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Winter Garden Single Family Homes For Sale - 550 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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  • 5715 ORANGE ORCHARD DR, WINTER GARDEN, FL 34787

    $730,0005 Days on yellowkey   MLS ID: O6400221

    2 Days Off yellowkey (back on 4/20/2026)

    For Sale O6400221 - 5715 ORANGE ORCHARD DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2240
       Built: 2021
    Monthly Fee: $115
       Tax: $9,328 (2025)
    Community: Wincey Grvs Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,892 (change assumption)
    Mortgage ($4,000) + Fees ($115) + Taxes in 2025 ($777)


    Taxes:$9,328

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8220 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $599,99951 Days on yellowkey   MLS ID: TB8482364

    INCREASED by $42,000 (7.5%) on 03/31/2026

    For Sale TB8482364 - 8220 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 19 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2016
    Monthly Fee: $335
       Tax: $7,983 (2025)
    Community: Waterleigh Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,288 (change assumption)
    Mortgage ($3,288) + Fees ($335) + Taxes in 2025 ($665)


    Taxes:$7,983

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17608 DEER ISLE CIR, WINTER GARDEN, FL 34787

    $1,025,000196 Days on yellowkey   MLS ID: O6350825

    REDUCED by $25,000 (2.4%) on 04/20/2026

    For Sale O6350825 - 17608 DEER ISLE CIR, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 3144
       Built: 1997
    Monthly Fee: $207
       Tax: $6,334 (2024)
    Community: Deer Island Ph 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,351 (change assumption)
    Mortgage ($5,616) + Fees ($207) + Taxes in 2024 ($528)


    Taxes:$6,334

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 17453 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $757,9904 Days on yellowkey   MLS ID: G5111222

    0 Days Off yellowkey (back on 4/19/2026)

    For Sale G5111222 - 17453 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787 2 photos

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

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,303 (change assumption)
    Mortgage ($4,153) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15878 MOONLIGHT BAY ST, WINTER GARDEN, FL 34787

    $559,00059 Days on yellowkey   MLS ID: O6384745

    REDUCED by $6,000 (1.1%) on 04/20/2026

    For Sale O6384745 - 15878 MOONLIGHT BAY ST, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2472
       Built: 2021
    Monthly Fee: $257
       Tax: $7,417 (2025)
    Community: Waterleigh Ph 3B 3C & 3D
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,938 (change assumption)
    Mortgage ($3,063) + Fees ($257) + Taxes in 2025 ($618)


    Taxes:$7,417

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 7720 SUMMERLAKE POINTE BLVD, WINTER GARDEN, FL 34787

    $800,0007 Days on yellowkey   MLS ID: O6399030

    For Sale O6399030 - 7720 SUMMERLAKE POINTE BLVD, WINTER GARDEN, FL 34787 42 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3893
       Built: 2013
    Monthly Fee: $252
       Tax: $7,628 (2025)
    Community: Summerlake
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,271 (change assumption)
    Mortgage ($4,383) + Fees ($252) + Taxes in 2025 ($636)


    Taxes:$7,628

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12934 CANOPY WOODS WAY WAY, WINTER GARDEN, FL 34787

    $1,350,00039 Days on yellowkey   MLS ID: O6390704

    REDUCED by $20,000 (1.5%) on 04/19/2026

    For Sale O6390704 - 12934 CANOPY WOODS WAY WAY, WINTER GARDEN, FL 34787 90 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3665
       Built: 2018
    Monthly Fee: $299
       Tax: $12,379 (2025)
    Community: Canopy Oaks Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,728 (change assumption)
    Mortgage ($7,397) + Fees ($299) + Taxes in 2025 ($1,032)


    Taxes:$12,379

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 3633 TURNINGWIND LN, WINTER GARDEN, FL 34787

    $750,0008 Days on yellowkey   MLS ID: S5147897

    0 Days Off yellowkey (back on 4/19/2026)

    For Sale S5147897 - 3633 TURNINGWIND LN, WINTER GARDEN, FL 34787 85 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3412
       Built: 2003
    Monthly Fee: $115
       Tax: $5,047 (2025)
    Community: Windward Cay 48 125
    Single Family


    Estimated Monthly Payment: $4,645 (change assumption)
    Mortgage ($4,109) + Fees ($115) + Taxes in 2025 ($421)


    Taxes:$5,047

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 16716 WINGSPREAD LOOP, WINTER GARDEN, FL 34787

    $495,00014 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


  • 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787

    $519,900237 Days on yellowkey   MLS ID: S5133690

    For Sale S5133690 - 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2035
       Built: 2001
    Monthly Fee: $33
       Tax: $6,403 (2024)
    Community: Tuscany Ph 02
    Single Family


    Estimated Monthly Payment: $3,415 (change assumption)
    Mortgage ($2,849) + Fees ($33) + Taxes in 2024 ($534)


    Taxes:$6,403

    Elementary School: Maxey Elem

    High School: Ocoee High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 13043 SANDCASTLE DRIVE, WINTER GARDEN, FL 34787

    $846,0008 Days on yellowkey   MLS ID: O6399529

    For Sale O6399529 - 13043 SANDCASTLE DRIVE, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1943
       Built: 2022
    Monthly Fee: $534
       Tax: $10,109 (2025)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,012 (change assumption)
    Mortgage ($4,636) + Fees ($534) + Taxes in 2025 ($842)


    Taxes:$10,109

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5340 BOWMAN DR, WINTER GARDEN, FL 34787

    $2,195,0009 Days 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


  • 17066 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $765,37737 Days on yellowkey   MLS ID: G5109739

    For Sale G5109739 - 17066 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3038
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,316 (change assumption)
    Mortgage ($4,194) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17060 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $819,39137 Days on yellowkey   MLS ID: G5109737

    For Sale G5109737 - 17060 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3117
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,630 (change assumption)
    Mortgage ($4,490) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17055 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $580,68242 Days on yellowkey   MLS ID: G5109480

    For Sale G5109480 - 17055 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,332 (change assumption)
    Mortgage ($3,182) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17054 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $688,32442 Days on yellowkey   MLS ID: G5109477

    For Sale G5109477 - 17054 HAGGERTY HOLLOW 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: $3,922 (change assumption)
    Mortgage ($3,772) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5983 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $858,014217 Days on yellowkey   MLS ID: G5102280

    For Sale G5102280 - 5983 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2879
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,851 (change assumption)
    Mortgage ($4,701) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6345 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $581,285217 Days on yellowkey   MLS ID: G5102273

    For Sale G5102273 - 6345 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 2 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1772
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,335 (change assumption)
    Mortgage ($3,185) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15075 TEA TREE DR, WINTER GARDEN, FL 34787

    $829,347219 Days on yellowkey   MLS ID: G5102184

    For Sale G5102184 - 15075 TEA TREE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3038
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,694 (change assumption)
    Mortgage ($4,544) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15162 CANOPY COVER DR, WINTER GARDEN, FL 34787

    $885,000146 Days on yellowkey   MLS ID: S5139203

    For Sale S5139203 - 15162 CANOPY COVER DR, WINTER GARDEN, FL 34787 70 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2049
       Built: 2023
    Monthly Fee: $545
       Tax: $1,939 (2023)
    Community: Del Webb Oasis Phase 2
    Single Family


    Estimated Monthly Payment: $5,556 (change assumption)
    Mortgage ($4,849) + Fees ($545) + Taxes in 2023 ($162)


    Taxes:$1,939

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None




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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.