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Winter Garden Homes For Sale & Real Estate - 709 homes

Winter Garden homes for sale are located in Orange County, Florida. Find homes in Winter Garden for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Garden houses.

Location: Winter Garden

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  • 11079 HANLON TERRACE ALY, WINTER GARDEN, FL 34787

    $389,990165 Days on yellowkey   MLS ID: O6358387

    REDUCED by $4,000 (1.0%) on 04/20/2026

    For Sale O6358387 - 11079 HANLON TERRACE ALY, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1868
       Built: 2021
    Monthly Fee: $339
       Tax: $6,256 (2024)
    Community: Winding Bay Preserve
    Townhouse


    Estimated Monthly Payment: $2,997 (change assumption)
    Mortgage ($2,137) + Fees ($339) + Taxes in 2024 ($521)


    Taxes:$6,256

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16126 PARKWYN ST, WINTER GARDEN, FL 34787

    $625,00039 Days on yellowkey   MLS ID: O6389811

    REDUCED by $4,000 (0.6%) on 04/20/2026

    For Sale O6389811 - 16126 PARKWYN ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2372
       Built: 2021
    Monthly Fee: $127
       Tax: $7,291 (2025)
    Community: Hawksmoor Ph 2
    Single Family


    Estimated Monthly Payment: $4,159 (change assumption)
    Mortgage ($3,425) + Fees ($127) + Taxes in 2025 ($608)


    Taxes:$7,291

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 18219 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $599,000137 Days on yellowkey   MLS ID: O6365155

    0 Days Off yellowkey (back on 2/27/2026)

    For Sale O6365155 - 18219 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2683
       Built: 2021
    Monthly Fee: $200
       Tax: $9,012 (2024)
    Community: Storey Grove Ph 3
    Single Family


    Estimated Monthly Payment: $4,233 (change assumption)
    Mortgage ($3,282) + Fees ($200) + Taxes in 2024 ($751)


    Taxes:$9,012

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787

    $929,00022 Days on yellowkey   MLS ID: O6394506

    REDUCED by $20,900 (2.2%) on 04/20/2026

    For Sale O6394506 - 1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3841
       Built: 2017
    Monthly Fee: $184
       Tax: $12,543 (2025)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $6,320 (change assumption)
    Mortgage ($5,090) + Fees ($184) + Taxes in 2025 ($1,045)


    Taxes:$12,543

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14345 WABASSO LOOP, WINTER GARDEN, FL 34787

    $735,00074 Days on yellowkey   MLS ID: O6376609

    For Sale O6376609 - 14345 WABASSO LOOP, WINTER GARDEN, FL 34787 31 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2878
       Built: 2022
    Monthly Fee: $192
       Tax: $10,615 (2025)
    Community: Tilden Place/Winter Garden
    Single Family


    Estimated Monthly Payment: $5,104 (change assumption)
    Mortgage ($4,027) + Fees ($192) + Taxes in 2025 ($885)


    Taxes:$10,615

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15182 SUNRISE GROVE CT, WINTER GARDEN, FL 34787

    $394,90045 Days on yellowkey   MLS ID: O6382211

    REDUCED by $4,100 (1.0%) on 04/20/2026

    For Sale O6382211 - 15182 SUNRISE GROVE CT, WINTER GARDEN, FL 34787 27 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1844
       Built: 2018
    Monthly Fee: $346
       Tax: $3,222 (2024)
    Community: Hickory Hammock Ph 2B
    Townhouse


    Estimated Monthly Payment: $2,778 (change assumption)
    Mortgage ($2,164) + Fees ($346) + Taxes in 2024 ($268)


    Taxes:$3,222

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 940 MARSH REED DR, WINTER GARDEN, FL 34787

    $799,9907 Days on yellowkey   MLS ID: O6397274

    For Sale O6397274 - 940 MARSH REED DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3493
       Built: 2015
    Monthly Fee: $128
       Tax: $10,543 (2025)
    Community: Johns Lake Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,390 (change assumption)
    Mortgage ($4,383) + Fees ($128) + Taxes in 2025 ($879)


    Taxes:$10,543

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 8807 FOUNTAIN PALM ALY, WINTER GARDEN, FL 34787

    $630,000Listed 04/20/2026 5:49AM   MLS ID: O6400597

    For Sale O6400597 - 8807 FOUNTAIN PALM ALY, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2581
       Built: 2018
    Monthly Fee: $600
       Tax: $6,298 (2025)
    Community: Lakeshore Preserve Ph 1
    Townhouse


    Estimated Monthly Payment: $4,577 (change assumption)
    Mortgage ($3,452) + Fees ($600) + Taxes in 2025 ($525)


    Taxes:$6,298

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16006 GILDEN WAY, WINTER GARDEN, FL 34787

    $1,085,00024 Days on yellowkey   MLS ID: O6392997

    REDUCED by $65,000 (5.7%) on 04/20/2026

    For Sale O6392997 - 16006 GILDEN WAY, WINTER GARDEN, FL 34787 64 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3617
       Built: 2023
    Monthly Fee: $225
       Tax: $12,929 (2025)
    Community: Encore At Ovation
    Single Family


    Estimated Monthly Payment: $7,247 (change assumption)
    Mortgage ($5,945) + Fees ($225) + Taxes in 2025 ($1,077)


    Taxes:$12,929

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 150 WINDTREE LN #150, WINTER GARDEN, FL 34787

    $195,000135 Days on yellowkey   MLS ID: O6365343

    REDUCED by $4,900 (2.5%) on 04/20/2026

    For Sale O6365343 - 150 WINDTREE LN #150, WINTER GARDEN, FL 34787 31 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1984
    Monthly Fee: $300
       Tax: $2,565 (2025)
    Community: Windree Gardens Ph 5
    Condo


    Estimated Monthly Payment: $1,582 (change assumption)
    Mortgage ($1,068) + Fees ($300) + Taxes in 2025 ($214)


    Taxes:$2,565

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 328 BAYSIDE AVE, WINTER GARDEN, FL 34787

    $445,0003 Days on yellowkey   MLS ID: O6396654

    For Sale O6396654 - 328 BAYSIDE AVE, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1235
       Built: 1986
    Monthly Fee: $7
       Tax: $5,354 (2025)
    Community: Kings Bay
    Single Family


    Estimated Monthly Payment: $2,891 (change assumption)
    Mortgage ($2,438) + Fees ($7) + Taxes in 2025 ($446)


    Taxes:$5,354

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,337,00021 Days on yellowkey   MLS ID: O6394059

    For Sale O6394059 - 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4019
       Built: 2018
    Monthly Fee: $188
       Tax: $17,895 (2025)
    Community: Canopy Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $9,005 (change assumption)
    Mortgage ($7,326) + Fees ($188) + Taxes in 2025 ($1,491)


    Taxes:$17,895

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787

    $1,200,00046 Days on yellowkey   MLS ID: O6384801

    For Sale O6384801 - 156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3170
       Built: 2018
    Monthly Fee: $188
       Tax: $7,979 (2024)
    Community: Stanton Estates
    Single Family


    Estimated Monthly Payment: $7,428 (change assumption)
    Mortgage ($6,575) + Fees ($188) + Taxes in 2024 ($665)


    Taxes:$7,979

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 17422 CHANNEL WAY, WINTER GARDEN, FL 34787

    $784,00055 Days on yellowkey   MLS ID: G5108709

    REDUCED by $11,000 (1.4%) on 04/17/2026

    For Sale G5108709 - 17422 CHANNEL WAY, WINTER GARDEN, FL 34787 44 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3261
       Built: 2019
    Monthly Fee: $215
       Tax: $9,958 (2025)
    Community: Waterside On Johns Lake
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,341 (change assumption)
    Mortgage ($4,296) + Fees ($215) + Taxes in 2025 ($830)


    Taxes:$9,958

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787

    $568,00084 Days on yellowkey   MLS ID: NS1087076

    REDUCED by $5,000 (0.9%) on 04/17/2026

    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: $3,593 (change assumption)
    Mortgage ($3,112) + Fees ($291) + Taxes in 2024 ($189)


    Taxes:$2,273

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 3242 IRISH PEACH DR, WINTER GARDEN, FL 34787

    $539,900402 Days on yellowkey   MLS ID: O6289752

    1 Days Off yellowkey (back on 4/20/2026)

    REDUCED by $10,100 (1.8%) on 04/17/2026

    For Sale O6289752 - 3242 IRISH PEACH DR, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2120
       Built: 2017
    Monthly Fee: $180
       Tax: $5,147 (2024)
    Community: Orchard Pk/Stillwater Xing Ph
    Single Family


    Estimated Monthly Payment: $3,567 (change assumption)
    Mortgage ($2,958) + Fees ($180) + Taxes in 2024 ($429)


    Taxes:$5,147

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 16149 WIND VIEW LN, WINTER GARDEN, FL 34787

    $498,00038 Days on yellowkey   MLS ID: O6389892

    REDUCED by $7,000 (1.4%) on 04/15/2026

    For Sale O6389892 - 16149 WIND VIEW LN, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2036
       Built: 2016
    Monthly Fee: $332
       Tax: $4,472 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $3,433 (change assumption)
    Mortgage ($2,729) + Fees ($332) + Taxes in 2025 ($373)


    Taxes:$4,472

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 4842 LIME RICKEY ALY, WINTER GARDEN, FL 34787

    $539,50067 Days on yellowkey   MLS ID: O6381954

    REDUCED by $400 (0.1%) on 04/20/2026

    For Sale O6381954 - 4842 LIME RICKEY ALY, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2114
       Built: 2023
    Monthly Fee: $148
       Tax: $8,002 (2024)
    Community: Silverleaf Reserve/Haml Ph 2A
    Single Family


    Estimated Monthly Payment: $3,771 (change assumption)
    Mortgage ($2,956) + Fees ($148) + Taxes in 2024 ($667)


    Taxes:$8,002

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9459 JAYWOOD RD, WINTER GARDEN, FL 34787

    $755,00049 Days on yellowkey   MLS ID: O6386488

    REDUCED by $5,000 (0.7%) on 04/20/2026

    For Sale O6386488 - 9459 JAYWOOD RD, WINTER GARDEN, FL 34787 55 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2020
    Monthly Fee: $261
       Tax: $6,669 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $4,954 (change assumption)
    Mortgage ($4,137) + Fees ($261) + Taxes in 2025 ($556)


    Taxes:$6,669

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15306 GILLIGAN CT, WINTER GARDEN, FL 34787

    $925,0003 Days on yellowkey   MLS ID: O6399653

    For Sale O6399653 - 15306 GILLIGAN CT, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3127
       Built: 2020
    Monthly Fee: $102
       Tax: $8,308 (2025)
    Community: Winding Bay Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,863 (change assumption)
    Mortgage ($5,068) + Fees ($102) + Taxes in 2025 ($692)


    Taxes:$8,308

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle




Why Bother Searching Elsewhere for Winter Garden Homes for Sale and Other Real Estate?

Winter Garden home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Winter Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Garden listings.



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.