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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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  • 10224 ATWATER BAY DR, WINTER GARDEN, FL 34787

    $799,0001 Day on yellowkey   MLS ID: S5147252

    For Sale S5147252 - 10224 ATWATER BAY DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3227
       Built: 2018
    Monthly Fee: $230
       Tax: $7,456 (2025)
    Community: Waterleigh Ph 2B
    Single Family


    Estimated Monthly Payment: $5,229 (change assumption)
    Mortgage ($4,378) + Fees ($230) + Taxes in 2025 ($621)


    Taxes:$7,456

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1035 CHASE DR, WINTER GARDEN, FL 34787

    $465,0004 Days on yellowkey   MLS ID: O6396474

    For Sale O6396474 - 1035 CHASE DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1793
       Built: 1995
    Monthly Fee: $44
       Tax: $3,337 (2025)
    Community: Island Pointe Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,870 (change assumption)
    Mortgage ($2,548) + Fees ($44) + Taxes in 2025 ($278)


    Taxes:$3,337

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $580,00055 Days on yellowkey   MLS ID: O6383534

    For Sale O6383534 - 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2415
       Built: 2022
    Monthly Fee: $101
       Tax: $7,566 (2024)
    Community: Winding Bay Ph 3
    Single Family


    Estimated Monthly Payment: $3,909 (change assumption)
    Mortgage ($3,178) + Fees ($101) + Taxes in 2024 ($630)


    Taxes:$7,566

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15306 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $568,00053 Days on yellowkey   MLS ID: O6384014

    For Sale O6384014 - 15306 LEBEAU LOOP, WINTER GARDEN, FL 34787 52 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2482
       Built: 2021
    Monthly Fee: $101
       Tax: $6,339 (2024)
    Community: Winding Bay Ph 3
    Single Family


    Estimated Monthly Payment: $3,741 (change assumption)
    Mortgage ($3,112) + Fees ($101) + Taxes in 2024 ($528)


    Taxes:$6,339

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15716 SWEET LEMON WAY, WINTER GARDEN, FL 34787

    $739,00084 Days on yellowkey   MLS ID: O6375190

    REDUCED by $26,000 (3.4%) on 04/13/2026

    For Sale O6375190 - 15716 SWEET LEMON WAY, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2945
       Built: 2021
    Monthly Fee: $118
       Tax: $9,510 (2025)
    Community: Highlands At Summerlake Groves
    Single Family


    Estimated Monthly Payment: $4,960 (change assumption)
    Mortgage ($4,049) + Fees ($118) + Taxes in 2025 ($793)


    Taxes:$9,510

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9256 GRAND ISLAND WAY, WINTER GARDEN, FL 34787

    $750,0004 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


  • 5596 THOMAS SQUARE DR, WINTER GARDEN, FL 34787

    $618,00043 Days on yellowkey   MLS ID: O6386791

    For Sale O6386791 - 5596 THOMAS SQUARE DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2458
       Built: 2015
    Monthly Fee: $324
       Tax: $8,569 (2025)
    Community: Overlook At Hamlin
    Single Family


    Estimated Monthly Payment: $4,424 (change assumption)
    Mortgage ($3,386) + Fees ($324) + Taxes in 2025 ($714)


    Taxes:$8,569

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16006 GILDEN WAY, WINTER GARDEN, FL 34787

    $1,150,00018 Days on yellowkey   MLS ID: O6392997

    For Sale O6392997 - 16006 GILDEN WAY, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3617
       Built: 2023
    Monthly Fee: $225
       Tax: $12,929 (2025)
    Community: Encore At Ovation
    Single Family


    Estimated Monthly Payment: $7,604 (change assumption)
    Mortgage ($6,301) + Fees ($225) + Taxes in 2025 ($1,077)


    Taxes:$12,929

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 8275 BAYVIEW CROSSING DR DR, WINTER GARDEN, FL 34787

    $565,0004 Days on yellowkey   MLS ID: TB8496196

    For Sale TB8496196 - 8275 BAYVIEW CROSSING DR DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2019
       Built: 2017
    Monthly Fee: $312
       Tax: $5,109 (2025)
    Community: Waterleigh Phase 1C
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,834 (change assumption)
    Mortgage ($3,096) + Fees ($312) + Taxes in 2025 ($426)


    Taxes:$5,109

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 10472 PETRILLO WAY, WINTER GARDEN, FL 34787

    $1,065,00060 Days on yellowkey   MLS ID: O6382263

    For Sale O6382263 - 10472 PETRILLO WAY, WINTER GARDEN, FL 34787 53 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4025
       Built: 2022
    Monthly Fee: $102
       Tax: $12,049 (2025)
    Community: Winding Bay Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,942 (change assumption)
    Mortgage ($5,835) + Fees ($102) + Taxes in 2025 ($1,004)


    Taxes:$12,049

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15381 HONEYBELL DR, WINTER GARDEN, FL 34787

    $426,00022 Days on yellowkey   MLS ID: O6391881

    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: $3,157 (change assumption)
    Mortgage ($2,334) + 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


  • 15226 SUNSET OVERLOOK CIR, WINTER GARDEN, FL 34787

    $1,100,00026 Days on yellowkey   MLS ID: O6390971

    REDUCED by $50,000 (4.3%) on 03/31/2026

    For Sale O6390971 - 15226 SUNSET OVERLOOK CIR, WINTER GARDEN, FL 34787 80 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3556
       Built: 2023
    Monthly Fee: $128
       Tax: $10,299 (2025)
    Community: Johns Lake Pointe
    Single Family


    Estimated Monthly Payment: $7,013 (change assumption)
    Mortgage ($6,027) + Fees ($128) + Taxes in 2025 ($858)


    Taxes:$10,299

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 238 N MAIN ST, WINTER GARDEN, FL 34787

    $600,0006 Days on yellowkey   MLS ID: O6397340

    For Sale O6397340 - 238 N MAIN ST, WINTER GARDEN, FL 34787 21 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1005
       Built: 1950   Tax: $5,389 (2025)
    Community: Orange Grove Sub
    Single Family


    Estimated Monthly Payment: $3,737 (change assumption)
    Mortgage ($3,288) + Taxes in 2025 ($449)


    Taxes:$5,389

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 2621 SHIREHALL LN, WINTER GARDEN, FL 34787

    $500,00039 Days on yellowkey   MLS ID: O6386585

    For Sale O6386585 - 2621 SHIREHALL LN, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2003
    Monthly Fee: $243
       Tax: $3,181 (2024)
    Community: Stoneybrook West Ut 04 48 48
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,248 (change assumption)
    Mortgage ($2,740) + Fees ($243) + Taxes in 2024 ($265)


    Taxes:$3,181

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1075 CHASE DR, WINTER GARDEN, FL 34787

    $625,00043 Days on yellowkey   MLS ID: O6386607

    For Sale O6386607 - 1075 CHASE DR, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2125
       Built: 2015
    Monthly Fee: $41
       Tax: $2,734 (2024)
    Community: Island Pointe Sub
    Single Family


    Estimated Monthly Payment: $3,693 (change assumption)
    Mortgage ($3,425) + Fees ($41) + Taxes in 2024 ($228)


    Taxes:$2,734

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14501 GROVE RESORT AVE #2527, WINTER GARDEN, FL 34787

    $270,000117 Days on yellowkey   MLS ID: O6368187

    SHORT SALE O6368187 - 14501 GROVE RESORT AVE #2527, WINTER GARDEN, FL 34787 36 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1544
       Built: 2018
    Monthly Fee: $1,103
       Tax: $8,868 (2024)
    Community: Grove Residence & Spa Hotel Condo Ii
    Condo


    Estimated Monthly Payment: $3,321 (change assumption)
    Mortgage ($1,479) + Fees ($1,103) + Taxes in 2024 ($739)


    Taxes:$8,868

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 8216 TOPSAIL PL, WINTER GARDEN, FL 34787

    $974,90028 Days on yellowkey   MLS ID: O6391155

    REDUCED by $14,100 (1.4%) on 04/13/2026

    For Sale O6391155 - 8216 TOPSAIL PL, WINTER GARDEN, FL 34787 67 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3055
       Built: 2022
    Monthly Fee: $360
       Tax: $12,728 (2025)
    Community: Lakeshore Preserve Ph 5
    Single Family


    Estimated Monthly Payment: $6,762 (change assumption)
    Mortgage ($5,342) + Fees ($360) + Taxes in 2025 ($1,061)


    Taxes:$12,728

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 14501 GROVE RESORT AVE #1612, WINTER GARDEN, FL 34787

    $299,000176 Days on yellowkey   MLS ID: S5136940

    For Sale S5136940 - 14501 GROVE RESORT AVE #1612, WINTER GARDEN, FL 34787 76 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1375
       Built: 2016
    Monthly Fee: $875
       Tax: $6,828 (2024)
    Community: Grove Resort And Spa Hotel Condo 1
    Condo


    Estimated Monthly Payment: $3,082 (change assumption)
    Mortgage ($1,638) + Fees ($875) + Taxes in 2024 ($569)


    Taxes:$6,828

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17006 SEVILLE ORANGE RD, WINTER GARDEN, FL 34787

    $718,79912 Days on yellowkey   MLS ID: TB8493597

    For Sale TB8493597 - 17006 SEVILLE ORANGE RD, WINTER GARDEN, FL 34787 11 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2224
       Built: 2026
    Monthly Fee: $84
       Tax: $2,363 (2025)
    Community: Northlake/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $4,219 (change assumption)
    Mortgage ($3,939) + Fees ($84) + Taxes in 2025 ($197)


    Taxes:$2,363

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15659 JUNGLE ALY, WINTER GARDEN, FL 34787

    $360,00024 Days on yellowkey   MLS ID: S5143684

    REDUCED by $85,000 (19.1%) on 03/31/2026

    For Sale S5143684 - 15659 JUNGLE ALY, WINTER GARDEN, FL 34787 16 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1732
       Built: 2021   Tax: $6,265 (2024)
    Community: Winding Bay Ph 2
    Townhouse


    Estimated Monthly Payment: $2,495 (change assumption)
    Mortgage ($1,973) + Taxes in 2024 ($522)


    Taxes:$6,265

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




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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.