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Winter Garden Homes For Sale & Real Estate - 712 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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  • 10031 MEMOIR AVE, WINTER GARDEN, FL 34787

    $415,0007 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


  • 15878 MOONLIGHT BAY ST, WINTER GARDEN, FL 34787

    $559,00057 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

    $800,0005 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

    $1,350,00037 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

    $750,0006 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


  • 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,990127 Days on yellowkey   MLS ID: O6367437

    For Sale O6367437 - 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $200
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,297 (change assumption)
    Mortgage ($4,931) + Fees ($200) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9803 AMBER CHESTNUT WAY, WINTER GARDEN, FL 34787

    $535,00076 Days on yellowkey   MLS ID: S5142809

    REDUCED by $10,000 (1.8%) on 04/19/2026

    For Sale S5142809 - 9803 AMBER CHESTNUT WAY, WINTER GARDEN, FL 34787 15 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2303
       Built: 2018
    Monthly Fee: $245
       Tax: $7,328 (2024)
    Community: Watermark
    Townhouse


    Estimated Monthly Payment: $3,787 (change assumption)
    Mortgage ($2,931) + Fees ($245) + Taxes in 2024 ($611)


    Taxes:$7,328

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 16716 WINGSPREAD LOOP, WINTER GARDEN, FL 34787

    $495,00012 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


  • 15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787

    $700,00025 Days on yellowkey   MLS ID: O6394429

    For Sale O6394429 - 15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2383
       Built: 2017
    Monthly Fee: $118
       Tax: $5,959 (2025)
    Community: Highlands/Summerlake Grvs Ph 1
    Single Family


    Estimated Monthly Payment: $4,450 (change assumption)
    Mortgage ($3,836) + Fees ($118) + Taxes in 2025 ($497)


    Taxes:$5,959

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 11193 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $839,99041 Days on yellowkey   MLS ID: O6389839

    REDUCED by $5,661 (0.7%) on 04/16/2026

    For Sale O6389839 - 11193 HOLLOW BAY DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,018 (change assumption)
    Mortgage ($4,603) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11858 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $539,990200 Days on yellowkey   MLS ID: O6349514

    For Sale O6349514 - 11858 SHINE VIEW LN, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,315 (change assumption)
    Mortgage ($2,959) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787

    $519,900235 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


  • 1532 SCARLET OAK LOOP #70B, WINTER GARDEN, FL 34787

    $349,00063 Days on yellowkey   MLS ID: S5143993

    For Sale S5143993 - 1532 SCARLET OAK LOOP #70B, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1544
       Built: 2012
    Monthly Fee: $282
       Tax: $3,423 (2024)
    Community: Tucker Oaks
    Townhouse


    Estimated Monthly Payment: $2,479 (change assumption)
    Mortgage ($1,912) + Fees ($282) + Taxes in 2024 ($285)


    Taxes:$3,423

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 10693 PETRILLO WAY, WINTER GARDEN, FL 34787

    $799,0005 Days on yellowkey   MLS ID: O6399081

    For Sale O6399081 - 10693 PETRILLO WAY, WINTER GARDEN, FL 34787 60 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3149
       Built: 2021
    Monthly Fee: $102
       Tax: $8,845 (2025)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $5,217 (change assumption)
    Mortgage ($4,378) + Fees ($102) + Taxes in 2025 ($737)


    Taxes:$8,845

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15563 ORCHID ROSE COURT, WINTER GARDEN, FL 34787

    $799,0005 Days on yellowkey   MLS ID: O6399638

    For Sale O6399638 - 15563 ORCHID ROSE COURT, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2808
       Built: 2026
    Monthly Fee: $544
       Tax: $545 (2025)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,967 (change assumption)
    Mortgage ($4,378) + Fees ($544) + Taxes in 2025 ($45)


    Taxes:$545

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13043 SANDCASTLE DRIVE, WINTER GARDEN, FL 34787

    $846,0006 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


  • 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $750,0007 Days on yellowkey   MLS ID: O6398720

    For Sale O6398720 - 2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3747
       Built: 2000
    Monthly Fee: $90
       Tax: $10,152 (2025)
    Community: Wintermere Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,045 (change assumption)
    Mortgage ($4,109) + Fees ($90) + Taxes in 2025 ($846)


    Taxes:$10,152

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 5340 BOWMAN DR, WINTER GARDEN, FL 34787

    $2,195,0007 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


  • 15381 HONEYBELL DR, WINTER GARDEN, FL 34787

    $419,00029 Days on yellowkey   MLS ID: O6391881

    REDUCED by $7,000 (1.6%) on 04/19/2026

    For Sale O6391881 - 15381 HONEYBELL DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2034
       Built: 2016
    Monthly Fee: $418
       Tax: $4,853 (2025)
    Community: Hamlin Reserve
    Townhouse


    Estimated Monthly Payment: $3,118 (change assumption)
    Mortgage ($2,296) + Fees ($418) + Taxes in 2025 ($404)


    Taxes:$4,853

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 17066 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $765,37735 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




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.