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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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  • 15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $653,99026 Days on yellowkey   MLS ID: S5153036

    REDUCED by $16,000 (2.4%) on 07/29/2026

    For Sale S5153036 - 15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787 41 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2930
       Built: 2024
    Monthly Fee: $202
       Tax: $9,669 (2025)
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $4,591 (change assumption)
    Mortgage ($3,583) + Fees ($202) + Taxes in 2025 ($806)


    Taxes:$9,669

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 227 W BAY ST, WINTER GARDEN, FL 34787

    $565,000Listed 07/29/2026 12:30PM   MLS ID: S5154601

    0 Days Off yellowkey (back on 7/29/2026)

    For Sale S5154601 - 227 W BAY ST, WINTER GARDEN, FL 34787 74 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1338
       Built: 1956   Tax: $5,193 (2025)
    Community: Cooper & Sewell Add
    Single Family


    Estimated Monthly Payment: $3,529 (change assumption)
    Mortgage ($3,096) + Taxes in 2025 ($433)


    Taxes:$5,193

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787

    $479,900334 Days on yellowkey   MLS ID: S5133690

    2 Days Off yellowkey (back on 7/29/2026)

    REDUCED by $20,000 (4.0%) on 07/14/2026

    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: $3,196 (change assumption)
    Mortgage ($2,630) + Fees ($33) + Taxes in 2024 ($534)


    Taxes:$6,403

    Elementary School: Maxey Elem

    High School: Ocoee High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • WINTER GARDEN, FL 34787

    $870,00015 Days on yellowkey   MLS ID: O6424765

    For Sale O6424765 - WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3078
       Built: 2007
    Monthly Fee: $260
       Tax: $10,499 (2025)
    Community: Bronsons Lndgs F & M
    Single Family


    Estimated Monthly Payment: $5,902 (change assumption)
    Mortgage ($4,767) + Fees ($260) + Taxes in 2025 ($875)


    Taxes:$10,499

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 7052 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787

    $775,0006 Days on yellowkey   MLS ID: S5154077

    For Sale S5154077 - 7052 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3264
       Built: 2016
    Monthly Fee: $270
       Tax: $6,080 (2025)
    Community: Lakeview Pointe At Horizon West
    Single Family


    Estimated Monthly Payment: $5,023 (change assumption)
    Mortgage ($4,246) + Fees ($270) + Taxes in 2025 ($507)


    Taxes:$6,080

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 2045 SANDY GARDEN LN, WINTER GARDEN, FL 34787

    $719,00020 Days on yellowkey   MLS ID: O6422461

    For Sale O6422461 - 2045 SANDY GARDEN LN, WINTER GARDEN, FL 34787 45 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2742
       Built: 2013
    Monthly Fee: $113
       Tax: $5,645 (2025)
    Community: Reserve/Carriage Point Ph 1
    Single Family


    Estimated Monthly Payment: $4,523 (change assumption)
    Mortgage ($3,940) + Fees ($113) + Taxes in 2025 ($470)


    Taxes:$5,645

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17070 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $575,00016 Days on yellowkey   MLS ID: O6424329

    For Sale O6424329 - 17070 WATER SPRING BLVD, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2215
       Built: 2022
    Monthly Fee: $291
       Tax: $7,640 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,078 (change assumption)
    Mortgage ($3,151) + Fees ($291) + Taxes in 2025 ($637)


    Taxes:$7,640

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1610 BEULAH RD, WINTER GARDEN, FL 34787

    $450,00041 Days on yellowkey   MLS ID: O6418153

    For Sale O6418153 - 1610 BEULAH RD, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2210
       Built: 1998
    Monthly Fee: $44
       Tax: $2,189 (2025)
    Community: Orange Cove
    Single Family


    Estimated Monthly Payment: $2,692 (change assumption)
    Mortgage ($2,466) + Fees ($44) + Taxes in 2025 ($182)


    Taxes:$2,189

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11265 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $859,99084 Days on yellowkey   MLS ID: O6405351

    REDUCED by $11,841 (1.4%) on 07/29/2026

    For Sale O6405351 - 11265 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: $200
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,078 (change assumption)
    Mortgage ($4,712) + Fees ($200) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11259 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $884,99034 Days on yellowkey   MLS ID: O6419946

    REDUCED by $5,000 (0.6%) on 07/29/2026

    For Sale O6419946 - 11259 HOLLOW BAY DR, WINTER GARDEN, FL 34787 68 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $208
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,223 (change assumption)
    Mortgage ($4,849) + Fees ($208) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12026 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $569,99085 Days on yellowkey   MLS ID: O6405058

    REDUCED by $27,805 (4.7%) on 07/29/2026

    For Sale O6405058 - 12026 SHINE VIEW LN, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,479 (change assumption)
    Mortgage ($3,123) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 217 W BAY ST, WINTER GARDEN, FL 34787

    $1,349,00081 Days on yellowkey   MLS ID: S5149527

    REDUCED by $46,000 (3.3%) on 07/21/2026

    For Sale S5149527 - 217 W BAY ST, WINTER GARDEN, FL 34787 89 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 2800
       Built: 2025   Tax: $5,958 (2025)
    Community: Cooper & Sewell Add
    Single Family


    Estimated Monthly Payment: $7,888 (change assumption)
    Mortgage ($7,392) + Taxes in 2025 ($497)


    Taxes:$5,958

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17085 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $939,88091 Days on yellowkey   MLS ID: G5111738

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

    For Sale G5111738 - 17085 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3409
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $5,272 (change assumption)
    Mortgage ($5,150) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12033 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $749,99034 Days on yellowkey   MLS ID: O6418908

    1 Days Off yellowkey (back on 7/29/2026)

    REDUCED by $30,000 (3.8%) on 07/21/2026

    For Sale O6418908 - 12033 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $169
       Tax: $2,512 (2025)
    Community: Encore At Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,488 (change assumption)
    Mortgage ($4,109) + Fees ($169) + Taxes in 2025 ($209)


    Taxes:$2,512

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 10007 LITTLE ALCOVE LOOP, WINTER GARDEN, FL 34787

    $989,900352 Days on yellowkey   MLS ID: S5132434

    REDUCED by $10,090 (1.0%) on 07/29/2026

    For Sale S5132434 - 10007 LITTLE ALCOVE LOOP, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2921
       Built: 2018
    Monthly Fee: $250
       Tax: $6,381 (2024)
    Community: Waterleigh Ph 2B
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,206 (change assumption)
    Mortgage ($5,424) + Fees ($250) + Taxes in 2024 ($532)


    Taxes:$6,381

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $529,990250 Days on yellowkey   MLS ID: O6362478

    REDUCED by $10,000 (1.9%) on 07/29/2026

    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: $3,260 (change assumption)
    Mortgage ($2,904) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12014 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $549,99020 Days on yellowkey   MLS ID: O6423746

    REDUCED by $5,000 (0.9%) on 07/29/2026

    For Sale O6423746 - 12014 SHINE VIEW LN, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,429 (change assumption)
    Mortgage ($3,014) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16816 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $534,99020 Days on yellowkey   MLS ID: O6423763

    REDUCED by $15,000 (2.7%) on 07/29/2026

    For Sale O6423763 - 16816 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,347 (change assumption)
    Mortgage ($2,931) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $529,990229 Days on yellowkey   MLS ID: O6367156

    REDUCED by $10,000 (1.9%) on 07/29/2026

    For Sale O6367156 - 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 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: $3,260 (change assumption)
    Mortgage ($2,904) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 10198 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $1,200,00027 Days on yellowkey   MLS ID: O6421817

    For Sale O6421817 - 10198 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 42 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3911
       Built: 2020
    Monthly Fee: $260
       Tax: $11,419 (2025)
    Community: Waterleigh Ph 2C-1
    Single Family


    Estimated Monthly Payment: $7,787 (change assumption)
    Mortgage ($6,575) + Fees ($260) + Taxes in 2025 ($952)


    Taxes:$11,419

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring 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.