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Winter Garden Single Family Homes For Sale - 729 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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  • 8289 TOPSAIL PL, WINTER GARDEN, FL 34787

    $890,00049 Days on yellowkey   MLS ID: S5151179

    2 Days Off yellowkey (back on 7/21/2026)

    REDUCED by $30,000 (3.3%) on 06/16/2026

    For Sale S5151179 - 8289 TOPSAIL PL, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2755
       Built: 2020
    Monthly Fee: $350
       Tax: $11,564 (2024)
    Community: Lakeshore Preserve Ph 5
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,190 (change assumption)
    Mortgage ($4,877) + Fees ($350) + Taxes in 2024 ($964)


    Taxes:$11,564

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 13822 JOMATT LOOP, WINTER GARDEN, FL 34787

    $975,00054 Days on yellowkey   MLS ID: O6411926

    0 Days Off yellowkey (back on 7/21/2026)

    REDUCED by $25,000 (2.5%) on 06/24/2026

    For Sale O6411926 - 13822 JOMATT LOOP, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3828
       Built: 2016
    Monthly Fee: $75
       Tax: $12,039 (2025)
    Community: Cypress Reserve Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,421 (change assumption)
    Mortgage ($5,342) + Fees ($75) + Taxes in 2025 ($1,003)


    Taxes:$12,039

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787

    $479,900327 Days on yellowkey   MLS ID: S5133690

    REDUCED by $20,000 (4.0%) on 07/14/2026

    For Sale S5133690 - 1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2035
       Built: 2001
    Monthly Fee: $33
       Tax: $6,403 (2024)
    Community: Tuscany Ph 02
    Single Family


    Estimated Monthly Payment: $3,196 (change assumption)
    Mortgage ($2,630) + Fees ($33) + Taxes in 2024 ($534)


    Taxes:$6,403

    Elementary School: Maxey Elem

    High School: Ocoee High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 261 ZACHARY WADE ST, WINTER GARDEN, FL 34787

    $1,599,000262 Days on yellowkey   MLS ID: O6357233

    REDUCED by $46,000 (2.8%) on 07/09/2026

    For Sale O6357233 - 261 ZACHARY WADE ST, WINTER GARDEN, FL 34787 59 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3728
       Built: 2005
    Monthly Fee: $67
       Tax: $15,019 (2024)
    Community: Lakeview Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $10,080 (change assumption)
    Mortgage ($8,761) + Fees ($67) + Taxes in 2024 ($1,252)


    Taxes:$15,019

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787

    $1,160,000244 Days on yellowkey   MLS ID: O6361968

    REDUCED by $10,000 (0.9%) on 07/21/2026

    For Sale O6361968 - 10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787 97 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4305
       Built: 2020
    Monthly Fee: $159
       Tax: $13,997 (2024)
    Community: Watermark Ph 4
    Single Family


    Estimated Monthly Payment: $7,681 (change assumption)
    Mortgage ($6,356) + Fees ($159) + Taxes in 2024 ($1,166)


    Taxes:$13,997

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 16082 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787

    $739,90019 Days on yellowkey   MLS ID: O6420606

    For Sale O6420606 - 16082 HAMPTON CROSSING DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2240
       Built: 2017
    Monthly Fee: $342
       Tax: $5,019 (2025)
    Community: Waterleigh Phase 1C
    Single Family


    Estimated Monthly Payment: $4,814 (change assumption)
    Mortgage ($4,054) + Fees ($342) + Taxes in 2025 ($418)


    Taxes:$5,019

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16153 WATER SPRING BLVD, WINTER GARDEN, FL 34787

    $549,990139 Days on yellowkey   MLS ID: O6387508

    For Sale O6387508 - 16153 WATER SPRING BLVD, WINTER GARDEN, FL 34787 53 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2042
       Built: 2020
    Monthly Fee: $108
       Tax: $6,865 (2024)
    Community: Storey Grove Ph 2
    Single Family


    Estimated Monthly Payment: $3,694 (change assumption)
    Mortgage ($3,014) + Fees ($108) + Taxes in 2024 ($572)


    Taxes:$6,865

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 12241 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $1,190,00079 Days on yellowkey   MLS ID: O6403198

    For Sale O6403198 - 12241 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 94 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3693
       Built: 2021
    Monthly Fee: $225
       Tax: $12,882 (2025)
    Community: Encore/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $7,819 (change assumption)
    Mortgage ($6,520) + Fees ($225) + Taxes in 2025 ($1,074)


    Taxes:$12,882

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 6174 WHISPERING GLEN, WINTER GARDEN, FL 34787

    $522,29070 Days on yellowkey   MLS ID: O6407807

    1 Days Off yellowkey (back on 7/21/2026)

    INCREASED by $4,000 (0.8%) on 07/19/2026

    For Sale O6407807 - 6174 WHISPERING GLEN, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1628
       Built: 2026
    Monthly Fee: $152
       Tax: $1,373 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,128 (change assumption)
    Mortgage ($2,862) + Fees ($152) + Taxes in 2024 ($114)


    Taxes:$1,373

    Elementary School: Vista Lakes Elem

    High School: Colonial High

    Tax Year: 2024

    Middle School: Odyssey Middle


  • 16098 MANGROVE RD, WINTER GARDEN, FL 34787

    $559,000188 Days on yellowkey   MLS ID: O6373125

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

    REDUCED by $9,000 (1.6%) on 07/02/2026

    For Sale O6373125 - 16098 MANGROVE RD, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2472
       Built: 2021
    Monthly Fee: $257
       Tax: $5,612 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,788 (change assumption)
    Mortgage ($3,063) + Fees ($257) + Taxes in 2025 ($468)


    Taxes:$5,612

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 688 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,470,0009 Days on yellowkey   MLS ID: R4911647

    1 Days Off yellowkey (back on 7/21/2026)

    For Sale R4911647 - 688 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 66 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4388
       Built: 2020
    Monthly Fee: $298
       Tax: $14,229 (2024)
    Community: Canopy Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $9,538 (change assumption)
    Mortgage ($8,055) + Fees ($298) + Taxes in 2024 ($1,186)


    Taxes:$14,229

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 5973 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $734,90052 Days on yellowkey   MLS ID: O6412179

    REDUCED by $5,100 (0.7%) on 07/21/2026

    For Sale O6412179 - 5973 CYPRESS HILL RD, WINTER GARDEN, FL 34787 44 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3532
       Built: 2017
    Monthly Fee: $195
       Tax: $9,630 (2025)
    Community: Independnece
    Single Family


    Estimated Monthly Payment: $5,024 (change assumption)
    Mortgage ($4,027) + Fees ($195) + Taxes in 2025 ($803)


    Taxes:$9,630

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 427 EGRET PLACE DR, WINTER GARDEN, FL 34787

    $1,095,00016 Days on yellowkey   MLS ID: O6422411

    For Sale O6422411 - 427 EGRET PLACE DR, WINTER GARDEN, FL 34787 64 photos

    Bed: 6   Bath: 5.0   Gar: 4
    Liv Area Sq Ft: 4693
       Built: 2013
    Monthly Fee: $128
       Tax: $12,983 (2025)
    Community: Johns Lake Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,210 (change assumption)
    Mortgage ($6,000) + Fees ($128) + Taxes in 2025 ($1,082)


    Taxes:$12,983

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15755 SWEET LIMETTA DR, WINTER GARDEN, FL 34787

    $809,900198 Days on yellowkey   MLS ID: O6370049

    INCREASED by $9,901 (1.2%) on 06/22/2026

    For Sale O6370049 - 15755 SWEET LIMETTA DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3633
       Built: 2018
    Monthly Fee: $110
       Tax: $11,264 (2025)
    Community: Highlands/Summerlake Grove Ph 2
    Single Family


    Estimated Monthly Payment: $5,486 (change assumption)
    Mortgage ($4,438) + Fees ($110) + Taxes in 2025 ($939)


    Taxes:$11,264

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13536 SUNSET LAKES CIR, WINTER GARDEN, FL 34787

    $1,025,00097 Days on yellowkey   MLS ID: O6399227

    REDUCED by $25,000 (2.4%) on 07/21/2026

    For Sale O6399227 - 13536 SUNSET LAKES CIR, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3389
       Built: 1998
    Monthly Fee: $69
       Tax: $10,940 (2025)
    Community: Sunset Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,597 (change assumption)
    Mortgage ($5,616) + Fees ($69) + Taxes in 2025 ($912)


    Taxes:$10,940

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15161 CANOE PL, WINTER GARDEN, FL 34787

    $1,100,00099 Days on yellowkey   MLS ID: O6398949

    REDUCED by $80,000 (6.8%) on 07/21/2026

    For Sale O6398949 - 15161 CANOE PL, WINTER GARDEN, FL 34787 67 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3816
       Built: 2019
    Monthly Fee: $385
       Tax: $13,235 (2025)
    Community: Lakeshore Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $7,515 (change assumption)
    Mortgage ($6,027) + Fees ($385) + Taxes in 2025 ($1,103)


    Taxes:$13,235

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 10750 PETRILLO WAY, WINTER GARDEN, FL 34787

    $749,00014 Days on yellowkey   MLS ID: O6423067

    REDUCED by $1,000 (0.1%) on 07/21/2026

    For Sale O6423067 - 10750 PETRILLO WAY, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2613
       Built: 2020
    Monthly Fee: $101
       Tax: $5,059 (2026)
    Community: Winding Bay Phase 1B
    Single Family


    Estimated Monthly Payment: $4,627 (change assumption)
    Mortgage ($4,104) + Fees ($101) + Taxes in 2026 ($422)


    Taxes:$5,059

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 7725 PURPLE FINCH ST, WINTER GARDEN, FL 34787

    $530,00055 Days on yellowkey   MLS ID: O6410286

    1 Days Off yellowkey (back on 7/21/2026)

    For Sale O6410286 - 7725 PURPLE FINCH ST, WINTER GARDEN, FL 34787 42 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2195
       Built: 2016
    Monthly Fee: $252
       Tax: $6,665 (2025)
    Community: Summerlake Pd Ph 3B
    Single Family


    Estimated Monthly Payment: $3,711 (change assumption)
    Mortgage ($2,904) + Fees ($252) + Taxes in 2025 ($555)


    Taxes:$6,665

    Elementary School: Summerlake Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14780 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $653,118127 Days on yellowkey   MLS ID: O6391463

    INCREASED by $10,118 (1.6%) on 07/21/2026

    For Sale O6391463 - 14780 FIELD DAISY DR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2441
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $3,808 (change assumption)
    Mortgage ($3,579) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16185 TALIESIN ST, WINTER GARDEN, FL 34787

    $649,99069 Days on yellowkey   MLS ID: O6407177

    REDUCED by $10,010 (1.5%) on 06/25/2026

    For Sale O6407177 - 16185 TALIESIN ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2372
       Built: 2020
    Monthly Fee: $127
       Tax: $6,048 (2025)
    Community: Hawksmoor
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,192 (change assumption)
    Mortgage ($3,562) + Fees ($127) + Taxes in 2025 ($504)


    Taxes:$6,048

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring 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.