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Winter Garden Single Family Homes For Sale - 730 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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  • 1144 HULL ISLAND DR, WINTER GARDEN, FL 34787

    $1,699,00027 Days on yellowkey   MLS ID: O6418306

    REDUCED by $50,000 (2.9%) on 07/09/2026

    For Sale O6418306 - 1144 HULL ISLAND DR, WINTER GARDEN, FL 34787 64 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4102
       Built: 2021
    Monthly Fee: $165
       Tax: $13,885 (2025)
    Community: Hull Island/Oakland
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,631 (change assumption)
    Mortgage ($9,309) + Fees ($165) + Taxes in 2025 ($1,157)


    Taxes:$13,885

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 12050 BRACCO ST, WINTER GARDEN, FL 34787

    $475,00095 Days on yellowkey   MLS ID: O6398494

    REDUCED by $14,900 (3.0%) on 07/16/2026

    For Sale O6398494 - 12050 BRACCO ST, WINTER GARDEN, FL 34787 73 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2023
    Monthly Fee: $110
       Tax: $7,195 (2025)
    Community: Highland Ridge
    Single Family


    Estimated Monthly Payment: $3,312 (change assumption)
    Mortgage ($2,603) + Fees ($110) + Taxes in 2025 ($600)


    Taxes:$7,195

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 10174 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $974,00087 Days on yellowkey   MLS ID: O6402434

    REDUCED by $25,000 (2.5%) on 07/08/2026

    For Sale O6402434 - 10174 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2758
       Built: 2020
    Monthly Fee: $250
       Tax: $7,946 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Single Family


    Estimated Monthly Payment: $6,249 (change assumption)
    Mortgage ($5,337) + Fees ($250) + Taxes in 2025 ($662)


    Taxes:$7,946

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 806 JOHNS POINT DR, WINTER GARDEN, FL 34787

    $1,075,00032 Days on yellowkey   MLS ID: O6418276

    0 Days Off yellowkey (back on 7/16/2026)

    For Sale O6418276 - 806 JOHNS POINT DR, WINTER GARDEN, FL 34787 98 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3552
       Built: 2003
    Monthly Fee: $173
       Tax: $10,300 (2025)
    Community: John's Cove
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,922 (change assumption)
    Mortgage ($5,890) + Fees ($173) + Taxes in 2025 ($858)


    Taxes:$10,300

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16466 OLIVE HILL DR, WINTER GARDEN, FL 34787

    $640,00049 Days on yellowkey   MLS ID: O6409922

    REDUCED by $20,000 (3.0%) on 07/16/2026

    For Sale O6409922 - 16466 OLIVE HILL DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2020
       Built: 2019
    Monthly Fee: $127
       Tax: $8,758 (2025)
    Community: Hawksmoor-Ph 1
    Single Family


    Estimated Monthly Payment: $4,364 (change assumption)
    Mortgage ($3,507) + Fees ($127) + Taxes in 2025 ($730)


    Taxes:$8,758

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 1343 CASTLEPORT RD, WINTER GARDEN, FL 34787

    $525,00041 Days on yellowkey   MLS ID: O6414756

    REDUCED by $10,000 (1.9%) on 07/01/2026

    For Sale O6414756 - 1343 CASTLEPORT RD, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2001
    Monthly Fee: $243
       Tax: $4,191 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,469 (change assumption)
    Mortgage ($2,877) + Fees ($243) + Taxes in 2025 ($349)


    Taxes:$4,191

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1801 BURDOCK DR, WINTER GARDEN, FL 34787

    $599,90027 Days on yellowkey   MLS ID: O6419427

    For Sale O6419427 - 1801 BURDOCK DR, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2534
       Built: 2008
    Monthly Fee: $90
       Tax: $3,695 (2025)
    Community: Carriage Pointe A-I & L
    Single Family


    Estimated Monthly Payment: $3,685 (change assumption)
    Mortgage ($3,287) + Fees ($90) + Taxes in 2025 ($308)


    Taxes:$3,695

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5330 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787

    $579,00021 Days on yellowkey   MLS ID: O6420269

    1 Days Off yellowkey (back on 7/16/2026)

    For Sale O6420269 - 5330 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2022
    Monthly Fee: $160
       Tax: $7,489 (2025)
    Community: Lakeside At Hamlin
    Single Family


    Estimated Monthly Payment: $3,957 (change assumption)
    Mortgage ($3,173) + Fees ($160) + Taxes in 2025 ($624)


    Taxes:$7,489

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 338 WINDFORD CT, WINTER GARDEN, FL 34787

    $330,00050 Days on yellowkey   MLS ID: O6413058

    For Sale O6413058 - 338 WINDFORD CT, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1050
       Built: 1996
    Monthly Fee: $40
       Tax: $2,089 (2025)
    Community: Park Ave Estates
    Single Family


    Estimated Monthly Payment: $2,022 (change assumption)
    Mortgage ($1,808) + Fees ($40) + Taxes in 2025 ($174)


    Taxes:$2,089

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 4004 REX DR, WINTER GARDEN, FL 34787

    $2,790,000110 Days on yellowkey   MLS ID: O6395737

    REDUCED by $110,000 (3.8%) on 07/16/2026

    For Sale O6395737 - 4004 REX DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1804
       Built: 1971   Tax: $3,688 (2025)
    Community: Lake Avalon Groves Rep
    Single Family


    Estimated Monthly Payment: $15,595 (change assumption)
    Mortgage ($15,287) + Taxes in 2025 ($307)


    Taxes:$3,688

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13361 SUNNY RETREAT LN, WINTER GARDEN, FL 34787

    $859,90023 Days on yellowkey   MLS ID: O6419110

    REDUCED by $10,000 (1.1%) on 07/16/2026

    For Sale O6419110 - 13361 SUNNY RETREAT LN, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3172
       Built: 2023
    Monthly Fee: $642
       Tax: $8,700 (2025)
    Community: Del Webb Oasis
    Single Family


    Estimated Monthly Payment: $6,079 (change assumption)
    Mortgage ($4,712) + Fees ($642) + Taxes in 2025 ($725)


    Taxes:$8,700

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17379 CHANNEL WAY, WINTER GARDEN, FL 34787

    $658,00049 Days on yellowkey   MLS ID: O6412749

    REDUCED by $10,000 (1.5%) on 07/16/2026

    For Sale O6412749 - 17379 CHANNEL WAY, WINTER GARDEN, FL 34787 61 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2782
       Built: 2019
    Monthly Fee: $215
       Tax: $9,049 (2025)
    Community: Waterside At Johns Lake
    Single Family


    Estimated Monthly Payment: $4,574 (change assumption)
    Mortgage ($3,605) + Fees ($215) + Taxes in 2025 ($754)


    Taxes:$9,049

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13184 DENDY WAY, WINTER GARDEN, FL 34787

    $664,000145 Days on yellowkey   MLS ID: O6384386

    For Sale O6384386 - 13184 DENDY WAY, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2211
       Built: 2025
    Monthly Fee: $139
       Tax: $2,677 (2025)
    Community: Horizon Isle
    Single Family


    Estimated Monthly Payment: $4,000 (change assumption)
    Mortgage ($3,638) + Fees ($139) + Taxes in 2025 ($223)


    Taxes:$2,677

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14788 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $530,000100 Days on yellowkey   MLS ID: O6398754

    1 Days Off yellowkey (back on 7/16/2026)

    REDUCED by $49,999 (8.6%) on 07/10/2026

    For Sale O6398754 - 14788 FIELD DAISY DR, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1992
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $3,133 (change assumption)
    Mortgage ($2,904) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 12438 CLEAR SAPPHIRE DR #223, WINTER GARDEN, FL 34787

    $684,990118 Days on yellowkey   MLS ID: O6393877

    4 Days Off yellowkey (back on 5/26/2026)

    REDUCED by $5,000 (0.7%) on 04/16/2026

    For Sale O6393877 - 12438 CLEAR SAPPHIRE DR #223, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $3,849 (change assumption)
    Mortgage ($3,753) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 15143 BLUE PEACOCK LN, WINTER GARDEN, FL 34787

    $589,00044 Days on yellowkey   MLS ID: O6414996

    REDUCED by $6,000 (1.0%) on 07/16/2026

    For Sale O6414996 - 15143 BLUE PEACOCK LN, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2420
       Built: 2024
    Monthly Fee: $96
       Tax: $8,683 (2025)
    Community: Osprey Ranch Ph 1
    Single Family


    Estimated Monthly Payment: $4,047 (change assumption)
    Mortgage ($3,227) + Fees ($96) + Taxes in 2025 ($724)


    Taxes:$8,683

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1743 FULLERS OAK LOOP, WINTER GARDEN, FL 34787

    $689,00025 Days on yellowkey   MLS ID: O6419299

    0 Days Off yellowkey (back on 7/16/2026)

    For Sale O6419299 - 1743 FULLERS OAK LOOP, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2536
       Built: 2017
    Monthly Fee: $251
       Tax: $5,698 (2025)
    Community: Fullers Oak
    Single Family


    Estimated Monthly Payment: $4,501 (change assumption)
    Mortgage ($3,775) + Fees ($251) + Taxes in 2025 ($475)


    Taxes:$5,698

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 11899 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $743,2718 Days on yellowkey   MLS ID: O6425088

    1 Days Off yellowkey (back on 7/16/2026)

    INCREASED by $1,935 (0.3%) on 07/15/2026

    For Sale O6425088 - 11899 SHINE VIEW LN, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $208
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,446 (change assumption)
    Mortgage ($4,073) + Fees ($208) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1701 E BAY ST, WINTER GARDEN, FL 34787

    $289,00046 Days on yellowkey   MLS ID: O6413973

    REDUCED by $6,000 (2.0%) on 07/16/2026

    For Sale O6413973 - 1701 E BAY ST, WINTER GARDEN, FL 34787 32 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 825
       Built: 1950   Tax: $2,560 (2025)
    Community: Joe Louis Park First Add
    Single Family


    Estimated Monthly Payment: $1,797 (change assumption)
    Mortgage ($1,584) + Taxes in 2025 ($213)


    Taxes:$2,560

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $589,990246 Days on yellowkey   MLS ID: O6361583

    1 Days Off yellowkey (back on 7/16/2026)

    REDUCED by $10,000 (1.7%) on 07/03/2026

    For Sale O6361583 - 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,588 (change assumption)
    Mortgage ($3,233) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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.