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Winter Garden Homes For Sale & Real Estate - 661 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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  • 9459 JAYWOOD RD, WINTER GARDEN, FL 34787

    $760,00043 Days on yellowkey   MLS ID: O6386488

    0 Days Off yellowkey (back on 3/31/2026)

    For Sale O6386488 - 9459 JAYWOOD RD, WINTER GARDEN, FL 34787 55 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2020
    Monthly Fee: $261
       Tax: $6,669 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $4,981 (change assumption)
    Mortgage ($4,164) + Fees ($261) + Taxes in 2025 ($556)


    Taxes:$6,669

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14327 WABASSO LOOP, WINTER GARDEN, FL 34787

    $899,990200 Days on yellowkey   MLS ID: O6347454

    For Sale O6347454 - 14327 WABASSO LOOP, WINTER GARDEN, FL 34787 48 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3710
       Built: 2022
    Monthly Fee: $200
       Tax: $12,141 (2024)
    Community: Tilden Place/Winter Garden
    Single Family


    Estimated Monthly Payment: $6,143 (change assumption)
    Mortgage ($4,931) + Fees ($200) + Taxes in 2024 ($1,012)


    Taxes:$12,141

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 233 SOUTHERN PECAN CIR #101, WINTER GARDEN, FL 34787

    $259,90019 Days on yellowkey   MLS ID: S5144851

    For Sale S5144851 - 233 SOUTHERN PECAN CIR #101, WINTER GARDEN, FL 34787 18 photos

    Bed: 2   Bath: 1.0   Gar: 1
    Liv Area Sq Ft: 966
       Built: 2005
    Monthly Fee: $343
       Tax: $2,537 (2024)
    Community: Southern Pines Condo
    Condo


    Estimated Monthly Payment: $1,978 (change assumption)
    Mortgage ($1,424) + Fees ($343) + Taxes in 2024 ($211)


    Taxes:$2,537

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787

    $554,990102 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


  • 15625 SYLVESTER PALM DR, WINTER GARDEN, FL 34787

    $1,115,00068 Days on yellowkey   MLS ID: O6379346

    For Sale O6379346 - 15625 SYLVESTER PALM DR, WINTER GARDEN, FL 34787 72 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 3886
       Built: 2018
    Monthly Fee: $360
       Tax: $9,571 (2024)
    Community: Lakeshore Preserve Ph 1
    Single Family


    Estimated Monthly Payment: $7,267 (change assumption)
    Mortgage ($6,109) + Fees ($360) + Taxes in 2024 ($798)


    Taxes:$9,571

    Elementary School: Panther Lake Elementary

    High School: None

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787

    $591,00043 Days on yellowkey   MLS ID: S5144794

    For Sale S5144794 - 4642 PRAIRIE CREEK ST, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 2149
       Built: 2021
    Monthly Fee: $281
       Tax: $6,500 (2024)
    Community: Enclave At Hamlin
    Single Family


    Estimated Monthly Payment: $4,061 (change assumption)
    Mortgage ($3,238) + Fees ($281) + Taxes in 2024 ($542)


    Taxes:$6,500

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7832 FREESTYLE LN, WINTER GARDEN, FL 34787

    $1,100,00070 Days on yellowkey   MLS ID: G5107680

    For Sale G5107680 - 7832 FREESTYLE LN, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2650
       Built: 2018
    Monthly Fee: $300
       Tax: $16,616 (2025)
    Community: Isles Of Lake Hancock
    Single Family


    Estimated Monthly Payment: $7,712 (change assumption)
    Mortgage ($6,027) + Fees ($300) + Taxes in 2025 ($1,385)


    Taxes:$16,616

    Elementary School: Independence Elementary

    High School: None

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13953 EASDALE ALY, WINTER GARDEN, FL 34787

    $509,90062 Days on yellowkey   MLS ID: O6381882

    For Sale O6381882 - 13953 EASDALE ALY, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1770
       Built: 2024
    Monthly Fee: $149
       Tax: $5,696 (2025)
    Community: Westhaven At Ovation
    Townhouse


    Estimated Monthly Payment: $3,418 (change assumption)
    Mortgage ($2,794) + Fees ($149) + Taxes in 2025 ($475)


    Taxes:$5,696

    Elementary School: Water Spring Elementary

    High School: None

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16149 WIND VIEW LN, WINTER GARDEN, FL 34787

    $505,00032 Days on yellowkey   MLS ID: O6389892

    For Sale O6389892 - 16149 WIND VIEW LN, WINTER GARDEN, FL 34787 46 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2036
       Built: 2016
    Monthly Fee: $332
       Tax: $4,472 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $3,472 (change assumption)
    Mortgage ($2,767) + Fees ($332) + Taxes in 2025 ($373)


    Taxes:$4,472

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 10089 SALT POINT DR, WINTER GARDEN, FL 34787

    $475,00015 Days on yellowkey   MLS ID: O6392385

    For Sale O6392385 - 10089 SALT POINT DR, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1654
       Built: 2022
    Monthly Fee: $260
       Tax: $6,886 (2025)
    Community: Waterleigh Ph 2E
    Townhouse


    Estimated Monthly Payment: $3,437 (change assumption)
    Mortgage ($2,603) + Fees ($260) + Taxes in 2025 ($574)


    Taxes:$6,886

    Elementary School: Avalon Elem

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14501 GROVE RESORT AVE #2138, WINTER GARDEN, FL 34787

    $190,00069 Days on yellowkey   MLS ID: O6379849

    For Sale O6379849 - 14501 GROVE RESORT AVE #2138, WINTER GARDEN, FL 34787 61 photos

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


    Estimated Monthly Payment: $2,610 (change assumption)
    Mortgage ($1,041) + Fees ($889) + Taxes in 2024 ($680)


    Taxes:$8,154

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11229 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $806,80185 Days on yellowkey   MLS ID: O6375011

    2 Days Off yellowkey (back on 3/31/2026)

    For Sale O6375011 - 11229 HOLLOW BAY DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 5   Bath: 4.5
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,785 (change assumption)
    Mortgage ($4,421) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11187 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $814,56696 Days on yellowkey   MLS ID: O6372260

    2 Days Off yellowkey (back on 3/31/2026)

    For Sale O6372260 - 11187 HOLLOW BAY DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 5   Bath: 4.0
    Liv Area Sq Ft: 2866
       Built: 2025
    Monthly Fee: $249
       Tax: $1,989 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,878 (change assumption)
    Mortgage ($4,463) + Fees ($249) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8220 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $539,95042 Days on yellowkey   MLS ID: TB8482364

    REDUCED by $18,049 (3.2%) on 03/31/2026

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

    Bed: 4   Bath: 3.5
    Liv Area Sq Ft: 2477
       Built: 2016
    Monthly Fee: $335
       Tax: $7,983 (2025)
    Community: Waterleigh Ph 1B
    Single Family


    Estimated Monthly Payment: $3,959 (change assumption)
    Mortgage ($2,959) + 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


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

    $849,99015 Days on yellowkey   MLS ID: O6394850

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

    Bed: 4   Bath: 3.0
    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


  • 5210 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787

    $730,00015 Days on yellowkey   MLS ID: O6394219

    For Sale O6394219 - 5210 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787 28 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 2477
       Built: 2023
    Monthly Fee: $165
       Tax: $9,345 (2025)
    Community: Silverleaf Reserve/Hamlin Ph 2
    Single Family


    Estimated Monthly Payment: $4,944 (change assumption)
    Mortgage ($4,000) + Fees ($165) + Taxes in 2025 ($779)


    Taxes:$9,345

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16302 HAMLIN HILLS RD, WINTER GARDEN, FL 34787

    $459,900249 Days on yellowkey   MLS ID: O6331200

    2 Days Off yellowkey (back on 12/19/2025)

    For Sale O6331200 - 16302 HAMLIN HILLS RD, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1644
       Built: 2024
    Monthly Fee: $225
       Tax: $954 (2024)
    Community: Hamlin Rdg
    Townhouse


    Estimated Monthly Payment: $2,824 (change assumption)
    Mortgage ($2,520) + Fees ($225) + Taxes in 2024 ($80)


    Taxes:$954

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 13732 FRESH IVY ST, WINTER GARDEN, FL 34787

    $580,000238 Days on yellowkey   MLS ID: O6337004

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

    For Sale O6337004 - 13732 FRESH IVY ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1889
       Built: 2024
    Monthly Fee: $544
       Tax: $2,180 (2024)
    Community: Del Webb Oasis Ph 3
    Single Family


    Estimated Monthly Payment: $3,904 (change assumption)
    Mortgage ($3,178) + Fees ($544) + Taxes in 2024 ($182)


    Taxes:$2,180

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16554 RAVEN ROCK PL, WINTER GARDEN, FL 34787

    $875,00031 Days on yellowkey   MLS ID: O6390742

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

    For Sale O6390742 - 16554 RAVEN ROCK PL, WINTER GARDEN, FL 34787 58 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3032
       Built: 2015
    Monthly Fee: $184
       Tax: $6,702 (2025)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $5,537 (change assumption)
    Mortgage ($4,794) + Fees ($184) + Taxes in 2025 ($559)


    Taxes:$6,702

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13526 FOX GLOVE ST, WINTER GARDEN, FL 34787

    $845,00021 Days on yellowkey   MLS ID: O6388630

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

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

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




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.