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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Beds: 5 to 5

Winter Garden - 175 properties found

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  • 3208 SAILING PIER AVE, WINTER GARDEN, FL 34787

    $1,049,90060 Days on yellowkey   MLS ID: O6402332

    For Sale O6402332 - 3208 SAILING PIER AVE, WINTER GARDEN, FL 34787 50 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3998
       Built: 2023
    Monthly Fee: $208
       Tax: $12,135 (2024)
    Community: Ests/Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $6,972 (change assumption)
    Mortgage ($5,753) + Fees ($208) + Taxes in 2024 ($1,011)


    Taxes:$12,135

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16783 TURTLE HATCH DR, WINTER GARDEN, FL 34787

    $1,199,99947 Days on yellowkey   MLS ID: O6404708

    0 Days Off yellowkey (back on 6/5/2026)

    REDUCED by $1 (0.0%) on 05/20/2026

    For Sale O6404708 - 16783 TURTLE HATCH DR, WINTER GARDEN, FL 34787 61 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3513
       Built: 2019
    Monthly Fee: $240
       Tax: $13,161 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Single Family


    Estimated Monthly Payment: $7,912 (change assumption)
    Mortgage ($6,575) + Fees ($240) + Taxes in 2025 ($1,097)


    Taxes:$13,161

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 6110 MERIWETHER CRES, WINTER GARDEN, FL 34787

    $690,00028 Days on yellowkey   MLS ID: O6411208

    0 Days Off yellowkey (back on 6/4/2026)

    For Sale O6411208 - 6110 MERIWETHER CRES, WINTER GARDEN, FL 34787 17 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2830
       Built: 2011
    Monthly Fee: $16
       Tax: $6,992 (2025)
    Community: Signature Lakes Ph 02 A B H I J
    Single Family


    Estimated Monthly Payment: $4,379 (change assumption)
    Mortgage ($3,781) + Fees ($16) + Taxes in 2025 ($583)


    Taxes:$6,992

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12904 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $1,032,000133 Days on yellowkey   MLS ID: O6381734

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

    INCREASED by $10,000 (1.0%) on 06/01/2026

    For Sale O6381734 - 12904 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3894
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $5,925 (change assumption)
    Mortgage ($5,655) + Fees ($77) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1432 MARBLE CREST WAY, WINTER GARDEN, FL 34787

    $824,50072 Days on yellowkey   MLS ID: O6398054

    4 Days Off yellowkey (back on 6/2/2026)

    For Sale O6398054 - 1432 MARBLE CREST WAY, WINTER GARDEN, FL 34787 82 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3734
       Built: 2005
    Monthly Fee: $243
       Tax: $7,963 (2025)
    Community: Stoneybrook West 44/134
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,424 (change assumption)
    Mortgage ($4,518) + Fees ($243) + Taxes in 2025 ($664)


    Taxes:$7,963

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 8018 BOWERY DR, WINTER GARDEN, FL 34787

    $699,900344 Days on yellowkey   MLS ID: O6325853

    For Sale O6325853 - 8018 BOWERY DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3075
       Built: 2017
    Monthly Fee: $208
       Tax: $5,724 (2024)
    Community: Lake Hancock Preserve
    Single Family


    Estimated Monthly Payment: $4,520 (change assumption)
    Mortgage ($3,835) + Fees ($208) + Taxes in 2024 ($477)


    Taxes:$5,724

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $950,00023 Days on yellowkey   MLS ID: O6412033

    For Sale O6412033 - 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3777
       Built: 2016
    Monthly Fee: $195
       Tax: $11,678 (2025)
    Community: Signature Lakes Ph 3B-4 3B-5 & 3
    Single Family


    Estimated Monthly Payment: $6,374 (change assumption)
    Mortgage ($5,205) + Fees ($195) + Taxes in 2025 ($973)


    Taxes:$11,678

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11223 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $809,990131 Days on yellowkey   MLS ID: O6382359

    1 Days Off yellowkey (back on 6/4/2026)

    REDUCED by $10,000 (1.2%) on 06/04/2026

    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: $4,854 (change assumption)
    Mortgage ($4,438) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2640 GROVE VIEW DR, WINTER GARDEN, FL 34787

    $784,90061 Days on yellowkey   MLS ID: O6401215

    REDUCED by $5,000 (0.6%) on 05/31/2026

    For Sale O6401215 - 2640 GROVE VIEW DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3738
       Built: 2001
    Monthly Fee: $90
       Tax: $10,261 (2025)
    Community: Wintermere Pointe Ph 02 46/141
    Single Family


    Estimated Monthly Payment: $5,246 (change assumption)
    Mortgage ($4,301) + Fees ($90) + Taxes in 2025 ($855)


    Taxes:$10,261

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16379 SILVER GROVE BLVD, WINTER GARDEN, FL 34787

    $950,00027 Days on yellowkey   MLS ID: O6411552

    For Sale O6411552 - 16379 SILVER GROVE BLVD, WINTER GARDEN, FL 34787 62 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3823
       Built: 2025
    Monthly Fee: $168
       Tax: $1,938 (2024)
    Community: Silverleaf Reserve At Hamlin Phase
    Single Family


    Estimated Monthly Payment: $5,535 (change assumption)
    Mortgage ($5,205) + Fees ($168) + Taxes in 2024 ($162)


    Taxes:$1,938

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 11283 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $909,46650 Days on yellowkey   MLS ID: O6405091

    2 Days Off yellowkey (back on 6/2/2026)

    For Sale O6405091 - 11283 HOLLOW BAY DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,348 (change assumption)
    Mortgage ($4,983) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15518 HONEY MANDARIN WAY, WINTER GARDEN, FL 34787

    $869,90082 Days on yellowkey   MLS ID: O6396204

    For Sale O6396204 - 15518 HONEY MANDARIN WAY, WINTER GARDEN, FL 34787 70 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3640
       Built: 2018
    Monthly Fee: $113
       Tax: $11,489 (2025)
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $5,837 (change assumption)
    Mortgage ($4,766) + Fees ($113) + Taxes in 2025 ($957)


    Taxes:$11,489

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12940 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $919,000135 Days on yellowkey   MLS ID: O6381140

    0 Days Off yellowkey (back on 2/14/2026)

    For Sale O6381140 - 12940 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3894
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $5,306 (change assumption)
    Mortgage ($5,035) + Fees ($77) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15047 GAULBERRY RUN, WINTER GARDEN, FL 34787

    $1,525,00039 Days on yellowkey   MLS ID: O6408283

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

    For Sale O6408283 - 15047 GAULBERRY RUN, WINTER GARDEN, FL 34787 78 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4964
       Built: 2013
    Monthly Fee: $198
       Tax: $10,739 (2026)
    Community: Signature Lks-Pcl 01D Ph 02
    Single Family


    Estimated Monthly Payment: $9,449 (change assumption)
    Mortgage ($8,356) + Fees ($198) + Taxes in 2026 ($895)


    Taxes:$10,739

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Bridgewater Middle


  • 17588 LAKE STAR RD, WINTER GARDEN, FL 34787

    $1,185,000104 Days on yellowkey   MLS ID: O6387269

    REDUCED by $10,000 (0.8%) on 04/25/2026

    For Sale O6387269 - 17588 LAKE STAR RD, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4026
       Built: 2024
    Monthly Fee: $84
       Tax: $3,806 (2024)
    Community: Northlake At Ovation
    Single Family


    Estimated Monthly Payment: $6,894 (change assumption)
    Mortgage ($6,493) + Fees ($84) + Taxes in 2024 ($317)


    Taxes:$3,806

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16271 HONEY HARVEST ST, WINTER GARDEN, FL 34787

    $699,990115 Days on yellowkey   MLS ID: O6386199

    REDUCED by $6,000 (0.8%) on 05/27/2026

    For Sale O6386199 - 16271 HONEY HARVEST ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2024
    Monthly Fee: $184
       Tax: $8,425 (2025)
    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,722 (change assumption)
    Mortgage ($3,835) + Fees ($184) + Taxes in 2025 ($702)


    Taxes:$8,425

    Elementary School: Whispering Oak Elem

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 15532 AVENUE OF THE ARBORS, WINTER GARDEN, FL 34787

    $1,999,94742 Days on yellowkey   MLS ID: O6405850

    REDUCED by $3 (0.0%) on 05/25/2026

    For Sale O6405850 - 15532 AVENUE OF THE ARBORS, WINTER GARDEN, FL 34787 84 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3837
       Built: 2016
    Monthly Fee: $195
       Tax: $17,089 (2025)
    Community: Signature Lakes Ph 02 A B H I J
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,577 (change assumption)
    Mortgage ($10,958) + Fees ($195) + Taxes in 2025 ($1,424)


    Taxes:$17,089

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 15591 GENTLE RAIN DR, WINTER GARDEN, FL 34787

    $730,00026 Days on yellowkey   MLS ID: O6411803

    For Sale O6411803 - 15591 GENTLE RAIN DR, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2896
       Built: 2025
    Monthly Fee: $99
       Tax: $1,890 (2025)
    Community: Osprey Ranch Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,256 (change assumption)
    Mortgage ($4,000) + Fees ($99) + Taxes in 2025 ($158)


    Taxes:$1,890

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13181 TOOLCROSS WAY, WINTER GARDEN, FL 34787

    $1,100,00026 Days on yellowkey   MLS ID: O6410984

    For Sale O6410984 - 13181 TOOLCROSS WAY, WINTER GARDEN, FL 34787 87 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3894
       Built: 2024
    Monthly Fee: $83
       Tax: $11,946 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $7,106 (change assumption)
    Mortgage ($6,027) + Fees ($83) + Taxes in 2025 ($996)


    Taxes:$11,946

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15143 KIRSTY ALY, WINTER GARDEN, FL 34787

    $654,900280 Days on yellowkey   MLS ID: O6344886

    REDUCED by $4,100 (0.6%) on 05/24/2026

    For Sale O6344886 - 15143 KIRSTY ALY, WINTER GARDEN, FL 34787 44 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2934
       Built: 2017
    Monthly Fee: $328
       Tax: $9,868 (2025)
    Community: Overlook 2/Hamlin Ph 2 & 5
    Single Family


    Estimated Monthly Payment: $4,739 (change assumption)
    Mortgage ($3,588) + Fees ($328) + Taxes in 2025 ($822)


    Taxes:$9,868

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle






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