REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Windermere Homes For Sale & Real Estate - 332 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

Sort:
  • 4906 AVIVA GARDEN CT, WINDERMERE, FL 34786

    $4,590,00054 Days on yellowkey   MLS ID: O6400218

    REDUCED by $100,000 (2.1%) on 06/01/2026

    For Sale O6400218 - 4906 AVIVA GARDEN CT, WINDERMERE, FL 34786 27 photos

    Bed: 3   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 6236
       Built: 2016
    Monthly Fee: $1,146
       Tax: $48,425 (2025)
    Community: Gardens/Isleworth Un #2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $30,331 (change assumption)
    Mortgage ($25,150) + Fees ($1,146) + Taxes in 2025 ($4,035)


    Taxes:$48,425

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12966 VENNETTA WAY, WINDERMERE, FL 34786

    $380,00045 Days on yellowkey   MLS ID: S5148828

    REDUCED by $6,000 (1.6%) on 06/01/2026

    For Sale S5148828 - 12966 VENNETTA WAY, WINDERMERE, FL 34786 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1644
       Built: 2008
    Monthly Fee: $380
       Tax: $3,153 (2025)
    Community: Lake Sawyer South Ph 3
    Townhouse


    Estimated Monthly Payment: $2,725 (change assumption)
    Mortgage ($2,082) + Fees ($380) + Taxes in 2025 ($263)


    Taxes:$3,153

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 1924 DOWN HOLLOW LN, WINDERMERE, FL 34786

    $1,680,00016 Days on yellowkey   MLS ID: O6398100

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

    For Sale O6398100 - 1924 DOWN HOLLOW LN, WINDERMERE, FL 34786 86 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1962
       Built: 1999   Tax: $8,460 (2025)
    Community: Acreage
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,910 (change assumption)
    Mortgage ($9,205) + Taxes in 2025 ($705)


    Taxes:$8,460

    Elementary School: Thornebrooke Elem

    High School: Olympia High

    Tax Year: 2025

    Middle School: Gotha Middle


  • 2068 ROBERTS POINT DR, WINDERMERE, FL 34786

    $2,250,00058 Days on yellowkey   MLS ID: O6397543

    REDUCED by $100,000 (4.3%) on 06/01/2026

    For Sale O6397543 - 2068 ROBERTS POINT DR, WINDERMERE, FL 34786 81 photos

    Bed: 5   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 4876
       Built: 1999
    Monthly Fee: $325
       Tax: $12,356 (2025)
    Community: Waterford Pointe Ph 02 Rep
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $13,683 (change assumption)
    Mortgage ($12,328) + Fees ($325) + Taxes in 2025 ($1,030)


    Taxes:$12,356

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 2230 RIDGEWIND WAY, WINDERMERE, FL 34786

    $1,349,00022 Days on yellowkey   MLS ID: O6410264

    For Sale O6410264 - 2230 RIDGEWIND WAY, WINDERMERE, FL 34786 38 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3064
       Built: 1999
    Monthly Fee: $220
       Tax: $8,790 (2025)
    Community: Estates At Windermere
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,344 (change assumption)
    Mortgage ($7,392) + Fees ($220) + Taxes in 2025 ($732)


    Taxes:$8,790

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 6820 THORNHILL CIR, WINDERMERE, FL 34786

    $520,00055 Days on yellowkey   MLS ID: V4948591

    For Sale V4948591 - 6820 THORNHILL CIR, WINDERMERE, FL 34786 14 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1725
       Built: 2009
    Monthly Fee: $82
       Tax: $7,228 (2025)
    Community: Lakes Of Windermere
    Single Family


    Estimated Monthly Payment: $3,534 (change assumption)
    Mortgage ($2,849) + Fees ($82) + Taxes in 2025 ($602)


    Taxes:$7,228

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2958 MARQUESAS CT, WINDERMERE, FL 34786

    $1,875,000222 Days on yellowkey   MLS ID: O6357302

    REDUCED by $10,000 (0.5%) on 05/19/2026

    For Sale O6357302 - 2958 MARQUESAS CT, WINDERMERE, FL 34786 32 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4716
       Built: 1984
    Monthly Fee: $215
       Tax: $15,228 (2024)
    Community: Lake Crescent Reserve
    Single Family


    Estimated Monthly Payment: $11,758 (change assumption)
    Mortgage ($10,274) + Fees ($215) + Taxes in 2024 ($1,269)


    Taxes:$15,228

    Elementary School: Windermere Elem

    High School: Olympia High

    Tax Year: 2024

    Middle School: Gotha Middle


  • 6552 HELMSLEY CIRCLE, WINDERMERE, FL 34786

    $469,00081 Days on yellowkey   MLS ID: O6392752

    0 Days Off yellowkey (back on 5/31/2026)

    REDUCED by $10,000 (2.1%) on 04/23/2026

    For Sale O6392752 - 6552 HELMSLEY CIRCLE, WINDERMERE, FL 34786 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1980
       Built: 2008
    Monthly Fee: $315
       Tax: $3,248 (2025)
    Community: Preston Square
    Townhouse


    Estimated Monthly Payment: $3,155 (change assumption)
    Mortgage ($2,570) + Fees ($315) + Taxes in 2025 ($271)


    Taxes:$3,248

    Elementary School: Sunset Park Elem

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 10870 BAYSHORE DR, WINDERMERE, FL 34786

    $2,895,000134 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


  • 12305 VIA DERNA PL, WINDERMERE, FL 34786

    $465,000144 Days on yellowkey   MLS ID: O6374964

    REDUCED by $5,000 (1.1%) on 04/17/2026

    For Sale O6374964 - 12305 VIA DERNA PL, WINDERMERE, FL 34786 24 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1891
       Built: 2014
    Monthly Fee: $316
       Tax: $5,016 (2025)
    Community: Carrington
    Townhouse


    Estimated Monthly Payment: $3,282 (change assumption)
    Mortgage ($2,548) + Fees ($316) + Taxes in 2025 ($418)


    Taxes:$5,016

    Elementary School: Bay Lake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 9669 WESTOVER CLUB CIR, WINDERMERE, FL 34786

    $750,000105 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

    $3,200,000264 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


  • 11564 MIZZON DR #930, WINDERMERE, FL 34786

    $325,00040 Days on yellowkey   MLS ID: O6404607

    REDUCED by $10,000 (3.0%) on 05/31/2026

    For Sale O6404607 - 11564 MIZZON DR #930, WINDERMERE, FL 34786 38 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1442
       Built: 2006   Tax: $4,561 (2025)
    Community: Lakeside/Lks/Windermere Condo
    Condo


    Estimated Monthly Payment: $2,161 (change assumption)
    Mortgage ($1,781) + Taxes in 2025 ($380)


    Taxes:$4,561

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9144 ISLEWORTH GARDENS DR, WINDERMERE, FL 34786

    $4,450,00065 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

    $550,00014 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

    $1,090,00014 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


  • 11326 LEDGEMENT LN, WINDERMERE, FL 34786

    $939,00023 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

    $1,299,00017 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

    $2,400,00017 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


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

    $320,00015 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




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.