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Windermere Single Family Homes For Sale - 266 homes

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

Location: Windermere

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  • 10870 BAYSHORE DR, WINDERMERE, FL 34786

    $2,895,000122 Days on yellowkey   MLS ID: O6371471

    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


  • 5128 BUTLER RIDGE DR, WINDERMERE, FL 34786

    $1,250,0003 Days on yellowkey   MLS ID: O6412016

    For Sale O6412016 - 5128 BUTLER RIDGE DR, WINDERMERE, FL 34786 34 photos

    Bed: 4   Bath: 3.0   Gar: 7
    Liv Area Sq Ft: 2816
       Built: 1989   Tax: $9,506 (2025)
    Community: Butler Ridge
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,641 (change assumption)
    Mortgage ($6,849) + Taxes in 2025 ($792)


    Taxes:$9,506

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9669 WESTOVER CLUB CIR, WINDERMERE, FL 34786

    $750,00093 Days on yellowkey   MLS ID: O6386605

    REDUCED by $100,000 (11.8%) on 04/08/2026

    For Sale O6386605 - 9669 WESTOVER CLUB CIR, WINDERMERE, FL 34786 28 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3435
       Built: 2001
    Monthly Fee: $115
       Tax: $11,111 (2024)
    Community: Westover Club Ph 01 44/139
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,150 (change assumption)
    Mortgage ($4,109) + Fees ($115) + Taxes in 2024 ($926)


    Taxes:$11,111

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 13448 BELLARIA CIR, WINDERMERE, FL 34786

    $3,200,000252 Days on yellowkey   MLS ID: O6346484

    For Sale O6346484 - 13448 BELLARIA CIR, WINDERMERE, FL 34786 65 photos

    Bed: 6   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 6308
       Built: 2014
    Monthly Fee: $483
       Tax: $29,164 (2024)
    Community: Bellaria
    Single Family


    Estimated Monthly Payment: $20,447 (change assumption)
    Mortgage ($17,534) + Fees ($483) + Taxes in 2024 ($2,430)


    Taxes:$29,164

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 9144 ISLEWORTH GARDENS DR, WINDERMERE, FL 34786

    $4,450,00053 Days on yellowkey   MLS ID: O6397842

    For Sale O6397842 - 9144 ISLEWORTH GARDENS DR, WINDERMERE, FL 34786 63 photos

    Bed: 3   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 5004
       Built: 2019
    Monthly Fee: $1,146
       Tax: $35,432 (2025)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $28,482 (change assumption)
    Mortgage ($24,383) + Fees ($1,146) + Taxes in 2025 ($2,953)


    Taxes:$35,432

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 6412 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786

    $550,0001 Day on yellowkey   MLS ID: O6412095

    For Sale O6412095 - 6412 GOLDEN DEWDROP TRL, WINDERMERE, FL 34786 38 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1984
       Built: 2012
    Monthly Fee: $130
       Tax: $6,210 (2025)
    Community: Windermere Lndgs Ph 02
    Single Family


    Estimated Monthly Payment: $3,661 (change assumption)
    Mortgage ($3,014) + Fees ($130) + Taxes in 2025 ($517)


    Taxes:$6,210

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1407 HEMPEL AVE, WINDERMERE, FL 34786

    $1,090,0001 Day on yellowkey   MLS ID: O6410840

    For Sale O6410840 - 1407 HEMPEL AVE, WINDERMERE, FL 34786 52 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2842
       Built: 1989   Tax: $10,727 (2025)
    Community: Gotha Town
    Single Family


    Estimated Monthly Payment: $6,866 (change assumption)
    Mortgage ($5,972) + Taxes in 2025 ($894)


    Taxes:$10,727

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9317 GLADYS GARDEN CT, WINDERMERE, FL 34786

    $7,999,0001 Day on yellowkey   MLS ID: O6410843

    For Sale O6410843 - 9317 GLADYS GARDEN CT, WINDERMERE, FL 34786 3 photos

    Bed: 6   Bath: 7.5   Gar: 4
    Liv Area Sq Ft: 8038
       Built: 2027
    Monthly Fee: $1,099
       Tax: $9,424 (2025)
    Community: Gardens/Isleworth
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $45,713 (change assumption)
    Mortgage ($43,829) + Fees ($1,099) + Taxes in 2025 ($785)


    Taxes:$9,424

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 11326 LEDGEMENT LN, WINDERMERE, FL 34786

    $939,00011 Days on yellowkey   MLS ID: O6409714

    For Sale O6409714 - 11326 LEDGEMENT LN, WINDERMERE, FL 34786 63 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3182
       Built: 2002
    Monthly Fee: $170
       Tax: $9,509 (2025)
    Community: Glenmuir 48 39
    Single Family


    Estimated Monthly Payment: $6,107 (change assumption)
    Mortgage ($5,145) + Fees ($170) + Taxes in 2025 ($792)


    Taxes:$9,509

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 2002 WATER KEY DR, WINDERMERE, FL 34786

    $1,299,0005 Days on yellowkey   MLS ID: O6408915

    0 Days Off yellowkey (back on 5/30/2026)

    For Sale O6408915 - 2002 WATER KEY DR, WINDERMERE, FL 34786 60 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3695
       Built: 2002
    Monthly Fee: $335
       Tax: $16,085 (2025)
    Community: Reserve At Waterford Pointe Ph 01
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,793 (change assumption)
    Mortgage ($7,118) + Fees ($335) + Taxes in 2025 ($1,340)


    Taxes:$16,085

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 10520 PARK RIDGE GOTHA RD, WINDERMERE, FL 34786

    $2,400,0005 Days on yellowkey   MLS ID: O6409659

    For Sale O6409659 - 10520 PARK RIDGE GOTHA RD, WINDERMERE, FL 34786 4 photos

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 3101
       Built: 1979   Tax: $3,341 (2025)
    Community: None
    Single Family


    Estimated Monthly Payment: $13,429 (change assumption)
    Mortgage ($13,150) + Taxes in 2025 ($278)


    Taxes:$3,341

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 2428 BUTLER BAY DR N, WINDERMERE, FL 34786

    $1,150,0003 Days on yellowkey   MLS ID: O6410967

    For Sale O6410967 - 2428 BUTLER BAY DR N, WINDERMERE, FL 34786 48 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3387
       Built: 1990
    Monthly Fee: $199
       Tax: $9,842 (2025)
    Community: Butler Bay
    Single Family


    Estimated Monthly Payment: $7,320 (change assumption)
    Mortgage ($6,301) + Fees ($199) + Taxes in 2025 ($820)


    Taxes:$9,842

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13048 LAKE ROPER CT., WINDERMERE, FL 34786

    $1,890,000262 Days on yellowkey   MLS ID: O6342354

    5 Days Off yellowkey (back on 5/30/2026)

    REDUCED by $60,000 (3.1%) on 04/22/2026

    For Sale O6342354 - 13048 LAKE ROPER CT., WINDERMERE, FL 34786 80 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4130
       Built: 2002
    Monthly Fee: $333
       Tax: $14,738 (2025)
    Community: Windermere Pointe
    Single Family


    Estimated Monthly Payment: $11,917 (change assumption)
    Mortgage ($10,356) + Fees ($333) + Taxes in 2025 ($1,228)


    Taxes:$14,738

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9057 BALMORAL MEWS SQ, WINDERMERE, FL 34786

    $1,859,00079 Days on yellowkey   MLS ID: O6390656

    REDUCED by $40,000 (2.1%) on 05/29/2026

    For Sale O6390656 - 9057 BALMORAL MEWS SQ, WINDERMERE, FL 34786 67 photos

    Bed: 6   Bath: 5.5   Gar: 4
    Liv Area Sq Ft: 5430
       Built: 1997
    Monthly Fee: $267
       Tax: $12,735 (2025)
    Community: Balmoral
    Single Family


    Estimated Monthly Payment: $11,514 (change assumption)
    Mortgage ($10,186) + Fees ($267) + Taxes in 2025 ($1,061)


    Taxes:$12,735

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 13106 ORANGE ISLE DR, WINDERMERE, FL 34786

    $870,000175 Days on yellowkey   MLS ID: O6361057

    INCREASED by $20,000 (2.4%) on 05/30/2026

    For Sale O6361057 - 13106 ORANGE ISLE DR, WINDERMERE, FL 34786 69 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3312
       Built: 2022
    Monthly Fee: $95
       Tax: $11,893 (2025)
    Community: Sanctuary/Lks/Windermere
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,853 (change assumption)
    Mortgage ($4,767) + Fees ($95) + Taxes in 2025 ($991)


    Taxes:$11,893

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 13124 FILLY CT, WINDERMERE, FL 34786

    $1,575,000402 Days on yellowkey   MLS ID: O6303140

    For Sale O6303140 - 13124 FILLY CT, WINDERMERE, FL 34786 51 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3300
       Built: 1989
    Monthly Fee: $46
       Tax: $15,459 (2024)
    Community: Farms
    Spa: No

    Single Family


    Estimated Monthly Payment: $9,964 (change assumption)
    Mortgage ($8,630) + Fees ($46) + Taxes in 2024 ($1,288)


    Taxes:$15,459

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 9222 TIBET POINTE CIR, WINDERMERE, FL 34786

    $2,599,00024 Days on yellowkey   MLS ID: O6405278

    REDUCED by $100,000 (3.7%) on 05/30/2026

    For Sale O6405278 - 9222 TIBET POINTE CIR, WINDERMERE, FL 34786 100 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 5323
       Built: 2009
    Monthly Fee: $298
       Tax: $27,697 (2025)
    Community: Keenes Pointe 46/104
    Single Family


    Estimated Monthly Payment: $16,847 (change assumption)
    Mortgage ($14,241) + Fees ($298) + Taxes in 2025 ($2,308)


    Taxes:$27,697

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5538 W LAKE BUTLER RD, WINDERMERE, FL 34786

    $3,195,000124 Days on yellowkey   MLS ID: O6376859

    REDUCED by $300,000 (8.6%) on 05/15/2026

    For Sale O6376859 - 5538 W LAKE BUTLER RD, WINDERMERE, FL 34786 71 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 6000
       Built: 1982
    Monthly Fee: $67
       Tax: $25,546 (2025)
    Community: Kelso On Lake Butler
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $19,702 (change assumption)
    Mortgage ($17,506) + Fees ($67) + Taxes in 2025 ($2,129)


    Taxes:$25,546

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 8409 VIVARO ISLE WAY, WINDERMERE, FL 34786

    $1,235,00021 Days on yellowkey   MLS ID: G5112154

    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: $7,857 (change assumption)
    Mortgage ($6,767) + 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


  • 325 MAGNOLIA ST, WINDERMERE, FL 34786

    $2,450,00076 Days on yellowkey   MLS ID: O6391047

    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




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.