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Winter Garden Homes For Sale & Real Estate - 951 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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  • 8289 TOPSAIL PL, WINTER GARDEN, FL 34787

    $890,00015 Days on yellowkey   MLS ID: S5151179

    REDUCED by $30,000 (3.3%) on 06/16/2026

    For Sale S5151179 - 8289 TOPSAIL PL, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2755
       Built: 2020
    Monthly Fee: $350
       Tax: $11,564 (2024)
    Community: Lakeshore Preserve Ph 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,190 (change assumption)
    Mortgage ($4,877) + Fees ($350) + Taxes in 2024 ($964)


    Taxes:$11,564

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15149 CANOE PL, WINTER GARDEN, FL 34787

    $798,89216 Days on yellowkey   MLS ID: O6412776

    REDUCED by $108 (0.0%) on 06/16/2026

    For Sale O6412776 - 15149 CANOE PL, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3081
       Built: 2019
    Monthly Fee: $385
       Tax: $9,388 (2025)
    Community: Lakeshore Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $5,545 (change assumption)
    Mortgage ($4,377) + Fees ($385) + Taxes in 2025 ($782)


    Taxes:$9,388

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7841 ICELAND GULL ST, WINTER GARDEN, FL 34787

    $730,00015 Days on yellowkey   MLS ID: O6413079

    REDUCED by $15,000 (2.0%) on 06/14/2026

    For Sale O6413079 - 7841 ICELAND GULL ST, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2765
       Built: 2013
    Monthly Fee: $252
       Tax: $4,898 (2025)
    Community: Summerlake Pd Ph 1B-A Rep
    Single Family


    Estimated Monthly Payment: $4,660 (change assumption)
    Mortgage ($4,000) + Fees ($252) + Taxes in 2025 ($408)


    Taxes:$4,898

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 8113 RED STOPPER LN, WINTER GARDEN, FL 34787

    $434,900108 Days on yellowkey   MLS ID: O6386525

    REDUCED by $9,100 (2.0%) on 06/16/2026

    For Sale O6386525 - 8113 RED STOPPER LN, WINTER GARDEN, FL 34787 62 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1725
       Built: 2017
    Monthly Fee: $315
       Tax: $4,284 (2024)
    Community: Summerlake Pd Ph 2C 2D 2E
    Townhouse


    Estimated Monthly Payment: $3,055 (change assumption)
    Mortgage ($2,383) + Fees ($315) + Taxes in 2024 ($357)


    Taxes:$4,284

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 113 W DIVISION ST, WINTER GARDEN, FL 34787

    $525,99051 Days on yellowkey   MLS ID: S5148787

    REDUCED by $13,910 (2.6%) on 06/16/2026

    For Sale S5148787 - 113 W DIVISION ST, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1487
       Built: 1951   Tax: $4,920 (2025)
    Community: Winter Garden Shores Rep
    Single Family


    Estimated Monthly Payment: $3,292 (change assumption)
    Mortgage ($2,882) + Taxes in 2025 ($410)


    Taxes:$4,920

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13780 FRESH IVY ST, WINTER GARDEN, FL 34787

    $865,00043 Days on yellowkey   MLS ID: O6403387

    REDUCED by $30,000 (3.4%) on 06/06/2026

    For Sale O6403387 - 13780 FRESH IVY ST, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2862
       Built: 2025
    Monthly Fee: $642
       Tax: $2,578 (2025)
    Community: Del Webb Oasis Ph 3
    Single Family


    Estimated Monthly Payment: $5,596 (change assumption)
    Mortgage ($4,740) + Fees ($642) + Taxes in 2025 ($215)


    Taxes:$2,578

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 503 FIRST CAPE CORAL DR, WINTER GARDEN, FL 34787

    $556,00093 Days on yellowkey   MLS ID: O6381166

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

    For Sale O6381166 - 503 FIRST CAPE CORAL DR, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2365
       Built: 2006
    Monthly Fee: $123
       Tax: $3,974 (2024)
    Community: Black Lake Park Ph 01
    Single Family


    Estimated Monthly Payment: $3,501 (change assumption)
    Mortgage ($3,046) + Fees ($123) + Taxes in 2024 ($331)


    Taxes:$3,974

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 12390 CLEAR SAPPHIRE, WINTER GARDEN, FL 34787

    $764,99080 Days on yellowkey   MLS ID: O6394850

    REDUCED by $5,000 (0.6%) on 06/16/2026

    For Sale O6394850 - 12390 CLEAR SAPPHIRE, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2552
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,288 (change assumption)
    Mortgage ($4,192) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 12547 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787

    $919,99015 Days on yellowkey   MLS ID: O6413409

    REDUCED by $5,000 (0.5%) on 06/16/2026

    For Sale O6413409 - 12547 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3291
       Built: 2026
    Monthly Fee: $96
       Tax: $13,460 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $6,259 (change assumption)
    Mortgage ($5,041) + Fees ($96) + Taxes in 2026 ($1,122)


    Taxes:$13,460

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 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


  • 14501 GROVE RESORT AVE #1629, WINTER GARDEN, FL 34787

    $290,00097 Days on yellowkey   MLS ID: S5144771

    For Sale S5144771 - 14501 GROVE RESORT AVE #1629, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1544
       Built: 2009   Tax: $5,068 (2025)
    Community: The Grove Resort
    Condo


    Estimated Monthly Payment: $2,011 (change assumption)
    Mortgage ($1,589) + Taxes in 2025 ($422)


    Taxes:$5,068

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring 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


  • 1437 SCARLET OAK LOOP, WINTER GARDEN, FL 34787

    $350,00013 Days on yellowkey   MLS ID: O6411620

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

    For Sale O6411620 - 1437 SCARLET OAK LOOP, WINTER GARDEN, FL 34787 71 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1684
       Built: 2014
    Monthly Fee: $300
       Tax: $3,213 (2025)
    Community: Tucker Oaks
    Townhouse


    Estimated Monthly Payment: $2,486 (change assumption)
    Mortgage ($1,918) + Fees ($300) + Taxes in 2025 ($268)


    Taxes:$3,213

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 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




Why Bother Searching Elsewhere for Winter Garden Homes for Sale and Other Real Estate?

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.