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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Price: $500,000 to $599,000

Winter Garden - 164 properties found

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  • 113 W DIVISION ST, WINTER GARDEN, FL 34787

    $525,99057 Days on yellowkey   MLS ID: S5148787

    REDUCED by $13,910 (2.6%) on 06/16/2026

    For Sale S5148787 - 113 W DIVISION ST, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1487
       Built: 1951   Tax: $4,920 (2025)
    Community: Winter Garden Shores Rep
    Single Family


    Estimated Monthly Payment: $3,292 (change assumption)
    Mortgage ($2,882) + Taxes in 2025 ($410)


    Taxes:$4,920

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 503 FIRST CAPE CORAL DR, WINTER GARDEN, FL 34787

    $556,00099 Days on yellowkey   MLS ID: O6381166

    1 Days Off yellowkey (back on 6/16/2026)

    For Sale O6381166 - 503 FIRST CAPE CORAL DR, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2365
       Built: 2006
    Monthly Fee: $123
       Tax: $3,974 (2024)
    Community: Black Lake Park Ph 01
    Single Family


    Estimated Monthly Payment: $3,501 (change assumption)
    Mortgage ($3,046) + Fees ($123) + Taxes in 2024 ($331)


    Taxes:$3,974

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 15336 FIRELIGHT DR, WINTER GARDEN, FL 34787

    $585,00014 Days on yellowkey   MLS ID: G5113550

    0 Days Off yellowkey (back on 6/15/2026)

    For Sale G5113550 - 15336 FIRELIGHT DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2242
       Built: 2007
    Monthly Fee: $167
       Tax: $4,649 (2025)
    Community: Belle Meade Ph 2
    Single Family


    Estimated Monthly Payment: $3,760 (change assumption)
    Mortgage ($3,205) + Fees ($167) + Taxes in 2025 ($387)


    Taxes:$4,649

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16153 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $549,990111 Days on yellowkey   MLS ID: O6387508

    For Sale O6387508 - 16153 WATER SPRING BLVD, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2042
       Built: 2020
    Monthly Fee: $108
       Tax: $6,865 (2024)
    Community: Storey Grove Ph 2
    Single Family


    Estimated Monthly Payment: $3,694 (change assumption)
    Mortgage ($3,014) + Fees ($108) + Taxes in 2024 ($572)


    Taxes:$6,865

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 1049 SPRING LANDING DR, WINTER GARDEN, FL 34787

    $547,90013 Days on yellowkey   MLS ID: O6412927

    1 Days Off yellowkey (back on 6/15/2026)

    For Sale O6412927 - 1049 SPRING LANDING DR, WINTER GARDEN, FL 34787 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2167
       Built: 1990
    Monthly Fee: $25
       Tax: $5,582 (2025)
    Community: Crown Point Spgs
    Single Family


    Estimated Monthly Payment: $3,492 (change assumption)
    Mortgage ($3,002) + Fees ($25) + Taxes in 2025 ($465)


    Taxes:$5,582

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787

    $560,000202 Days on yellowkey   MLS ID: O6365057

    0 Days Off yellowkey (back on 5/22/2026)

    REDUCED by $5,000 (0.9%) on 05/12/2026

    For Sale O6365057 - 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2018
    Monthly Fee: $245
       Tax: $8,615 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $4,031 (change assumption)
    Mortgage ($3,068) + Fees ($245) + Taxes in 2025 ($718)


    Taxes:$8,615

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 6279 SUNNY TIME AVENUE, WINTER GARDEN, FL 34787

    $546,49026 Days on yellowkey   MLS ID: O6412141

    2 Days Off yellowkey (back on 6/14/2026)

    REDUCED by $15,500 (2.8%) on 06/06/2026

    For Sale O6412141 - 6279 SUNNY TIME AVENUE, WINTER GARDEN, FL 34787 28 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1913
       Built: 2026
    Monthly Fee: $152
       Tax: $1,372 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,261 (change assumption)
    Mortgage ($2,994) + Fees ($152) + Taxes in 2024 ($114)


    Taxes:$1,372

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 5960 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $597,99644 Days on yellowkey   MLS ID: G5112227

    INCREASED by $40,873 (7.3%) on 06/10/2026

    For Sale G5112227 - 5960 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 5 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1772
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,427 (change assumption)
    Mortgage ($3,277) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 921 BENDING OAK TRL, WINTER GARDEN, FL 34787

    $549,90047 Days on yellowkey   MLS ID: O6405328

    REDUCED by $20,000 (3.5%) on 06/11/2026

    For Sale O6405328 - 921 BENDING OAK TRL, WINTER GARDEN, FL 34787 79 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2517
       Built: 2012
    Monthly Fee: $125
       Tax: $3,791 (2025)
    Community: Oaks/Brandy Lake 01 Rep A & B
    Single Family


    Estimated Monthly Payment: $3,454 (change assumption)
    Mortgage ($3,013) + Fees ($125) + Taxes in 2025 ($316)


    Taxes:$3,791

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15073 VALVERSE ALY, WINTER GARDEN, FL 34787

    $515,00013 Days on yellowkey   MLS ID: O6416182

    For Sale O6416182 - 15073 VALVERSE ALY, WINTER GARDEN, FL 34787 38 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1892
       Built: 2017
    Monthly Fee: $339
       Tax: $4,172 (2025)
    Community: Overlook 2/Hamlin Ph 2 & 5
    Single Family


    Estimated Monthly Payment: $3,509 (change assumption)
    Mortgage ($2,822) + Fees ($339) + Taxes in 2025 ($348)


    Taxes:$4,172

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 913 BENDING OAK TRL, WINTER GARDEN, FL 34787

    $530,00013 Days on yellowkey   MLS ID: O6409986

    1 Days Off yellowkey (back on 6/14/2026)

    For Sale O6409986 - 913 BENDING OAK TRL, WINTER GARDEN, FL 34787 28 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2212
       Built: 2012
    Monthly Fee: $125
       Tax: $3,860 (2025)
    Community: Oaks/Brandy Lake 01 Rep A & B
    Single Family


    Estimated Monthly Payment: $3,351 (change assumption)
    Mortgage ($2,904) + Fees ($125) + Taxes in 2025 ($322)


    Taxes:$3,860

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787

    $545,00048 Days on yellowkey   MLS ID: O6402423

    For Sale O6402423 - 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787 24 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2016
    Monthly Fee: $253
       Tax: $5,148 (2025)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,668 (change assumption)
    Mortgage ($2,986) + Fees ($253) + Taxes in 2025 ($429)


    Taxes:$5,148

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $555,00075 Days on yellowkey   MLS ID: TB8496196

    REDUCED by $10,000 (1.8%) on 06/09/2026

    For Sale TB8496196 - 8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 96 photos

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

    Single Family


    Estimated Monthly Payment: $3,779 (change assumption)
    Mortgage ($3,041) + 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


  • 279 DOE RUN DR, WINTER GARDEN, FL 34787

    $599,00026 Days on yellowkey   MLS ID: TB8513595

    For Sale TB8513595 - 279 DOE RUN DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2435
       Built: 2005
    Monthly Fee: $57
       Tax: $2,489 (2025)
    Community: Deerfield Place 57/1
    Single Family


    Estimated Monthly Payment: $3,547 (change assumption)
    Mortgage ($3,282) + Fees ($57) + Taxes in 2025 ($207)


    Taxes:$2,489

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1061 PORTMOOR WAY, WINTER GARDEN, FL 34787

    $535,00020 Days on yellowkey   MLS ID: G5113349

    For Sale G5113349 - 1061 PORTMOOR WAY, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1804
       Built: 2001
    Monthly Fee: $243
       Tax: $6,801 (2025)
    Community: Stoneybrook West 44/134
    Single Family


    Estimated Monthly Payment: $3,741 (change assumption)
    Mortgage ($2,931) + Fees ($243) + Taxes in 2025 ($567)


    Taxes:$6,801

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 5460 BOWMAN DR, WINTER GARDEN, FL 34787

    $585,00047 Days on yellowkey   MLS ID: O6402308

    REDUCED by $30,000 (4.9%) on 06/10/2026

    For Sale O6402308 - 5460 BOWMAN DR, WINTER GARDEN, FL 34787 69 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2016
    Monthly Fee: $328
       Tax: $8,917 (2025)
    Community: Overlook At Hamlin
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,276 (change assumption)
    Mortgage ($3,205) + Fees ($328) + Taxes in 2025 ($743)


    Taxes:$8,917

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12554 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $599,000273 Days on yellowkey   MLS ID: O6346537

    1 Days Off yellowkey (back on 6/13/2026)

    For Sale O6346537 - 12554 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 42 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2743
       Built: 2025
    Monthly Fee: $96
       Tax: $1,862 (2024)
    Community: Osprey Ranch-Ph 1
    Single Family


    Estimated Monthly Payment: $3,533 (change assumption)
    Mortgage ($3,282) + Fees ($96) + Taxes in 2024 ($155)


    Taxes:$1,862

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2202 ROMANUM DR, WINTER GARDEN, FL 34787

    $565,00069 Days on yellowkey   MLS ID: O6398743

    REDUCED by $14,900 (2.6%) on 06/07/2026

    For Sale O6398743 - 2202 ROMANUM DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1889
       Built: 2015
    Monthly Fee: $211
       Tax: $3,839 (2025)
    Community: Alexander Ridge
    Single Family


    Estimated Monthly Payment: $3,627 (change assumption)
    Mortgage ($3,096) + Fees ($211) + Taxes in 2025 ($320)


    Taxes:$3,839

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5754 SURPRISE LILY DR, WINTER GARDEN, FL 34787

    $515,00012 Days on yellowkey   MLS ID: S5151845

    For Sale S5151845 - 5754 SURPRISE LILY DR, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2128
       Built: 2021
    Monthly Fee: $91
       Tax: $8,266 (2025)
    Community: Hamilton Gardens Ph 2A 2B
    Single Family


    Estimated Monthly Payment: $3,602 (change assumption)
    Mortgage ($2,822) + Fees ($91) + Taxes in 2025 ($689)


    Taxes:$8,266

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6475 BREEZE FILLED LN, WINTER GARDEN, FL 34787

    $585,00012 Days on yellowkey   MLS ID: O6416512

    For Sale O6416512 - 6475 BREEZE FILLED LN, WINTER GARDEN, FL 34787 43 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2231
       Built: 2025
    Monthly Fee: $147
       Tax: $2,107 (2025)
    Community: Silverleaf Oaks At Hamlin Phase 3A
    Single Family


    Estimated Monthly Payment: $3,528 (change assumption)
    Mortgage ($3,205) + Fees ($147) + Taxes in 2025 ($176)


    Taxes:$2,107

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle






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.