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Winter Garden Homes For Sale & Real Estate - 715 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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  • 14446 WHITTRIDGE DR, WINTER GARDEN, FL 34787

    $450,00055 Days on yellowkey   MLS ID: O6378698

    2 Days Off yellowkey (back on 4/21/2026)

    For Sale O6378698 - 14446 WHITTRIDGE DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1650
       Built: 2005
    Monthly Fee: $195
       Tax: $5,006 (2024)
    Community: Signature Lks-Pcl 01B
    Single Family


    Estimated Monthly Payment: $3,078 (change assumption)
    Mortgage ($2,466) + Fees ($195) + Taxes in 2024 ($417)


    Taxes:$5,006

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 15456 GILLIGAN CT, WINTER GARDEN, FL 34787

    $600,000264 Days on yellowkey   MLS ID: A4660262

    REDUCED by $20,000 (3.2%) on 04/21/2026

    For Sale A4660262 - 15456 GILLIGAN CT, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2571
       Built: 2020
    Monthly Fee: $102
       Tax: $8,702 (2024)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $4,115 (change assumption)
    Mortgage ($3,288) + Fees ($102) + Taxes in 2024 ($725)


    Taxes:$8,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1698 JUNIPER HAMMOCK ST, WINTER GARDEN, FL 34787

    $1,450,0004 Days on yellowkey   MLS ID: V4948569

    For Sale V4948569 - 1698 JUNIPER HAMMOCK ST, WINTER GARDEN, FL 34787 78 photos

    Bed: 7   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 4700
       Built: 2019
    Monthly Fee: $97
       Tax: $9,199 (2025)
    Community: Mcallister Lndg
    Single Family


    Estimated Monthly Payment: $8,809 (change assumption)
    Mortgage ($7,945) + Fees ($97) + Taxes in 2025 ($767)


    Taxes:$9,199

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787

    $823,90025 Days on yellowkey   MLS ID: O6393190

    REDUCED by $1,000 (0.1%) on 04/19/2026

    For Sale O6393190 - 15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787 82 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3902
       Built: 2005
    Monthly Fee: $243
       Tax: $7,653 (2025)
    Community: Stoneybrook West
    Single Family


    Estimated Monthly Payment: $5,395 (change assumption)
    Mortgage ($4,514) + Fees ($243) + Taxes in 2025 ($638)


    Taxes:$7,653

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 515 9TH ST, WINTER GARDEN, FL 34787

    $279,90063 Days on yellowkey   MLS ID: O6383185

    5 Days Off yellowkey (back on 4/21/2026)

    For Sale O6383185 - 515 9TH ST, WINTER GARDEN, FL 34787 32 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 770
       Built: 1951   Tax: $1,285 (2024)
    Community: Merchants Sub
    Single Family


    Estimated Monthly Payment: $1,641 (change assumption)
    Mortgage ($1,534) + Taxes in 2024 ($107)


    Taxes:$1,285

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1286 WINTER GREEN WAY, WINTER GARDEN, FL 34787

    $239,900157 Days on yellowkey   MLS ID: G5104510

    For Sale G5104510 - 1286 WINTER GREEN WAY, WINTER GARDEN, FL 34787 30 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1144
       Built: 1985
    Monthly Fee: $63
       Tax: $1,159 (2024)
    Community: Village Grove Ph 02
    Townhouse


    Estimated Monthly Payment: $1,474 (change assumption)
    Mortgage ($1,314) + Fees ($63) + Taxes in 2024 ($97)


    Taxes:$1,159

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 8807 FOUNTAIN PALM ALY, WINTER GARDEN, FL 34787

    $630,0001 Day on yellowkey   MLS ID: O6400597

    For Sale O6400597 - 8807 FOUNTAIN PALM ALY, WINTER GARDEN, FL 34787 27 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2581
       Built: 2018
    Monthly Fee: $600
       Tax: $6,298 (2025)
    Community: Lakeshore Preserve Ph 1
    Townhouse


    Estimated Monthly Payment: $4,577 (change assumption)
    Mortgage ($3,452) + Fees ($600) + Taxes in 2025 ($525)


    Taxes:$6,298

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5618 WATER ROSE RD, WINTER GARDEN, FL 34787

    $395,000Listed 04/20/2026 6:27PM   MLS ID: O6400788

    For Sale O6400788 - 5618 WATER ROSE RD, WINTER GARDEN, FL 34787 27 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1755
       Built: 2016
    Monthly Fee: $402
       Tax: $6,527 (2025)
    Community: Signature Lakes Ph 3B-6
    Townhouse


    Estimated Monthly Payment: $3,110 (change assumption)
    Mortgage ($2,164) + Fees ($402) + Taxes in 2025 ($544)


    Taxes:$6,527

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 12529 DALLINGTON TER, WINTER GARDEN, FL 34787

    $884,9901 Day on yellowkey   MLS ID: O6400678

    For Sale O6400678 - 12529 DALLINGTON TER, WINTER GARDEN, FL 34787 66 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3519
       Built: 2006
    Monthly Fee: $130
       Tax: $6,735 (2025)
    Community: Foxcrest A-N & P
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,540 (change assumption)
    Mortgage ($4,849) + Fees ($130) + Taxes in 2025 ($561)


    Taxes:$6,735

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 13067 TOLLCROSS WAY, WINTER GARDEN, FL 34787

    $599,00099 Days on yellowkey   MLS ID: O6367311

    For Sale O6367311 - 13067 TOLLCROSS WAY, WINTER GARDEN, FL 34787 64 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1906
       Built: 2024
    Monthly Fee: $96
       Tax: $2,239 (2024)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,565 (change assumption)
    Mortgage ($3,282) + Fees ($96) + Taxes in 2024 ($187)


    Taxes:$2,239

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: None


  • 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787

    $619,990154 Days on yellowkey   MLS ID: O6361583

    1 Days Off yellowkey (back on 4/15/2026)

    For Sale O6361583 - 11864 SHINE VIEW LN, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,753 (change assumption)
    Mortgage ($3,397) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17652 JAPONICA BLOOM DRIVE, WINTER GARDEN, FL 34787

    $749,990188 Days on yellowkey   MLS ID: TB8438268

    1 Days Off yellowkey (back on 3/30/2026)

    For Sale TB8438268 - 17652 JAPONICA BLOOM DRIVE, WINTER GARDEN, FL 34787 44 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3545
       Built: 2025
    Monthly Fee: $84
       Tax: $14,531 (2024)
    Community: Northlake At Ovation Phase 2 & 3
    Single Family


    Estimated Monthly Payment: $5,404 (change assumption)
    Mortgage ($4,109) + Fees ($84) + Taxes in 2024 ($1,211)


    Taxes:$14,531

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $748,000383 Days on yellowkey   MLS ID: O6280496

    For Sale O6280496 - 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2023
    Monthly Fee: $250
       Tax: $9,777 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $5,163 (change assumption)
    Mortgage ($4,099) + Fees ($250) + Taxes in 2024 ($815)


    Taxes:$9,777

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 14501 GROVE RESORT AVE, WINTER GARDEN, FL 34787

    $349,900Listed 04/20/2026 7:27PM   MLS ID: S5148274

    For Sale S5148274 - 14501 GROVE RESORT AVE, WINTER GARDEN, FL 34787 10 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1265
       Built: 2009
    Monthly Fee: $608
       Tax: $6,218 (2025)
    Community: Grove Resort And Spa
    Condo


    Estimated Monthly Payment: $3,043 (change assumption)
    Mortgage ($1,917) + Fees ($608) + Taxes in 2025 ($518)


    Taxes:$6,218

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11079 HANLON TERRACE ALY, WINTER GARDEN, FL 34787

    $389,990166 Days on yellowkey   MLS ID: O6358387

    REDUCED by $4,000 (1.0%) on 04/20/2026

    For Sale O6358387 - 11079 HANLON TERRACE ALY, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1868
       Built: 2021
    Monthly Fee: $339
       Tax: $6,256 (2024)
    Community: Winding Bay Preserve
    Townhouse


    Estimated Monthly Payment: $2,997 (change assumption)
    Mortgage ($2,137) + Fees ($339) + Taxes in 2024 ($521)


    Taxes:$6,256

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 9256 GRAND ISLAND WAY, WINTER GARDEN, FL 34787

    $750,00011 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


  • 13393 SUNSET LAKES CIR, WINTER GARDEN, FL 34787

    $867,0009 Days on yellowkey   MLS ID: O6398468

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

    For Sale O6398468 - 13393 SUNSET LAKES CIR, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2186
       Built: 1994
    Monthly Fee: $69
       Tax: $6,434 (2025)
    Community: Sunset Lakes
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,356 (change assumption)
    Mortgage ($4,751) + Fees ($69) + Taxes in 2025 ($536)


    Taxes:$6,434

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12438 CLEAR SAPPHIRE DR #223, WINTER GARDEN, FL 34787

    $684,99026 Days on yellowkey   MLS ID: O6393877

    REDUCED by $5,000 (0.7%) on 04/16/2026

    For Sale O6393877 - 12438 CLEAR SAPPHIRE DR #223, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3460
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $3,849 (change assumption)
    Mortgage ($3,753) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 14326 MURCOTT BLOSSOM BLVD, WINTER GARDEN, FL 34787

    $511,50052 Days on yellowkey   MLS ID: O6386513

    For Sale O6386513 - 14326 MURCOTT BLOSSOM BLVD, WINTER GARDEN, FL 34787 56 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1936
       Built: 2018
    Monthly Fee: $249
       Tax: $4,788 (2024)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,451 (change assumption)
    Mortgage ($2,803) + Fees ($249) + Taxes in 2024 ($399)


    Taxes:$4,788

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 12390 CLEAR SAPPHIRE #260, WINTER GARDEN, FL 34787

    $849,99022 Days on yellowkey   MLS ID: O6394850

    For Sale O6394850 - 12390 CLEAR SAPPHIRE #260, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2552
       Built: 2026
    Monthly Fee: $96

    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,753 (change assumption)
    Mortgage ($4,657) + Fees ($96) + Taxes in 2026 ($0)


    Taxes:$0

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None




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.