007
    Monthly Fee: $489
       Tax: $4,561 (2025)
    Community: Lakeside At Lakes Of Windermere
    Condo


    Estimated Monthly Payment: $2,677 (change assumption)
    Mortgage ($1,808) + Fees ($489) + Taxes in 2025 ($380)


    Taxes:$4,561

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 715 MAGNOLIA ST, WINDERMERE, FL 34786

    $1,175,00095 Days on yellowkey   MLS ID: S5147648

    REDUCED by $75,000 (6.0%) on 04/27/2026

    For Sale S5147648 - 715 MAGNOLIA ST, WINDERMERE, FL 34786 44 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3390
       Built: 1999   Tax: $5,631 (2024)
    Community: Windermere Town
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,907 (change assumption)
    Mortgage ($6,438) + Taxes in 2024 ($469)


    Taxes:$5,631

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 5413 WALSH POND CT, WINDERMERE, FL 34786

    $798,000113 Days on yellowkey   MLS ID: O6391919

    REDUCED by $2,000 (0.3%) on 07/05/2026

    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: $5,390 (change assumption)
    Mortgage ($4,372) + 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


  • 8236 PROCIDA ISLE LN, WINDERMERE, FL 34786

    $1,080,000145 Days on yellowkey   MLS ID: O6383546

    REDUCED by $20,000 (1.8%) on 06/19/2026

    For Sale O6383546 - 8236 PROCIDA ISLE LN, WINDERMERE, FL 34786 27 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4176
       Built: 2018
    Monthly Fee: $299
       Tax: $12,887 (2025)
    Community: Windermere Isle Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,291 (change assumption)
    Mortgage ($5,918) + Fees ($299) + Taxes in 2025 ($1,074)


    Taxes:$12,887

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 6417 LAKE BURDEN VIEW DR, WINDERMERE, FL 34786

    $2,960,00015 Days on yellowkey   MLS ID: O6418943

    For Sale O6418943 - 6417 LAKE BURDEN VIEW DR, WINDERMERE, FL 34786 86 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 5935
       Built: 2006
    Monthly Fee: $298
       Tax: $25,461 (2025)
    Community: Keenes Pointe
    Single Family


    Estimated Monthly Payment: $18,639 (change assumption)
    Mortgage ($16,219) + Fees ($298) + Taxes in 2025 ($2,122)


    Taxes:$25,461

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 7409 FAIRGROVE AVE, WINDERMERE, FL 34786

    $765,99017 Days on yellowkey   MLS ID: O6420597

    For Sale O6420597 - 7409 FAIRGROVE AVE, WINDERMERE, FL 34786 29 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3285
       Built: 2015
    Monthly Fee: $198
       Tax: $10,018 (2025)
    Community: Windermere Sound
    Single Family


    Estimated Monthly Payment: $5,230 (change assumption)
    Mortgage ($4,197) + Fees ($198) + Taxes in 2025 ($835)


    Taxes:$10,018

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 412 FOREST ST, WINDERMERE, FL 34786

    $840,00037 Days on yellowkey   MLS ID: O6414200

    0 Days Off yellowkey (back on 7/3/2026)

    For Sale O6414200 - 412 FOREST ST, WINDERMERE, FL 34786 34 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2539
       Built: 1973   Tax: $4,939 (2025)
    Community: Windermere Town
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,014 (change assumption)
    Mortgage ($4,603) + Taxes in 2025 ($412)


    Taxes:$4,939

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 13324 LONGACRE DR, WINDERMERE, FL 34786

    $510,00036 Days on yellowkey   MLS ID: S5151263

    2 Days Off yellowkey (back on 7/3/2026)

    For Sale S5151263 - 13324 LONGACRE DR, WINDERMERE, FL 34786 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2058
       Built: 2013
    Monthly Fee: $115
       Tax: $7,924 (2025)
    Community: Windermere Terrace
    Single Family


    Estimated Monthly Payment: $3,570 (change assumption)
    Mortgage ($2,794) + Fees ($115) + Taxes in 2025 ($660)


    Taxes:$7,924

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 8552 POWDER RIDGE TRL, WINDERMERE, FL 34786

    $680,000140 Days on yellowkey   MLS ID: S5144276

    0 Days Off yellowkey (back on 7/3/2026)

    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


  • 10870 BAYSHORE DR, WINDERMERE, FL 34786

    $2,895,000166 Days on yellowkey   MLS ID: O6371471

    1 Days Off yellowkey (back on 7/3/2026)

    REDUCED by $100,000 (3.3%) on 05/11/2026

    For Sale O6371471 - 10870 BAYSHORE DR, WINDERMERE, FL 34786 60 photos

    Bed: 4   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4693
       Built: 1999   Tax: $27,527 (2024)
    Community: Lake Down Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $18,157 (change assumption)
    Mortgage ($15,863) + Taxes in 2024 ($2,294)


    Taxes:$27,527

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 7180 BEEK ST, WINDERMERE, FL 34786

    $780,000113 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


  • 13219 CHARFIELD ST, WINDERMERE, FL 34786

    $565,00013 Days on yellowkey   MLS ID: O6420991

    For Sale O6420991 - 13219 CHARFIELD ST, WINDERMERE, FL 34786 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1706
       Built: 2009
    Monthly Fee: $81
       Tax: $6,800 (2025)
    Community: Lake Sawyer South Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,743 (change assumption)
    Mortgage ($3,096) + Fees ($81) + Taxes in 2025 ($567)


    Taxes:$6,800

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 4071 ISABELLA CIR, WINDERMERE, FL 34786

    $3,290,00035 Days on yellowkey   MLS ID: O6413509

    1 Days Off yellowkey (back on 7/2/2026)

    For Sale O6413509 - 4071 ISABELLA CIR, WINDERMERE, FL 34786 100 photos

    Bed: 5   Bath: 7.5   Gar: 4
    Liv Area Sq Ft: 7058
       Built: 2017
    Monthly Fee: $480
       Tax: $35,637 (2025)
    Community: Casabella
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $21,477 (change assumption)
    Mortgage ($18,027) + Fees ($480) + Taxes in 2025 ($2,970)


    Taxes:$35,637

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12718 WINDERMERE ISLES PL, WINDERMERE, FL 34786

    $1,480,00090 Days on yellowkey   MLS ID: O6399958

    REDUCED by $10,000 (0.7%) on 07/02/2026

    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: $8,794 (change assumption)
    Mortgage ($8,109) + 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




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.