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Windermere Homes For Sale & Real Estate - 336 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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  • 9669 WESTOVER CLUB CIR, WINDERMERE, FL 34786

    $750,000112 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

    $3,200,000271 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

    $4,450,00072 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

    $550,00021 Days 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

    $1,090,00021 Days 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


  • 2002 WATER KEY DR, WINDERMERE, FL 34786

    $1,299,00024 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


  • 11434 JASPER KAY TER #106, WINDERMERE, FL 34786

    $320,00022 Days on yellowkey   MLS ID: S5150874

    For Sale S5150874 - 11434 JASPER KAY TER #106, WINDERMERE, FL 34786 49 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1455
       Built: 2007
    Monthly Fee: $485
       Tax: $4,640 (2025)
    Community: Lakeside/Lks/Windermere
    Condo


    Estimated Monthly Payment: $2,625 (change assumption)
    Mortgage ($1,753) + Fees ($485) + Taxes in 2025 ($387)


    Taxes:$4,640

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13048 LAKE ROPER CT., WINDERMERE, FL 34786

    $1,890,000281 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


  • 13106 ORANGE ISLE DR, WINDERMERE, FL 34786

    $870,000194 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

    $1,575,000421 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


  • 9960 6TH ST, WINDERMERE, FL 34786

    $3,750,00022 Days on yellowkey   MLS ID: O6412077

    For Sale O6412077 - 9960 6TH ST, WINDERMERE, FL 34786 1 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 6182
       Built: 2027   Tax: $5,791 (2025)
    Community: Gotha Town
    Single Family


    Estimated Monthly Payment: $21,030 (change assumption)
    Mortgage ($20,547) + Taxes in 2025 ($483)


    Taxes:$5,791

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 12132 MONTALCINO CIR, WINDERMERE, FL 34786

    $3,790,000227 Days on yellowkey   MLS ID: O6319854

    0 Days Off yellowkey (back on 5/29/2026)

    REDUCED by $160,000 (4.1%) on 05/13/2026

    For Sale O6319854 - 12132 MONTALCINO CIR, WINDERMERE, FL 34786 90 photos

    Bed: 6   Bath: 7.0   Gar: 3
    Liv Area Sq Ft: 5709
       Built: 2016
    Monthly Fee: $242
       Tax: $38,798 (2024)
    Community: Casa Del Lago Rep
    Single Family


    Estimated Monthly Payment: $24,242 (change assumption)
    Mortgage ($20,767) + Fees ($242) + Taxes in 2024 ($3,233)


    Taxes:$38,798

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 11822 SILVERLAKE PARK DR, WINDERMERE, FL 34786

    $495,00023 Days on yellowkey   MLS ID: O6409301

    For Sale O6409301 - 11822 SILVERLAKE PARK DR, WINDERMERE, FL 34786 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1829
       Built: 2014
    Monthly Fee: $85
       Tax: $6,641 (2025)
    Community: Windermere Trls Ph 1C
    Single Family


    Estimated Monthly Payment: $3,351 (change assumption)
    Mortgage ($2,712) + Fees ($85) + Taxes in 2025 ($553)


    Taxes:$6,641

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 5001 LATROBE DR, WINDERMERE, FL 34786

    $3,299,99995 Days on yellowkey   MLS ID: O6389183

    REDUCED by $200,000 (5.7%) on 05/28/2026

    For Sale O6389183 - 5001 LATROBE DR, WINDERMERE, FL 34786 40 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4417
       Built: 1990
    Monthly Fee: $1,043
       Tax: $30,452 (2024)
    Community: Isleworth
    Spa: No

    Single Family


    Estimated Monthly Payment: $21,662 (change assumption)
    Mortgage ($18,082) + Fees ($1,043) + Taxes in 2024 ($2,538)


    Taxes:$30,452

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6219 TIROCO WAY, WINDERMERE, FL 34786

    $2,600,000104 Days on yellowkey   MLS ID: O6387454

    For Sale O6387454 - 6219 TIROCO WAY, WINDERMERE, FL 34786 41 photos

    Bed: 7   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5221
       Built: 2014
    Monthly Fee: $310
       Tax: $27,796 (2025)
    Community: Waterstone
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $16,873 (change assumption)
    Mortgage ($14,246) + Fees ($310) + Taxes in 2025 ($2,316)


    Taxes:$27,796

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 5199 LATROBE DR, WINDERMERE, FL 34786

    $5,300,00024 Days on yellowkey   MLS ID: O6409961

    For Sale O6409961 - 5199 LATROBE DR, WINDERMERE, FL 34786 64 photos

    Bed: 6   Bath: 6.5   Gar: 4
    Liv Area Sq Ft: 4665
       Built: 1993
    Monthly Fee: $1,224
       Tax: $37,241 (2025)
    Community: Isleworth
    Single Family


    Estimated Monthly Payment: $33,368 (change assumption)
    Mortgage ($29,040) + Fees ($1,224) + Taxes in 2025 ($3,103)


    Taxes:$37,241

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Chain of Lakes Middle


  • 10624 REAMS RD, WINDERMERE, FL 34786

    $475,000303 Days on yellowkey   MLS ID: O6338130

    REDUCED by $12,000 (2.5%) on 05/28/2026

    For Sale O6338130 - 10624 REAMS RD, WINDERMERE, FL 34786 61 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2092
       Built: 2014
    Monthly Fee: $81
       Tax: $5,459 (2024)
    Community: Windermere Trls Ph 1C
    Single Family


    Estimated Monthly Payment: $3,139 (change assumption)
    Mortgage ($2,603) + Fees ($81) + Taxes in 2024 ($455)


    Taxes:$5,459

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 12623 PARK AVE, WINDERMERE, FL 34786

    $3,800,00025 Days on yellowkey   MLS ID: O6410693

    For Sale O6410693 - 12623 PARK AVE, WINDERMERE, FL 34786 87 photos

    Bed: 5   Bath: 6.0   Gar: 6
    Liv Area Sq Ft: 7120
       Built: 2023
    Monthly Fee: $687
       Tax: $23,243 (2025)
    Community: Chaine De Lac
    Single Family


    Estimated Monthly Payment: $23,445 (change assumption)
    Mortgage ($20,821) + Fees ($687) + Taxes in 2025 ($1,937)


    Taxes:$23,243

    Elementary School: Windermere Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14422 DESERT HAVEN ST #4206, WINDERMERE, FL 34786

    $385,00053 Days on yellowkey   MLS ID: S5148708

    For Sale S5148708 - 14422 DESERT HAVEN ST #4206, WINDERMERE, FL 34786 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1840
       Built: 2013
    Monthly Fee: $541
       Tax: $4,948 (2025)
    Community: Oasis Cove Ii/Lakeside Village
    Townhouse


    Estimated Monthly Payment: $3,063 (change assumption)
    Mortgage ($2,110) + Fees ($541) + Taxes in 2025 ($412)


    Taxes:$4,948

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8360 VIVARO ISLE WAY, WINDERMERE, FL 34786

    $690,00025 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




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.