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Winter Garden Homes For Sale & Real Estate - 726 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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  • 13846 FRESH IVY ST, WINTER GARDEN, FL 34787

    $649,900204 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


  • 1325 FETTLER WAY, WINTER GARDEN, FL 34787

    $289,90012 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


  • 8024 BLUEJACK OAK DR, WINTER GARDEN, FL 34787

    $490,000131 Days on yellowkey   MLS ID: O6366553

    2 Days Off yellowkey (back on 3/9/2026)

    For Sale O6366553 - 8024 BLUEJACK OAK DR, WINTER GARDEN, FL 34787 62 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1784
       Built: 2018
    Monthly Fee: $312
       Tax: $4,624 (2025)
    Community: Summerlake
    Townhouse


    Estimated Monthly Payment: $3,382 (change assumption)
    Mortgage ($2,685) + Fees ($312) + Taxes in 2025 ($385)


    Taxes:$4,624

    Elementary School: Summerlake Elementary

    High School: None

    Tax Year: 2025

    Middle School: None


  • 276 SUMMER PINE ST, WINTER GARDEN, FL 34787

    $875,00060 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

    $515,00048 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

    $515,0003 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

    $609,61165 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


  • 18173 CIDER MILL LN, WINTER GARDEN, FL 34787

    $419,990Listed 04/22/2026 1:21PM   MLS ID: O6401425

    For Sale O6401425 - 18173 CIDER MILL LN, WINTER GARDEN, FL 34787 0 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1567
       Built: 2025
    Monthly Fee: $204
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,624 (change assumption)
    Mortgage ($2,301) + Fees ($204) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16828 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $581,190Listed 04/22/2026 11:17AM   MLS ID: O6401359

    For Sale O6401359 - 16828 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2026
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,540 (change assumption)
    Mortgage ($3,185) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12513 SCARLETT SAGE CT, WINTER GARDEN, FL 34787

    $875,000Listed 04/22/2026 11:09AM   MLS ID: O6393138

    For Sale O6393138 - 12513 SCARLETT SAGE CT, WINTER GARDEN, FL 34787 45 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3570
       Built: 2001
    Monthly Fee: $104
       Tax: $9,264 (2025)
    Community: Cambridge Crossing Ph 01A 45/21
    Single Family


    Estimated Monthly Payment: $5,670 (change assumption)
    Mortgage ($4,794) + Fees ($104) + Taxes in 2025 ($772)


    Taxes:$9,264

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9008 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $824,950275 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


  • 9849 LOST CREEK DR, WINTER GARDEN, FL 34787

    $990,000517 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


  • 10031 MEMOIR AVE, WINTER GARDEN, FL 34787

    $415,0008 Days on yellowkey   MLS ID: O6399210

    For Sale O6399210 - 10031 MEMOIR AVE, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1636
       Built: 2018
    Monthly Fee: $268
       Tax: $5,910 (2025)
    Community: Storey Grove Ph 1B-1
    Townhouse


    Estimated Monthly Payment: $3,034 (change assumption)
    Mortgage ($2,274) + Fees ($268) + Taxes in 2025 ($493)


    Taxes:$5,910

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14014 LANYARD WAY, WINTER GARDEN, FL 34787

    $778,206Listed 04/21/2026 5:35PM   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

    $455,000139 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

    $775,000172 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


  • 15524 AVIATION ALY, WINTER GARDEN, FL 34787

    $570,00011 Days on yellowkey   MLS ID: O6398331

    INCREASED by $100 (0.0%) on 04/22/2026

    For Sale O6398331 - 15524 AVIATION ALY, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2414
       Built: 2015
    Monthly Fee: $328
       Tax: $8,711 (2025)
    Community: Overlook 2/Hamlin Ph 1 & 6
    Single Family


    Estimated Monthly Payment: $4,177 (change assumption)
    Mortgage ($3,123) + Fees ($328) + Taxes in 2025 ($726)


    Taxes:$8,711

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14280 BRAEMAR ST, WINTER GARDEN, FL 34787

    $559,900Listed 04/22/2026 11:50AM   MLS ID: TB8500322

    For Sale TB8500322 - 14280 BRAEMAR ST, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2023
    Monthly Fee: $100
       Tax: $7,928 (2025)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,829 (change assumption)
    Mortgage ($3,068) + Fees ($100) + Taxes in 2025 ($661)


    Taxes:$7,928

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14645 SCOTT KEY DR, WINTER GARDEN, FL 34787

    $890,00096 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

    $2,445,000Listed 04/21/2026 7:35PM   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.