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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 2500 to 2999

Winter Garden - 136 properties found

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  • 9062 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $785,000204 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


  • 7526 SPRING VALLEY ST, WINTER GARDEN, FL 34787

    $676,24514 Days on yellowkey   MLS ID: G5111448

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

    For Sale G5111448 - 7526 SPRING VALLEY ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2680
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,855 (change assumption)
    Mortgage ($3,705) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15327 GILLIGAN CT, WINTER GARDEN, FL 34787

    $664,80021 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


  • 13386 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787

    $799,99069 Days on yellowkey   MLS ID: S5144786

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

    For Sale S5144786 - 13386 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2856
       Built: 2026
    Monthly Fee: $125
       Tax: $500 (2025)
    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $4,550 (change assumption)
    Mortgage ($4,383) + Fees ($125) + Taxes in 2025 ($42)


    Taxes:$500

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $609,61180 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


  • 11223 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $819,99083 Days on yellowkey   MLS ID: O6382359

    REDUCED by $9,746 (1.2%) on 04/22/2026

    For Sale O6382359 - 11223 HOLLOW BAY DR, WINTER GARDEN, FL 34787 10 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,909 (change assumption)
    Mortgage ($4,493) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16143 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787

    $875,595101 Days on yellowkey   MLS ID: G5107301

    0 Days Off yellowkey (back on 1/26/2026)

    For Sale G5107301 - 16143 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,948 (change assumption)
    Mortgage ($4,798) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15456 GILLIGAN CT, WINTER GARDEN, FL 34787

    $600,000280 Days on yellowkey   MLS ID: A4660262

    REDUCED by $20,000 (3.2%) on 04/21/2026

    For Sale A4660262 - 15456 GILLIGAN CT, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2571
       Built: 2020
    Monthly Fee: $102
       Tax: $8,702 (2024)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $4,115 (change assumption)
    Mortgage ($3,288) + Fees ($102) + Taxes in 2024 ($725)


    Taxes:$8,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14345 WABASSO LOOP, WINTER GARDEN, FL 34787

    $735,00091 Days on yellowkey   MLS ID: O6376609

    For Sale O6376609 - 14345 WABASSO LOOP, WINTER GARDEN, FL 34787 31 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2878
       Built: 2022
    Monthly Fee: $192
       Tax: $10,615 (2025)
    Community: Tilden Place/Winter Garden
    Single Family


    Estimated Monthly Payment: $5,104 (change assumption)
    Mortgage ($4,027) + Fees ($192) + Taxes in 2025 ($885)


    Taxes:$10,615

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9459 JAYWOOD RD, WINTER GARDEN, FL 34787

    $755,00066 Days on yellowkey   MLS ID: O6386488

    REDUCED by $5,000 (0.7%) on 04/20/2026

    For Sale O6386488 - 9459 JAYWOOD RD, WINTER GARDEN, FL 34787 55 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2020
    Monthly Fee: $261
       Tax: $6,669 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $4,954 (change assumption)
    Mortgage ($4,137) + Fees ($261) + Taxes in 2025 ($556)


    Taxes:$6,669

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17453 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $757,99018 Days on yellowkey   MLS ID: G5111222

    0 Days Off yellowkey (back on 4/19/2026)

    For Sale G5111222 - 17453 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,303 (change assumption)
    Mortgage ($4,153) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 393 LAKE AMBERLEIGH DR, WINTER GARDEN, FL 34787

    $615,000112 Days on yellowkey   MLS ID: O6374079

    For Sale O6374079 - 393 LAKE AMBERLEIGH DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2684
       Built: 2002
    Monthly Fee: $117
       Tax: $2,690 (2025)
    Community: Amberleigh
    Single Family


    Estimated Monthly Payment: $3,711 (change assumption)
    Mortgage ($3,370) + Fees ($117) + Taxes in 2025 ($224)


    Taxes:$2,690

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $725,00070 Days on yellowkey   MLS ID: O6386008

    For Sale O6386008 - 18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 37 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2832
       Built: 2023
    Monthly Fee: $281
       Tax: $497 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,295 (change assumption)
    Mortgage ($3,973) + Fees ($281) + Taxes in 2024 ($41)


    Taxes:$497

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $745,000136 Days on yellowkey   MLS ID: S5140531

    For Sale S5140531 - 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2924
       Built: 2023
    Monthly Fee: $300
       Tax: $1,706 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,524 (change assumption)
    Mortgage ($4,082) + Fees ($300) + Taxes in 2024 ($142)


    Taxes:$1,706

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 815 BURLAND CIR, WINTER GARDEN, FL 34787

    $575,900141 Days on yellowkey   MLS ID: O6368127

    1 Days Off yellowkey (back on 4/16/2026)

    For Sale O6368127 - 815 BURLAND CIR, WINTER GARDEN, FL 34787 38 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2994
       Built: 2005
    Monthly Fee: $53
       Tax: $8,110 (2025)
    Community: Fullers Xing Ph 03 A-G
    Single Family


    Estimated Monthly Payment: $3,884 (change assumption)
    Mortgage ($3,156) + Fees ($53) + Taxes in 2025 ($676)


    Taxes:$8,110

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 6441 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $617,99022 Days on yellowkey   MLS ID: G5111080

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale G5111080 - 6441 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $150
       Tax: $298 (2025)
    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,561 (change assumption)
    Mortgage ($3,386) + Fees ($150) + Taxes in 2025 ($25)


    Taxes:$298

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6050 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $712,63422 Days on yellowkey   MLS ID: G5111051

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale G5111051 - 6050 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 2 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,055 (change assumption)
    Mortgage ($3,905) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15359 MARITIME PINE DR, WINTER GARDEN, FL 34787

    $828,10523 Days on yellowkey   MLS ID: G5110994

    0 Days Off yellowkey (back on 4/14/2026)

    For Sale G5110994 - 15359 MARITIME PINE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,687 (change assumption)
    Mortgage ($4,537) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1923 JEAN MARIE DR, WINTER GARDEN, FL 34787

    $580,000110 Days on yellowkey   MLS ID: G5106903

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale G5106903 - 1923 JEAN MARIE DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2916
       Built: 2007
    Monthly Fee: $90
       Tax: $4,275 (2024)
    Community: Carriage Pointe A-I & L
    Single Family


    Estimated Monthly Payment: $3,624 (change assumption)
    Mortgage ($3,178) + Fees ($90) + Taxes in 2024 ($356)


    Taxes:$4,275

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6226 MANUSCRIPT ST, WINTER GARDEN, FL 34787

    $627,900180 Days on yellowkey   MLS ID: O6359078

    1 Days Off yellowkey (back on 4/15/2026)

    REDUCED by $8,000 (1.3%) on 04/02/2026

    For Sale O6359078 - 6226 MANUSCRIPT ST, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2849
       Built: 2012
    Monthly Fee: $168
       Tax: $7,134 (2024)
    Community: Signature Lakes Ph 02 A B H I J
    Single Family


    Estimated Monthly Payment: $4,203 (change assumption)
    Mortgage ($3,440) + Fees ($168) + Taxes in 2024 ($595)


    Taxes:$7,134

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None






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