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Winter Garden Homes For Sale & Real Estate - 727 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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  • 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


  • 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


  • 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


  • 16029 TOLLINGTON ALY, WINTER GARDEN, FL 34787

    $619,5005 Days on yellowkey   MLS ID: P4938378

    For Sale P4938378 - 16029 TOLLINGTON ALY, WINTER GARDEN, FL 34787 55 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2341
       Built: 2020
    Monthly Fee: $225
       Tax: $8,643 (2025)
    Community: Encore/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $4,340 (change assumption)
    Mortgage ($3,394) + Fees ($225) + Taxes in 2025 ($720)


    Taxes:$8,643

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 12390 CLEAR SAPPHIRE #260, WINTER GARDEN, FL 34787

    $849,99023 Days on yellowkey   MLS ID: O6394850

    For Sale O6394850 - 12390 CLEAR SAPPHIRE #260, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2552
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,753 (change assumption)
    Mortgage ($4,657) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 12438 CLEAR SAPPHIRE DR #223, WINTER GARDEN, FL 34787

    $684,99027 Days on yellowkey   MLS ID: O6393877

    REDUCED by $5,000 (0.7%) on 04/16/2026

    For Sale O6393877 - 12438 CLEAR SAPPHIRE DR #223, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $3,849 (change assumption)
    Mortgage ($3,753) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 3167 WINESAP WAY, WINTER GARDEN, FL 34787

    $575,000Listed 04/22/2026 8:01AM   MLS ID: O6400764

    For Sale O6400764 - 3167 WINESAP WAY, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2115
       Built: 2016
    Monthly Fee: $190
       Tax: $5,408 (2025)
    Community: Orchard Pk/Stillwater Xing
    Single Family


    Estimated Monthly Payment: $3,791 (change assumption)
    Mortgage ($3,151) + Fees ($190) + Taxes in 2025 ($451)


    Taxes:$5,408

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 131 OAK LAUREL DR, WINTER GARDEN, FL 34787

    $869,00096 Days on yellowkey   MLS ID: O6374501

    REDUCED by $26,000 (2.9%) on 04/06/2026

    For Sale O6374501 - 131 OAK LAUREL DR, WINTER GARDEN, FL 34787 42 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1906
       Built: 2019
    Monthly Fee: $475
       Tax: $10,586 (2025)
    Community: Park Place/Winter Garden
    Townhouse


    Estimated Monthly Payment: $6,119 (change assumption)
    Mortgage ($4,762) + Fees ($475) + Taxes in 2025 ($882)


    Taxes:$10,586

    Elementary School: Dillard Street Elem

    High School: None

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 8012 BLUEJACK OAK DR, WINTER GARDEN, FL 34787

    $549,000Listed 04/22/2026 10:36AM   MLS ID: FC317938

    For Sale FC317938 - 8012 BLUEJACK OAK DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2222
       Built: 2018
    Monthly Fee: $315
       Tax: $8,103 (2025)
    Community: Summerlake Pd Ph 2C 2D 2E
    Townhouse


    Estimated Monthly Payment: $3,998 (change assumption)
    Mortgage ($3,008) + Fees ($315) + Taxes in 2025 ($675)


    Taxes:$8,103

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787

    $929,00024 Days on yellowkey   MLS ID: O6394506

    REDUCED by $20,900 (2.2%) on 04/20/2026

    For Sale O6394506 - 1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3841
       Built: 2017
    Monthly Fee: $184
       Tax: $12,543 (2025)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $6,320 (change assumption)
    Mortgage ($5,090) + Fees ($184) + Taxes in 2025 ($1,045)


    Taxes:$12,543

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 3407 CURRENT AVE, WINTER GARDEN, FL 34787

    $699,0005 Days on yellowkey   MLS ID: O6400102

    For Sale O6400102 - 3407 CURRENT AVE, WINTER GARDEN, FL 34787 43 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3747
       Built: 2020
    Monthly Fee: $152
       Tax: $10,520 (2025)
    Community: Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $4,859 (change assumption)
    Mortgage ($3,830) + Fees ($152) + Taxes in 2025 ($877)


    Taxes:$10,520

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill 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.