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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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  • 15280 MARITIME PINE DR, WINTER GARDEN, FL 34787

    $988,539273 Days on yellowkey   MLS ID: G5102291

    For Sale G5102291 - 15280 MARITIME PINE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3550
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $5,567 (change assumption)
    Mortgage ($5,417) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 3351 HANGING TIDE ST, WINTER GARDEN, FL 34787

    $635,00035 Days on yellowkey   MLS ID: O6407746

    0 Days Off yellowkey (back on 6/12/2026)

    For Sale O6407746 - 3351 HANGING TIDE ST, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2741
       Built: 2021
    Monthly Fee: $152
       Tax: $7,521 (2025)
    Community: Lakeview Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $4,258 (change assumption)
    Mortgage ($3,479) + Fees ($152) + Taxes in 2025 ($627)


    Taxes:$7,521

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 7808 WINTER WREN ST, WINTER GARDEN, FL 34787

    $579,00056 Days on yellowkey   MLS ID: O6400269

    0 Days Off yellowkey (back on 6/12/2026)

    REDUCED by $9,000 (1.5%) on 06/04/2026

    For Sale O6400269 - 7808 WINTER WREN ST, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2274
       Built: 2015
    Monthly Fee: $252
       Tax: $8,119 (2025)
    Community: Summerlake
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,101 (change assumption)
    Mortgage ($3,173) + Fees ($252) + Taxes in 2025 ($677)


    Taxes:$8,119

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 642 MEDORA WAY, WINTER GARDEN, FL 34787

    $1,137,1509 Days on yellowkey   MLS ID: O6413483

    For Sale O6413483 - 642 MEDORA WAY, WINTER GARDEN, FL 34787 14 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2995
       Built: 2026
    Monthly Fee: $155
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Single Family


    Estimated Monthly Payment: $6,469 (change assumption)
    Mortgage ($6,231) + Fees ($155) + Taxes in 2025 ($83)


    Taxes:$993

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 650 MEDORA WAY, WINTER GARDEN, FL 34787

    $1,157,1909 Days on yellowkey   MLS ID: O6413464

    For Sale O6413464 - 650 MEDORA WAY, WINTER GARDEN, FL 34787 12 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2902
       Built: 2026
    Monthly Fee: $155
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Single Family


    Estimated Monthly Payment: $6,578 (change assumption)
    Mortgage ($6,341) + Fees ($155) + Taxes in 2025 ($83)


    Taxes:$993

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 17090 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $534,90050 Days on yellowkey   MLS ID: G5111718

    1 Days Off yellowkey (back on 6/12/2026)

    REDUCED by $5,000 (0.9%) on 06/02/2026

    For Sale G5111718 - 17090 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2148
       Built: 2019
    Monthly Fee: $215
       Tax: $7,499 (2025)
    Community: Waterside/Johns Lk-Ph 2A
    Single Family


    Estimated Monthly Payment: $3,771 (change assumption)
    Mortgage ($2,931) + Fees ($215) + Taxes in 2025 ($625)


    Taxes:$7,499

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14989 APOLLO BOND DR, WINTER GARDEN, FL 34787

    $405,000124 Days on yellowkey   MLS ID: O6378685

    REDUCED by $10,000 (2.4%) on 06/12/2026

    For Sale O6378685 - 14989 APOLLO BOND DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1789
       Built: 2019
    Monthly Fee: $241
       Tax: $3,914 (2024)
    Community: Watermark Ph 3
    Townhouse


    Estimated Monthly Payment: $2,786 (change assumption)
    Mortgage ($2,219) + Fees ($241) + Taxes in 2024 ($326)


    Taxes:$3,914

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 17125 STILLNESS ALY, WINTER GARDEN, FL 34787

    $580,9337 Days on yellowkey   MLS ID: G5113666

    For Sale G5113666 - 17125 STILLNESS ALY, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2083
       Built: 2026
    Monthly Fee: $121

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $3,304 (change assumption)
    Mortgage ($3,183) + Fees ($121) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 181 ZACHARY WADE ST, WINTER GARDEN, FL 34787

    $600,00019 Days on yellowkey   MLS ID: O6412174

    For Sale O6412174 - 181 ZACHARY WADE ST, WINTER GARDEN, FL 34787 64 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2940
       Built: 2002
    Monthly Fee: $67
       Tax: $7,609 (2025)
    Community: Lakeview Reserve
    Single Family


    Estimated Monthly Payment: $3,989 (change assumption)
    Mortgage ($3,288) + Fees ($67) + Taxes in 2025 ($634)


    Taxes:$7,609

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16425 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787

    $435,000113 Days on yellowkey   MLS ID: O6383709

    REDUCED by $25,000 (5.4%) on 05/16/2026

    For Sale O6383709 - 16425 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1662
       Built: 2021
    Monthly Fee: $284
       Tax: $6,683 (2024)
    Community: Hawksmoor-Ph 3
    Townhouse


    Estimated Monthly Payment: $3,224 (change assumption)
    Mortgage ($2,384) + Fees ($284) + Taxes in 2024 ($557)


    Taxes:$6,683

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16217 LAKE JOHNS CIR, WINTER GARDEN, FL 34787

    $1,200,00030 Days on yellowkey   MLS ID: O6409098

    1 Days Off yellowkey (back on 5/29/2026)

    For Sale O6409098 - 16217 LAKE JOHNS CIR, WINTER GARDEN, FL 34787 65 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4659
       Built: 1973   Tax: $3,817 (2025)
    Community: Lake Johns Shores
    Single Family


    Estimated Monthly Payment: $6,893 (change assumption)
    Mortgage ($6,575) + Taxes in 2025 ($318)


    Taxes:$3,817

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $724,900102 Days on yellowkey   MLS ID: O6388830

    0 Days Off yellowkey (back on 5/1/2026)

    For Sale O6388830 - 18386 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2924
       Built: 2024
    Monthly Fee: $280
       Tax: $10,366 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,116 (change assumption)
    Mortgage ($3,972) + Fees ($280) + Taxes in 2024 ($864)


    Taxes:$10,366

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: None


  • 9508 QUIET LN, WINTER GARDEN, FL 34787

    $1,400,00029 Days on yellowkey   MLS ID: O6408432

    For Sale O6408432 - 9508 QUIET LN, WINTER GARDEN, FL 34787 42 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3728
       Built: 2001
    Monthly Fee: $17
       Tax: $9,906 (2026)
    Community: Valley View
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,514 (change assumption)
    Mortgage ($7,671) + Fees ($17) + Taxes in 2026 ($825)


    Taxes:$9,906

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2026

    Middle School: Windy Hill Middle


  • 611 SIGLER DR, WINTER GARDEN, FL 34787

    $899,7609 Days on yellowkey   MLS ID: O6415005

    For Sale O6415005 - 611 SIGLER DR, WINTER GARDEN, FL 34787 14 photos

    Bed: 4   Bath: 3.5   Gar: 22
    Liv Area Sq Ft: 2432
       Built: 2026
    Monthly Fee: $155
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Single Family


    Estimated Monthly Payment: $5,168 (change assumption)
    Mortgage ($4,930) + Fees ($155) + Taxes in 2025 ($83)


    Taxes:$993

    Elementary School: Dillard Street Elem

    High School: None

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 636 SIGLER DR, WINTER GARDEN, FL 34787

    $611,6109 Days on yellowkey   MLS ID: O6413662

    For Sale O6413662 - 636 SIGLER DR, WINTER GARDEN, FL 34787 13 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1634
       Built: 2026
    Monthly Fee: $275
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Townhouse


    Estimated Monthly Payment: $3,709 (change assumption)
    Mortgage ($3,351) + Fees ($275) + Taxes in 2025 ($83)


    Taxes:$993

    Elementary School: Dillard Street Elem

    High School: None

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14501 GROVE RESORT AVE #2101, WINTER GARDEN, FL 34787

    $460,000238 Days on yellowkey   MLS ID: O6353080

    For Sale O6353080 - 14501 GROVE RESORT AVE #2101, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1544
       Built: 2018
    Monthly Fee: $826
       Tax: $8,802 (2024)
    Community: Grove Resort And Spa Hotel Condo 1
    Condo


    Estimated Monthly Payment: $4,080 (change assumption)
    Mortgage ($2,520) + Fees ($826) + Taxes in 2024 ($734)


    Taxes:$8,802

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15456 GILLIGAN CT, WINTER GARDEN, FL 34787

    $550,000322 Days on yellowkey   MLS ID: A4660262

    REDUCED by $25,000 (4.3%) on 06/12/2026

    For Sale A4660262 - 15456 GILLIGAN CT, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2571
       Built: 2020
    Monthly Fee: $102
       Tax: $8,702 (2024)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $3,841 (change assumption)
    Mortgage ($3,014) + Fees ($102) + Taxes in 2024 ($725)


    Taxes:$8,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15121 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787

    $874,9007 Days on yellowkey   MLS ID: O6416065

    For Sale O6416065 - 15121 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787 43 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4042
       Built: 2016
    Monthly Fee: $180
       Tax: $552 (2024)
    Community: Signature Lakes Ph 3B-4
    Single Family


    Estimated Monthly Payment: $5,020 (change assumption)
    Mortgage ($4,794) + Fees ($180) + Taxes in 2024 ($46)


    Taxes:$552

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 16893 BROADWATER AVE, WINTER GARDEN, FL 34787

    $2,795,9007 Days on yellowkey   MLS ID: O6415972

    For Sale O6415972 - 16893 BROADWATER AVE, WINTER GARDEN, FL 34787 76 photos

    Bed: 7   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 6289
       Built: 2019
    Monthly Fee: $383
       Tax: $25,448 (2025)
    Community: Waterside 90'S
    Single Family


    Estimated Monthly Payment: $17,823 (change assumption)
    Mortgage ($15,320) + Fees ($383) + Taxes in 2025 ($2,121)


    Taxes:$25,448

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13303 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787

    $424,9907 Days on yellowkey   MLS ID: G5113612

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale G5113612 - 13303 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1715
       Built: 2026
    Monthly Fee: $216

    Community: Serenade At Ovation
    Townhouse


    Estimated Monthly Payment: $2,545 (change assumption)
    Mortgage ($2,329) + Fees ($216) + Taxes in 2024 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring 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.