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Winter Garden Homes For Sale & Real Estate - 973 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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  • 14411 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787

    $885,00052 Days on yellowkey   MLS ID: O6413972

    REDUCED by $10,000 (1.1%) on 07/24/2026

    For Sale O6413972 - 14411 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787 72 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4010
       Built: 2005
    Monthly Fee: $182
       Tax: $11,924 (2025)
    Community: Bay Isle 48 17
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,025 (change assumption)
    Mortgage ($4,849) + Fees ($182) + Taxes in 2025 ($994)


    Taxes:$11,924

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 6131 ELFIN HERB WAY, WINTER GARDEN, FL 34787

    $435,00052 Days on yellowkey   MLS ID: O6414015

    REDUCED by $15,000 (3.3%) on 07/24/2026

    For Sale O6414015 - 6131 ELFIN HERB WAY, WINTER GARDEN, FL 34787 78 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1714
       Built: 2020
    Monthly Fee: $289
       Tax: $5,990 (2025)
    Community: Hamilton Gardens
    Townhouse


    Estimated Monthly Payment: $3,172 (change assumption)
    Mortgage ($2,384) + Fees ($289) + Taxes in 2025 ($499)


    Taxes:$5,990

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: None


  • 2025 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787

    $715,00020 Days on yellowkey   MLS ID: O6422627

    For Sale O6422627 - 2025 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 2655
       Built: 1999
    Monthly Fee: $92
       Tax: $2,506 (2025)
    Community: Wintermere Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,219 (change assumption)
    Mortgage ($3,918) + Fees ($92) + Taxes in 2025 ($209)


    Taxes:$2,506

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14501 GROVE RESORT AVE #3523, WINTER GARDEN, FL 34787

    $200,00060 Days on yellowkey   MLS ID: O6411650

    0 Days Off yellowkey (back on 7/24/2026)

    FORECLOSURE O6411650 - 14501 GROVE RESORT AVE #3523, WINTER GARDEN, FL 34787 78 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1265
       Built: 2018   Tax: $6,847 (2025)
    Community: Grove Resort & Spa
    Spa: Yes

    Condo


    Estimated Monthly Payment: $1,666 (change assumption)
    Mortgage ($1,096) + Taxes in 2025 ($571)


    Taxes:$6,847

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7840 WINTER WREN ST, WINTER GARDEN, FL 34787

    $519,90027 Days on yellowkey   MLS ID: O6421167

    REDUCED by $6,000 (1.1%) on 07/24/2026

    For Sale O6421167 - 7840 WINTER WREN ST, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2004
       Built: 2015
    Monthly Fee: $251
       Tax: $7,385 (2025)
    Community: Summerlake Pd Ph 1B Rep
    Single Family


    Estimated Monthly Payment: $3,715 (change assumption)
    Mortgage ($2,849) + Fees ($251) + Taxes in 2025 ($615)


    Taxes:$7,385

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 721 S WOODLAND ST, WINTER GARDEN, FL 34787

    $440,00031 Days on yellowkey   MLS ID: O6419636

    REDUCED by $10,000 (2.2%) on 07/23/2026

    For Sale O6419636 - 721 S WOODLAND ST, WINTER GARDEN, FL 34787 24 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1034
       Built: 1955   Tax: $508 (2025)
    Community: Borders & Woosley Sub
    Single Family


    Estimated Monthly Payment: $2,453 (change assumption)
    Mortgage ($2,411) + Taxes in 2025 ($42)


    Taxes:$508

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14501 GROVE RESORT AVE #3205, WINTER GARDEN, FL 34787

    $325,000984 Days on yellowkey   MLS ID: O6157343

    For Sale O6157343 - 14501 GROVE RESORT AVE #3205, WINTER GARDEN, FL 34787 25 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1265
       Built: 2018   Tax: $4,196 (2023)
    Community: Grove Resort And Spa Hotel
    Condo


    Estimated Monthly Payment: $2,130 (change assumption)
    Mortgage ($1,781) + Taxes in 2023 ($350)


    Taxes:$4,196

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 15665 CITRUS HARVEST RD, WINTER GARDEN, FL 34787

    $699,90086 Days on yellowkey   MLS ID: O6400896

    REDUCED by $20,000 (2.8%) on 07/11/2026

    For Sale O6400896 - 15665 CITRUS HARVEST RD, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2016
    Monthly Fee: $235
       Tax: $5,441 (2025)
    Community: Hickory Hammock Ph 2A
    Single Family


    Estimated Monthly Payment: $4,523 (change assumption)
    Mortgage ($3,835) + Fees ($235) + Taxes in 2025 ($453)


    Taxes:$5,441

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14327 WABASSO LOOP, WINTER GARDEN, FL 34787

    $869,990304 Days on yellowkey   MLS ID: O6347454

    REDUCED by $30,000 (3.3%) on 07/24/2026

    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: $5,979 (change assumption)
    Mortgage ($4,767) + Fees ($200) + Taxes in 2024 ($1,012)


    Taxes:$12,141

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2200 ROMANUM DR, WINTER GARDEN, FL 34787

    $550,00073 Days on yellowkey   MLS ID: O6408190

    0 Days Off yellowkey (back on 6/29/2026)

    REDUCED by $10,000 (1.8%) on 06/24/2026

    For Sale O6408190 - 2200 ROMANUM DR, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2561
       Built: 2015
    Monthly Fee: $211
       Tax: $8,843 (2025)
    Community: Alexander Rdg
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,962 (change assumption)
    Mortgage ($3,014) + Fees ($211) + Taxes in 2025 ($737)


    Taxes:$8,843

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14099 LOCHEND WAY, WINTER GARDEN, FL 34787

    $468,00087 Days on yellowkey   MLS ID: O6404015

    REDUCED by $11,900 (2.5%) on 07/24/2026

    For Sale O6404015 - 14099 LOCHEND WAY, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1720
       Built: 2024
    Monthly Fee: $150
       Tax: $6,752 (2025)
    Community: Westhaven/Ovation
    Townhouse


    Estimated Monthly Payment: $3,277 (change assumption)
    Mortgage ($2,564) + Fees ($150) + Taxes in 2025 ($563)


    Taxes:$6,752

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787

    $535,00081 Days on yellowkey   MLS ID: O6402423

    REDUCED by $10,000 (1.8%) on 06/25/2026

    For Sale O6402423 - 7190 ENCHANTED LAKE DR, WINTER GARDEN, FL 34787 17 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2016
    Monthly Fee: $253
       Tax: $5,148 (2025)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,613 (change assumption)
    Mortgage ($2,931) + Fees ($253) + Taxes in 2025 ($429)


    Taxes:$5,148

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787

    $765,000123 Days on yellowkey   MLS ID: O6393987

    1 Days Off yellowkey (back on 7/24/2026)

    REDUCED by $30,000 (3.8%) on 05/08/2026

    For Sale O6393987 - 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4307
       Built: 2014
    Monthly Fee: $114
       Tax: $5,670 (2025)
    Community: Reserve/Carriage Pointe Ph 1
    Single Family


    Estimated Monthly Payment: $4,778 (change assumption)
    Mortgage ($4,192) + Fees ($114) + Taxes in 2025 ($472)


    Taxes:$5,670

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787

    $669,99024 Days on yellowkey   MLS ID: S5153036

    INCREASED by $20,100 (3.1%) on 07/14/2026

    For Sale S5153036 - 15026 SUMMER HARVEST ST, WINTER GARDEN, FL 34787 41 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2930
       Built: 2024
    Monthly Fee: $202
       Tax: $9,669 (2025)
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $4,679 (change assumption)
    Mortgage ($3,671) + Fees ($202) + Taxes in 2025 ($806)


    Taxes:$9,669

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 10294 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $449,90074 Days on yellowkey   MLS ID: O6407798

    REDUCED by $10,000 (2.2%) on 07/16/2026

    For Sale O6407798 - 10294 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 56 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1689
       Built: 2019
    Monthly Fee: $245
       Tax: $7,600 (2025)
    Community: Waterleigh Ph 2C-1
    Single Family


    Estimated Monthly Payment: $3,343 (change assumption)
    Mortgage ($2,465) + Fees ($245) + Taxes in 2025 ($633)


    Taxes:$7,600

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1142 DUNBROOKE ST, WINTER GARDEN, FL 34787

    $515,00039 Days on yellowkey   MLS ID: O6417527

    1 Days Off yellowkey (back on 6/26/2026)

    For Sale O6417527 - 1142 DUNBROOKE ST, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2068
       Built: 2005
    Monthly Fee: $53
       Tax: $4,251 (2025)
    Community: Chapin Station
    Single Family


    Estimated Monthly Payment: $3,229 (change assumption)
    Mortgage ($2,822) + Fees ($53) + Taxes in 2025 ($354)


    Taxes:$4,251

    Elementary School: Maxey Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 455 WESTPOINT GARDEN CIR, WINTER GARDEN, FL 34787

    $330,00017 Days on yellowkey   MLS ID: O6423147

    2 Days Off yellowkey (back on 7/24/2026)

    For Sale O6423147 - 455 WESTPOINT GARDEN CIR, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1588
       Built: 2006
    Monthly Fee: $123
       Tax: $4,229 (2025)
    Community: Westpoint Townhomes
    Townhouse


    Estimated Monthly Payment: $2,284 (change assumption)
    Mortgage ($1,808) + Fees ($123) + Taxes in 2025 ($352)


    Taxes:$4,229

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3399 BUOY CIR, WINTER GARDEN, FL 34787

    $1,204,90033 Days on yellowkey   MLS ID: O6419829

    REDUCED by $20,000 (1.6%) on 07/24/2026

    For Sale O6419829 - 3399 BUOY CIR, WINTER GARDEN, FL 34787 34 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 5277
       Built: 2020
    Monthly Fee: $128
       Tax: $17,116 (2025)
    Community: Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $8,156 (change assumption)
    Mortgage ($6,602) + Fees ($128) + Taxes in 2025 ($1,426)


    Taxes:$17,116

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12050 BRACCO ST, WINTER GARDEN, FL 34787

    $475,000100 Days on yellowkey   MLS ID: O6398494

    REDUCED by $14,900 (3.0%) on 07/16/2026

    For Sale O6398494 - 12050 BRACCO ST, WINTER GARDEN, FL 34787 77 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2023
    Monthly Fee: $110
       Tax: $7,195 (2025)
    Community: Highland Ridge
    Single Family


    Estimated Monthly Payment: $3,312 (change assumption)
    Mortgage ($2,603) + Fees ($110) + Taxes in 2025 ($600)


    Taxes:$7,195

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1005 CHASE DR, WINTER GARDEN, FL 34787

    $599,99960 Days on yellowkey   MLS ID: O6411451

    REDUCED by $1 (0.0%) on 07/09/2026

    For Sale O6411451 - 1005 CHASE DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2319
       Built: 2005
    Monthly Fee: $68
       Tax: $7,087 (2025)
    Community: Island Pointe Sub
    Single Family


    Estimated Monthly Payment: $3,946 (change assumption)
    Mortgage ($3,288) + Fees ($68) + Taxes in 2025 ($591)


    Taxes:$7,087

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview 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.