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Winter Garden Homes For Sale & Real Estate - 984 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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  • 5150 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787

    $950,00080 Days on yellowkey   MLS ID: O6404827

    REDUCED by $20,000 (2.1%) on 07/03/2026

    For Sale O6404827 - 5150 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787 42 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3461
       Built: 2023
    Monthly Fee: $168
       Tax: $12,730 (2025)
    Community: Silverleaf Reserve/Hamlin Ph 2
    Single Family


    Estimated Monthly Payment: $6,434 (change assumption)
    Mortgage ($5,205) + Fees ($168) + Taxes in 2025 ($1,061)


    Taxes:$12,730

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8921 FOUNTAIN PALM ALY, WINTER GARDEN, FL 34787

    $559,00042 Days on yellowkey   MLS ID: O6415441

    0 Days Off yellowkey (back on 7/3/2026)

    For Sale O6415441 - 8921 FOUNTAIN PALM ALY, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2134
       Built: 2018
    Monthly Fee: $600
       Tax: $5,906 (2025)
    Community: Lakeshore Preserve Ph 1
    Spa: Yes

    Townhouse


    Estimated Monthly Payment: $4,155 (change assumption)
    Mortgage ($3,063) + Fees ($600) + Taxes in 2025 ($492)


    Taxes:$5,906

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16031 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787

    $560,00082 Days on yellowkey   MLS ID: O6404448

    For Sale O6404448 - 16031 PEBBLE BLUFF LOOP, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2487
       Built: 2018
    Monthly Fee: $257
       Tax: $9,371 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $4,106 (change assumption)
    Mortgage ($3,068) + Fees ($257) + Taxes in 2025 ($781)


    Taxes:$9,371

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 4863 LACEWING DR, WINTER GARDEN, FL 34787

    $540,000106 Days on yellowkey   MLS ID: O6397857

    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


  • 2230 ROMANUM DR, WINTER GARDEN, FL 34787

    $565,000134 Days on yellowkey   MLS ID: O6389947

    1 Days Off yellowkey (back on 5/17/2026)

    For Sale O6389947 - 2230 ROMANUM DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2562
       Built: 2014
    Monthly Fee: $207
       Tax: $8,425 (2025)
    Community: Alexander Rdg
    Single Family


    Estimated Monthly Payment: $4,005 (change assumption)
    Mortgage ($3,096) + Fees ($207) + Taxes in 2025 ($702)


    Taxes:$8,425

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15353 OAK APPLE CT, WINTER GARDEN, FL 34787

    $347,500121 Days on yellowkey   MLS ID: O6393663

    REDUCED by $2,500 (0.7%) on 05/27/2026

    For Sale O6393663 - 15353 OAK APPLE CT, WINTER GARDEN, FL 34787 16 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1699
       Built: 2008
    Monthly Fee: $283
       Tax: $1,863 (2025)
    Community: Tucker Oaks Bldg 5
    Townhouse


    Estimated Monthly Payment: $2,342 (change assumption)
    Mortgage ($1,904) + Fees ($283) + Taxes in 2025 ($155)


    Taxes:$1,863

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 33 TIMBERCREEK PINES CIR, WINTER GARDEN, FL 34787

    $535,00064 Days on yellowkey   MLS ID: O6408941

    REDUCED by $10,000 (1.8%) on 07/03/2026

    For Sale O6408941 - 33 TIMBERCREEK PINES CIR, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1584
       Built: 2004
    Monthly Fee: $46
       Tax: $7,326 (2025)
    Community: Timbercreek Pines A B C & D
    Single Family


    Estimated Monthly Payment: $3,588 (change assumption)
    Mortgage ($2,931) + Fees ($46) + Taxes in 2025 ($610)


    Taxes:$7,326

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 417 SOUTHERN PECAN CIR #201, WINTER GARDEN, FL 34787

    $275,00022 Days on yellowkey   MLS ID: O6421941

    For Sale O6421941 - 417 SOUTHERN PECAN CIR #201, WINTER GARDEN, FL 34787 19 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1264
       Built: 2005
    Monthly Fee: $489
       Tax: $3,366 (2025)
    Community: Southern Pines Condo
    Condo


    Estimated Monthly Payment: $2,276 (change assumption)
    Mortgage ($1,507) + Fees ($489) + Taxes in 2025 ($281)


    Taxes:$3,366

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 689 BETHUNE AVE, WINTER GARDEN, FL 34787

    $434,00022 Days on yellowkey   MLS ID: O6421715

    For Sale O6421715 - 689 BETHUNE AVE, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1434
       Built: 1950   Tax: $2,330 (2025)
    Community: Joe Louis Park Q162
    Single Family


    Estimated Monthly Payment: $2,572 (change assumption)
    Mortgage ($2,378) + Taxes in 2025 ($194)


    Taxes:$2,330

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16330 BRISK BREEZE ALY, WINTER GARDEN, FL 34787

    $525,000204 Days on yellowkey   MLS ID: G5106012

    REDUCED by $15,000 (2.8%) on 06/19/2026

    For Sale G5106012 - 16330 BRISK BREEZE ALY, WINTER GARDEN, FL 34787 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2018
    Monthly Fee: $245
       Tax: $7,556 (2024)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $3,751 (change assumption)
    Mortgage ($2,877) + Fees ($245) + Taxes in 2024 ($630)


    Taxes:$7,556

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $650,000477 Days on yellowkey   MLS ID: O6280496

    0 Days Off yellowkey (back on 7/2/2026)

    REDUCED by $98,000 (13.1%) on 06/10/2026

    SHORT SALE O6280496 - 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2023
    Monthly Fee: $250
       Tax: $9,777 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,626 (change assumption)
    Mortgage ($3,562) + Fees ($250) + Taxes in 2024 ($815)


    Taxes:$9,777

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15073 VALVERSE ALY, WINTER GARDEN, FL 34787

    $499,99943 Days on yellowkey   MLS ID: O6416182

    0 Days Off yellowkey (back on 7/2/2026)

    REDUCED by $15,001 (2.9%) on 06/24/2026

    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: $3,426 (change assumption)
    Mortgage ($2,740) + 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


  • 15648 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $699,00042 Days on yellowkey   MLS ID: G5113473

    0 Days Off yellowkey (back on 7/2/2026)

    REDUCED by $30,000 (4.1%) on 06/28/2026

    For Sale G5113473 - 15648 SHOREBIRD LN, WINTER GARDEN, FL 34787 93 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2018
    Monthly Fee: $360
       Tax: $7,052 (2025)
    Community: Lakeshore Preserve Ph 1
    Single Family


    Estimated Monthly Payment: $4,778 (change assumption)
    Mortgage ($3,830) + Fees ($360) + Taxes in 2025 ($588)


    Taxes:$7,052

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 16425 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787

    $435,000149 Days on yellowkey   MLS ID: O6383709

    REDUCED by $25,000 (5.4%) on 05/16/2026

    For Sale O6383709 - 16425 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1662
       Built: 2021
    Monthly Fee: $284
       Tax: $6,683 (2024)
    Community: Hawksmoor-Ph 3
    Townhouse


    Estimated Monthly Payment: $3,224 (change assumption)
    Mortgage ($2,384) + Fees ($284) + Taxes in 2024 ($557)


    Taxes:$6,683

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15039 GROVESIDE RD, WINTER GARDEN, FL 34787

    $497,380104 Days on yellowkey   MLS ID: O6398354

    2 Days Off yellowkey (back on 7/2/2026)

    INCREASED by $5,000 (1.0%) on 06/17/2026

    For Sale O6398354 - 15039 GROVESIDE RD, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1846
       Built: 2026
    Monthly Fee: $247
       Tax: $1,375 (2025)
    Community: Parkview At Hamlin
    Townhouse


    Estimated Monthly Payment: $3,087 (change assumption)
    Mortgage ($2,725) + Fees ($247) + Taxes in 2025 ($115)


    Taxes:$1,375

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 2022 BOSS HEWETT ST, WINTER GARDEN, FL 34787

    $679,00036 Days on yellowkey   MLS ID: O6417697

    1 Days Off yellowkey (back on 7/2/2026)

    For Sale O6417697 - 2022 BOSS HEWETT ST, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2281
       Built: 2022
    Monthly Fee: $171
       Tax: $7,948 (2025)
    Community: Hull Island/Oakland Ph 2
    Single Family


    Estimated Monthly Payment: $4,554 (change assumption)
    Mortgage ($3,720) + Fees ($171) + Taxes in 2025 ($662)


    Taxes:$7,948

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • WINTER GARDEN, FL 34787

    $217,50023 Days on yellowkey   MLS ID: O6420656

    For Sale O6420656 - WINTER GARDEN, FL 34787 16 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 942
       Built: 2005
    Monthly Fee: $378
       Tax: $2,727 (2025)
    Community: Southern Pines Condo
    Spa: No

    Condo


    Estimated Monthly Payment: $1,797 (change assumption)
    Mortgage ($1,192) + Fees ($378) + Taxes in 2025 ($227)


    Taxes:$2,727

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16503 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787

    $459,00029 Days on yellowkey   MLS ID: O6420071

    REDUCED by $20,000 (4.2%) on 07/02/2026

    For Sale O6420071 - 16503 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2025
    Monthly Fee: $204
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,838 (change assumption)
    Mortgage ($2,515) + Fees ($204) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16509 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787

    $414,99029 Days on yellowkey   MLS ID: O6420095

    REDUCED by $32,510 (7.3%) on 07/02/2026

    For Sale O6420095 - 16509 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787 63 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1567
       Built: 2025
    Monthly Fee: $208
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,601 (change assumption)
    Mortgage ($2,274) + Fees ($208) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16558 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787

    $464,99029 Days on yellowkey   MLS ID: O6420061

    REDUCED by $5,510 (1.2%) on 07/02/2026

    For Sale O6420061 - 16558 BARBOURS CREEK WAY, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2025
    Monthly Fee: $204
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,870 (change assumption)
    Mortgage ($2,548) + Fees ($204) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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.