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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Beds: 4 to 4

Winter Garden - 262 properties found

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  • 9409 EMERALD BERRY DR, WINTER GARDEN, FL 34787

    $875,00062 Days on yellowkey   MLS ID: S5144953

    0 Days Off yellowkey (back on 4/25/2026)

    For Sale S5144953 - 9409 EMERALD BERRY DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2923
       Built: 2024
    Monthly Fee: $85

    Community: Summerlake Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,879 (change assumption)
    Mortgage ($4,794) + Fees ($85) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 7580 SPRING VALLEY ST, WINTER GARDEN, FL 34787

    $693,23010 Days on yellowkey   MLS ID: G5111519

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

    For Sale G5111519 - 7580 SPRING VALLEY ST, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,920 (change assumption)
    Mortgage ($3,798) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9062 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $785,000201 Days on yellowkey   MLS ID: O6352763

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

    For Sale O6352763 - 9062 SONOMA COAST DR, WINTER GARDEN, FL 34787 69 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2909
       Built: 2021
    Monthly Fee: $261
       Tax: $10,736 (2024)
    Community: Waterleigh Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $5,457 (change assumption)
    Mortgage ($4,301) + Fees ($261) + Taxes in 2024 ($895)


    Taxes:$10,736

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 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


  • 15306 GILLIGAN CT, WINTER GARDEN, FL 34787

    $925,00017 Days on yellowkey   MLS ID: O6399653

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

    For Sale O6399653 - 15306 GILLIGAN CT, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3127
       Built: 2020
    Monthly Fee: $102
       Tax: $8,308 (2025)
    Community: Winding Bay Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,863 (change assumption)
    Mortgage ($5,068) + Fees ($102) + Taxes in 2025 ($692)


    Taxes:$8,308

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 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


  • 15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787

    $645,900563 Days on yellowkey   MLS ID: O6250356

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

    REDUCED by $3,900 (0.6%) on 04/17/2026

    For Sale O6250356 - 15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3359
       Built: 2001
    Monthly Fee: $233
       Tax: $8,538 (2023)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,484 (change assumption)
    Mortgage ($3,539) + Fees ($233) + Taxes in 2023 ($712)


    Taxes:$8,538

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2023

    Middle School: SunRidge Middle


  • 15327 GILLIGAN CT, WINTER GARDEN, FL 34787

    $664,80018 Days on yellowkey   MLS ID: O6398756

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

    For Sale O6398756 - 15327 GILLIGAN CT, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2506
       Built: 2021
    Monthly Fee: $103
       Tax: $7,266 (2025)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $4,351 (change assumption)
    Mortgage ($3,643) + Fees ($103) + Taxes in 2025 ($606)


    Taxes:$7,266

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 3439 BUOY CIR, WINTER GARDEN, FL 34787

    $734,99048 Days on yellowkey   MLS ID: O6386482

    REDUCED by $13,010 (1.7%) on 04/23/2026

    For Sale O6386482 - 3439 BUOY CIR, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 2920
       Built: 2019
    Monthly Fee: $152
       Tax: $7,013 (2025)
    Community: Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $4,764 (change assumption)
    Mortgage ($4,027) + Fees ($152) + Taxes in 2025 ($584)


    Taxes:$7,013

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 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


  • 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $609,61177 Days on yellowkey   MLS ID: G5108288

    0 Days Off yellowkey (back on 4/7/2026)

    For Sale G5108288 - 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2520
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,462 (change assumption)
    Mortgage ($3,340) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14645 SCOTT KEY DR, WINTER GARDEN, FL 34787

    $890,000108 Days on yellowkey   MLS ID: G5106818

    0 Days Off yellowkey (back on 4/21/2026)

    For Sale G5106818 - 14645 SCOTT KEY DR, WINTER GARDEN, FL 34787 72 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3427
       Built: 2016   Tax: $10,465 (2024)
    Community: Watermark Ph 1B
    Single Family


    Estimated Monthly Payment: $5,749 (change assumption)
    Mortgage ($4,877) + Taxes in 2024 ($872)


    Taxes:$10,465

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin 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






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