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Winter Garden Homes For Sale & Real Estate - 759 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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  • 13846 FRESH IVY ST, WINTER GARDEN, FL 34787

    $649,900209 Days on yellowkey   MLS ID: O6346706

    For Sale O6346706 - 13846 FRESH IVY ST, WINTER GARDEN, FL 34787 51 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2108
       Built: 2024
    Monthly Fee: $534
       Tax: $2,180 (2024)
    Community: Del Webb Oasis Ph 3
    Single Family


    Estimated Monthly Payment: $4,277 (change assumption)
    Mortgage ($3,561) + Fees ($534) + Taxes in 2024 ($182)


    Taxes:$2,180

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 16920 RESEDA ALY, WINTER GARDEN, FL 34787

    $385,0006 Days on yellowkey   MLS ID: O6400124

    For Sale O6400124 - 16920 RESEDA ALY, WINTER GARDEN, FL 34787 21 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1568
       Built: 2020
    Monthly Fee: $285
       Tax: $6,193 (2025)
    Community: Waterleigh Ph 3A
    Townhouse


    Estimated Monthly Payment: $2,911 (change assumption)
    Mortgage ($2,110) + Fees ($285) + Taxes in 2025 ($516)


    Taxes:$6,193

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 7692 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787

    $875,0003 Days on yellowkey   MLS ID: O6401130

    For Sale O6401130 - 7692 GREEN MOUNTAIN WAY, WINTER GARDEN, FL 34787 45 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3855
       Built: 2016
    Monthly Fee: $252
       Tax: $7,767 (2025)
    Community: Summerlake Pd Ph 3A
    Single Family


    Estimated Monthly Payment: $5,694 (change assumption)
    Mortgage ($4,794) + Fees ($252) + Taxes in 2025 ($647)


    Taxes:$7,767

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14280 BRAEMAR ST, WINTER GARDEN, FL 34787

    $559,9005 Days on yellowkey   MLS ID: TB8500322

    For Sale TB8500322 - 14280 BRAEMAR ST, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2023
    Monthly Fee: $100
       Tax: $7,928 (2025)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,829 (change assumption)
    Mortgage ($3,068) + Fees ($100) + Taxes in 2025 ($661)


    Taxes:$7,928

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3167 WINESAP WAY, WINTER GARDEN, FL 34787

    $575,0005 Days on yellowkey   MLS ID: O6400764

    For Sale O6400764 - 3167 WINESAP WAY, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2115
       Built: 2016
    Monthly Fee: $190
       Tax: $5,408 (2025)
    Community: Orchard Pk/Stillwater Xing
    Single Family


    Estimated Monthly Payment: $3,791 (change assumption)
    Mortgage ($3,151) + Fees ($190) + Taxes in 2025 ($451)


    Taxes:$5,408

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 6166 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787

    $664,90013 Days on yellowkey   MLS ID: O6399123

    REDUCED by $10,100 (1.5%) on 04/20/2026

    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: $4,316 (change assumption)
    Mortgage ($3,643) + 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


  • 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,317,00028 Days on yellowkey   MLS ID: O6394059

    REDUCED by $20,000 (1.5%) on 04/25/2026

    For Sale O6394059 - 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4019
       Built: 2018
    Monthly Fee: $188
       Tax: $17,895 (2025)
    Community: Canopy Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $8,896 (change assumption)
    Mortgage ($7,216) + Fees ($188) + Taxes in 2025 ($1,491)


    Taxes:$17,895

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787

    $929,00029 Days on yellowkey   MLS ID: O6394506

    REDUCED by $20,900 (2.2%) on 04/20/2026

    For Sale O6394506 - 1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3841
       Built: 2017
    Monthly Fee: $184
       Tax: $12,543 (2025)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $6,320 (change assumption)
    Mortgage ($5,090) + Fees ($184) + Taxes in 2025 ($1,045)


    Taxes:$12,543

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17326 BAL HARBOUR DR, WINTER GARDEN, FL 34787

    $769,00032 Days on yellowkey   MLS ID: O6393857

    REDUCED by $5,000 (0.6%) on 04/24/2026

    For Sale O6393857 - 17326 BAL HARBOUR DR, WINTER GARDEN, FL 34787 81 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3196
       Built: 2018
    Monthly Fee: $215
       Tax: $11,210 (2025)
    Community: Waterside/Johns Lk-Ph 2B
    Single Family


    Estimated Monthly Payment: $5,363 (change assumption)
    Mortgage ($4,214) + Fees ($215) + Taxes in 2025 ($934)


    Taxes:$11,210

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9256 GRAND ISLAND WAY, WINTER GARDEN, FL 34787

    $750,00017 Days on yellowkey   MLS ID: O6397917

    For Sale O6397917 - 9256 GRAND ISLAND WAY, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2507
       Built: 2017
    Monthly Fee: $164
       Tax: $6,475 (2025)
    Community: Watermark Ph 2C
    Single Family


    Estimated Monthly Payment: $4,813 (change assumption)
    Mortgage ($4,109) + Fees ($164) + Taxes in 2025 ($540)


    Taxes:$6,475

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13526 FOX GLOVE ST, WINTER GARDEN, FL 34787

    $845,00034 Days on yellowkey   MLS ID: O6388630

    For Sale O6388630 - 13526 FOX GLOVE ST, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3866
       Built: 2005
    Monthly Fee: $243
       Tax: $11,960 (2025)
    Community: Stoneybrook West
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,870 (change assumption)
    Mortgage ($4,630) + Fees ($243) + Taxes in 2025 ($997)


    Taxes:$11,960

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 2230 ROMANUM DR, WINTER GARDEN, FL 34787

    $565,00046 Days on yellowkey   MLS ID: O6389947

    For Sale O6389947 - 2230 ROMANUM DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2562
       Built: 2014
    Monthly Fee: $207
       Tax: $8,425 (2025)
    Community: Alexander Rdg
    Single Family


    Estimated Monthly Payment: $4,005 (change assumption)
    Mortgage ($3,096) + Fees ($207) + Taxes in 2025 ($702)


    Taxes:$8,425

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787

    $554,990115 Days on yellowkey   MLS ID: O6370363

    For Sale O6370363 - 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2021
    Monthly Fee: $281
       Tax: $8,150 (2024)
    Community: Enclave/Hamlin
    Single Family


    Estimated Monthly Payment: $4,001 (change assumption)
    Mortgage ($3,041) + Fees ($281) + Taxes in 2024 ($679)


    Taxes:$8,150

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 7363 MEZZANO LN, WINTER GARDEN, FL 34787

    $479,999235 Days on yellowkey   MLS ID: O6340083

    For Sale O6340083 - 7363 MEZZANO LN, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2023
    Monthly Fee: $159
       Tax: $6,986 (2025)
    Community: Mezzano
    Townhouse


    Estimated Monthly Payment: $3,371 (change assumption)
    Mortgage ($2,630) + Fees ($159) + Taxes in 2025 ($582)


    Taxes:$6,986

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787

    $950,00058 Days on yellowkey   MLS ID: O6386394

    REDUCED by $15,000 (1.6%) on 04/16/2026

    For Sale O6386394 - 9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3087
       Built: 2018
    Monthly Fee: $164
       Tax: $11,801 (2025)
    Community: Watermark Ph 2B
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,353 (change assumption)
    Mortgage ($5,205) + Fees ($164) + Taxes in 2025 ($983)


    Taxes:$11,801

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14626 BLACK QUILL DR, WINTER GARDEN, FL 34787

    $799,90011 Days on yellowkey   MLS ID: O6399975

    0 Days Off yellowkey (back on 4/26/2026)

    For Sale O6399975 - 14626 BLACK QUILL DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2907
       Built: 2016
    Monthly Fee: $215
       Tax: $6,816 (2025)
    Community: Overlook At Hamlin
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,166 (change assumption)
    Mortgage ($4,383) + Fees ($215) + Taxes in 2025 ($568)


    Taxes:$6,816

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 3208 SAILING PIER AVE, WINTER GARDEN, FL 34787

    $1,049,9001 Day on yellowkey   MLS ID: O6402332

    For Sale O6402332 - 3208 SAILING PIER AVE, WINTER GARDEN, FL 34787 50 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3998
       Built: 2023
    Monthly Fee: $208
       Tax: $12,135 (2024)
    Community: Ests/Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $6,972 (change assumption)
    Mortgage ($5,753) + Fees ($208) + Taxes in 2024 ($1,011)


    Taxes:$12,135

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17406 HONEYBELL TANGELO CT, WINTER GARDEN, FL 34787

    $847,0001 Day on yellowkey   MLS ID: O6402286

    For Sale O6402286 - 17406 HONEYBELL TANGELO CT, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3427
       Built: 2026
    Monthly Fee: $83

    Community: Northlake At Ovation
    Single Family


    Estimated Monthly Payment: $4,724 (change assumption)
    Mortgage ($4,641) + Fees ($83) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 345 WINTER ST, WINTER GARDEN, FL 34787

    $285,0003 Days on yellowkey   MLS ID: O6402105

    INCREASED by $5,100 (1.8%) on 04/26/2026

    For Sale O6402105 - 345 WINTER ST, WINTER GARDEN, FL 34787 18 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 700
       Built: 1951   Tax: $211 (2025)
    Community: Shadow Lawn
    Single Family


    Estimated Monthly Payment: $1,579 (change assumption)
    Mortgage ($1,562) + Taxes in 2025 ($18)


    Taxes:$211

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2640 GROVE VIEW DR, WINTER GARDEN, FL 34787

    $795,0003 Days on yellowkey   MLS ID: O6401215

    For Sale O6401215 - 2640 GROVE VIEW DR, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3738
       Built: 2001
    Monthly Fee: $90
       Tax: $10,261 (2025)
    Community: Wintermere Pointe Ph 02 46/141
    Single Family


    Estimated Monthly Payment: $5,301 (change assumption)
    Mortgage ($4,356) + Fees ($90) + Taxes in 2025 ($855)


    Taxes:$10,261

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge 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.