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Winter Garden Single Family Homes For Sale - 503 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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  • 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787

    $339,9001 Day on yellowkey   MLS ID: O6398208

    For Sale O6398208 - 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787 4 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1988   Tax: $2,702 (2025)
    Community: East Garden Manor Add 03
    Single Family


    Estimated Monthly Payment: $2,088 (change assumption)
    Mortgage ($1,862) + Taxes in 2025 ($225)


    Taxes:$2,702

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16716 WINGSPREAD LOOP, WINTER GARDEN, FL 34787

    $495,0006 Days on yellowkey   MLS ID: O6397108

    For Sale O6397108 - 16716 WINGSPREAD LOOP, WINTER GARDEN, FL 34787 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1676
       Built: 2019
    Monthly Fee: $127
       Tax: $5,006 (2025)
    Community: Hawksmoor-Ph 1
    Single Family


    Estimated Monthly Payment: $3,256 (change assumption)
    Mortgage ($2,712) + Fees ($127) + Taxes in 2025 ($417)


    Taxes:$5,006

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1209 CASTLEPORT RD, WINTER GARDEN, FL 34787

    $664,90032 Days on yellowkey   MLS ID: O6390760

    REDUCED by $10,090 (1.5%) on 04/14/2026

    For Sale O6390760 - 1209 CASTLEPORT RD, WINTER GARDEN, FL 34787 36 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2001
    Monthly Fee: $243
       Tax: $4,030 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,222 (change assumption)
    Mortgage ($3,643) + Fees ($243) + Taxes in 2025 ($336)


    Taxes:$4,030

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 604 FOSTER AVE, WINTER GARDEN, FL 34787

    $400,0004 Days on yellowkey   MLS ID: O6389095

    For Sale O6389095 - 604 FOSTER AVE, WINTER GARDEN, FL 34787 32 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1275
       Built: 1975   Tax: $1,633 (2024)
    Community: Westchester Place
    Single Family


    Estimated Monthly Payment: $2,328 (change assumption)
    Mortgage ($2,192) + Taxes in 2024 ($136)


    Taxes:$1,633

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 12055 BRACCO ST, WINTER GARDEN, FL 34787

    $429,000126 Days on yellowkey   MLS ID: O6366675

    REDUCED by $11,000 (2.5%) on 04/14/2026

    For Sale O6366675 - 12055 BRACCO ST, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1668
       Built: 2023
    Monthly Fee: $105
       Tax: $6,881 (2024)
    Community: Highland Ridge
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,029 (change assumption)
    Mortgage ($2,351) + Fees ($105) + Taxes in 2024 ($573)


    Taxes:$6,881

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14168 LARKSPUR LAKE DR, WINTER GARDEN, FL 34787

    $2,999,990203 Days on yellowkey   MLS ID: O6346469

    REDUCED by $333,389 (10.0%) on 04/14/2026

    For Sale O6346469 - 14168 LARKSPUR LAKE DR, WINTER GARDEN, FL 34787 19 photos

    Bed: 6   Bath: 7.0   Gar: 4
    Liv Area Sq Ft: 6442
       Built: 2025
    Monthly Fee: $112
       Tax: $6,673 (2024)
    Community: Shorefront Cove
    Single Family


    Estimated Monthly Payment: $17,106 (change assumption)
    Mortgage ($16,438) + Fees ($112) + Taxes in 2024 ($556)


    Taxes:$6,673

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787

    $585,00044 Days on yellowkey   MLS ID: S5144794

    REDUCED by $6,000 (1.0%) on 04/14/2026

    For Sale S5144794 - 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2149
       Built: 2021
    Monthly Fee: $281
       Tax: $6,500 (2024)
    Community: Enclave At Hamlin
    Single Family


    Estimated Monthly Payment: $4,028 (change assumption)
    Mortgage ($3,205) + Fees ($281) + Taxes in 2024 ($542)


    Taxes:$6,500

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16548 RAVEN ROCK PL, WINTER GARDEN, FL 34787

    $1,459,90051 Days on yellowkey   MLS ID: S5144064

    For Sale S5144064 - 16548 RAVEN ROCK PL, WINTER GARDEN, FL 34787 36 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4263
       Built: 2017
    Monthly Fee: $178
       Tax: $16,938 (2024)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $9,589 (change assumption)
    Mortgage ($7,999) + Fees ($178) + Taxes in 2024 ($1,411)


    Taxes:$16,938

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14834 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $545,00014 Days on yellowkey   MLS ID: O6395079

    For Sale O6395079 - 14834 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2049
       Built: 2014
    Monthly Fee: $252
       Tax: $3,824 (2025)
    Community: Summerlake Pd Ph 1B-A Rep
    Single Family


    Estimated Monthly Payment: $3,557 (change assumption)
    Mortgage ($2,986) + Fees ($252) + Taxes in 2025 ($319)


    Taxes:$3,824

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 931 KYLEE ALY, WINTER GARDEN, FL 34787

    $849,00041 Days on yellowkey   MLS ID: O6387922

    REDUCED by $26,000 (3.0%) on 04/14/2026

    For Sale O6387922 - 931 KYLEE ALY, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2831
       Built: 2022
    Monthly Fee: $401
       Tax: $9,637 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $5,856 (change assumption)
    Mortgage ($4,652) + Fees ($401) + Taxes in 2025 ($803)


    Taxes:$9,637

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15594 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $1,258,0009 Days on yellowkey   MLS ID: S5147208

    For Sale S5147208 - 15594 SHOREBIRD LN, WINTER GARDEN, FL 34787 84 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3022
       Built: 2020
    Monthly Fee: $360
       Tax: $17,905 (2025)
    Community: Lakeshore Preserve Ph 4
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,745 (change assumption)
    Mortgage ($6,893) + Fees ($360) + Taxes in 2025 ($1,492)


    Taxes:$17,905

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 2015 SANDY GARDEN LN, WINTER GARDEN, FL 34787

    $765,000103 Days on yellowkey   MLS ID: O6370025

    For Sale O6370025 - 2015 SANDY GARDEN LN, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3871
       Built: 2015
    Monthly Fee: $113
       Tax: $10,989 (2025)
    Community: Reserve At Carriage Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,220 (change assumption)
    Mortgage ($4,192) + Fees ($113) + Taxes in 2025 ($916)


    Taxes:$10,989

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12112 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $540,000125 Days on yellowkey   MLS ID: O6366467

    REDUCED by $10,000 (1.8%) on 04/14/2026

    For Sale O6366467 - 12112 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2801
       Built: 2021
    Monthly Fee: $192
       Tax: $9,460 (2025)
    Community: Encore At Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,939 (change assumption)
    Mortgage ($2,959) + Fees ($192) + Taxes in 2025 ($788)


    Taxes:$9,460

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16788 MUSKGRASS DR, WINTER GARDEN, FL 34787

    $1,600,00040 Days on yellowkey   MLS ID: O6388174

    For Sale O6388174 - 16788 MUSKGRASS DR, WINTER GARDEN, FL 34787 77 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4733
       Built: 2025
    Monthly Fee: $86

    Community: Lake Star At Ovation Phase 1B
    Single Family


    Estimated Monthly Payment: $8,853 (change assumption)
    Mortgage ($8,767) + Fees ($86) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $1,025,00072 Days on yellowkey   MLS ID: O6378658

    For Sale O6378658 - 8768 SONOMA COAST DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 3416
       Built: 2022
    Monthly Fee: $271
       Tax: $11,513 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,847 (change assumption)
    Mortgage ($5,616) + Fees ($271) + Taxes in 2024 ($959)


    Taxes:$11,513

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 5340 BOWMAN DR, WINTER GARDEN, FL 34787

    $2,195,0001 Day on yellowkey   MLS ID: O6398618

    For Sale O6398618 - 5340 BOWMAN DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 6.5   Gar: 3
    Liv Area Sq Ft: 5749
       Built: 2017
    Monthly Fee: $230
       Tax: $16,854 (2026)
    Community: The Cove At Hamlin
    Single Family


    Estimated Monthly Payment: $13,662 (change assumption)
    Mortgage ($12,027) + Fees ($230) + Taxes in 2026 ($1,405)


    Taxes:$16,854

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2026

    Middle School: Bridgewater Middle


  • 16768 SANCTUARY DR, WINTER GARDEN, FL 34787

    $1,575,00086 Days on yellowkey   MLS ID: O6374904

    REDUCED by $15,000 (0.9%) on 04/14/2026

    For Sale O6374904 - 16768 SANCTUARY DR, WINTER GARDEN, FL 34787 82 photos

    Bed: 5   Bath: 4.5   Gar: 4
    Liv Area Sq Ft: 4258
       Built: 2021
    Monthly Fee: $165
       Tax: $13,171 (2024)
    Community: Sanctuary/Twin Waters
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,893 (change assumption)
    Mortgage ($8,630) + Fees ($165) + Taxes in 2024 ($1,098)


    Taxes:$13,171

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 15312 GILLIGAN CT, WINTER GARDEN, FL 34787

    $1,150,00083 Days on yellowkey   MLS ID: O6372954

    0 Days Off yellowkey (back on 4/14/2026)

    For Sale O6372954 - 15312 GILLIGAN CT, WINTER GARDEN, FL 34787 69 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3652
       Built: 2020
    Monthly Fee: $102
       Tax: $9,787 (2024)
    Community: Winding Bay Ii Llc
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,219 (change assumption)
    Mortgage ($6,301) + Fees ($102) + Taxes in 2024 ($816)


    Taxes:$9,787

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 17156 INGRAM BLUFF DR, WINTER GARDEN, FL 34787

    $606,44028 Days on yellowkey   MLS ID: G5109791

    0 Days Off yellowkey (back on 3/18/2026)

    For Sale G5109791 - 17156 INGRAM BLUFF DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,463 (change assumption)
    Mortgage ($3,323) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14241 COLONIAL POINTE DR, WINTER GARDEN, FL 34787

    $1,390,00069 Days on yellowkey   MLS ID: O6379808

    3 Days Off yellowkey (back on 4/14/2026)

    For Sale O6379808 - 14241 COLONIAL POINTE DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 7   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5001
       Built: 2017
    Monthly Fee: $215
       Tax: $9,308 (2024)
    Community: Overlook 2 At Hamlin
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,607 (change assumption)
    Mortgage ($7,616) + Fees ($215) + Taxes in 2024 ($776)


    Taxes:$9,308

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin 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.