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Windermere Single Family Homes For Sale in Windermere - 66 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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  • 8266 BRYCE CANYON AVE, WINDERMERE, FL 34786

    $484,50035 Days on yellowkey   MLS ID: O6410344

    REDUCED by $5,000 (1.0%) on 07/09/2026

    For Sale O6410344 - 8266 BRYCE CANYON AVE, WINDERMERE, FL 34786 57 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1825
       Built: 2016
    Monthly Fee: $81
       Tax: $5,441 (2025)
    Community: Windermere Trls Ph 3B
    Single Family


    Estimated Monthly Payment: $3,189 (change assumption)
    Mortgage ($2,655) + Fees ($81) + Taxes in 2025 ($453)


    Taxes:$5,441

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 1002 OAKDALE ST, WINDERMERE, FL 34786

    $950,00093 Days on yellowkey   MLS ID: TB8495717

    REDUCED by $15,000 (1.6%) on 07/11/2026

    For Sale TB8495717 - 1002 OAKDALE ST, WINDERMERE, FL 34786 60 photos

    Bed: 4   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 3516
       Built: 1973   Tax: $8,799 (2025)
    Community: Windermere Town
    Single Family


    Estimated Monthly Payment: $5,939 (change assumption)
    Mortgage ($5,205) + Taxes in 2025 ($733)


    Taxes:$8,799

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8355 TORCELLO ISLE DR, WINDERMERE, FL 34786

    $925,00064 Days on yellowkey   MLS ID: O6407061

    REDUCED by $25,000 (2.6%) on 07/10/2026

    For Sale O6407061 - 8355 TORCELLO ISLE DR, WINDERMERE, FL 34786 73 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4202
       Built: 2019
    Monthly Fee: $299
       Tax: $9,036 (2025)
    Community: Windermere Isle
    Single Family


    Estimated Monthly Payment: $6,120 (change assumption)
    Mortgage ($5,068) + Fees ($299) + Taxes in 2025 ($753)


    Taxes:$9,036

    Elementary School: Castleview Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2 CHASE RD, WINDERMERE, FL 34786

    $2,200,000302 Days on yellowkey   MLS ID: O6345197

    0 Days Off yellowkey (back on 7/10/2026)

    REDUCED by $1,000,000 (31.3%) on 06/16/2026

    For Sale O6345197 - 2 CHASE RD, WINDERMERE, FL 34786 3 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3889
       Built: 2026   Tax: $3,100 (2024)
    Community: Windermere
    Single Family


    Estimated Monthly Payment: $12,313 (change assumption)
    Mortgage ($12,054) + Taxes in 2024 ($258)


    Taxes:$3,100

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Chain of Lakes Middle


  • 8394 LOOKOUT POINTE DR, WINDERMERE, FL 34786

    $1,150,00038 Days on yellowkey   MLS ID: O6413196

    0 Days Off yellowkey (back on 7/9/2026)

    For Sale O6413196 - 8394 LOOKOUT POINTE DR, WINDERMERE, FL 34786 67 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


  • 12580 CRAGSIDE LN, WINDERMERE, FL 34786

    $624,00021 Days on yellowkey   MLS ID: O6418877

    3 Days Off yellowkey (back on 7/9/2026)

    For Sale O6418877 - 12580 CRAGSIDE LN, WINDERMERE, FL 34786 62 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2776
       Built: 2003
    Monthly Fee: $82
       Tax: $4,199 (2025)
    Community: Lakes Windermere Ph 01 49 108
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,851 (change assumption)
    Mortgage ($3,419) + Fees ($82) + Taxes in 2025 ($350)


    Taxes:$4,199

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 12633 HADDON DR, WINDERMERE, FL 34786

    $650,00049 Days on yellowkey   MLS ID: O6411199

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

    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


  • 7011 NOBLETON DR, WINDERMERE, FL 34786

    $580,00046 Days on yellowkey   MLS ID: O6412101

    For Sale O6412101 - 7011 NOBLETON DR, WINDERMERE, FL 34786 85 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 2460
       Built: 2003
    Monthly Fee: $82
       Tax: $9,209 (2025)
    Community: Lakes Windermere Ph 01 49 108
    Single Family


    Estimated Monthly Payment: $4,027 (change assumption)
    Mortgage ($3,178) + Fees ($82) + Taxes in 2025 ($767)


    Taxes:$9,209

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2009 WOODY DR, WINDERMERE, FL 34786

    $1,200,00010 Days on yellowkey   MLS ID: O6422132

    For Sale O6422132 - 2009 WOODY DR, WINDERMERE, FL 34786 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3540
       Built: 1974
    Monthly Fee: $85
       Tax: $6,392 (2024)
    Community: Windermere Downs
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,193 (change assumption)
    Mortgage ($6,575) + Fees ($85) + Taxes in 2024 ($533)


    Taxes:$6,392

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 8715 QUIET MEADOWS TRL, WINDERMERE, FL 34786

    $825,00052 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


  • 715 MAGNOLIA ST, WINDERMERE, FL 34786

    $1,175,00096 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


  • 8236 PROCIDA ISLE LN, WINDERMERE, FL 34786

    $1,080,000146 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


  • 7409 FAIRGROVE AVE, WINDERMERE, FL 34786

    $765,99018 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

    $840,00038 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

    $510,00037 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

    $680,000141 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


  • 7180 BEEK ST, WINDERMERE, FL 34786

    $780,000114 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


  • 12718 WINDERMERE ISLES PL, WINDERMERE, FL 34786

    $1,480,00091 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


  • 13137 PENSHURST LN, WINDERMERE, FL 34786

    $560,00015 Days on yellowkey   MLS ID: O6421270

    For Sale O6421270 - 13137 PENSHURST LN, WINDERMERE, FL 34786 46 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1948
       Built: 2007
    Monthly Fee: $80
       Tax: $3,439 (2025)
    Community: Lakes/Windermere Ph 03 P & Q
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,435 (change assumption)
    Mortgage ($3,068) + Fees ($80) + Taxes in 2025 ($287)


    Taxes:$3,439

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 516 JENNIFER LN, WINDERMERE, FL 34786

    $1,295,00021 Days on yellowkey   MLS ID: O6419731

    0 Days Off yellowkey (back on 6/29/2026)

    For Sale O6419731 - 516 JENNIFER LN, WINDERMERE, FL 34786 71 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3021
       Built: 1982
    Monthly Fee: $333
       Tax: $6,252 (2025)
    Community: Windermere Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,950 (change assumption)
    Mortgage ($7,096) + Fees ($333) + Taxes in 2025 ($521)


    Taxes:$6,252

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes 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.