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Displaying: For Sale

Location: Winter Garden

Property Type(s): Single Family

Price: $500,000 to $599,000

Winter Garden - 126 properties found

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  • 9354 MCLAREN ALY, WINTER GARDEN, FL 34787

    $529,50053 Days on yellowkey   MLS ID: O6390060

    0 Days Off yellowkey (back on 5/2/2026)

    REDUCED by $15,500 (2.8%) on 04/17/2026

    For Sale O6390060 - 9354 MCLAREN ALY, WINTER GARDEN, FL 34787 59 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2014
       Built: 2020
    Monthly Fee: $257
       Tax: $614 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,209 (change assumption)
    Mortgage ($2,901) + Fees ($257) + Taxes in 2025 ($51)


    Taxes:$614

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787

    $554,990122 Days on yellowkey   MLS ID: O6370363

    For Sale O6370363 - 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2021
    Monthly Fee: $281
       Tax: $8,150 (2024)
    Community: Enclave/Hamlin
    Single Family


    Estimated Monthly Payment: $4,001 (change assumption)
    Mortgage ($3,041) + Fees ($281) + Taxes in 2024 ($679)


    Taxes:$8,150

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 199 E CREST AVE, WINTER GARDEN, FL 34787

    $525,00011 Days on yellowkey   MLS ID: O6401923

    For Sale O6401923 - 199 E CREST AVE, WINTER GARDEN, FL 34787 21 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1659
       Built: 1984   Tax: $6,857 (2025)
    Community: Garden Heights Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,448 (change assumption)
    Mortgage ($2,877) + Taxes in 2025 ($571)


    Taxes:$6,857

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17058 QUICKSILVER AVE, WINTER GARDEN, FL 34787

    $539,000147 Days on yellowkey   MLS ID: O6365686

    For Sale O6365686 - 17058 QUICKSILVER AVE, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2492
       Built: 2021
    Monthly Fee: $215
       Tax: $7,682 (2024)
    Community: Waterside/Johns Lake Ph 2C
    Single Family


    Estimated Monthly Payment: $3,809 (change assumption)
    Mortgage ($2,953) + Fees ($215) + Taxes in 2024 ($640)


    Taxes:$7,682

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 15613 PORTER RD, WINTER GARDEN, FL 34787

    $575,0006 Days on yellowkey   MLS ID: O6397283

    For Sale O6397283 - 15613 PORTER RD, WINTER GARDEN, FL 34787 48 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2089
       Built: 2015
    Monthly Fee: $252
       Tax: $8,171 (2025)
    Community: Summerlake Ph 2C 2D 2E
    Single Family


    Estimated Monthly Payment: $4,084 (change assumption)
    Mortgage ($3,151) + Fees ($252) + Taxes in 2025 ($681)


    Taxes:$8,171

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17055 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $580,68253 Days on yellowkey   MLS ID: G5109480

    0 Days Off yellowkey (back on 4/29/2026)

    For Sale G5109480 - 17055 HAGGERTY HOLLOW DR, 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: $3,332 (change assumption)
    Mortgage ($3,182) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 512 GARDEN HEIGHTS DR, WINTER GARDEN, FL 34787

    $577,90094 Days on yellowkey   MLS ID: S5142675

    REDUCED by $7,100 (1.2%) on 04/23/2026

    For Sale S5142675 - 512 GARDEN HEIGHTS DR, WINTER GARDEN, FL 34787 61 photos

    Bed: 4   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1700
       Built: 1974   Tax: $3,743 (2024)
    Community: Garden Heights
    Single Family


    Estimated Monthly Payment: $3,478 (change assumption)
    Mortgage ($3,166) + Taxes in 2024 ($312)


    Taxes:$3,743

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 1032 BURLAND CIR, WINTER GARDEN, FL 34787

    $519,9906 Days on yellowkey   MLS ID: O6401764

    For Sale O6401764 - 1032 BURLAND CIR, WINTER GARDEN, FL 34787 58 photos

    Bed: 5   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2487
       Built: 2005
    Monthly Fee: $64
       Tax: $6,728 (2025)
    Community: Fullers Xing Ph 03 A-G
    Single Family


    Estimated Monthly Payment: $3,474 (change assumption)
    Mortgage ($2,849) + Fees ($64) + Taxes in 2025 ($561)


    Taxes:$6,728

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16933 OAKBORO ST, WINTER GARDEN, FL 34787

    $560,00043 Days on yellowkey   MLS ID: R4910916

    For Sale R4910916 - 16933 OAKBORO ST, WINTER GARDEN, FL 34787 32 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2020
    Monthly Fee: $257
       Tax: $3,651 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,630 (change assumption)
    Mortgage ($3,068) + Fees ($257) + Taxes in 2025 ($304)


    Taxes:$3,651

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13151 CALMING BREEZE WAY, WINTER GARDEN, FL 34787

    $565,000153 Days on yellowkey   MLS ID: O6363957

    REDUCED by $4,000 (0.7%) on 05/02/2026

    For Sale O6363957 - 13151 CALMING BREEZE WAY, WINTER GARDEN, FL 34787 39 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: $3,867 (change assumption)
    Mortgage ($3,096) + 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


  • 14280 BRAEMAR ST, WINTER GARDEN, FL 34787

    $559,90012 Days on yellowkey   MLS ID: TB8500322

    For Sale TB8500322 - 14280 BRAEMAR ST, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2023
    Monthly Fee: $100
       Tax: $7,928 (2025)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,829 (change assumption)
    Mortgage ($3,068) + Fees ($100) + Taxes in 2025 ($661)


    Taxes:$7,928

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14834 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $525,00033 Days on yellowkey   MLS ID: O6395079

    REDUCED by $10,000 (1.9%) on 05/01/2026

    For Sale O6395079 - 14834 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2049
       Built: 2014
    Monthly Fee: $252
       Tax: $3,824 (2025)
    Community: Summerlake Pd Ph 1B-A Rep
    Single Family


    Estimated Monthly Payment: $3,447 (change assumption)
    Mortgage ($2,877) + Fees ($252) + Taxes in 2025 ($319)


    Taxes:$3,824

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787

    $565,000151 Days on yellowkey   MLS ID: O6365057

    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: $4,059 (change assumption)
    Mortgage ($3,096) + 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


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $590,000249 Days on yellowkey   MLS ID: O6337436

    For Sale O6337436 - 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787 89 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2292
       Built: 2023
    Monthly Fee: $245
       Tax: $9,031 (2024)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $4,230 (change assumption)
    Mortgage ($3,233) + Fees ($245) + Taxes in 2024 ($753)


    Taxes:$9,031

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787

    $529,99998 Days on yellowkey   MLS ID: NS1087076

    REDUCED by $38,001 (6.7%) on 05/02/2026

    For Sale NS1087076 - 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787 23 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2024
    Monthly Fee: $291
       Tax: $2,273 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,384 (change assumption)
    Mortgage ($2,904) + Fees ($291) + Taxes in 2024 ($189)


    Taxes:$2,273

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 10043 SEQUEL ALY, WINTER GARDEN, FL 34787

    $569,00070 Days on yellowkey   MLS ID: O6384246

    REDUCED by $1,000 (0.2%) on 04/23/2026

    For Sale O6384246 - 10043 SEQUEL ALY, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2502
       Built: 2018
    Monthly Fee: $100
       Tax: $8,237 (2024)
    Community: Storey Grove Ph 1B-2
    Single Family


    Estimated Monthly Payment: $3,904 (change assumption)
    Mortgage ($3,118) + Fees ($100) + Taxes in 2024 ($686)


    Taxes:$8,237

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13360 SUNNY RETREAT LN, WINTER GARDEN, FL 34787

    $585,00097 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: $534
       Tax: $7,519 (2024)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,366 (change assumption)
    Mortgage ($3,205) + Fees ($534) + Taxes in 2024 ($627)


    Taxes:$7,519

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12362 BRACCO ST, WINTER GARDEN, FL 34787

    $515,0003 Days on yellowkey   MLS ID: O6404125

    For Sale O6404125 - 12362 BRACCO ST, WINTER GARDEN, FL 34787 17 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2094
       Built: 2023
    Monthly Fee: $105
       Tax: $8,231 (2025)
    Community: Highland Rdg Ph 2
    Single Family


    Estimated Monthly Payment: $3,613 (change assumption)
    Mortgage ($2,822) + Fees ($105) + Taxes in 2025 ($686)


    Taxes:$8,231

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787

    $519,900248 Days on yellowkey   MLS ID: S5133690

    For Sale S5133690 - 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2035
       Built: 2001
    Monthly Fee: $33
       Tax: $6,403 (2024)
    Community: Tuscany Ph 02
    Single Family


    Estimated Monthly Payment: $3,415 (change assumption)
    Mortgage ($2,849) + Fees ($33) + Taxes in 2024 ($534)


    Taxes:$6,403

    Elementary School: Maxey Elem

    High School: Ocoee High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 15524 AVIATION ALY, WINTER GARDEN, FL 34787

    $560,00023 Days on yellowkey   MLS ID: O6398331

    REDUCED by $10,000 (1.8%) on 04/29/2026

    For Sale O6398331 - 15524 AVIATION ALY, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2414
       Built: 2015
    Monthly Fee: $328
       Tax: $8,711 (2025)
    Community: Overlook 2/Hamlin Ph 1 & 6
    Single Family


    Estimated Monthly Payment: $4,122 (change assumption)
    Mortgage ($3,068) + Fees ($328) + Taxes in 2025 ($726)


    Taxes:$8,711

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater 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.