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Winter Garden Homes For Sale & Real Estate - 799 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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  • 5526 TINY RD, WINTER GARDEN, FL 34787

    $1,675,000276 Days on yellowkey   MLS ID: O6334009

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

    For Sale O6334009 - 5526 TINY RD, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2474
       Built: 2007   Tax: $10,165 (2024)
    Community: None
    Single Family


    Estimated Monthly Payment: $10,025 (change assumption)
    Mortgage ($9,178) + Taxes in 2024 ($847)


    Taxes:$10,165

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15126 AQUA SOL LN, WINTER GARDEN, FL 34787

    $399,50038 Days on yellowkey   MLS ID: O6395617

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

    For Sale O6395617 - 15126 AQUA SOL LN, WINTER GARDEN, FL 34787 64 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1579
       Built: 2024
    Monthly Fee: $596
       Tax: $7,371 (2025)
    Community: Del Webb Oasis
    Villa


    Estimated Monthly Payment: $3,399 (change assumption)
    Mortgage ($2,189) + Fees ($596) + Taxes in 2025 ($614)


    Taxes:$7,371

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1073 VINSETTA CIR, WINTER GARDEN, FL 34787

    $725,000294 Days on yellowkey   MLS ID: O6328215

    INCREASED by $10,000 (1.4%) on 04/02/2026

    For Sale O6328215 - 1073 VINSETTA CIR, WINTER GARDEN, FL 34787 72 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3568
       Built: 2014
    Monthly Fee: $95
       Tax: $5,710 (2024)
    Community: Avalon Reserve Village 1
    Single Family


    Estimated Monthly Payment: $4,543 (change assumption)
    Mortgage ($3,973) + Fees ($95) + Taxes in 2024 ($476)


    Taxes:$5,710

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 2031 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $489,00045 Days on yellowkey   MLS ID: O6394075

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

    For Sale O6394075 - 2031 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 17 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2000
    Monthly Fee: $90
       Tax: $4,516 (2025)
    Community: Wintermere Pointe
    Single Family


    Estimated Monthly Payment: $3,146 (change assumption)
    Mortgage ($2,679) + Fees ($90) + Taxes in 2025 ($376)


    Taxes:$4,516

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16434 HAMLIN HILLS RD, WINTER GARDEN, FL 34787

    $480,00037 Days on yellowkey   MLS ID: O6396052

    For Sale O6396052 - 16434 HAMLIN HILLS RD, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1729
       Built: 2025
    Monthly Fee: $225
       Tax: $252 (2025)
    Community: Hamlin Ridge
    Townhouse


    Estimated Monthly Payment: $2,876 (change assumption)
    Mortgage ($2,630) + Fees ($225) + Taxes in 2025 ($21)


    Taxes:$252

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787

    $874,99038 Days on yellowkey   MLS ID: O6395693

    For Sale O6395693 - 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787 35 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2650
       Built: 2026
    Monthly Fee: $240
       Tax: $1,955 (2025)
    Community: Winter Grove
    Single Family


    Estimated Monthly Payment: $5,197 (change assumption)
    Mortgage ($4,794) + Fees ($240) + Taxes in 2025 ($163)


    Taxes:$1,955

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 17061 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $565,99039 Days on yellowkey   MLS ID: G5110436

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

    For Sale G5110436 - 17061 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,223 (change assumption)
    Mortgage ($3,101) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14501 GROVE RESORT AVE #2541, WINTER GARDEN, FL 34787

    $310,000347 Days on yellowkey   MLS ID: O6313000

    For Sale O6313000 - 14501 GROVE RESORT AVE #2541, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1396
       Built: 2018
    Monthly Fee: $889
       Tax: $8,154 (2024)
    Community: Grove Resort And Spa Hotel Condominium
    Condo


    Estimated Monthly Payment: $3,267 (change assumption)
    Mortgage ($1,699) + Fees ($889) + Taxes in 2024 ($680)


    Taxes:$8,154

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 5778 LAUREL CHERRY AVE, WINTER GARDEN, FL 34787

    $540,00039 Days on yellowkey   MLS ID: O6395452

    For Sale O6395452 - 5778 LAUREL CHERRY AVE, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2524
       Built: 2016
    Monthly Fee: $195
       Tax: $9,031 (2025)
    Community: Signature Lakes
    Single Family


    Estimated Monthly Payment: $3,906 (change assumption)
    Mortgage ($2,959) + Fees ($195) + Taxes in 2025 ($753)


    Taxes:$9,031

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14501 GROVE RESORT AVE #1110, WINTER GARDEN, FL 34787

    $185,00039 Days on yellowkey   MLS ID: A4688528

    For Sale A4688528 - 14501 GROVE RESORT AVE #1110, WINTER GARDEN, FL 34787 35 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1265
       Built: 2016
    Monthly Fee: $805
       Tax: $6,081 (2025)
    Community: Grove Resort
    Condo


    Estimated Monthly Payment: $2,325 (change assumption)
    Mortgage ($1,014) + Fees ($805) + Taxes in 2025 ($507)


    Taxes:$6,081

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 327 S LAKEVIEW AVE, WINTER GARDEN, FL 34787

    $849,00041 Days on yellowkey   MLS ID: O6394438

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

    For Sale O6394438 - 327 S LAKEVIEW AVE, WINTER GARDEN, FL 34787 72 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 2225
       Built: 2014   Tax: $2,758 (2025)
    Community: G T Smith Sub 3
    Single Family


    Estimated Monthly Payment: $4,882 (change assumption)
    Mortgage ($4,652) + Taxes in 2025 ($230)


    Taxes:$2,758

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • WINTER GARDEN, FL 34787

    $510,88039 Days on yellowkey   MLS ID: G5110456

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

    For Sale G5110456 - WINTER GARDEN, FL 34787 2 photos

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

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $2,949 (change assumption)
    Mortgage ($2,799) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • WINTER GARDEN, FL 34787

    $955,89339 Days on yellowkey   MLS ID: G5110454

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

    For Sale G5110454 - WINTER GARDEN, FL 34787 1 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $5,388 (change assumption)
    Mortgage ($5,238) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7655 SILVER MEADOW ST, WINTER GARDEN, FL 34787

    $511,70539 Days on yellowkey   MLS ID: G5110445

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

    For Sale G5110445 - 7655 SILVER MEADOW ST, WINTER GARDEN, FL 34787 2 photos

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

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $2,954 (change assumption)
    Mortgage ($2,804) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15255 MARITIME PINE DR, WINTER GARDEN, FL 34787

    $923,25039 Days on yellowkey   MLS ID: G5110443

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

    For Sale G5110443 - 15255 MARITIME PINE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3498
       Built: 2026
    Monthly Fee: $150
       Tax: $298 (2025)
    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $5,234 (change assumption)
    Mortgage ($5,059) + Fees ($150) + Taxes in 2025 ($25)


    Taxes:$298

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17362 WILD DAISY DR, WINTER GARDEN, FL 34787

    $829,95339 Days on yellowkey   MLS ID: G5110442

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

    For Sale G5110442 - 17362 WILD DAISY DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $125

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,673 (change assumption)
    Mortgage ($4,548) + Fees ($125) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17465 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $849,35839 Days on yellowkey   MLS ID: G5110441

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

    For Sale G5110441 - 17465 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $125

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,779 (change assumption)
    Mortgage ($4,654) + Fees ($125) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17368 WILD DAISY DR, WINTER GARDEN, FL 34787

    $909,77839 Days on yellowkey   MLS ID: G5110440

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

    For Sale G5110440 - 17368 WILD DAISY DR, WINTER GARDEN, FL 34787 3 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $125

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $5,110 (change assumption)
    Mortgage ($4,985) + Fees ($125) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13001 HARVEST RAIN AVE, WINTER GARDEN, FL 34787

    $750,00054 Days on yellowkey   MLS ID: O6391387

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

    For Sale O6391387 - 13001 HARVEST RAIN AVE, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2858
       Built: 2026
    Monthly Fee: $140

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,249 (change assumption)
    Mortgage ($4,109) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14740 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $510,00081 Days on yellowkey   MLS ID: O6383531

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

    For Sale O6383531 - 14740 FIELD DAISY DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1992
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $3,023 (change assumption)
    Mortgage ($2,794) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring 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.