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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 2000 to 2499

Winter Garden - 170 properties found

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  • 16149 WIND VIEW LN, WINTER GARDEN, FL 34787

    $498,00052 Days on yellowkey   MLS ID: O6389892

    REDUCED by $7,000 (1.4%) on 04/15/2026

    For Sale O6389892 - 16149 WIND VIEW LN, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2036
       Built: 2016
    Monthly Fee: $332
       Tax: $4,472 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $3,433 (change assumption)
    Mortgage ($2,729) + Fees ($332) + Taxes in 2025 ($373)


    Taxes:$4,472

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17549 SEIDNER RD, WINTER GARDEN, FL 34787

    $950,00037 Days on yellowkey   MLS ID: O6392430

    1 Days Off yellowkey (back on 4/18/2026)

    For Sale O6392430 - 17549 SEIDNER RD, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2130
       Built: 1985
    Monthly Fee: $3
       Tax: $3,947 (2025)
    Community: Lake Avalon Heights
    Single Family


    Estimated Monthly Payment: $5,537 (change assumption)
    Mortgage ($5,205) + Fees ($3) + Taxes in 2025 ($329)


    Taxes:$3,947

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5531 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $610,00095 Days on yellowkey   MLS ID: O6378167

    1 Days Off yellowkey (back on 4/24/2026)

    For Sale O6378167 - 5531 CYPRESS HILL RD, WINTER GARDEN, FL 34787 62 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2204
       Built: 2016
    Monthly Fee: $188
       Tax: $8,644 (2025)
    Community: Orchard Hills Ph 2 Signature Lakes
    Single Family


    Estimated Monthly Payment: $4,251 (change assumption)
    Mortgage ($3,342) + Fees ($188) + Taxes in 2025 ($720)


    Taxes:$8,644

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 776 RAINFALL DR, WINTER GARDEN, FL 34787

    $550,00011 Days on yellowkey   MLS ID: O6400904

    For Sale O6400904 - 776 RAINFALL DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2238
       Built: 2007
    Monthly Fee: $92
       Tax: $7,884 (2025)
    Community: Black Lake Park Ph 02
    Single Family


    Estimated Monthly Payment: $3,763 (change assumption)
    Mortgage ($3,014) + Fees ($92) + Taxes in 2025 ($657)


    Taxes:$7,884

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1075 CHASE DR, WINTER GARDEN, FL 34787

    $625,00063 Days on yellowkey   MLS ID: O6386607

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6386607 - 1075 CHASE DR, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2125
       Built: 2015
    Monthly Fee: $41
       Tax: $2,734 (2024)
    Community: Island Pointe Sub
    Single Family


    Estimated Monthly Payment: $3,693 (change assumption)
    Mortgage ($3,425) + Fees ($41) + Taxes in 2024 ($228)


    Taxes:$2,734

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16467 OLIVE HILL DR, WINTER GARDEN, FL 34787

    $599,900600 Days on yellowkey   MLS ID: O6240446

    2 Days Off yellowkey (back on 6/27/2025)

    For Sale O6240446 - 16467 OLIVE HILL DR, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2355
       Built: 2019
    Monthly Fee: $115
       Tax: $7,249 (2023)
    Community: Hawksmoor Ph 1
    Single Family


    Estimated Monthly Payment: $4,006 (change assumption)
    Mortgage ($3,287) + Fees ($115) + Taxes in 2023 ($604)


    Taxes:$7,249

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 205 SURPRISE DR, WINTER GARDEN, FL 34787

    $1,200,000151 Days on yellowkey   MLS ID: O6365188

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6365188 - 205 SURPRISE DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2171
       Built: 1950   Tax: $3,406 (2024)
    Community: Winter Garden Shores Rep
    Single Family


    Estimated Monthly Payment: $6,859 (change assumption)
    Mortgage ($6,575) + Taxes in 2024 ($284)


    Taxes:$3,406

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $580,00075 Days on yellowkey   MLS ID: O6383534

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6383534 - 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2415
       Built: 2022
    Monthly Fee: $101
       Tax: $7,566 (2024)
    Community: Winding Bay Ph 3
    Single Family


    Estimated Monthly Payment: $3,909 (change assumption)
    Mortgage ($3,178) + Fees ($101) + Taxes in 2024 ($630)


    Taxes:$7,566

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15306 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $568,00073 Days on yellowkey   MLS ID: O6384014

    1 Days Off yellowkey (back on 4/23/2026)

    For Sale O6384014 - 15306 LEBEAU LOOP, WINTER GARDEN, FL 34787 52 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2482
       Built: 2021
    Monthly Fee: $101
       Tax: $6,339 (2024)
    Community: Winding Bay Ph 3
    Single Family


    Estimated Monthly Payment: $3,741 (change assumption)
    Mortgage ($3,112) + Fees ($101) + Taxes in 2024 ($528)


    Taxes:$6,339

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17865 ADRIFT RD, WINTER GARDEN, FL 34787

    $599,000285 Days on yellowkey   MLS ID: O6329586

    For Sale O6329586 - 17865 ADRIFT RD, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2484
       Built: 2023
    Monthly Fee: $277
       Tax: $9,155 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,322 (change assumption)
    Mortgage ($3,282) + Fees ($277) + Taxes in 2024 ($763)


    Taxes:$9,155

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $634,99012 Days on yellowkey   MLS ID: O6401373

    For Sale O6401373 - 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2494
       Built: 2026
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,835 (change assumption)
    Mortgage ($3,479) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15401 PORTER RD, WINTER GARDEN, FL 34787

    $558,000125 Days on yellowkey   MLS ID: S5140743

    For Sale S5140743 - 15401 PORTER RD, WINTER GARDEN, FL 34787 59 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2455
       Built: 2015
    Monthly Fee: $242
       Tax: $8,271 (2024)
    Community: Summerlake
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,989 (change assumption)
    Mortgage ($3,057) + Fees ($242) + Taxes in 2024 ($689)


    Taxes:$8,271

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 9008 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $824,950287 Days on yellowkey   MLS ID: O6328849

    For Sale O6328849 - 9008 SONOMA COAST DR, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2348
       Built: 2022
    Monthly Fee: $258
       Tax: $10,553 (2024)
    Community: Waterleigh Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $5,658 (change assumption)
    Mortgage ($4,520) + Fees ($258) + Taxes in 2024 ($879)


    Taxes:$10,553

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16271 SILVER GROVE BLVD, WINTER GARDEN, FL 34787

    $680,000383 Days on yellowkey   MLS ID: O6299810

    For Sale O6299810 - 16271 SILVER GROVE BLVD, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2093
       Built: 2023
    Monthly Fee: $148
       Tax: $1,854 (2023)
    Community: Silverleaf Reserve At Hamlin
    Single Family


    Estimated Monthly Payment: $4,028 (change assumption)
    Mortgage ($3,726) + Fees ($148) + Taxes in 2023 ($154)


    Taxes:$1,854

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787

    $997,00023 Days on yellowkey   MLS ID: O6397262

    For Sale O6397262 - 14140 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2346
       Built: 1984
    Monthly Fee: $71
       Tax: $10,303 (2025)
    Community: Country Lakes
    Single Family


    Estimated Monthly Payment: $6,392 (change assumption)
    Mortgage ($5,463) + Fees ($71) + Taxes in 2025 ($859)


    Taxes:$10,303

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5596 THOMAS SQUARE DR, WINTER GARDEN, FL 34787

    $618,00063 Days on yellowkey   MLS ID: O6386791

    For Sale O6386791 - 5596 THOMAS SQUARE DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2458
       Built: 2015
    Monthly Fee: $324
       Tax: $8,569 (2025)
    Community: Overlook At Hamlin
    Single Family


    Estimated Monthly Payment: $4,424 (change assumption)
    Mortgage ($3,386) + Fees ($324) + Taxes in 2025 ($714)


    Taxes:$8,569

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11241 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $789,99095 Days on yellowkey   MLS ID: O6378044

    REDUCED by $10,000 (1.3%) on 04/22/2026

    For Sale O6378044 - 11241 HOLLOW BAY DR, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $248
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,742 (change assumption)
    Mortgage ($4,329) + Fees ($248) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $564,990164 Days on yellowkey   MLS ID: O6362478

    REDUCED by $7,565 (1.3%) on 04/22/2026

    For Sale O6362478 - 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,452 (change assumption)
    Mortgage ($3,096) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11858 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $534,990213 Days on yellowkey   MLS ID: O6349514

    REDUCED by $5,000 (0.9%) on 04/22/2026

    For Sale O6349514 - 11858 SHINE VIEW LN, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,287 (change assumption)
    Mortgage ($2,931) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $584,990105 Days on yellowkey   MLS ID: O6374947

    REDUCED by $5,710 (1.0%) on 04/22/2026

    For Sale O6374947 - 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,570 (change assumption)
    Mortgage ($3,205) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None






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.