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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Living Area Square Feet: 1500 to 1999

Winter Garden - 76 properties found

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  • 420 E CYPRESS ST, WINTER GARDEN, FL 34787

    $420,00022 Days on yellowkey   MLS ID: O6412414

    REDUCED by $5,000 (1.2%) on 06/18/2026

    For Sale O6412414 - 420 E CYPRESS ST, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1616
       Built: 1950   Tax: $5,517 (2025)
    Community: Overstreet Crate
    Single Family


    Estimated Monthly Payment: $2,761 (change assumption)
    Mortgage ($2,301) + Taxes in 2025 ($460)


    Taxes:$5,517

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14788 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $579,99971 Days on yellowkey   MLS ID: O6398754

    REDUCED by $37,501 (6.1%) on 06/16/2026

    For Sale O6398754 - 14788 FIELD DAISY DR, WINTER GARDEN, FL 34787 44 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: $3,407 (change assumption)
    Mortgage ($3,178) + 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


  • 17806 SEDONA ST, WINTER GARDEN, FL 34787

    $672,50913 Days on yellowkey   MLS ID: O6415594

    INCREASED by $34,300 (5.4%) on 06/15/2026

    For Sale O6415594 - 17806 SEDONA ST, WINTER GARDEN, FL 34787 28 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1843
       Built: 2026
    Monthly Fee: $140

    Community: Esplanade At Mckinnon Groves
    Single Family


    Estimated Monthly Payment: $3,825 (change assumption)
    Mortgage ($3,685) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 14536 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787

    $450,000355 Days on yellowkey   MLS ID: O6320739

    SHORT SALE O6320739 - 14536 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787 23 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1904
       Built: 2016
    Monthly Fee: $159
       Tax: $7,554 (2024)
    Community: Watermark Ph 2C
    Single Family


    Estimated Monthly Payment: $3,254 (change assumption)
    Mortgage ($2,466) + Fees ($159) + Taxes in 2024 ($630)


    Taxes:$7,554

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 1968 PANTHEON DR, WINTER GARDEN, FL 34787

    $529,90047 Days on yellowkey   MLS ID: O6404386

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

    For Sale O6404386 - 1968 PANTHEON DR, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1971
       Built: 2015
    Monthly Fee: $211
       Tax: $3,832 (2025)
    Community: Alexander Rdg
    Single Family


    Estimated Monthly Payment: $3,434 (change assumption)
    Mortgage ($2,903) + Fees ($211) + Taxes in 2025 ($319)


    Taxes:$3,832

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 11117 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $507,00040 Days on yellowkey   MLS ID: O6407552

    REDUCED by $13,000 (2.5%) on 06/17/2026

    For Sale O6407552 - 11117 BOSTWICK ALY, WINTER GARDEN, FL 34787 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1685
       Built: 2022
    Monthly Fee: $291
       Tax: $6,722 (2025)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $3,629 (change assumption)
    Mortgage ($2,778) + Fees ($291) + Taxes in 2025 ($560)


    Taxes:$6,722

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 7558 BISHOP SQUARE DR, WINTER GARDEN, FL 34787

    $554,9007 Days on yellowkey   MLS ID: O6417556

    For Sale O6417556 - 7558 BISHOP SQUARE DR, WINTER GARDEN, FL 34787 16 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1952
       Built: 2017
    Monthly Fee: $214
       Tax: $7,627 (2024)
    Community: West Lake Hancock Estates
    Single Family


    Estimated Monthly Payment: $3,890 (change assumption)
    Mortgage ($3,040) + Fees ($214) + Taxes in 2024 ($636)


    Taxes:$7,627

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 10294 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $459,90040 Days on yellowkey   MLS ID: O6407798

    REDUCED by $9,000 (1.9%) on 06/15/2026

    For Sale O6407798 - 10294 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 58 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1689
       Built: 2019
    Monthly Fee: $245
       Tax: $7,600 (2025)
    Community: Waterleigh Ph 2C-1
    Single Family


    Estimated Monthly Payment: $3,398 (change assumption)
    Mortgage ($2,520) + Fees ($245) + Taxes in 2025 ($633)


    Taxes:$7,600

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 6279 SUNNY TIME AVENUE, WINTER GARDEN, FL 34787

    $546,49025 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

    $597,99643 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


  • 15073 VALVERSE ALY, WINTER GARDEN, FL 34787

    $515,00012 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


  • 12103 EASTMOOR DR, WINTER GARDEN, FL 34787

    $445,00033 Days on yellowkey   MLS ID: O6409071

    REDUCED by $5,000 (1.1%) on 06/04/2026

    For Sale O6409071 - 12103 EASTMOOR DR, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1604
       Built: 2024
    Monthly Fee: $225
       Tax: $6,795 (2025)
    Community: Encore/Ovation Ph 4B
    Single Family


    Estimated Monthly Payment: $3,230 (change assumption)
    Mortgage ($2,438) + Fees ($225) + Taxes in 2025 ($566)


    Taxes:$6,795

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1061 PORTMOOR WAY, WINTER GARDEN, FL 34787

    $535,00019 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


  • 12253 S BRACCO ST, WINTER GARDEN, FL 34787

    $499,00022 Days on yellowkey   MLS ID: S5150840

    For Sale S5150840 - 12253 S BRACCO ST, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1788
       Built: 2024
    Monthly Fee: $110
       Tax: $6,803 (2025)
    Community: Highland Rdg Ph 2
    Single Family


    Estimated Monthly Payment: $3,411 (change assumption)
    Mortgage ($2,734) + Fees ($110) + Taxes in 2025 ($567)


    Taxes:$6,803

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 2202 ROMANUM DR, WINTER GARDEN, FL 34787

    $565,00068 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


  • 4863 LACEWING DR, WINTER GARDEN, FL 34787

    $540,00075 Days on yellowkey   MLS ID: O6397857

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

    For Sale O6397857 - 4863 LACEWING DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1788
       Built: 2023
    Monthly Fee: $171
       Tax: $6,905 (2025)
    Community: Silverleaf Reserve Bungalows
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,705 (change assumption)
    Mortgage ($2,959) + Fees ($171) + Taxes in 2025 ($575)


    Taxes:$6,905

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 936 KYLEE ALY, WINTER GARDEN, FL 34787

    $675,00089 Days on yellowkey   MLS ID: O6393910

    4 Days Off yellowkey (back on 6/11/2026)

    For Sale O6393910 - 936 KYLEE ALY, WINTER GARDEN, FL 34787 60 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1772
       Built: 2022
    Monthly Fee: $356
       Tax: $6,058 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $4,559 (change assumption)
    Mortgage ($3,699) + Fees ($356) + Taxes in 2025 ($505)


    Taxes:$6,058

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Legacy Middle


  • 13026 SUNSET GARDEN LN, WINTER GARDEN, FL 34787

    $547,16067 Days on yellowkey   MLS ID: O6400188

    INCREASED by $3,000 (0.6%) on 04/30/2026

    For Sale O6400188 - 13026 SUNSET GARDEN LN, WINTER GARDEN, FL 34787 6 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1908
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,269 (change assumption)
    Mortgage ($2,998) + 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


  • 1253 BRANDY LAKE VIEW CIR, WINTER GARDEN, FL 34787

    $474,90050 Days on yellowkey   MLS ID: O6404570

    1 Days Off yellowkey (back on 5/28/2026)

    For Sale O6404570 - 1253 BRANDY LAKE VIEW CIR, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1702
       Built: 1998
    Monthly Fee: $89
       Tax: $3,024 (2025)
    Community: Brandy Creek
    Single Family


    Estimated Monthly Payment: $2,943 (change assumption)
    Mortgage ($2,602) + Fees ($89) + Taxes in 2025 ($252)


    Taxes:$3,024

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 411 MILLWOOD PL, WINTER GARDEN, FL 34787

    $459,00013 Days on yellowkey   MLS ID: TB8518055

    For Sale TB8518055 - 411 MILLWOOD PL, WINTER GARDEN, FL 34787 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1696
       Built: 2014
    Monthly Fee: $72
       Tax: $6,471 (2025)
    Community: Covington Chase Ph 2A
    Single Family


    Estimated Monthly Payment: $3,126 (change assumption)
    Mortgage ($2,515) + Fees ($72) + Taxes in 2025 ($539)


    Taxes:$6,471

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.