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Winter Garden Homes For Sale & Real Estate - 758 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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  • 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $750,00010 Days on yellowkey   MLS ID: O6398720

    For Sale O6398720 - 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3747
       Built: 2000
    Monthly Fee: $90
       Tax: $10,152 (2025)
    Community: Wintermere Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,045 (change assumption)
    Mortgage ($4,109) + Fees ($90) + Taxes in 2025 ($846)


    Taxes:$10,152

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1325 FETTLER WAY, WINTER GARDEN, FL 34787

    $289,90014 Days on yellowkey   MLS ID: O6393936

    For Sale O6393936 - 1325 FETTLER WAY, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1440
       Built: 2004
    Monthly Fee: $61
       Tax: $3,653 (2025)
    Community: Westside Twnhms-Ph 05 A B & C
    Townhouse


    Estimated Monthly Payment: $1,954 (change assumption)
    Mortgage ($1,588) + Fees ($61) + Taxes in 2025 ($304)


    Taxes:$3,653

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16396 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787

    $484,99014 Days on yellowkey   MLS ID: O6396532

    For Sale O6396532 - 16396 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2021
    Monthly Fee: $286
       Tax: $7,102 (2025)
    Community: Hawksmoor Ph 3
    Townhouse


    Estimated Monthly Payment: $3,535 (change assumption)
    Mortgage ($2,657) + Fees ($286) + Taxes in 2025 ($592)


    Taxes:$7,102

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 2478 PRAIRIE VIEW DR, WINTER GARDEN, FL 34787

    $499,9003 Days on yellowkey   MLS ID: O6400594

    For Sale O6400594 - 2478 PRAIRIE VIEW DR, WINTER GARDEN, FL 34787 21 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2766
       Built: 2002
    Monthly Fee: $90
       Tax: $8,172 (2025)
    Community: Wintermere Pointe Ph 02 46/141
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,510 (change assumption)
    Mortgage ($2,739) + Fees ($90) + Taxes in 2025 ($681)


    Taxes:$8,172

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14971 APOLLO BOND DR, WINTER GARDEN, FL 34787

    $414,900247 Days on yellowkey   MLS ID: O6337468

    For Sale O6337468 - 14971 APOLLO BOND DR, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1655
       Built: 2019
    Monthly Fee: $253
       Tax: $6,577 (2025)
    Community: Watermark Ph 3
    Townhouse


    Estimated Monthly Payment: $3,074 (change assumption)
    Mortgage ($2,273) + Fees ($253) + Taxes in 2025 ($548)


    Taxes:$6,577

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 10693 PETRILLO WAY, WINTER GARDEN, FL 34787

    $799,0008 Days on yellowkey   MLS ID: O6399081

    For Sale O6399081 - 10693 PETRILLO WAY, WINTER GARDEN, FL 34787 60 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3149
       Built: 2021
    Monthly Fee: $102
       Tax: $8,845 (2025)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $5,217 (change assumption)
    Mortgage ($4,378) + Fees ($102) + Taxes in 2025 ($737)


    Taxes:$8,845

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15401 PORTER RD, WINTER GARDEN, FL 34787

    $558,000115 Days on yellowkey   MLS ID: S5140743

    For Sale S5140743 - 15401 PORTER RD, WINTER GARDEN, FL 34787 59 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2455
       Built: 2015
    Monthly Fee: $242
       Tax: $8,271 (2024)
    Community: Summerlake
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,989 (change assumption)
    Mortgage ($3,057) + Fees ($242) + Taxes in 2024 ($689)


    Taxes:$8,271

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


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

    $195,000139 Days on yellowkey   MLS ID: O6365343

    REDUCED by $4,900 (2.5%) on 04/20/2026

    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: $1,582 (change assumption)
    Mortgage ($1,068) + 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


  • 2621 SHIREHALL LN, WINTER GARDEN, FL 34787

    $475,00049 Days on yellowkey   MLS ID: O6386585

    REDUCED by $25,000 (5.0%) on 04/17/2026

    For Sale O6386585 - 2621 SHIREHALL LN, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2003
    Monthly Fee: $243
       Tax: $3,181 (2024)
    Community: Stoneybrook West Ut 04 48 48
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,111 (change assumption)
    Mortgage ($2,603) + Fees ($243) + Taxes in 2024 ($265)


    Taxes:$3,181

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 650 SETTING SUN DR, WINTER GARDEN, FL 34787

    $740,00037 Days on yellowkey   MLS ID: O6390644

    1 Days Off yellowkey (back on 4/22/2026)

    For Sale O6390644 - 650 SETTING SUN DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3605
       Built: 2006
    Monthly Fee: $123
       Tax: $9,067 (2025)
    Community: Black Lake Park Ph 01
    Single Family


    Estimated Monthly Payment: $4,933 (change assumption)
    Mortgage ($4,055) + Fees ($123) + Taxes in 2025 ($756)


    Taxes:$9,067

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 276 SUMMER PINE ST, WINTER GARDEN, FL 34787

    $875,00062 Days on yellowkey   MLS ID: O6384565

    REDUCED by $5,000 (0.6%) on 04/22/2026

    For Sale O6384565 - 276 SUMMER PINE ST, WINTER GARDEN, FL 34787 25 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3147
       Built: 2025
    Monthly Fee: $240
       Tax: $1,914 (2024)
    Community: Winter Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,194 (change assumption)
    Mortgage ($4,794) + Fees ($240) + Taxes in 2024 ($160)


    Taxes:$1,914

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 16242 OUTLOOK SHORE ALY, WINTER GARDEN, FL 34787

    $515,00050 Days on yellowkey   MLS ID: O6388026

    For Sale O6388026 - 16242 OUTLOOK SHORE ALY, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2014
       Built: 2018
    Monthly Fee: $257
       Tax: $7,296 (2024)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $3,687 (change assumption)
    Mortgage ($2,822) + Fees ($257) + Taxes in 2024 ($608)


    Taxes:$7,296

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16749 HARPER COVE DR, WINTER GARDEN, FL 34787

    $515,0005 Days on yellowkey   MLS ID: O6400511

    For Sale O6400511 - 16749 HARPER COVE DR, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2014
       Built: 2019
    Monthly Fee: $257
       Tax: $7,287 (2024)
    Community: Waterleigh Ph 2C-1
    Single Family


    Estimated Monthly Payment: $3,686 (change assumption)
    Mortgage ($2,822) + Fees ($257) + Taxes in 2024 ($607)


    Taxes:$7,287

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $609,61167 Days on yellowkey   MLS ID: G5108288

    0 Days Off yellowkey (back on 4/7/2026)

    For Sale G5108288 - 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2520
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,462 (change assumption)
    Mortgage ($3,340) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9008 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $824,950277 Days on yellowkey   MLS ID: O6328849

    For Sale O6328849 - 9008 SONOMA COAST DR, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2348
       Built: 2022
    Monthly Fee: $258
       Tax: $10,553 (2024)
    Community: Waterleigh Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $5,658 (change assumption)
    Mortgage ($4,520) + Fees ($258) + Taxes in 2024 ($879)


    Taxes:$10,553

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 14014 LANYARD WAY, WINTER GARDEN, FL 34787

    $778,2063 Days on yellowkey   MLS ID: G5111358

    0 Days Off yellowkey (back on 4/21/2026)

    For Sale G5111358 - 14014 LANYARD WAY, WINTER GARDEN, FL 34787 3 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3076
       Built: 2026
    Monthly Fee: $160

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $4,424 (change assumption)
    Mortgage ($4,264) + Fees ($160) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: None


  • 12036 HOLYSTONE ST, WINTER GARDEN, FL 34787

    $455,000141 Days on yellowkey   MLS ID: S5139531

    For Sale S5139531 - 12036 HOLYSTONE ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2022
    Monthly Fee: $256
       Tax: $6,116 (2024)
    Community: Waterleigh Ph 4A
    Townhouse


    Estimated Monthly Payment: $3,259 (change assumption)
    Mortgage ($2,493) + Fees ($256) + Taxes in 2024 ($510)


    Taxes:$6,116

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14372 SUNBRIDGE CIR, WINTER GARDEN, FL 34787

    $775,000174 Days on yellowkey   MLS ID: O6356579

    For Sale O6356579 - 14372 SUNBRIDGE CIR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3468
       Built: 2016
    Monthly Fee: $166
       Tax: $5,745 (2023)
    Community: Bradford Crk Ph Ii
    Single Family


    Estimated Monthly Payment: $4,891 (change assumption)
    Mortgage ($4,246) + Fees ($166) + Taxes in 2023 ($479)


    Taxes:$5,745

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2023

    Middle School: SunRidge Middle


  • 14645 SCOTT KEY DR, WINTER GARDEN, FL 34787

    $890,00098 Days on yellowkey   MLS ID: G5106818

    0 Days Off yellowkey (back on 4/21/2026)

    For Sale G5106818 - 14645 SCOTT KEY DR, WINTER GARDEN, FL 34787 72 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3427
       Built: 2016   Tax: $10,465 (2024)
    Community: Watermark Ph 1B
    Single Family


    Estimated Monthly Payment: $5,749 (change assumption)
    Mortgage ($4,877) + Taxes in 2024 ($872)


    Taxes:$10,465

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 7460 JOHN HANCOCK DR, WINTER GARDEN, FL 34787

    $2,445,0003 Days on yellowkey   MLS ID: O6400891

    For Sale O6400891 - 7460 JOHN HANCOCK DR, WINTER GARDEN, FL 34787 89 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4817
       Built: 2020
    Monthly Fee: $210
       Tax: $17,060 (2025)
    Community: Overlook At Hamlin
    Single Family


    Estimated Monthly Payment: $15,029 (change assumption)
    Mortgage ($13,397) + Fees ($210) + Taxes in 2025 ($1,422)


    Taxes:$17,060

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater 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.