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Winter Garden Single Family Homes For Sale - 691 homes

Winter Garden Single Family Homes for Sale are located in Orange County, Florida. Find single family homes for sale in Winter Garden with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Garden single family houses.

Location: Winter Garden

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  • 5211 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787

    $799,000152 Days on yellowkey   MLS ID: O6373067

    REDUCED by $20,000 (2.4%) on 05/16/2026

    For Sale O6373067 - 5211 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2909
       Built: 2023
    Monthly Fee: $165
       Tax: $9,990 (2024)
    Community: Silverleaf Reserve/Hamlin Ph 2
    Single Family


    Estimated Monthly Payment: $5,375 (change assumption)
    Mortgage ($4,378) + Fees ($165) + Taxes in 2024 ($833)


    Taxes:$9,990

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 1261 E FULLERS CROSS RD, WINTER GARDEN, FL 34787

    $675,00065 Days on yellowkey   MLS ID: O6397098

    1 Days Off yellowkey (back on 5/7/2026)

    For Sale O6397098 - 1261 E FULLERS CROSS RD, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1832
       Built: 1991   Tax: $2,367 (2025)
    Community: 0000
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,896 (change assumption)
    Mortgage ($3,699) + Taxes in 2025 ($197)


    Taxes:$2,367

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15058 SUNSTAR WAY, WINTER GARDEN, FL 34787

    $1,900,00015 Days on yellowkey   MLS ID: O6411520

    0 Days Off yellowkey (back on 6/8/2026)

    For Sale O6411520 - 15058 SUNSTAR WAY, WINTER GARDEN, FL 34787 50 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3607
       Built: 2021
    Monthly Fee: $110
       Tax: $645 (2025)
    Community: Highlands/Summerlake Grvs Ph 3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,574 (change assumption)
    Mortgage ($10,411) + Fees ($110) + Taxes in 2025 ($54)


    Taxes:$645

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1005 CHASE DR, WINTER GARDEN, FL 34787

    $615,00016 Days on yellowkey   MLS ID: O6411451

    For Sale O6411451 - 1005 CHASE DR, WINTER GARDEN, FL 34787 39 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: $4,028 (change assumption)
    Mortgage ($3,370) + 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


  • 11205 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $939,99082 Days on yellowkey   MLS ID: O6392839

    1 Days Off yellowkey (back on 5/15/2026)

    REDUCED by $10,000 (1.1%) on 05/15/2026

    For Sale O6392839 - 11205 HOLLOW BAY DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,566 (change assumption)
    Mortgage ($5,151) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15162 CANOPY COVER DR, WINTER GARDEN, FL 34787

    $880,000197 Days on yellowkey   MLS ID: S5139203

    REDUCED by $5,000 (0.6%) on 04/29/2026

    For Sale S5139203 - 15162 CANOPY COVER DR, WINTER GARDEN, FL 34787 69 photos

    Bed: 2   Bath: 2.0   Gar: 3
    Liv Area Sq Ft: 2049
       Built: 2023
    Monthly Fee: $545
       Tax: $1,939 (2023)
    Community: Del Webb Oasis Phase 2
    Single Family


    Estimated Monthly Payment: $5,528 (change assumption)
    Mortgage ($4,822) + Fees ($545) + Taxes in 2023 ($162)


    Taxes:$1,939

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 14372 BREDA CENTER LOOP, WINTER GARDEN, FL 34787

    $580,000107 Days on yellowkey   MLS ID: O6385377

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

    For Sale O6385377 - 14372 BREDA CENTER LOOP, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2700
       Built: 2016
    Monthly Fee: $196
       Tax: $4,460 (2025)
    Community: Lake Hancock Preserve
    Single Family


    Estimated Monthly Payment: $3,746 (change assumption)
    Mortgage ($3,178) + Fees ($196) + Taxes in 2025 ($372)


    Taxes:$4,460

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $745,000173 Days on yellowkey   MLS ID: S5140531

    For Sale S5140531 - 18344 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2924
       Built: 2023
    Monthly Fee: $300
       Tax: $1,706 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,524 (change assumption)
    Mortgage ($4,082) + Fees ($300) + Taxes in 2024 ($142)


    Taxes:$1,706

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 705 GARDEN WEST TER, WINTER GARDEN, FL 34787

    $1,275,00040 Days on yellowkey   MLS ID: O6403363

    REDUCED by $25,000 (1.9%) on 06/08/2026

    For Sale O6403363 - 705 GARDEN WEST TER, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2698
       Built: 2020
    Monthly Fee: $232
       Tax: $10,345 (2025)
    Community: Garden West
    Single Family


    Estimated Monthly Payment: $8,080 (change assumption)
    Mortgage ($6,986) + Fees ($232) + Taxes in 2025 ($862)


    Taxes:$10,345

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15130 OVATION DR, WINTER GARDEN, FL 34787

    $840,00010 Days on yellowkey   MLS ID: O6413647

    For Sale O6413647 - 15130 OVATION DR, WINTER GARDEN, FL 34787 55 photos

    Bed: 7   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4688
       Built: 2009
    Monthly Fee: $167
       Tax: $6,472 (2025)
    Community: Belle Meade Ph 02 H
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,309 (change assumption)
    Mortgage ($4,603) + Fees ($167) + Taxes in 2025 ($539)


    Taxes:$6,472

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17379 CHANNEL WAY, WINTER GARDEN, FL 34787

    $689,00010 Days on yellowkey   MLS ID: O6412749

    REDUCED by $10,000 (1.4%) on 06/05/2026

    For Sale O6412749 - 17379 CHANNEL WAY, WINTER GARDEN, FL 34787 61 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2782
       Built: 2019
    Monthly Fee: $215
       Tax: $9,049 (2025)
    Community: Waterside At Johns Lake
    Single Family


    Estimated Monthly Payment: $4,744 (change assumption)
    Mortgage ($3,775) + Fees ($215) + Taxes in 2025 ($754)


    Taxes:$9,049

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $569,990145 Days on yellowkey   MLS ID: O6374947

    REDUCED by $5,000 (0.9%) on 06/04/2026

    For Sale O6374947 - 16840 HOBE SOUND CT, WINTER GARDEN, FL 34787 13 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,488 (change assumption)
    Mortgage ($3,123) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $546,990204 Days on yellowkey   MLS ID: O6362478

    REDUCED by $8,000 (1.4%) on 06/04/2026

    For Sale O6362478 - 16845 HOBE SOUND CT, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2025
    Monthly Fee: $190
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,353 (change assumption)
    Mortgage ($2,997) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13212 SOCIAL LN, WINTER GARDEN, FL 34787

    $595,00058 Days on yellowkey   MLS ID: O6398708

    For Sale O6398708 - 13212 SOCIAL LN, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2526
       Built: 2005
    Monthly Fee: $100
       Tax: $4,474 (2025)
    Community: Regency Oaks F
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,733 (change assumption)
    Mortgage ($3,260) + Fees ($100) + Taxes in 2025 ($373)


    Taxes:$4,474

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 17422 CHANNEL WAY, WINTER GARDEN, FL 34787

    $767,000109 Days on yellowkey   MLS ID: G5108709

    1 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $7,000 (0.9%) on 05/11/2026

    For Sale G5108709 - 17422 CHANNEL WAY, WINTER GARDEN, FL 34787 44 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3261
       Built: 2019
    Monthly Fee: $215
       Tax: $9,958 (2025)
    Community: Waterside On Johns Lake
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,247 (change assumption)
    Mortgage ($4,203) + Fees ($215) + Taxes in 2025 ($830)


    Taxes:$9,958

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6166 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787

    $649,00060 Days on yellowkey   MLS ID: O6399123

    3 Days Off yellowkey (back on 6/7/2026)

    REDUCED by $15,900 (2.4%) on 06/02/2026

    For Sale O6399123 - 6166 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787 73 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2818
       Built: 2018
    Monthly Fee: $142
       Tax: $6,366 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $4,229 (change assumption)
    Mortgage ($3,556) + Fees ($142) + Taxes in 2025 ($531)


    Taxes:$6,366

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 205 HORSTFIELD DR, WINTER GARDEN, FL 34787

    $315,00022 Days on yellowkey   MLS ID: O6410222

    REDUCED by $7,500 (2.3%) on 06/08/2026

    For Sale O6410222 - 205 HORSTFIELD DR, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1048
       Built: 1998
    Monthly Fee: $40
       Tax: $1,983 (2025)
    Community: Park Ave Estates
    Single Family


    Estimated Monthly Payment: $1,931 (change assumption)
    Mortgage ($1,726) + Fees ($40) + Taxes in 2025 ($165)


    Taxes:$1,983

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 11264 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,99065 Days on yellowkey   MLS ID: O6397733

    3 Days Off yellowkey (back on 6/8/2026)

    REDUCED by $20,000 (2.2%) on 06/04/2026

    For Sale O6397733 - 11264 HOLLOW BAY DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,296 (change assumption)
    Mortgage ($4,931) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13043 SANDCASTLE DRIVE, WINTER GARDEN, FL 34787

    $899,00059 Days on yellowkey   MLS ID: O6399529

    1 Days Off yellowkey (back on 6/7/2026)

    INCREASED by $23,000 (2.6%) on 05/09/2026

    For Sale O6399529 - 13043 SANDCASTLE DRIVE, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1943
       Built: 2022
    Monthly Fee: $534
       Tax: $10,109 (2025)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,302 (change assumption)
    Mortgage ($4,926) + Fees ($534) + Taxes in 2025 ($842)


    Taxes:$10,109

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14240 COLONIAL POINTE DR, WINTER GARDEN, FL 34787

    $1,250,00012 Days on yellowkey   MLS ID: O6412255

    REDUCED by $25,000 (2.0%) on 06/06/2026

    For Sale O6412255 - 14240 COLONIAL POINTE DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4816
       Built: 2018
    Monthly Fee: $209
       Tax: $10,516 (2025)
    Community: West Lake Hancock Estates
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,934 (change assumption)
    Mortgage ($6,849) + Fees ($209) + Taxes in 2025 ($876)


    Taxes:$10,516

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle




Why Bother Searching Elsewhere for Winter Garden Single Family Homes for Sale?

Winter Garden home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden single family homes. 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 single family home 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.