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Winter Garden Homes For Sale & Real Estate - 947 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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  • 241 N DILLARD ST, WINTER GARDEN, FL 34787

    $1,499,999248 Days on yellowkey   MLS ID: O6353975

    REDUCED by $100,001 (6.3%) on 04/13/2026

    For Sale O6353975 - 241 N DILLARD ST, WINTER GARDEN, FL 34787 52 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3507
       Built: 1953   Tax: $2,959 (2024)
    Community: J L Dillard Sub 3
    Single Family


    Estimated Monthly Payment: $8,466 (change assumption)
    Mortgage ($8,219) + Taxes in 2024 ($247)


    Taxes:$2,959

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 8955 LAKESHORE POINTE DR, WINTER GARDEN, FL 34787

    $639,990300 Days on yellowkey   MLS ID: O6337042

    For Sale O6337042 - 8955 LAKESHORE POINTE DR, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2539
       Built: 2018
    Monthly Fee: $600
       Tax: $8,886 (2024)
    Community: Lakeshore Preserve Ph 1
    Townhouse


    Estimated Monthly Payment: $4,847 (change assumption)
    Mortgage ($3,507) + Fees ($600) + Taxes in 2024 ($741)


    Taxes:$8,886

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 9355 TYRELLA PINE TRL, WINTER GARDEN, FL 34787

    $459,00092 Days on yellowkey   MLS ID: O6391856

    0 Days Off yellowkey (back on 6/5/2026)

    REDUCED by $8,000 (1.7%) on 05/30/2026

    For Sale O6391856 - 9355 TYRELLA PINE TRL, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1670
       Built: 2016
    Monthly Fee: $148
       Tax: $657 (2025)
    Community: Watermark Ph 1B
    Single Family


    Estimated Monthly Payment: $2,718 (change assumption)
    Mortgage ($2,515) + Fees ($148) + Taxes in 2025 ($55)


    Taxes:$657

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16783 TURTLE HATCH DR, WINTER GARDEN, FL 34787

    $1,199,99948 Days on yellowkey   MLS ID: O6404708

    0 Days Off yellowkey (back on 6/5/2026)

    REDUCED by $1 (0.0%) on 05/20/2026

    For Sale O6404708 - 16783 TURTLE HATCH DR, WINTER GARDEN, FL 34787 61 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3513
       Built: 2019
    Monthly Fee: $240
       Tax: $13,161 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Single Family


    Estimated Monthly Payment: $7,912 (change assumption)
    Mortgage ($6,575) + Fees ($240) + Taxes in 2025 ($1,097)


    Taxes:$13,161

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 68 N PARK AVE, WINTER GARDEN, FL 34787

    $1,799,00069 Days on yellowkey   MLS ID: O6400066

    REDUCED by $50,000 (2.7%) on 06/05/2026

    For Sale O6400066 - 68 N PARK AVE, WINTER GARDEN, FL 34787 61 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3555
       Built: 2021
    Monthly Fee: $325
       Tax: $15,594 (2025)
    Community: 30 North Park
    Townhouse


    Estimated Monthly Payment: $11,482 (change assumption)
    Mortgage ($9,857) + Fees ($325) + Taxes in 2025 ($1,300)


    Taxes:$15,594

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • WINTER GARDEN, FL 34787

    $855,52021 Days on yellowkey   MLS ID: G5113317

    0 Days Off yellowkey (back on 6/4/2026)

    For Sale G5113317 - WINTER GARDEN, FL 34787 3 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $125

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,813 (change assumption)
    Mortgage ($4,688) + Fees ($125) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • WINTER GARDEN, FL 34787

    $909,99021 Days on yellowkey   MLS ID: G5113315

    0 Days Off yellowkey (back on 6/4/2026)

    For Sale G5113315 - WINTER GARDEN, FL 34787 3 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $125

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $5,111 (change assumption)
    Mortgage ($4,986) + Fees ($125) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14451 WINDSOR HALL WAY, WINTER GARDEN, FL 34787

    $510,00038 Days on yellowkey   MLS ID: O6408731

    0 Days Off yellowkey (back on 6/4/2026)

    For Sale O6408731 - 14451 WINDSOR HALL WAY, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1814
       Built: 2016
    Monthly Fee: $192
       Tax: $5,900 (2025)
    Community: Lake Hancock Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,478 (change assumption)
    Mortgage ($2,794) + Fees ($192) + Taxes in 2025 ($492)


    Taxes:$5,900

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6110 MERIWETHER CRES, WINTER GARDEN, FL 34787

    $690,00029 Days on yellowkey   MLS ID: O6411208

    0 Days Off yellowkey (back on 6/4/2026)

    For Sale O6411208 - 6110 MERIWETHER CRES, WINTER GARDEN, FL 34787 17 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2830
       Built: 2011
    Monthly Fee: $16
       Tax: $6,992 (2025)
    Community: Signature Lakes Ph 02 A B H I J
    Single Family


    Estimated Monthly Payment: $4,379 (change assumption)
    Mortgage ($3,781) + Fees ($16) + Taxes in 2025 ($583)


    Taxes:$6,992

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 168 WINDTREE LN #203, WINTER GARDEN, FL 34787

    $202,900255 Days on yellowkey   MLS ID: O6351954

    REDUCED by $6,500 (3.1%) on 06/04/2026

    For Sale O6351954 - 168 WINDTREE LN #203, WINTER GARDEN, FL 34787 27 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1985
    Monthly Fee: $260
       Tax: $2,004 (2024)
    Community: Windtree Gardens Ph 6
    Condo


    Estimated Monthly Payment: $1,539 (change assumption)
    Mortgage ($1,112) + Fees ($260) + Taxes in 2024 ($167)


    Taxes:$2,004

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 12904 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $1,032,000134 Days on yellowkey   MLS ID: O6381734

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

    INCREASED by $10,000 (1.0%) on 06/01/2026

    For Sale O6381734 - 12904 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3894
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $5,925 (change assumption)
    Mortgage ($5,655) + Fees ($77) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 925 BAINBRIDGE LOOP, WINTER GARDEN, FL 34787

    $815,00062 Days on yellowkey   MLS ID: O6402075

    For Sale O6402075 - 925 BAINBRIDGE LOOP, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3580
       Built: 2008
    Monthly Fee: $72
       Tax: $4,880 (2025)
    Community: Covington Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,944 (change assumption)
    Mortgage ($4,466) + Fees ($72) + Taxes in 2025 ($407)


    Taxes:$4,880

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $599,990219 Days on yellowkey   MLS ID: O6361583

    REDUCED by $25,000 (4.0%) on 06/04/2026

    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: $3,643 (change assumption)
    Mortgage ($3,288) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1432 MARBLE CREST WAY, WINTER GARDEN, FL 34787

    $824,50073 Days on yellowkey   MLS ID: O6398054

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

    For Sale O6398054 - 1432 MARBLE CREST WAY, WINTER GARDEN, FL 34787 82 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3734
       Built: 2005
    Monthly Fee: $243
       Tax: $7,963 (2025)
    Community: Stoneybrook West 44/134
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,424 (change assumption)
    Mortgage ($4,518) + Fees ($243) + Taxes in 2025 ($664)


    Taxes:$7,963

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $599,99064 Days on yellowkey   MLS ID: O6401373

    REDUCED by $25,000 (4.0%) on 06/04/2026

    For Sale O6401373 - 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2494
       Built: 2026
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,643 (change assumption)
    Mortgage ($3,288) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13846 FRESH IVY ST, WINTER GARDEN, FL 34787

    $649,900268 Days on yellowkey   MLS ID: O6346706

    For Sale O6346706 - 13846 FRESH IVY ST, WINTER GARDEN, FL 34787 51 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2108
       Built: 2024
    Monthly Fee: $534
       Tax: $2,180 (2024)
    Community: Del Webb Oasis Ph 3
    Single Family


    Estimated Monthly Payment: $4,277 (change assumption)
    Mortgage ($3,561) + Fees ($534) + Taxes in 2024 ($182)


    Taxes:$2,180

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 8018 BOWERY DR, WINTER GARDEN, FL 34787

    $699,900345 Days on yellowkey   MLS ID: O6325853

    For Sale O6325853 - 8018 BOWERY DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3075
       Built: 2017
    Monthly Fee: $208
       Tax: $5,724 (2024)
    Community: Lake Hancock Preserve
    Single Family


    Estimated Monthly Payment: $4,520 (change assumption)
    Mortgage ($3,835) + Fees ($208) + Taxes in 2024 ($477)


    Taxes:$5,724

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $950,00024 Days on yellowkey   MLS ID: O6412033

    For Sale O6412033 - 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3777
       Built: 2016
    Monthly Fee: $195
       Tax: $11,678 (2025)
    Community: Signature Lakes Ph 3B-4 3B-5 & 3
    Single Family


    Estimated Monthly Payment: $6,374 (change assumption)
    Mortgage ($5,205) + Fees ($195) + Taxes in 2025 ($973)


    Taxes:$11,678

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14501 GROVE RESORT AVE #2138, WINTER GARDEN, FL 34787

    $190,000141 Days on yellowkey   MLS ID: O6379849

    5 Days Off yellowkey (back on 6/4/2026)

    For Sale O6379849 - 14501 GROVE RESORT AVE #2138, WINTER GARDEN, FL 34787 61 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1396
       Built: 2018
    Monthly Fee: $998
       Tax: $8,154 (2024)
    Community: Grove Resort And Spa Hotel Condominium U
    Condo


    Estimated Monthly Payment: $2,719 (change assumption)
    Mortgage ($1,041) + Fees ($998) + Taxes in 2024 ($680)


    Taxes:$8,154

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 92 WINDTREE LN #201, WINTER GARDEN, FL 34787

    $218,000170 Days on yellowkey   MLS ID: O6371247

    For Sale O6371247 - 92 WINDTREE LN #201, WINTER GARDEN, FL 34787 17 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1984
    Monthly Fee: $300
       Tax: $2,362 (2024)
    Community: Windtree Gardens Condo Ph 03
    Condo


    Estimated Monthly Payment: $1,691 (change assumption)
    Mortgage ($1,194) + Fees ($300) + Taxes in 2024 ($197)


    Taxes:$2,362

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle




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.