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Winter Garden Single Family Homes For Sale - 727 homes

Winter Garden Single Family Homes for Sale are located in Orange County, Florida. Find single family homes for sale in Winter Garden with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Garden single family houses.

Location: Winter Garden

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  • 944 KYLEE ALY, WINTER GARDEN, FL 34787

    $779,9006 Days on yellowkey   MLS ID: O6425976

    0 Days Off yellowkey (back on 7/20/2026)

    For Sale O6425976 - 944 KYLEE ALY, WINTER GARDEN, FL 34787 60 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2831
       Built: 2022
    Monthly Fee: $401
       Tax: $11,438 (2026)
    Community: Oakland Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,627 (change assumption)
    Mortgage ($4,273) + Fees ($401) + Taxes in 2026 ($953)


    Taxes:$11,438

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2026

    Middle School: Lakeview Middle


  • 13019 SERENE GLADE RD, WINTER GARDEN, FL 34787

    $549,99042 Days on yellowkey   MLS ID: G5113698

    REDUCED by $20,000 (3.5%) on 06/17/2026

    For Sale G5113698 - 13019 SERENE GLADE RD, WINTER GARDEN, FL 34787 61 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2078
       Built: 2026
    Monthly Fee: $121

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $3,135 (change assumption)
    Mortgage ($3,014) + Fees ($121) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5320 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787

    $695,9909 Days on yellowkey   MLS ID: O6424081

    For Sale O6424081 - 5320 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787 67 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3366
       Built: 2024
    Monthly Fee: $176
       Tax: $10,233 (2025)
    Community: Lakeside/Hamlin
    Single Family


    Estimated Monthly Payment: $4,842 (change assumption)
    Mortgage ($3,814) + Fees ($176) + Taxes in 2025 ($853)


    Taxes:$10,233

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1642 CHANDELLE LN, WINTER GARDEN, FL 34787

    $689,90023 Days on yellowkey   MLS ID: G5114093

    REDUCED by $20,000 (2.8%) on 07/20/2026

    For Sale G5114093 - 1642 CHANDELLE LN, WINTER GARDEN, FL 34787 46 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2918
       Built: 2006
    Monthly Fee: $167
       Tax: $8,474 (2025)
    Community: Belle Meade-Ph I B D & G
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,653 (change assumption)
    Mortgage ($3,780) + Fees ($167) + Taxes in 2025 ($706)


    Taxes:$8,474

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14629 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $484,90022 Days on yellowkey   MLS ID: O6421797

    REDUCED by $8,000 (1.6%) on 07/20/2026

    For Sale O6421797 - 14629 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2223
       Built: 2012
    Monthly Fee: $242
       Tax: $8,151 (2025)
    Community: Summerlake Pd Ph 01B
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,578 (change assumption)
    Mortgage ($2,657) + Fees ($242) + Taxes in 2025 ($679)


    Taxes:$8,151

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787

    $549,90071 Days on yellowkey   MLS ID: O6408082

    REDUCED by $15,100 (2.7%) on 07/20/2026

    For Sale O6408082 - 14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787 17 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2258
       Built: 2004
    Monthly Fee: $253
       Tax: $8,397 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,966 (change assumption)
    Mortgage ($3,013) + Fees ($253) + Taxes in 2025 ($700)


    Taxes:$8,397

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 11031 JACKSON CV, WINTER GARDEN, FL 34787

    $715,0008 Days on yellowkey   MLS ID: O6425544

    For Sale O6425544 - 11031 JACKSON CV, WINTER GARDEN, FL 34787 70 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2023
    Monthly Fee: $300
       Tax: $10,935 (2025)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,129 (change assumption)
    Mortgage ($3,918) + Fees ($300) + Taxes in 2025 ($911)


    Taxes:$10,935

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1503 COLUSO DR, WINTER GARDEN, FL 34787

    $443,00062 Days on yellowkey   MLS ID: O6410109

    REDUCED by $20,000 (4.3%) on 07/17/2026

    For Sale O6410109 - 1503 COLUSO DR, WINTER GARDEN, FL 34787 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2187
       Built: 1988   Tax: $1,952 (2025)
    Community: Magnolia Wood Fifth Add
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,590 (change assumption)
    Mortgage ($2,427) + Taxes in 2025 ($163)


    Taxes:$1,952

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15411 GILLIGAN CT, WINTER GARDEN, FL 34787

    $559,90030 Days on yellowkey   MLS ID: O6418437

    REDUCED by $10,000 (1.8%) on 07/20/2026

    For Sale O6418437 - 15411 GILLIGAN CT, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2152
       Built: 2021
    Monthly Fee: $104
       Tax: $6,721 (2025)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $3,732 (change assumption)
    Mortgage ($3,068) + Fees ($104) + Taxes in 2025 ($560)


    Taxes:$6,721

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $875,00053 Days on yellowkey   MLS ID: O6412033

    REDUCED by $75,000 (7.9%) on 07/20/2026

    For Sale O6412033 - 6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3777
       Built: 2016
    Monthly Fee: $195
       Tax: $11,678 (2025)
    Community: Signature Lakes Ph 3B-4 3B-5 & 3
    Single Family


    Estimated Monthly Payment: $5,963 (change assumption)
    Mortgage ($4,794) + Fees ($195) + Taxes in 2025 ($973)


    Taxes:$11,678

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 16044 CITRUS KNOLL DR, WINTER GARDEN, FL 34787

    $1,100,00022 Days on yellowkey   MLS ID: O6419284

    For Sale O6419284 - 16044 CITRUS KNOLL DR, WINTER GARDEN, FL 34787 90 photos

    Bed: 5   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 3617
       Built: 2016
    Monthly Fee: $235
       Tax: $13,692 (2025)
    Community: Hickory Hammock Ph 1D
    Single Family


    Estimated Monthly Payment: $7,403 (change assumption)
    Mortgage ($6,027) + Fees ($235) + Taxes in 2025 ($1,141)


    Taxes:$13,692

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14511 ISLEVIEW DR, WINTER GARDEN, FL 34787

    $3,330,00086 Days on yellowkey   MLS ID: O6403188

    3 Days Off yellowkey (back on 7/20/2026)

    For Sale O6403188 - 14511 ISLEVIEW DR, WINTER GARDEN, FL 34787 65 photos

    Bed: 6   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 5290
       Built: 2001
    Monthly Fee: $300
       Tax: $32,571 (2025)
    Community: Isles Lake Hancock
    Single Family


    Estimated Monthly Payment: $21,260 (change assumption)
    Mortgage ($18,246) + Fees ($300) + Taxes in 2025 ($2,714)


    Taxes:$32,571

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13092 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787

    $850,00036 Days on yellowkey   MLS ID: O6417386

    For Sale O6417386 - 13092 SUNRISE HARVEST DR, WINTER GARDEN, FL 34787 44 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2993
       Built: 2024
    Monthly Fee: $140
       Tax: $9,934 (2025)
    Community: Harvest/Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,625 (change assumption)
    Mortgage ($4,657) + Fees ($140) + Taxes in 2025 ($828)


    Taxes:$9,934

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9606 WOODCRANE DR, WINTER GARDEN, FL 34787

    $525,00063 Days on yellowkey   MLS ID: O6410113

    2 Days Off yellowkey (back on 7/20/2026)

    For Sale O6410113 - 9606 WOODCRANE DR, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2101
       Built: 2017
    Monthly Fee: $164
       Tax: $5,079 (2025)
    Community: Watermark Ph 2B
    Single Family


    Estimated Monthly Payment: $3,464 (change assumption)
    Mortgage ($2,877) + Fees ($164) + Taxes in 2025 ($423)


    Taxes:$5,079

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 46 W VINING ST, WINTER GARDEN, FL 34787

    $544,90067 Days on yellowkey   MLS ID: O6408720

    REDUCED by $5,000 (0.9%) on 07/20/2026

    For Sale O6408720 - 46 W VINING ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1273
       Built: 1938   Tax: $6,287 (2025)
    Community: Ellman Park
    Single Family


    Estimated Monthly Payment: $3,510 (change assumption)
    Mortgage ($2,986) + Taxes in 2025 ($524)


    Taxes:$6,287

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 17035 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $485,00053 Days on yellowkey   MLS ID: O6411409

    REDUCED by $14,999 (3.0%) on 07/20/2026

    For Sale O6411409 - 17035 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1692
       Built: 2017
    Monthly Fee: $215
       Tax: $3,704 (2025)
    Community: Waterside/Johns Lake Ph 2A
    Single Family


    Estimated Monthly Payment: $3,181 (change assumption)
    Mortgage ($2,657) + Fees ($215) + Taxes in 2025 ($309)


    Taxes:$3,704

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 729 MEADOW GLADE DR, WINTER GARDEN, FL 34787

    $525,00071 Days on yellowkey   MLS ID: O6407943

    REDUCED by $4,000 (0.8%) on 06/16/2026

    For Sale O6407943 - 729 MEADOW GLADE DR, WINTER GARDEN, FL 34787 59 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2011
    Monthly Fee: $72
       Tax: $3,138 (2025)
    Community: Covington Park A B D E F G & J
    Single Family


    Estimated Monthly Payment: $3,210 (change assumption)
    Mortgage ($2,877) + Fees ($72) + Taxes in 2025 ($262)


    Taxes:$3,138

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15187 HARROWGATE WAY, WINTER GARDEN, FL 34787

    $425,00099 Days on yellowkey   MLS ID: TB8497081

    REDUCED by $10,000 (2.3%) on 07/20/2026

    For Sale TB8497081 - 15187 HARROWGATE WAY, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1296
       Built: 2003
    Monthly Fee: $46
       Tax: $5,808 (2025)
    Community: Stone Crk
    Single Family


    Estimated Monthly Payment: $2,859 (change assumption)
    Mortgage ($2,329) + Fees ($46) + Taxes in 2025 ($484)


    Taxes:$5,808

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9611 LOST CREEK DR, WINTER GARDEN, FL 34787

    $745,000191 Days on yellowkey   MLS ID: O6373845

    REDUCED by $20,000 (2.6%) on 07/20/2026

    For Sale O6373845 - 9611 LOST CREEK DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2909
       Built: 2021
    Monthly Fee: $260
       Tax: $11,300 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $5,284 (change assumption)
    Mortgage ($4,082) + Fees ($260) + Taxes in 2025 ($942)


    Taxes:$11,300

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787

    $765,00021 Days on yellowkey   MLS ID: S5152807

    0 Days Off yellowkey (back on 7/10/2026)

    For Sale S5152807 - 15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787 61 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3902
       Built: 2005
    Monthly Fee: $243
       Tax: $8,428 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,137 (change assumption)
    Mortgage ($4,192) + Fees ($243) + Taxes in 2025 ($702)


    Taxes:$8,428

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle




Why Bother Searching Elsewhere for Winter Garden Single Family Homes for Sale?

Winter Garden home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden single family homes. 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 single family home 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.