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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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  • 14372 BREDA CENTER LOOP, WINTER GARDEN, FL 34787

    $580,000118 Days on yellowkey   MLS ID: O6385377

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

    For Sale O6385377 - 14372 BREDA CENTER LOOP, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2700
       Built: 2016
    Monthly Fee: $196
       Tax: $4,460 (2025)
    Community: Lake Hancock Preserve
    Single Family


    Estimated Monthly Payment: $3,746 (change assumption)
    Mortgage ($3,178) + Fees ($196) + Taxes in 2025 ($372)


    Taxes:$4,460

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $569,990156 Days on yellowkey   MLS ID: O6374947

    REDUCED by $5,000 (0.9%) on 06/04/2026

    For Sale O6374947 - 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787 13 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,488 (change assumption)
    Mortgage ($3,123) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $546,990215 Days on yellowkey   MLS ID: O6362478

    REDUCED by $8,000 (1.4%) on 06/04/2026

    For Sale O6362478 - 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,353 (change assumption)
    Mortgage ($2,997) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13212 SOCIAL LN, WINTER GARDEN, FL 34787

    $595,00069 Days on yellowkey   MLS ID: O6398708

    For Sale O6398708 - 13212 SOCIAL LN, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2526
       Built: 2005
    Monthly Fee: $100
       Tax: $4,474 (2025)
    Community: Regency Oaks F
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,733 (change assumption)
    Mortgage ($3,260) + Fees ($100) + Taxes in 2025 ($373)


    Taxes:$4,474

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787

    $550,00078 Days on yellowkey   MLS ID: O6396757

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

    REDUCED by $20,000 (3.5%) on 04/21/2026

    For Sale O6396757 - 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1979
       Built: 2019
    Monthly Fee: $142
       Tax: $8,155 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $3,835 (change assumption)
    Mortgage ($3,014) + Fees ($142) + Taxes in 2025 ($680)


    Taxes:$8,155

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 13360 SUNNY RETREAT LN, WINTER GARDEN, FL 34787

    $585,000148 Days on yellowkey   MLS ID: S5142297

    For Sale S5142297 - 13360 SUNNY RETREAT LN, WINTER GARDEN, FL 34787 62 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2000
       Built: 2022
    Monthly Fee: $642
       Tax: $7,519 (2024)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,474 (change assumption)
    Mortgage ($3,205) + Fees ($642) + Taxes in 2024 ($627)


    Taxes:$7,519

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787

    $580,00041 Days on yellowkey   MLS ID: O6408082

    For Sale O6408082 - 14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787 17 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2258
       Built: 2004
    Monthly Fee: $253
       Tax: $8,397 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,131 (change assumption)
    Mortgage ($3,178) + Fees ($253) + Taxes in 2025 ($700)


    Taxes:$8,397

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16754 OAKBORO ST, WINTER GARDEN, FL 34787

    $535,00048 Days on yellowkey   MLS ID: O6404652

    REDUCED by $4,000 (0.7%) on 06/05/2026

    For Sale O6404652 - 16754 OAKBORO ST, WINTER GARDEN, FL 34787 85 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $254
       Tax: $8,808 (2025)
    Community: Waterleigh Ph 3B 3C 3D
    Single Family


    Estimated Monthly Payment: $3,919 (change assumption)
    Mortgage ($2,931) + Fees ($254) + Taxes in 2025 ($734)


    Taxes:$8,808

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14451 WINDSOR HALL WAY, WINTER GARDEN, FL 34787

    $510,00037 Days on yellowkey   MLS ID: O6408731

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

    For Sale O6408731 - 14451 WINDSOR HALL WAY, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1814
       Built: 2016
    Monthly Fee: $192
       Tax: $5,900 (2025)
    Community: Lake Hancock Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,478 (change assumption)
    Mortgage ($2,794) + Fees ($192) + Taxes in 2025 ($492)


    Taxes:$5,900

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $546,990194 Days on yellowkey   MLS ID: O6367156

    REDUCED by $8,000 (1.4%) on 06/04/2026

    For Sale O6367156 - 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,353 (change assumption)
    Mortgage ($2,997) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7531 SILVER VALLEY ST, WINTER GARDEN, FL 34787

    $552,27521 Days on yellowkey   MLS ID: G5113297

    0 Days Off yellowkey (back on 6/3/2026)

    For Sale G5113297 - 7531 SILVER VALLEY ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,176 (change assumption)
    Mortgage ($3,026) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13023 INKWELL ALY, WINTER GARDEN, FL 34787

    $515,00035 Days on yellowkey   MLS ID: O6409443

    0 Days Off yellowkey (back on 6/3/2026)

    For Sale O6409443 - 13023 INKWELL ALY, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2042
       Built: 2020
    Monthly Fee: $268
       Tax: $5,162 (2025)
    Community: Storey Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,520 (change assumption)
    Mortgage ($2,822) + Fees ($268) + Taxes in 2025 ($430)


    Taxes:$5,162

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13151 CALMING BREEZE WAY, WINTER GARDEN, FL 34787

    $553,000204 Days on yellowkey   MLS ID: O6363957

    REDUCED by $12,000 (2.1%) on 06/01/2026

    For Sale O6363957 - 13151 CALMING BREEZE WAY, WINTER GARDEN, FL 34787 30 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2096
       Built: 2024
    Monthly Fee: $125
       Tax: $7,757 (2025)
    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $3,801 (change assumption)
    Mortgage ($3,030) + Fees ($125) + Taxes in 2025 ($646)


    Taxes:$7,757

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 46 W VINING ST, WINTER GARDEN, FL 34787

    $549,90037 Days on yellowkey   MLS ID: O6408720

    REDUCED by $20,000 (3.5%) on 06/03/2026

    For Sale O6408720 - 46 W VINING ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1273
       Built: 1938   Tax: $6,287 (2025)
    Community: Ellman Park
    Single Family


    Estimated Monthly Payment: $3,537 (change assumption)
    Mortgage ($3,013) + Taxes in 2025 ($524)


    Taxes:$6,287

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16461 OLIVE HILL DR, WINTER GARDEN, FL 34787

    $569,900142 Days on yellowkey   MLS ID: O6379181

    REDUCED by $19,000 (3.2%) on 06/03/2026

    For Sale O6379181 - 16461 OLIVE HILL DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2008
       Built: 2019
    Monthly Fee: $127
       Tax: $7,241 (2024)
    Community: Hawksmoor
    Single Family


    Estimated Monthly Payment: $3,853 (change assumption)
    Mortgage ($3,123) + Fees ($127) + Taxes in 2024 ($603)


    Taxes:$7,241

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 6339 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $591,830279 Days on yellowkey   MLS ID: G5102274

    1 Days Off yellowkey (back on 11/19/2025)

    For Sale G5102274 - 6339 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,393 (change assumption)
    Mortgage ($3,243) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6174 WHISPERING GLEN, WINTER GARDEN, FL 34787

    $518,29042 Days on yellowkey   MLS ID: O6407807

    REDUCED by $28,000 (5.1%) on 06/02/2026

    For Sale O6407807 - 6174 WHISPERING GLEN, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1628
       Built: 2026
    Monthly Fee: $152
       Tax: $1,373 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,106 (change assumption)
    Mortgage ($2,840) + Fees ($152) + Taxes in 2024 ($114)


    Taxes:$1,373

    Elementary School: Vista Lakes Elem

    High School: Colonial High

    Tax Year: 2024

    Middle School: Odyssey Middle


  • 14257 LAGOON COVE LN, WINTER GARDEN, FL 34787

    $530,000155 Days on yellowkey   MLS ID: O6375296

    REDUCED by $10,000 (1.9%) on 06/01/2026

    For Sale O6375296 - 14257 LAGOON COVE LN, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2365
       Built: 2007
    Monthly Fee: $123
       Tax: $8,178 (2025)
    Community: Black Lake Park Ph 02
    Single Family


    Estimated Monthly Payment: $3,709 (change assumption)
    Mortgage ($2,904) + Fees ($123) + Taxes in 2025 ($682)


    Taxes:$8,178

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16098 MANGROVE RD, WINTER GARDEN, FL 34787

    $575,000160 Days on yellowkey   MLS ID: O6373125

    REDUCED by $10,000 (1.7%) on 06/02/2026

    For Sale O6373125 - 16098 MANGROVE RD, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2472
       Built: 2021
    Monthly Fee: $257
       Tax: $5,612 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,875 (change assumption)
    Mortgage ($3,151) + Fees ($257) + Taxes in 2025 ($468)


    Taxes:$5,612

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787

    $575,000114 Days on yellowkey   MLS ID: S5144794

    REDUCED by $5,000 (0.9%) on 06/01/2026

    For Sale S5144794 - 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2149
       Built: 2021
    Monthly Fee: $281
       Tax: $6,500 (2024)
    Community: Enclave At Hamlin
    Single Family


    Estimated Monthly Payment: $3,973 (change assumption)
    Mortgage ($3,151) + Fees ($281) + Taxes in 2024 ($542)


    Taxes:$6,500

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None






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.