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Winter Garden Single Family Homes For Sale - 711 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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  • 12541 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787

    $819,99016 Days on yellowkey   MLS ID: O6412476

    REDUCED by $10,000 (1.2%) on 06/16/2026

    For Sale O6412476 - 12541 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 2026
    Monthly Fee: $96
       Tax: $10,790 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $5,488 (change assumption)
    Mortgage ($4,493) + Fees ($96) + Taxes in 2026 ($899)


    Taxes:$10,790

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 931 KYLEE ALY, WINTER GARDEN, FL 34787

    $766,00044 Days on yellowkey   MLS ID: O6404673

    REDUCED by $1,000 (0.1%) on 06/16/2026

    For Sale O6404673 - 931 KYLEE ALY, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2831
       Built: 2022
    Monthly Fee: $393
       Tax: $9,637 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $5,393 (change assumption)
    Mortgage ($4,197) + Fees ($393) + Taxes in 2025 ($803)


    Taxes:$9,637

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 1005 CHASE DR, WINTER GARDEN, FL 34787

    $615,00021 Days on yellowkey   MLS ID: O6411451

    For Sale O6411451 - 1005 CHASE DR, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2319
       Built: 2005
    Monthly Fee: $68
       Tax: $7,087 (2025)
    Community: Island Pointe Sub
    Single Family


    Estimated Monthly Payment: $4,028 (change assumption)
    Mortgage ($3,370) + Fees ($68) + Taxes in 2025 ($591)


    Taxes:$7,087

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 13856 GLYNSHEL DR, WINTER GARDEN, FL 34787

    $850,0003 Days on yellowkey   MLS ID: O6416757

    For Sale O6416757 - 13856 GLYNSHEL DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3538
       Built: 2003
    Monthly Fee: $167
       Tax: $11,261 (2025)
    Community: Glynwood
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,763 (change assumption)
    Mortgage ($4,657) + Fees ($167) + Taxes in 2025 ($938)


    Taxes:$11,261

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 617 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,139,00098 Days on yellowkey   MLS ID: O6389100

    REDUCED by $11,000 (1.0%) on 06/01/2026

    For Sale O6389100 - 617 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3624
       Built: 2019
    Monthly Fee: $255
       Tax: $16,181 (2025)
    Community: Canopy Oaks Ph 1
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,844 (change assumption)
    Mortgage ($6,241) + Fees ($255) + Taxes in 2025 ($1,348)


    Taxes:$16,181

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16736 OAKBORO ST, WINTER GARDEN, FL 34787

    $563,90091 Days on yellowkey   MLS ID: O6388784

    0 Days Off yellowkey (back on 5/30/2026)

    REDUCED by $11,100 (1.9%) on 05/12/2026

    For Sale O6388784 - 16736 OAKBORO ST, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $257
       Tax: $6,967 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,927 (change assumption)
    Mortgage ($3,090) + Fees ($257) + Taxes in 2024 ($581)


    Taxes:$6,967

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2609 SLAGROVE CT, WINTER GARDEN, FL 34787

    $519,000170 Days on yellowkey   MLS ID: O6369515

    REDUCED by $11,000 (2.1%) on 06/16/2026

    For Sale O6369515 - 2609 SLAGROVE CT, WINTER GARDEN, FL 34787 44 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2383
       Built: 2003
    Monthly Fee: $205
       Tax: $4,293 (2024)
    Community: Stoneybrook West Ut 04 Rep 49 121
    Single Family


    Estimated Monthly Payment: $3,407 (change assumption)
    Mortgage ($2,844) + Fees ($205) + Taxes in 2024 ($358)


    Taxes:$4,293

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13843 LANYARD WAY, WINTER GARDEN, FL 34787

    $619,00018 Days on yellowkey   MLS ID: O6412130

    REDUCED by $29,000 (4.5%) on 06/16/2026

    For Sale O6412130 - 13843 LANYARD WAY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2568
       Built: 2022
    Monthly Fee: $225
       Tax: $9,717 (2025)
    Community: Encore/Ovation Ph 3
    Single Family


    Estimated Monthly Payment: $4,426 (change assumption)
    Mortgage ($3,392) + Fees ($225) + Taxes in 2025 ($810)


    Taxes:$9,717

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 18053 CIDER MILL LN, WINTER GARDEN, FL 34787

    $790,86170 Days on yellowkey   MLS ID: O6397726

    2 Days Off yellowkey (back on 6/16/2026)

    INCREASED by $3,020 (0.4%) on 06/12/2026

    For Sale O6397726 - 18053 CIDER MILL LN, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,698 (change assumption)
    Mortgage ($4,333) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14902 ARRENA RD, WINTER GARDEN, FL 34787

    $638,000608 Days on yellowkey   MLS ID: O6248982

    REDUCED by $10,000 (1.5%) on 06/16/2026

    For Sale O6248982 - 14902 ARRENA RD, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3392
       Built: 2001   Tax: $7,754 (2023)
    Community: Arrowhead Lakes
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,142 (change assumption)
    Mortgage ($3,496) + Taxes in 2023 ($646)


    Taxes:$7,754

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 14001 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787

    $1,175,00050 Days on yellowkey   MLS ID: O6403044

    For Sale O6403044 - 14001 COUNTRY ESTATE DR, WINTER GARDEN, FL 34787 75 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3698
       Built: 1988
    Monthly Fee: $71
       Tax: $6,208 (2025)
    Community: Country Lakes
    Single Family


    Estimated Monthly Payment: $7,027 (change assumption)
    Mortgage ($6,438) + Fees ($71) + Taxes in 2025 ($517)


    Taxes:$6,208

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 7187 WILD STRAWBERRY RUN, WINTER GARDEN, FL 34787

    $723,00046 Days on yellowkey   MLS ID: O6403837

    For Sale O6403837 - 7187 WILD STRAWBERRY RUN, WINTER GARDEN, FL 34787 56 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3602
       Built: 2007
    Monthly Fee: $200
       Tax: $11,214 (2025)
    Community: Signature Lks-Pcl 01D Ph 02
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,096 (change assumption)
    Mortgage ($3,962) + Fees ($200) + Taxes in 2025 ($935)


    Taxes:$11,214

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6334 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $913,3133 Days on yellowkey   MLS ID: G5113852

    0 Days Off yellowkey (back on 6/15/2026)

    For Sale G5113852 - 6334 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 49 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3543
       Built: 2026
    Monthly Fee: $150
       Tax: $298 (2025)
    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $5,179 (change assumption)
    Mortgage ($5,004) + Fees ($150) + Taxes in 2025 ($25)


    Taxes:$298

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 519 TEAGARDEN CT, WINTER GARDEN, FL 34787

    $898,0003 Days on yellowkey   MLS ID: O6416709

    For Sale O6416709 - 519 TEAGARDEN CT, WINTER GARDEN, FL 34787 23 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3061
       Built: 2002
    Monthly Fee: $30
       Tax: $3,496 (2025)
    Community: Teacup Spgs Cove
    Single Family


    Estimated Monthly Payment: $5,242 (change assumption)
    Mortgage ($4,920) + Fees ($30) + Taxes in 2025 ($291)


    Taxes:$3,496

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15154 TEA TREE DR, WINTER GARDEN, FL 34787

    $994,7333 Days on yellowkey   MLS ID: G5113803

    For Sale G5113803 - 15154 TEA TREE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3839
       Built: 2026
    Monthly Fee: $150
       Tax: $298 (2025)
    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $5,625 (change assumption)
    Mortgage ($5,450) + Fees ($150) + Taxes in 2025 ($25)


    Taxes:$298

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14776 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787

    $880,0003 Days on yellowkey   MLS ID: O6416354

    For Sale O6416354 - 14776 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787 72 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2876
       Built: 2017
    Monthly Fee: $187
       Tax: $11,232 (2025)
    Community: Orchard Hills Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,945 (change assumption)
    Mortgage ($4,822) + Fees ($187) + Taxes in 2025 ($936)


    Taxes:$11,232

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 925 EASLEY AVE, WINTER GARDEN, FL 34787

    $1,175,0003 Days on yellowkey   MLS ID: O6412977

    For Sale O6412977 - 925 EASLEY AVE, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2667
       Built: 2016
    Monthly Fee: $208
       Tax: $12,692 (2025)
    Community: Oakland Park
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,704 (change assumption)
    Mortgage ($6,438) + Fees ($208) + Taxes in 2025 ($1,058)


    Taxes:$12,692

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15160 TEA TREE DR, WINTER GARDEN, FL 34787

    $879,8065 Days on yellowkey   MLS ID: G5113740

    For Sale G5113740 - 15160 TEA TREE DR, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,971 (change assumption)
    Mortgage ($4,821) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14241 SUNRIDGE BLVD, WINTER GARDEN, FL 34787

    $749,8006 Days on yellowkey   MLS ID: O6416383

    0 Days Off yellowkey (back on 6/15/2026)

    For Sale O6416383 - 14241 SUNRIDGE BLVD, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2952
       Built: 2019
    Monthly Fee: $75
       Tax: $4,240 (2025)
    Community: Cypress Reserve Ph 1
    Single Family


    Estimated Monthly Payment: $4,537 (change assumption)
    Mortgage ($4,108) + Fees ($75) + Taxes in 2025 ($353)


    Taxes:$4,240

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 217 W BAY ST, WINTER GARDEN, FL 34787

    $1,395,00040 Days on yellowkey   MLS ID: S5149527

    REDUCED by $55,000 (3.8%) on 06/15/2026

    For Sale S5149527 - 217 W BAY ST, WINTER GARDEN, FL 34787 79 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: $8,140 (change assumption)
    Mortgage ($7,644) + Taxes in 2025 ($497)


    Taxes:$5,958

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.