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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Winter Garden - 581 properties found

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  • 1209 CASTLEPORT RD, WINTER GARDEN, FL 34787

    $664,90052 Days on yellowkey   MLS ID: O6390760

    REDUCED by $10,090 (1.5%) on 04/14/2026

    For Sale O6390760 - 1209 CASTLEPORT RD, WINTER GARDEN, FL 34787 36 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2001
    Monthly Fee: $243
       Tax: $4,030 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,222 (change assumption)
    Mortgage ($3,643) + Fees ($243) + Taxes in 2025 ($336)


    Taxes:$4,030

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14168 LARKSPUR LAKE DR, WINTER GARDEN, FL 34787

    $2,999,990223 Days on yellowkey   MLS ID: O6346469

    REDUCED by $333,389 (10.0%) on 04/14/2026

    For Sale O6346469 - 14168 LARKSPUR LAKE DR, WINTER GARDEN, FL 34787 19 photos

    Bed: 6   Bath: 7.0   Gar: 4
    Liv Area Sq Ft: 6442
       Built: 2025
    Monthly Fee: $112
       Tax: $6,673 (2024)
    Community: Shorefront Cove
    Single Family


    Estimated Monthly Payment: $17,106 (change assumption)
    Mortgage ($16,438) + Fees ($112) + Taxes in 2024 ($556)


    Taxes:$6,673

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 931 KYLEE ALY, WINTER GARDEN, FL 34787

    $849,00061 Days on yellowkey   MLS ID: O6387922

    REDUCED by $26,000 (3.0%) on 04/14/2026

    For Sale O6387922 - 931 KYLEE ALY, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2831
       Built: 2022
    Monthly Fee: $401
       Tax: $9,637 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $5,856 (change assumption)
    Mortgage ($4,652) + Fees ($401) + Taxes in 2025 ($803)


    Taxes:$9,637

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15312 GILLIGAN CT, WINTER GARDEN, FL 34787

    $1,150,000103 Days on yellowkey   MLS ID: O6372954

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

    For Sale O6372954 - 15312 GILLIGAN CT, WINTER GARDEN, FL 34787 69 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3652
       Built: 2020
    Monthly Fee: $102
       Tax: $9,787 (2024)
    Community: Winding Bay Ii Llc
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,219 (change assumption)
    Mortgage ($6,301) + Fees ($102) + Taxes in 2024 ($816)


    Taxes:$9,787

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 17156 INGRAM BLUFF DR, WINTER GARDEN, FL 34787

    $606,44048 Days on yellowkey   MLS ID: G5109791

    0 Days Off yellowkey (back on 3/18/2026)

    For Sale G5109791 - 17156 INGRAM BLUFF DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,463 (change assumption)
    Mortgage ($3,323) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14241 COLONIAL POINTE DR, WINTER GARDEN, FL 34787

    $1,390,00089 Days on yellowkey   MLS ID: O6379808

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

    For Sale O6379808 - 14241 COLONIAL POINTE DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 7   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5001
       Built: 2017
    Monthly Fee: $215
       Tax: $9,308 (2024)
    Community: Overlook 2 At Hamlin
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,607 (change assumption)
    Mortgage ($7,616) + Fees ($215) + Taxes in 2024 ($776)


    Taxes:$9,308

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 14788 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $617,50022 Days on yellowkey   MLS ID: O6398754

    For Sale O6398754 - 14788 FIELD DAISY DR, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1992
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $3,612 (change assumption)
    Mortgage ($3,383) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14006 FRASIER STREET, WINTER GARDEN, FL 34787

    $659,00022 Days on yellowkey   MLS ID: O6398760

    For Sale O6398760 - 14006 FRASIER STREET, WINTER GARDEN, FL 34787 79 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2098
       Built: 2023
    Monthly Fee: $100
       Tax: $8,274 (2025)
    Community: Highland Ridge
    Single Family


    Estimated Monthly Payment: $4,400 (change assumption)
    Mortgage ($3,611) + Fees ($100) + Taxes in 2025 ($689)


    Taxes:$8,274

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15442 ENCHANTED MELODY WAY, WINTER GARDEN, FL 34787

    $609,85045 Days on yellowkey   MLS ID: S5146095

    REDUCED by $3,050 (0.5%) on 04/13/2026

    For Sale S5146095 - 15442 ENCHANTED MELODY WAY, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2420
       Built: 2024
    Monthly Fee: $95
       Tax: $8,065 (2025)
    Community: Osprey Ranch Ph I
    Single Family


    Estimated Monthly Payment: $4,109 (change assumption)
    Mortgage ($3,342) + Fees ($95) + Taxes in 2025 ($672)


    Taxes:$8,065

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 7680 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787

    $658,90026 Days on yellowkey   MLS ID: O6389013

    1 Days Off yellowkey (back on 4/13/2026)

    For Sale O6389013 - 7680 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787 58 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2385
       Built: 2016
    Monthly Fee: $252
       Tax: $8,915 (2025)
    Community: Summerlake Pd Ph 3A
    Single Family


    Estimated Monthly Payment: $4,605 (change assumption)
    Mortgage ($3,610) + Fees ($252) + Taxes in 2025 ($743)


    Taxes:$8,915

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14058 FRASIER ST, WINTER GARDEN, FL 34787

    $459,00074 Days on yellowkey   MLS ID: V4947394

    For Sale V4947394 - 14058 FRASIER ST, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1996
       Built: 2023
    Monthly Fee: $110
       Tax: $7,893 (2024)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,283 (change assumption)
    Mortgage ($2,515) + Fees ($110) + Taxes in 2024 ($658)


    Taxes:$7,893

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15324 GILLIGAN CT, WINTER GARDEN, FL 34787

    $950,00040 Days on yellowkey   MLS ID: O6393498

    0 Days Off yellowkey (back on 4/13/2026)

    For Sale O6393498 - 15324 GILLIGAN CT, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2794
       Built: 2020
    Monthly Fee: $102
       Tax: $641 (2025)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $5,361 (change assumption)
    Mortgage ($5,205) + Fees ($102) + Taxes in 2025 ($53)


    Taxes:$641

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8275 BAYVIEW CROSSING DR DR, WINTER GARDEN, FL 34787

    $565,00025 Days on yellowkey   MLS ID: TB8496196

    For Sale TB8496196 - 8275 BAYVIEW CROSSING DR DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2019
       Built: 2017
    Monthly Fee: $312
       Tax: $5,109 (2025)
    Community: Waterleigh Phase 1C
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,834 (change assumption)
    Mortgage ($3,096) + Fees ($312) + Taxes in 2025 ($426)


    Taxes:$5,109

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 238 N MAIN ST, WINTER GARDEN, FL 34787

    $600,00027 Days on yellowkey   MLS ID: O6397340

    For Sale O6397340 - 238 N MAIN ST, WINTER GARDEN, FL 34787 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1005
       Built: 1950   Tax: $5,389 (2025)
    Community: Orange Grove Sub
    Single Family


    Estimated Monthly Payment: $3,737 (change assumption)
    Mortgage ($3,288) + Taxes in 2025 ($449)


    Taxes:$5,389

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 17006 SEVILLE ORANGE RD, WINTER GARDEN, FL 34787

    $718,79933 Days on yellowkey   MLS ID: TB8493597

    For Sale TB8493597 - 17006 SEVILLE ORANGE RD, WINTER GARDEN, FL 34787 11 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2224
       Built: 2026
    Monthly Fee: $84
       Tax: $2,363 (2025)
    Community: Northlake/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $4,219 (change assumption)
    Mortgage ($3,939) + Fees ($84) + Taxes in 2025 ($197)


    Taxes:$2,363

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $548,00090 Days on yellowkey   MLS ID: O6379918

    5 Days Off yellowkey (back on 4/13/2026)

    For Sale O6379918 - 12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2062
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,273 (change assumption)
    Mortgage ($3,003) + 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


  • 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787

    $795,00040 Days on yellowkey   MLS ID: O6393987

    For Sale O6393987 - 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4307
       Built: 2014
    Monthly Fee: $114
       Tax: $5,670 (2025)
    Community: Reserve/Carriage Pointe Ph 1
    Single Family


    Estimated Monthly Payment: $4,943 (change assumption)
    Mortgage ($4,356) + Fees ($114) + Taxes in 2025 ($472)


    Taxes:$5,670

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17031 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $646,09023 Days on yellowkey   MLS ID: G5110934

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale G5110934 - 17031 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2680
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,680 (change assumption)
    Mortgage ($3,540) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17428 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $740,20523 Days on yellowkey   MLS ID: G5110933

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale G5110933 - 17428 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3412
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,196 (change assumption)
    Mortgage ($4,056) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5637 TIGER WAY, WINTER GARDEN, FL 34787

    $765,00023 Days on yellowkey   MLS ID: O6398378

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale O6398378 - 5637 TIGER WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2917
       Built: 2018
    Monthly Fee: $214
       Tax: $12,077 (2025)
    Community: Overlook 2/Hamlin Ph 3
    Single Family


    Estimated Monthly Payment: $5,412 (change assumption)
    Mortgage ($4,192) + Fees ($214) + Taxes in 2025 ($1,006)


    Taxes:$12,077

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle






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