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Winter Garden Single Family Homes For Sale - 520 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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  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $590,000231 Days on yellowkey   MLS ID: O6337436

    For Sale O6337436 - 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787 89 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2292
       Built: 2023
    Monthly Fee: $245
       Tax: $9,031 (2024)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $4,230 (change assumption)
    Mortgage ($3,233) + Fees ($245) + Taxes in 2024 ($753)


    Taxes:$9,031

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15852 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $779,000148 Days on yellowkey   MLS ID: O6361580

    REDUCED by $20,000 (2.5%) on 04/15/2026

    For Sale O6361580 - 15852 SHOREBIRD LN, WINTER GARDEN, FL 34787 71 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2766
       Built: 2019
    Monthly Fee: $385
       Tax: $10,928 (2024)
    Community: Lakeshore Preserve Ph 5
    Single Family


    Estimated Monthly Payment: $5,564 (change assumption)
    Mortgage ($4,268) + Fees ($385) + Taxes in 2024 ($911)


    Taxes:$10,928

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 17458 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $625,5807 Days on yellowkey   MLS ID: G5110835

    0 Days Off yellowkey (back on 4/9/2026)

    For Sale G5110835 - 17458 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2235
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,578 (change assumption)
    Mortgage ($3,428) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16143 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787

    $875,59580 Days on yellowkey   MLS ID: G5107301

    0 Days Off yellowkey (back on 1/26/2026)

    For Sale G5107301 - 16143 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,948 (change assumption)
    Mortgage ($4,798) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $725,00049 Days on yellowkey   MLS ID: O6386008

    For Sale O6386008 - 18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 37 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2832
       Built: 2023
    Monthly Fee: $281
       Tax: $497 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,295 (change assumption)
    Mortgage ($3,973) + Fees ($281) + Taxes in 2024 ($41)


    Taxes:$497

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15456 GILLIGAN CT, WINTER GARDEN, FL 34787

    $620,000259 Days on yellowkey   MLS ID: A4660262

    REDUCED by $5,000 (0.8%) on 04/15/2026

    For Sale A4660262 - 15456 GILLIGAN CT, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2571
       Built: 2020
    Monthly Fee: $102
       Tax: $8,702 (2024)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $4,224 (change assumption)
    Mortgage ($3,397) + Fees ($102) + Taxes in 2024 ($725)


    Taxes:$8,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17222 DANCY ORANGE CT, WINTER GARDEN, FL 34787

    $965,00055 Days on yellowkey   MLS ID: O6383910

    REDUCED by $25,000 (2.5%) on 04/06/2026

    For Sale O6383910 - 17222 DANCY ORANGE CT, WINTER GARDEN, FL 34787 56 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3787
       Built: 2023
    Monthly Fee: $83
       Tax: $11,862 (2024)
    Community: Northlake/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $6,359 (change assumption)
    Mortgage ($5,288) + Fees ($83) + Taxes in 2024 ($989)


    Taxes:$11,862

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 1021 TEMPLE GROVE PL, WINTER GARDEN, FL 34787

    $1,995,00043 Days on yellowkey   MLS ID: O6387876

    For Sale O6387876 - 1021 TEMPLE GROVE PL, WINTER GARDEN, FL 34787 59 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3185
       Built: 2020   Tax: $17,100 (2025)
    Community: Emerald Acres
    Single Family


    Estimated Monthly Payment: $12,356 (change assumption)
    Mortgage ($10,931) + Taxes in 2025 ($1,425)


    Taxes:$17,100

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13813 PEACH ORCHARD WAY, WINTER GARDEN, FL 34787

    $850,0009 Days on yellowkey   MLS ID: O6392351

    For Sale O6392351 - 13813 PEACH ORCHARD WAY, WINTER GARDEN, FL 34787 40 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3793
       Built: 2018
    Monthly Fee: $190
       Tax: $7,249 (2025)
    Community: Orchard Pk/Stillwater Xing Ph
    Single Family


    Estimated Monthly Payment: $5,452 (change assumption)
    Mortgage ($4,657) + Fees ($190) + Taxes in 2025 ($604)


    Taxes:$7,249

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 16137 WIND VIEW LN, WINTER GARDEN, FL 34787

    $575,000236 Days on yellowkey   MLS ID: O6335769

    REDUCED by $14,000 (2.4%) on 04/13/2026

    For Sale O6335769 - 16137 WIND VIEW LN, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2016
    Monthly Fee: $283
       Tax: $6,800 (2024)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,000 (change assumption)
    Mortgage ($3,151) + Fees ($283) + Taxes in 2024 ($567)


    Taxes:$6,800

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 14571 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $519,900119 Days on yellowkey   MLS ID: O6368387

    For Sale O6368387 - 14571 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2063
       Built: 2012
    Monthly Fee: $251
       Tax: $7,507 (2024)
    Community: Summerlake Pd Ph 01A
    Single Family


    Estimated Monthly Payment: $3,725 (change assumption)
    Mortgage ($2,849) + Fees ($251) + Taxes in 2024 ($626)


    Taxes:$7,507

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 15393 SANDFIELD LOOP, WINTER GARDEN, FL 34787

    $935,00017 Days on yellowkey   MLS ID: O6391325

    REDUCED by $50,000 (5.1%) on 04/15/2026

    For Sale O6391325 - 15393 SANDFIELD LOOP, WINTER GARDEN, FL 34787 60 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4303
       Built: 2014
    Monthly Fee: $114
       Tax: $7,809 (2025)
    Community: Reserve At Carriage Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,888 (change assumption)
    Mortgage ($5,123) + Fees ($114) + Taxes in 2025 ($651)


    Taxes:$7,809

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 813 MARSH REED DR, WINTER GARDEN, FL 34787

    $609,000296 Days on yellowkey   MLS ID: O6321149

    For Sale O6321149 - 813 MARSH REED DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3148
       Built: 2015
    Monthly Fee: $128
       Tax: $8,220 (2024)
    Community: Johns Lake Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,150 (change assumption)
    Mortgage ($3,337) + Fees ($128) + Taxes in 2024 ($685)


    Taxes:$8,220

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787

    $470,00022 Days on yellowkey   MLS ID: O6393056

    REDUCED by $4,900 (1.0%) on 04/15/2026

    For Sale O6393056 - 16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2020
    Monthly Fee: $257
       Tax: $4,805 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,233 (change assumption)
    Mortgage ($2,575) + Fees ($257) + Taxes in 2025 ($400)


    Taxes:$4,805

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15226 SUNSET OVERLOOK CIR, WINTER GARDEN, FL 34787

    $1,100,00028 Days on yellowkey   MLS ID: O6390971

    REDUCED by $50,000 (4.3%) on 03/31/2026

    For Sale O6390971 - 15226 SUNSET OVERLOOK CIR, WINTER GARDEN, FL 34787 80 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3556
       Built: 2023
    Monthly Fee: $128
       Tax: $10,299 (2025)
    Community: Johns Lake Pointe
    Single Family


    Estimated Monthly Payment: $7,013 (change assumption)
    Mortgage ($6,027) + Fees ($128) + Taxes in 2025 ($858)


    Taxes:$10,299

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • WINTER GARDEN, FL 34787

    $1,695,0003 Days on yellowkey   MLS ID: O6396808

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6396808 - WINTER GARDEN, FL 34787 61 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2957
       Built: 2015
    Monthly Fee: $235
       Tax: $11,222 (2025)
    Community: Hlckory Hammock Ph 1D
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,458 (change assumption)
    Mortgage ($9,287) + Fees ($235) + Taxes in 2025 ($935)


    Taxes:$11,222

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $619,990149 Days on yellowkey   MLS ID: O6361583

    1 Days Off yellowkey (back on 4/15/2026)

    For Sale O6361583 - 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,753 (change assumption)
    Mortgage ($3,397) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5367 GOLDEN APPLE DR, WINTER GARDEN, FL 34787

    $614,90045 Days on yellowkey   MLS ID: O6380252

    REDUCED by $10,000 (1.6%) on 04/15/2026

    For Sale O6380252 - 5367 GOLDEN APPLE DR, WINTER GARDEN, FL 34787 21 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2270
       Built: 2021
    Monthly Fee: $115
       Tax: $8,949 (2024)
    Community: Wincey Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $4,230 (change assumption)
    Mortgage ($3,369) + Fees ($115) + Taxes in 2024 ($746)


    Taxes:$8,949

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16736 OAKBORO ST, WINTER GARDEN, FL 34787

    $575,00028 Days on yellowkey   MLS ID: O6388784

    REDUCED by $10,000 (1.7%) on 04/15/2026

    For Sale O6388784 - 16736 OAKBORO ST, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $257
       Tax: $6,967 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,988 (change assumption)
    Mortgage ($3,151) + Fees ($257) + Taxes in 2024 ($581)


    Taxes:$6,967

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6166 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787

    $675,0002 Days on yellowkey   MLS ID: O6399123

    For Sale O6399123 - 6166 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2818
       Built: 2018
    Monthly Fee: $142
       Tax: $6,366 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $4,371 (change assumption)
    Mortgage ($3,699) + Fees ($142) + Taxes in 2025 ($531)


    Taxes:$6,366

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater 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.