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Winter Garden Homes For Sale & Real Estate - 954 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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  • 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $569,990157 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


  • 13212 SOCIAL LN, WINTER GARDEN, FL 34787

    $595,00070 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

    $767,000121 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


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

    $310,00076 Days on yellowkey   MLS ID: O6397663

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

    REDUCED by $9,900 (3.1%) on 05/20/2026

    For Sale O6397663 - 431 SOUTHERN PECAN CIR #201, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1499
       Built: 2005
    Monthly Fee: $576
       Tax: $4,273 (2025)
    Community: Southern Pines Condo
    Condo


    Estimated Monthly Payment: $2,631 (change assumption)
    Mortgage ($1,699) + Fees ($576) + Taxes in 2025 ($356)


    Taxes:$4,273

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14501 GROVE RESORT AVE #2615, WINTER GARDEN, FL 34787

    $249,00065 Days on yellowkey   MLS ID: S5148328

    For Sale S5148328 - 14501 GROVE RESORT AVE #2615, WINTER GARDEN, FL 34787 15 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1265
       Built: 2018   Tax: $7,667 (2025)
    Community: Grove Residence & Spa Hotel Condo Ii
    Condo


    Estimated Monthly Payment: $2,003 (change assumption)
    Mortgage ($1,364) + Taxes in 2025 ($639)


    Taxes:$7,667

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14501 GROVE RESORT AVE #3524, WINTER GARDEN, FL 34787

    $299,00065 Days on yellowkey   MLS ID: S5148318

    For Sale S5148318 - 14501 GROVE RESORT AVE #3524, WINTER GARDEN, FL 34787 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1265
       Built: 2018   Tax: $7,257 (2025)
    Community: Grove Residence & Spa Hotel Condo Ii
    Condo


    Estimated Monthly Payment: $2,243 (change assumption)
    Mortgage ($1,638) + Taxes in 2025 ($605)


    Taxes:$7,257

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11264 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,99077 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


  • 15213 HAMLIN PARK DR, WINTER GARDEN, FL 34787

    $489,99030 Days on yellowkey   MLS ID: TB8512228

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

    For Sale TB8512228 - 15213 HAMLIN PARK DR, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2072
       Built: 2026
    Monthly Fee: $248
       Tax: $1,375 (2025)
    Community: Parkview/Hamlin
    Townhouse


    Estimated Monthly Payment: $3,047 (change assumption)
    Mortgage ($2,685) + Fees ($248) + Taxes in 2025 ($115)


    Taxes:$1,375

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13043 SANDCASTLE DRIVE, WINTER GARDEN, FL 34787

    $899,00071 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

    $599,990150 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


  • 14501 GROVE RESORT AVE #3109, WINTER GARDEN, FL 34787

    $299,900113 Days on yellowkey   MLS ID: O6386655

    REDUCED by $15,000 (4.8%) on 06/07/2026

    For Sale O6386655 - 14501 GROVE RESORT AVE #3109, WINTER GARDEN, FL 34787 59 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1434
       Built: 2018
    Monthly Fee: $1,025
       Tax: $4,503 (2025)
    Community: Grove Residence & Spa Hotel Condo 2
    Spa: Yes

    Condo


    Estimated Monthly Payment: $3,043 (change assumption)
    Mortgage ($1,643) + Fees ($1,025) + Taxes in 2025 ($375)


    Taxes:$4,503

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787

    $339,90072 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


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

    $639,99034 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


  • 8170 BLUEJACK OAK DR, WINTER GARDEN, FL 34787

    $460,00070 Days on yellowkey   MLS ID: O6399484

    REDUCED by $5,000 (1.1%) on 06/03/2026

    For Sale O6399484 - 8170 BLUEJACK OAK DR, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1853
       Built: 2016
    Monthly Fee: $315
       Tax: $4,738 (2025)
    Community: Summerlake Pd Ph 2C 2D 2E
    Townhouse


    Estimated Monthly Payment: $3,230 (change assumption)
    Mortgage ($2,520) + Fees ($315) + Taxes in 2025 ($395)


    Taxes:$4,738

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 205 SURPRISE DR, WINTER GARDEN, FL 34787

    $1,200,000203 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


  • 8530 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,499,00020 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


  • 6238 SUNNY TIME AVENUE, WINTER GARDEN, FL 34787

    $438,89025 Days on yellowkey   MLS ID: O6412326

    REDUCED by $6,000 (1.3%) on 06/02/2026

    For Sale O6412326 - 6238 SUNNY TIME AVENUE, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1683
       Built: 2024
    Monthly Fee: $286
       Tax: $892 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,765 (change assumption)
    Mortgage ($2,405) + Fees ($286) + Taxes in 2024 ($74)


    Taxes:$892

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 13360 SUNNY RETREAT LN, WINTER GARDEN, FL 34787

    $585,000149 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

    $339,90043 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


  • 14501 GROVE RESORT AVE #2604, WINTER GARDEN, FL 34787

    $195,000134 Days on yellowkey   MLS ID: O6367873

    REDUCED by $10,000 (4.9%) on 06/06/2026

    FORECLOSURE O6367873 - 14501 GROVE RESORT AVE #2604, WINTER GARDEN, FL 34787 23 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1375
       Built: 2009   Tax: $8,091 (2025)
    Community: Grove Residence & Spa Hotel Condo Ii
    Condo


    Estimated Monthly Payment: $1,743 (change assumption)
    Mortgage ($1,068) + Taxes in 2025 ($674)


    Taxes:$8,091

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle




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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.