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Winter Garden Single Family Homes For Sale - 729 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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  • 2006 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $750,00022 Days on yellowkey   MLS ID: O6420951

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

    For Sale O6420951 - 2006 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 50 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3011
       Built: 1999
    Monthly Fee: $90
       Tax: $5,441 (2025)
    Community: Wintermere Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,653 (change assumption)
    Mortgage ($4,109) + Fees ($90) + Taxes in 2025 ($453)


    Taxes:$5,441

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14050 FAIRWAY WILLOW LN, WINTER GARDEN, FL 34787

    $714,999120 Days on yellowkey   MLS ID: O6392994

    REDUCED by $34,001 (4.5%) on 07/17/2026

    For Sale O6392994 - 14050 FAIRWAY WILLOW LN, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 1989
    Monthly Fee: $322
       Tax: $4,924 (2025)
    Community: Woodbridge On Green
    Single Family


    Estimated Monthly Payment: $4,650 (change assumption)
    Mortgage ($3,918) + Fees ($322) + Taxes in 2025 ($410)


    Taxes:$4,924

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17070 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $575,0009 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


  • 16149 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787

    $1,005,995247 Days on yellowkey   MLS ID: G5104655

    0 Days Off yellowkey (back on 11/17/2025)

    For Sale G5104655 - 16149 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787 2 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3764
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $5,662 (change assumption)
    Mortgage ($5,512) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15512 FOUNTAIN COVE CT, WINTER GARDEN, FL 34787

    $728,0007 Days on yellowkey   MLS ID: O6425554

    For Sale O6425554 - 15512 FOUNTAIN COVE CT, WINTER GARDEN, FL 34787 55 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3227
       Built: 2017
    Monthly Fee: $342
       Tax: $11,367 (2025)
    Community: Waterleigh Ph 1A
    Single Family


    Estimated Monthly Payment: $5,278 (change assumption)
    Mortgage ($3,989) + Fees ($342) + Taxes in 2025 ($947)


    Taxes:$11,367

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15415 SHONAN GOLD DR, WINTER GARDEN, FL 34787

    $549,9906 Days on yellowkey   MLS ID: O6424833

    For Sale O6424833 - 15415 SHONAN GOLD DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1979
       Built: 2019
    Monthly Fee: $142
       Tax: $8,414 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $3,857 (change assumption)
    Mortgage ($3,014) + Fees ($142) + Taxes in 2025 ($701)


    Taxes:$8,414

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 341 E LAFAYETTE ST, WINTER GARDEN, FL 34787

    $179,00014 Days on yellowkey   MLS ID: O6423558

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

    For Sale O6423558 - 341 E LAFAYETTE ST, WINTER GARDEN, FL 34787 7 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1106
       Built: 1948   Tax: $2,897 (2025)
    Community: Solomon Sub
    Single Family


    Estimated Monthly Payment: $1,222 (change assumption)
    Mortgage ($981) + Taxes in 2025 ($241)


    Taxes:$2,897

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16746 TURTLE HATCH DR, WINTER GARDEN, FL 34787

    $1,265,00063 Days on yellowkey   MLS ID: O6406556

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

    For Sale O6406556 - 16746 TURTLE HATCH DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 6   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4451
       Built: 2018
    Monthly Fee: $215
       Tax: $9,540 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Single Family


    Estimated Monthly Payment: $7,941 (change assumption)
    Mortgage ($6,931) + Fees ($215) + Taxes in 2025 ($795)


    Taxes:$9,540

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16681 SILVER BROOK WAY, WINTER GARDEN, FL 34787

    $539,79028 Days on yellowkey   MLS ID: O6419693

    REDUCED by $16,000 (2.9%) on 07/16/2026

    For Sale O6419693 - 16681 SILVER BROOK WAY, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1896
       Built: 2024
    Monthly Fee: $152
       Tax: $1,372 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,224 (change assumption)
    Mortgage ($2,958) + Fees ($152) + Taxes in 2024 ($114)


    Taxes:$1,372

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 1815 AMERICUS MINOR DR, WINTER GARDEN, FL 34787

    $499,9907 Days on yellowkey   MLS ID: O6425157

    For Sale O6425157 - 1815 AMERICUS MINOR DR, WINTER GARDEN, FL 34787 9 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2199
       Built: 2002
    Monthly Fee: $44
       Tax: $6,178 (2025)
    Community: Fullers Crossing Ph 02 49 31
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,298 (change assumption)
    Mortgage ($2,740) + Fees ($44) + Taxes in 2025 ($515)


    Taxes:$6,178

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 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


  • 10301 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787

    $525,00055 Days on yellowkey   MLS ID: O6411527

    REDUCED by $5,000 (0.9%) on 07/16/2026

    For Sale O6411527 - 10301 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787 23 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2078
       Built: 2020
    Monthly Fee: $154
       Tax: $7,738 (2024)
    Community: Watermark Ph 4
    Single Family


    Estimated Monthly Payment: $3,675 (change assumption)
    Mortgage ($2,877) + Fees ($154) + Taxes in 2024 ($645)


    Taxes:$7,738

    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.