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Winter Garden Homes For Sale & Real Estate - 965 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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  • 12042 GRANDROSE ALY, WINTER GARDEN, FL 34787

    $420,00041 Days on yellowkey   MLS ID: S5152170

    For Sale S5152170 - 12042 GRANDROSE ALY, WINTER GARDEN, FL 34787 21 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1732
       Built: 2022
    Monthly Fee: $320
       Tax: $4,111 (2025)
    Community: Winding Bay Ph 2
    Townhouse


    Estimated Monthly Payment: $2,964 (change assumption)
    Mortgage ($2,301) + Fees ($320) + Taxes in 2025 ($343)


    Taxes:$4,111

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13552 AUTUMN HARVEST AVE, WINTER GARDEN, FL 34787

    $515,00081 Days on yellowkey   MLS ID: O6404264

    REDUCED by $15,000 (2.8%) on 06/19/2026

    For Sale O6404264 - 13552 AUTUMN HARVEST AVE, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1955
       Built: 2025
    Monthly Fee: $343
       Tax: $2,022 (2025)
    Community: Harvest/Ovation
    Townhouse


    Estimated Monthly Payment: $3,333 (change assumption)
    Mortgage ($2,822) + Fees ($343) + Taxes in 2025 ($169)


    Taxes:$2,022

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9362 WOODCRANE DR, WINTER GARDEN, FL 34787

    $459,30043 Days on yellowkey   MLS ID: O6417277

    SHORT SALE O6417277 - 9362 WOODCRANE DR, WINTER GARDEN, FL 34787 8 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2058
       Built: 2015
    Monthly Fee: $151
       Tax: $7,210 (2025)
    Community: Watermark Ph 1B
    Single Family


    Estimated Monthly Payment: $3,268 (change assumption)
    Mortgage ($2,517) + Fees ($151) + Taxes in 2025 ($601)


    Taxes:$7,210

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13722 FOX GLOVE ST, WINTER GARDEN, FL 34787

    $755,000204 Days on yellowkey   MLS ID: O6371378

    0 Days Off yellowkey (back on 6/18/2026)

    REDUCED by $4,990 (0.7%) on 06/01/2026

    For Sale O6371378 - 13722 FOX GLOVE ST, WINTER GARDEN, FL 34787 56 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3082
       Built: 2004
    Monthly Fee: $247
       Tax: $10,614 (2024)
    Community: Stoneybrook West Ut 04 48 48
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,268 (change assumption)
    Mortgage ($4,137) + Fees ($247) + Taxes in 2024 ($885)


    Taxes:$10,614

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 11 WINDTREE LN #B, WINTER GARDEN, FL 34787

    $195,00071 Days on yellowkey   MLS ID: O6409169

    1 Days Off yellowkey (back on 6/18/2026)

    For Sale O6409169 - 11 WINDTREE LN #B, WINTER GARDEN, FL 34787 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1983
    Monthly Fee: $300
       Tax: $2,664 (2025)
    Community: Windtree Gardens Condo Ph 01
    Condo


    Estimated Monthly Payment: $1,590 (change assumption)
    Mortgage ($1,068) + Fees ($300) + Taxes in 2025 ($222)


    Taxes:$2,664

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 214 S WOODLAND ST, WINTER GARDEN, FL 34787

    $800,00056 Days on yellowkey   MLS ID: O6413395

    For Sale O6413395 - 214 S WOODLAND ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2868
       Built: 1925   Tax: $2,450 (2025)
    Community: Fries Winter Garden
    Single Family


    Estimated Monthly Payment: $4,588 (change assumption)
    Mortgage ($4,383) + Taxes in 2025 ($204)


    Taxes:$2,450

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 9849 LOST CREEK DR, WINTER GARDEN, FL 34787

    $990,000615 Days on yellowkey   MLS ID: O6258009

    1 Days Off yellowkey (back on 6/18/2026)

    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


  • 811 CIVITAS WAY, WINTER GARDEN, FL 34787

    $2,199,00075 Days on yellowkey   MLS ID: O6403760

    REDUCED by $51,000 (2.3%) on 06/18/2026

    For Sale O6403760 - 811 CIVITAS WAY, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 5138
       Built: 2017
    Monthly Fee: $208
       Tax: $24,126 (2025)
    Community: Oakland Park Un # 2A
    Single Family


    Estimated Monthly Payment: $14,268 (change assumption)
    Mortgage ($12,049) + Fees ($208) + Taxes in 2025 ($2,011)


    Taxes:$24,126

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 13706 WERRINGTON DR, WINTER GARDEN, FL 34787

    $715,000265 Days on yellowkey   MLS ID: S5138020

    For Sale S5138020 - 13706 WERRINGTON DR, WINTER GARDEN, FL 34787 77 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2807
       Built: 2022
    Monthly Fee: $192
       Tax: $8,345 (2023)
    Community: Encore At Ovation-Ph 3
    Single Family


    Estimated Monthly Payment: $4,805 (change assumption)
    Mortgage ($3,918) + Fees ($192) + Taxes in 2023 ($695)


    Taxes:$8,345

    Elementary School: Water Spring Elementary

    High School: None

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 16175 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787

    $920,308265 Days on yellowkey   MLS ID: G5104189

    0 Days Off yellowkey (back on 11/6/2025)

    For Sale G5104189 - 16175 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3108
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $5,193 (change assumption)
    Mortgage ($5,043) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13392 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787

    $764,99046 Days on yellowkey   MLS ID: G5113739

    0 Days Off yellowkey (back on 6/17/2026)

    For Sale G5113739 - 13392 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787 26 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3076
       Built: 2026
    Monthly Fee: $160

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $4,352 (change assumption)
    Mortgage ($4,192) + Fees ($160) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: None


  • 17066 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $765,377134 Days on yellowkey   MLS ID: G5109739

    0 Days Off yellowkey (back on 6/17/2026)

    For Sale G5109739 - 17066 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3038
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,316 (change assumption)
    Mortgage ($4,194) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 11117 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $507,00076 Days on yellowkey   MLS ID: O6407552

    REDUCED by $13,000 (2.5%) on 06/17/2026

    For Sale O6407552 - 11117 BOSTWICK ALY, WINTER GARDEN, FL 34787 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1685
       Built: 2022
    Monthly Fee: $291
       Tax: $6,722 (2025)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $3,629 (change assumption)
    Mortgage ($2,778) + Fees ($291) + Taxes in 2025 ($560)


    Taxes:$6,722

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15327 HERON HIDEAWAY CIR, WINTER GARDEN, FL 34787

    $885,000172 Days on yellowkey   MLS ID: G5107891

    REDUCED by $30,000 (3.3%) on 06/17/2026

    For Sale G5107891 - 15327 HERON HIDEAWAY CIR, WINTER GARDEN, FL 34787 96 photos

    Bed: 7   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4267
       Built: 2012
    Monthly Fee: $128
       Tax: $11,470 (2025)
    Community: Johns Lake Pointe A & S
    Single Family


    Estimated Monthly Payment: $5,933 (change assumption)
    Mortgage ($4,849) + Fees ($128) + Taxes in 2025 ($956)


    Taxes:$11,470

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15138 SHONAN GOLD DR, WINTER GARDEN, FL 34787

    $2,799,95043 Days on yellowkey   MLS ID: O6417357

    For Sale O6417357 - 15138 SHONAN GOLD DR, WINTER GARDEN, FL 34787 94 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 5551
       Built: 2019
    Monthly Fee: $230
       Tax: $35,838 (2025)
    Community: Overlook 2/Hamlin Ph 3 & 4
    Spa: No

    Single Family


    Estimated Monthly Payment: $18,558 (change assumption)
    Mortgage ($15,342) + Fees ($230) + Taxes in 2025 ($2,987)


    Taxes:$35,838

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6225 FLOWERING CHERRY BEND DR, WINTER GARDEN, FL 34787

    $846,09543 Days on yellowkey   MLS ID: G5113896

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

    For Sale G5113896 - 6225 FLOWERING CHERRY BEND DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3412
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,786 (change assumption)
    Mortgage ($4,636) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15367 GILLIGAN CT, WINTER GARDEN, FL 34787

    $590,00044 Days on yellowkey   MLS ID: O6417175

    For Sale O6417175 - 15367 GILLIGAN CT, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2156
       Built: 2020
    Monthly Fee: $300
       Tax: $7,397 (2025)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $4,149 (change assumption)
    Mortgage ($3,233) + Fees ($300) + Taxes in 2025 ($616)


    Taxes:$7,397

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14501 GROVE RESORT AVE #1726, WINTER GARDEN, FL 34787

    $174,99943 Days on yellowkey   MLS ID: S5151998

    For Sale S5151998 - 14501 GROVE RESORT AVE #1726, WINTER GARDEN, FL 34787 40 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1265
       Built: 2016
    Monthly Fee: $904
       Tax: $6,319 (2025)
    Community: The Grove Resort And Spa
    Condo


    Estimated Monthly Payment: $2,389 (change assumption)
    Mortgage ($959) + Fees ($904) + Taxes in 2025 ($527)


    Taxes:$6,319

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14501 GROVE RESORT AVE #2528, WINTER GARDEN, FL 34787

    $229,000224 Days on yellowkey   MLS ID: O6361791

    INCREASED by $30,000 (15.1%) on 05/29/2026

    FORECLOSURE O6361791 - 14501 GROVE RESORT AVE #2528, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1544
       Built: 2009   Tax: $8,631 (2025)
    Community: Grove Resort And Spa Hotel Condo 1
    Condo


    Estimated Monthly Payment: $1,974 (change assumption)
    Mortgage ($1,255) + Taxes in 2025 ($719)


    Taxes:$8,631

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 113 W DIVISION ST, WINTER GARDEN, FL 34787

    $525,99092 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




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.