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Winter Garden Homes For Sale & Real Estate - 661 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

    $1,499,999176 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 51 photos

    Bed: 3   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


  • 9849 LOST CREEK DR, WINTER GARDEN, FL 34787

    $990,000509 Days on yellowkey   MLS ID: O6258009

    For Sale O6258009 - 9849 LOST CREEK DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2021
    Monthly Fee: $250
       Tax: $10,950 (2023)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,587 (change assumption)
    Mortgage ($5,425) + Fees ($250) + Taxes in 2023 ($913)


    Taxes:$10,950

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 12915 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $594,00064 Days on yellowkey   MLS ID: O6381156

    For Sale O6381156 - 12915 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2143
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,526 (change assumption)
    Mortgage ($3,255) + 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


  • 150 WINDTREE LN #150, WINTER GARDEN, FL 34787

    $199,900129 Days on yellowkey   MLS ID: O6365343

    For Sale O6365343 - 150 WINDTREE LN #150, WINTER GARDEN, FL 34787 31 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1984
    Monthly Fee: $300
       Tax: $2,565 (2025)
    Community: Windree Gardens Ph 5
    Condo


    Estimated Monthly Payment: $1,609 (change assumption)
    Mortgage ($1,095) + Fees ($300) + Taxes in 2025 ($214)


    Taxes:$2,565

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787

    $548,00069 Days on yellowkey   MLS ID: O6379918

    5 Days Off yellowkey (back on 4/13/2026)

    For Sale O6379918 - 12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2062
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,273 (change assumption)
    Mortgage ($3,003) + 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


  • 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787

    $565,000131 Days on yellowkey   MLS ID: O6365057

    For Sale O6365057 - 16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2018
    Monthly Fee: $245
       Tax: $8,615 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $4,059 (change assumption)
    Mortgage ($3,096) + Fees ($245) + Taxes in 2025 ($718)


    Taxes:$8,615

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16736 OAKBORO ST, WINTER GARDEN, FL 34787

    $585,00026 Days on yellowkey   MLS ID: O6388784

    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: $4,043 (change assumption)
    Mortgage ($3,205) + Fees ($257) + Taxes in 2024 ($581)


    Taxes:$6,967

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787

    $795,00019 Days on yellowkey   MLS ID: O6393987

    For Sale O6393987 - 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4307
       Built: 2014
    Monthly Fee: $114
       Tax: $5,670 (2025)
    Community: Reserve/Carriage Pointe Ph 1
    Single Family


    Estimated Monthly Payment: $4,943 (change assumption)
    Mortgage ($4,356) + Fees ($114) + Taxes in 2025 ($472)


    Taxes:$5,670

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16137 WIND VIEW LN, WINTER GARDEN, FL 34787

    $575,000234 Days on yellowkey   MLS ID: O6335769

    REDUCED by $14,000 (2.4%) on 04/13/2026

    For Sale O6335769 - 16137 WIND VIEW LN, WINTER GARDEN, FL 34787 19 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2016
    Monthly Fee: $283
       Tax: $6,800 (2024)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,000 (change assumption)
    Mortgage ($3,151) + Fees ($283) + Taxes in 2024 ($567)


    Taxes:$6,800

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16856 HYPATIA ALY, WINTER GARDEN, FL 34787

    $459,99940 Days on yellowkey   MLS ID: O6387941

    For Sale O6387941 - 16856 HYPATIA ALY, WINTER GARDEN, FL 34787 74 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2019
    Monthly Fee: $250
       Tax: $6,769 (2024)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,335 (change assumption)
    Mortgage ($2,520) + Fees ($250) + Taxes in 2024 ($564)


    Taxes:$6,769

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9728 NANCY DREW ALY, WINTER GARDEN, FL 34787

    $524,990169 Days on yellowkey   MLS ID: O6355911

    3 Days Off yellowkey (back on 4/13/2026)

    For Sale O6355911 - 9728 NANCY DREW ALY, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2475
       Built: 2020
    Monthly Fee: $108
       Tax: $8,203 (2024)
    Community: Storey Grove Ph 2
    Single Family


    Estimated Monthly Payment: $3,668 (change assumption)
    Mortgage ($2,877) + Fees ($108) + Taxes in 2024 ($684)


    Taxes:$8,203

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16209 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787

    $399,00019 Days on yellowkey   MLS ID: O6392111

    3 Days Off yellowkey (back on 4/13/2026)

    For Sale O6392111 - 16209 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1626
       Built: 2020
    Monthly Fee: $286
       Tax: $5,581 (2025)
    Community: Hawksmoor-Ph 3
    Townhouse


    Estimated Monthly Payment: $2,937 (change assumption)
    Mortgage ($2,186) + Fees ($286) + Taxes in 2025 ($465)


    Taxes:$5,581

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14051 GROVE RESORT AVE #1705, WINTER GARDEN, FL 34787

    $215,00075 Days on yellowkey   MLS ID: O6371816

    For Sale O6371816 - 14051 GROVE RESORT AVE #1705, WINTER GARDEN, FL 34787 15 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1265
       Built: 2016
    Monthly Fee: $904
       Tax: $6,487 (2024)
    Community: The Grove Resort And Spa
    Spa: No

    Condo


    Estimated Monthly Payment: $2,623 (change assumption)
    Mortgage ($1,178) + Fees ($904) + Taxes in 2024 ($541)


    Taxes:$6,487

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 17031 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $646,0901 Day on yellowkey   MLS ID: G5110934

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale G5110934 - 17031 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2680
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,680 (change assumption)
    Mortgage ($3,540) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17428 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $740,2051 Day on yellowkey   MLS ID: G5110933

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale G5110933 - 17428 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3412
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,196 (change assumption)
    Mortgage ($4,056) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13393 SUNSET LAKES CIR, WINTER GARDEN, FL 34787

    $867,0001 Day on yellowkey   MLS ID: O6398468

    For Sale O6398468 - 13393 SUNSET LAKES CIR, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2186
       Built: 1994
    Monthly Fee: $69
       Tax: $6,434 (2025)
    Community: Sunset Lakes
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,356 (change assumption)
    Mortgage ($4,751) + Fees ($69) + Taxes in 2025 ($536)


    Taxes:$6,434

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5637 TIGER WAY, WINTER GARDEN, FL 34787

    $765,0001 Day on yellowkey   MLS ID: O6398378

    0 Days Off yellowkey (back on 4/12/2026)

    For Sale O6398378 - 5637 TIGER WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2917
       Built: 2018
    Monthly Fee: $214
       Tax: $12,077 (2025)
    Community: Overlook 2/Hamlin Ph 3
    Single Family


    Estimated Monthly Payment: $5,412 (change assumption)
    Mortgage ($4,192) + Fees ($214) + Taxes in 2025 ($1,006)


    Taxes:$12,077

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15183 SERENADE DR, WINTER GARDEN, FL 34787

    $789,0002 Days on yellowkey   MLS ID: O6398436

    For Sale O6398436 - 15183 SERENADE DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 7   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4438
       Built: 2010
    Monthly Fee: $167
       Tax: $3,859 (2024)
    Community: Belle Meade Ph 02 H
    Single Family


    Estimated Monthly Payment: $4,812 (change assumption)
    Mortgage ($4,323) + Fees ($167) + Taxes in 2024 ($322)


    Taxes:$3,859

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 15907 MARINA BAY DR, WINTER GARDEN, FL 34787

    $450,0002 Days on yellowkey   MLS ID: O6398406

    For Sale O6398406 - 15907 MARINA BAY DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1818
       Built: 2020
    Monthly Fee: $286
       Tax: $7,110 (2025)
    Community: Hawksmoor-Ph 1
    Townhouse


    Estimated Monthly Payment: $3,344 (change assumption)
    Mortgage ($2,466) + Fees ($286) + Taxes in 2025 ($593)


    Taxes:$7,110

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6309 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $709,990208 Days on yellowkey   MLS ID: G5102289

    0 Days Off yellowkey (back on 9/18/2025)

    For Sale G5102289 - 6309 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,040 (change assumption)
    Mortgage ($3,890) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle




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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.