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Winter Garden Single Family Homes For Sale - 713 homes

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

Location: Winter Garden

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  • 14372 BREDA CENTER LOOP, WINTER GARDEN, FL 34787

    $580,000114 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

    $569,990152 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

    $546,990211 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

    $595,00065 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


  • 17422 CHANNEL WAY, WINTER GARDEN, FL 34787

    $767,000116 Days on yellowkey   MLS ID: G5108709

    1 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $7,000 (0.9%) on 05/11/2026

    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: $5,247 (change assumption)
    Mortgage ($4,203) + 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


  • 6166 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787

    $649,00067 Days on yellowkey   MLS ID: O6399123

    3 Days Off yellowkey (back on 6/7/2026)

    REDUCED by $15,900 (2.4%) on 06/02/2026

    For Sale O6399123 - 6166 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787 73 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2818
       Built: 2018
    Monthly Fee: $142
       Tax: $6,366 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $4,229 (change assumption)
    Mortgage ($3,556) + Fees ($142) + Taxes in 2025 ($531)


    Taxes:$6,366

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11264 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,99072 Days on yellowkey   MLS ID: O6397733

    3 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $20,000 (2.2%) on 06/04/2026

    For Sale O6397733 - 11264 HOLLOW BAY DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,296 (change assumption)
    Mortgage ($4,931) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13043 SANDCASTLE DRIVE, WINTER GARDEN, FL 34787

    $899,00066 Days on yellowkey   MLS ID: O6399529

    1 Days Off yellowkey (back on 6/7/2026)

    INCREASED by $23,000 (2.6%) on 05/09/2026

    For Sale O6399529 - 13043 SANDCASTLE DRIVE, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1943
       Built: 2022
    Monthly Fee: $534
       Tax: $10,109 (2025)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,302 (change assumption)
    Mortgage ($4,926) + Fees ($534) + Taxes in 2025 ($842)


    Taxes:$10,109

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16827 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $599,990145 Days on yellowkey   MLS ID: O6376919

    REDUCED by $15,000 (2.4%) on 06/04/2026

    For Sale O6376919 - 16827 HOBE SOUND CT, WINTER GARDEN, FL 34787 21 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $248
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,701 (change assumption)
    Mortgage ($3,288) + Fees ($248) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 18422 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $815,00018 Days on yellowkey   MLS ID: O6412770

    For Sale O6412770 - 18422 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 66 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3231
       Built: 2024
    Monthly Fee: $300
       Tax: $10,531 (2025)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,643 (change assumption)
    Mortgage ($4,466) + Fees ($300) + Taxes in 2025 ($878)


    Taxes:$10,531

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787

    $339,90067 Days on yellowkey   MLS ID: O6398208

    For Sale O6398208 - 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1988   Tax: $2,702 (2025)
    Community: East Garden Manor Add 03
    Single Family


    Estimated Monthly Payment: $2,088 (change assumption)
    Mortgage ($1,862) + Taxes in 2025 ($225)


    Taxes:$2,702

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 9354 MEADOW HUNT WAY, WINTER GARDEN, FL 34787

    $525,00056 Days on yellowkey   MLS ID: O6400695

    For Sale O6400695 - 9354 MEADOW HUNT WAY, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2079
       Built: 2017
    Monthly Fee: $164
       Tax: $4,974 (2025)
    Community: Watermark
    Single Family


    Estimated Monthly Payment: $3,455 (change assumption)
    Mortgage ($2,877) + Fees ($164) + Taxes in 2025 ($415)


    Taxes:$4,974

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12410 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $639,99029 Days on yellowkey   MLS ID: O6409937

    For Sale O6409937 - 12410 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1860
       Built: 2022
    Monthly Fee: $225
       Tax: $7,966 (2025)
    Community: Encore At Ovation
    Single Family


    Estimated Monthly Payment: $4,396 (change assumption)
    Mortgage ($3,507) + Fees ($225) + Taxes in 2025 ($664)


    Taxes:$7,966

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 205 SURPRISE DR, WINTER GARDEN, FL 34787

    $1,200,000198 Days on yellowkey   MLS ID: O6365188

    For Sale O6365188 - 205 SURPRISE DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2171
       Built: 1950   Tax: $3,406 (2024)
    Community: Winter Garden Shores Rep
    Single Family


    Estimated Monthly Payment: $6,859 (change assumption)
    Mortgage ($6,575) + Taxes in 2024 ($284)


    Taxes:$3,406

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 630 GRASSY STONE DR, WINTER GARDEN, FL 34787

    $545,00015 Days on yellowkey   MLS ID: O6414101

    1 Days Off yellowkey (back on 6/7/2026)

    For Sale O6414101 - 630 GRASSY STONE DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2210
       Built: 2013
    Monthly Fee: $72
       Tax: $4,479 (2025)
    Community: Covington Chase Ph 2B
    Single Family


    Estimated Monthly Payment: $3,431 (change assumption)
    Mortgage ($2,986) + Fees ($72) + Taxes in 2025 ($373)


    Taxes:$4,479

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787

    $550,00074 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


  • 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,499,00015 Days on yellowkey   MLS ID: O6413249

    For Sale O6413249 - 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4130
       Built: 2018
    Monthly Fee: $266
       Tax: $2,479 (2025)
    Community: Waterleigh Ph 1A
    Single Family


    Estimated Monthly Payment: $8,686 (change assumption)
    Mortgage ($8,213) + Fees ($266) + Taxes in 2025 ($207)


    Taxes:$2,479

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13360 SUNNY RETREAT LN, WINTER GARDEN, FL 34787

    $585,000144 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


  • 342 WINDFORD CT, WINTER GARDEN, FL 34787

    $339,90038 Days on yellowkey   MLS ID: O6407632

    REDUCED by $10,000 (2.9%) on 06/06/2026

    For Sale O6407632 - 342 WINDFORD CT, WINTER GARDEN, FL 34787 17 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1194
       Built: 1996
    Monthly Fee: $40
       Tax: $4,266 (2025)
    Community: Park Ave Estates
    Single Family


    Estimated Monthly Payment: $2,258 (change assumption)
    Mortgage ($1,862) + Fees ($40) + Taxes in 2025 ($356)


    Taxes:$4,266

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15025 PIGEON PLUM LN, WINTER GARDEN, FL 34787

    $599,99039 Days on yellowkey   MLS ID: O6404948

    1 Days Off yellowkey (back on 5/16/2026)

    For Sale O6404948 - 15025 PIGEON PLUM LN, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2605
       Built: 2016
    Monthly Fee: $252
       Tax: $6,086 (2025)
    Community: Summerlake Pd Ph 2C
    Single Family


    Estimated Monthly Payment: $4,047 (change assumption)
    Mortgage ($3,288) + Fees ($252) + Taxes in 2025 ($507)


    Taxes:$6,086

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle




Why Bother Searching Elsewhere for Winter Garden Single Family Homes for Sale?

Winter Garden home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden single family homes. 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 single family home 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.