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Windermere Homes for Sale in Windermere - 85 homes

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

Location: Windermere, Windermere

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  • 8632 ABBOTSBURY DR, WINDERMERE, FL 34786

    $625,00039 Days on yellowkey   MLS ID: O6406433

    For Sale O6406433 - 8632 ABBOTSBURY DR, WINDERMERE, FL 34786 32 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2720
       Built: 2004
    Monthly Fee: $167
       Tax: $8,567 (2025)
    Community: Lakes/Windermere-Peachtree
    Single Family


    Estimated Monthly Payment: $4,305 (change assumption)
    Mortgage ($3,425) + Fees ($167) + Taxes in 2025 ($714)


    Taxes:$8,567

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 6601 DUNCASTER ST, WINDERMERE, FL 34786

    $628,0005 Days on yellowkey   MLS ID: O6416272

    For Sale O6416272 - 6601 DUNCASTER ST, WINDERMERE, FL 34786 65 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3001
       Built: 2006
    Monthly Fee: $82
       Tax: $9,473 (2025)
    Community: Lakes/Windermere Ph 02A
    Single Family


    Estimated Monthly Payment: $4,312 (change assumption)
    Mortgage ($3,441) + Fees ($82) + Taxes in 2025 ($789)


    Taxes:$9,473

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 1700 LAKE ROBERTS CT, WINDERMERE, FL 34786

    $1,450,00021 Days on yellowkey   MLS ID: O6410847

    For Sale O6410847 - 1700 LAKE ROBERTS CT, WINDERMERE, FL 34786 45 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3929
       Built: 2002
    Monthly Fee: $216
       Tax: $10,637 (2025)
    Community: Butler Bay,Windermere Club
    Single Family


    Estimated Monthly Payment: $9,047 (change assumption)
    Mortgage ($7,945) + Fees ($216) + Taxes in 2025 ($886)


    Taxes:$10,637

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12633 HADDON DR, WINDERMERE, FL 34786

    $650,00019 Days on yellowkey   MLS ID: O6411199

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

    For Sale O6411199 - 12633 HADDON DR, WINDERMERE, FL 34786 53 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3000
       Built: 2003
    Monthly Fee: $82
       Tax: $7,410 (2025)
    Community: Lakes Windermere
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,261 (change assumption)
    Mortgage ($3,562) + Fees ($82) + Taxes in 2025 ($617)


    Taxes:$7,410

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 13013 OVERSTREET RD, WINDERMERE, FL 34786

    $649,994110 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


  • 8409 VIVARO ISLE WAY, WINDERMERE, FL 34786

    $1,187,00036 Days on yellowkey   MLS ID: G5112154

    0 Days Off yellowkey (back on 6/10/2026)

    REDUCED by $48,000 (3.9%) on 06/03/2026

    For Sale G5112154 - 8409 VIVARO ISLE WAY, WINDERMERE, FL 34786 92 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4176
       Built: 2019
    Monthly Fee: $299
       Tax: $9,493 (2025)
    Community: Windermere Isle
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,594 (change assumption)
    Mortgage ($6,504) + Fees ($299) + Taxes in 2025 ($791)


    Taxes:$9,493

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 7612 FAIRGROVE AVE, WINDERMERE, FL 34786

    $440,00041 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


  • 8394 LOOKOUT POINTE DR, WINDERMERE, FL 34786

    $1,150,0008 Days on yellowkey   MLS ID: O6413196

    For Sale O6413196 - 8394 LOOKOUT POINTE DR, WINDERMERE, FL 34786 66 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3971
       Built: 2016
    Monthly Fee: $8
       Tax: $13,647 (2025)
    Community: Windermere Trls Ph 3B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,446 (change assumption)
    Mortgage ($6,301) + Fees ($8) + Taxes in 2025 ($1,137)


    Taxes:$13,647

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786

    $322,000152 Days on yellowkey   MLS ID: TB8465266

    0 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $3,000 (0.9%) on 05/14/2026

    For Sale TB8465266 - 8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786 70 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1442
       Built: 2006   Tax: $4,422 (2024)
    Community: Lakeside/Lks/Windermere Ph 3
    Condo


    Estimated Monthly Payment: $2,133 (change assumption)
    Mortgage ($1,764) + Taxes in 2024 ($368)


    Taxes:$4,422

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9257 OUTLOOK ROCK TRL, WINDERMERE, FL 34786

    $879,999128 Days on yellowkey   MLS ID: S5143447

    0 Days Off yellowkey (back on 6/10/2026)

    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


  • 7174 BEEK ST, WINDERMERE, FL 34786

    $725,00043 Days on yellowkey   MLS ID: O6402279

    0 Days Off yellowkey (back on 6/1/2026)

    For Sale O6402279 - 7174 BEEK ST, WINDERMERE, FL 34786 47 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2464
       Built: 2013
    Monthly Fee: $115
       Tax: $5,627 (2025)
    Community: Windermere Terrace
    Single Family


    Estimated Monthly Payment: $4,556 (change assumption)
    Mortgage ($3,973) + Fees ($115) + Taxes in 2025 ($469)


    Taxes:$5,627

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 11861 VERMILLION AVE, WINDERMERE, FL 34786

    $475,00014 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


  • 715 MAGNOLIA ST, WINDERMERE, FL 34786

    $1,175,00066 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: 5   Bath: 4.0   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


  • 13542 GORGONA ISLE DR, WINDERMERE, FL 34786

    $895,00095 Days on yellowkey   MLS ID: O6390582

    REDUCED by $55,000 (5.8%) on 04/25/2026

    For Sale O6390582 - 13542 GORGONA ISLE DR, WINDERMERE, FL 34786 16 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2224
       Built: 2018
    Monthly Fee: $268
       Tax: $9,762 (2024)
    Community: Windermere Isle
    Single Family


    Estimated Monthly Payment: $5,985 (change assumption)
    Mortgage ($4,904) + Fees ($268) + Taxes in 2024 ($814)


    Taxes:$9,762

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 1316 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786

    $2,290,00078 Days on yellowkey   MLS ID: S5146178

    REDUCED by $90,000 (3.8%) on 05/29/2026

    For Sale S5146178 - 1316 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786 63 photos

    Bed: 5   Bath: 6.5   Gar: 2
    Liv Area Sq Ft: 5448
       Built: 2019
    Monthly Fee: $250
       Tax: $1,982 (2025)
    Community: Estancia/Windermere
    Single Family


    Estimated Monthly Payment: $12,963 (change assumption)
    Mortgage ($12,548) + Fees ($250) + Taxes in 2025 ($165)


    Taxes:$1,982

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 4474 BEGONIA CT, WINDERMERE, FL 34786

    $1,170,00052 Days on yellowkey   MLS ID: O6402227

    REDUCED by $100,000 (7.9%) on 05/13/2026

    For Sale O6402227 - 4474 BEGONIA CT, WINDERMERE, FL 34786 41 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4380
       Built: 1998
    Monthly Fee: $133
       Tax: $7,670 (2025)
    Community: Magnolia Park Windermere
    Single Family


    Estimated Monthly Payment: $7,183 (change assumption)
    Mortgage ($6,411) + Fees ($133) + Taxes in 2025 ($639)


    Taxes:$7,670

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 2509 RIDGEWIND WAY, WINDERMERE, FL 34786

    $1,460,00040 Days on yellowkey   MLS ID: O6402522

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

    For Sale O6402522 - 2509 RIDGEWIND WAY, WINDERMERE, FL 34786 39 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3844
       Built: 1998
    Monthly Fee: $220
       Tax: $19,706 (2025)
    Community: Estates At Windermere
    Single Family


    Estimated Monthly Payment: $9,862 (change assumption)
    Mortgage ($8,000) + Fees ($220) + Taxes in 2025 ($1,642)


    Taxes:$19,706

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 11903 CAVE RUN AVE, WINDERMERE, FL 34786

    $750,00085 Days on yellowkey   MLS ID: O6392757

    0 Days Off yellowkey (back on 6/5/2026)

    For Sale O6392757 - 11903 CAVE RUN AVE, WINDERMERE, FL 34786 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3413
       Built: 2014
    Monthly Fee: $81
       Tax: $10,874 (2025)
    Community: Windermere Trls Ph 1C
    Single Family


    Estimated Monthly Payment: $5,097 (change assumption)
    Mortgage ($4,109) + Fees ($81) + Taxes in 2025 ($906)


    Taxes:$10,874

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 325 MAGNOLIA ST, WINDERMERE, FL 34786

    $2,450,00091 Days on yellowkey   MLS ID: O6391047

    0 Days Off yellowkey (back on 6/5/2026)

    REDUCED by $25,000 (1.0%) on 05/30/2026

    For Sale O6391047 - 325 MAGNOLIA ST, WINDERMERE, FL 34786 52 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3975
       Built: 1954   Tax: $24,094 (2025)
    Community: Windermere Town
    Single Family


    Estimated Monthly Payment: $15,432 (change assumption)
    Mortgage ($13,424) + Taxes in 2025 ($2,008)


    Taxes:$24,094

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 12319 CRUXBURY DR, WINDERMERE, FL 34786

    $405,00018 Days on yellowkey   MLS ID: O6411226

    0 Days Off yellowkey (back on 6/5/2026)

    For Sale O6411226 - 12319 CRUXBURY DR, WINDERMERE, FL 34786 58 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1429
       Built: 2006
    Monthly Fee: $200
       Tax: $1,935 (2025)
    Community: Lakes/Windermere-Lk Reams Twhm
    Townhouse


    Estimated Monthly Payment: $2,580 (change assumption)
    Mortgage ($2,219) + Fees ($200) + Taxes in 2025 ($161)


    Taxes:$1,935

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School




Why Bother Searching Elsewhere for Windermere Homes for Sale and Other Windermere 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. 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.