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Winter Garden Single Family Homes For Sale - 674 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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  • 5074 BREEZY ACRES ST, WINTER GARDEN, FL 34787

    $969,900163 Days on yellowkey   MLS ID: O6369788

    REDUCED by $5,100 (0.5%) on 06/02/2026

    For Sale O6369788 - 5074 BREEZY ACRES ST, WINTER GARDEN, FL 34787 59 photos

    Bed: 7   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 4720
       Built: 2021
    Monthly Fee: $115
       Tax: $11,152 (2023)
    Community: Wincey Groves
    Single Family


    Estimated Monthly Payment: $6,359 (change assumption)
    Mortgage ($5,314) + Fees ($115) + Taxes in 2023 ($929)


    Taxes:$11,152

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Hamlin Middle


  • 231 DOE RUN DR, WINTER GARDEN, FL 34787

    $500,00011 Days on yellowkey   MLS ID: O6412284

    For Sale O6412284 - 231 DOE RUN DR, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1972
       Built: 2006
    Monthly Fee: $57
       Tax: $3,202 (2025)
    Community: Deerfield Place A-G
    Single Family


    Estimated Monthly Payment: $3,063 (change assumption)
    Mortgage ($2,740) + Fees ($57) + Taxes in 2025 ($267)


    Taxes:$3,202

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1061 PORTMOOR WAY, WINTER GARDEN, FL 34787

    $535,0006 Days on yellowkey   MLS ID: G5113349

    For Sale G5113349 - 1061 PORTMOOR WAY, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1804
       Built: 2001
    Monthly Fee: $243
       Tax: $6,801 (2025)
    Community: Stoneybrook West 44/134
    Single Family


    Estimated Monthly Payment: $3,741 (change assumption)
    Mortgage ($2,931) + Fees ($243) + Taxes in 2025 ($567)


    Taxes:$6,801

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 2123 PORTCASTLE CIR, WINTER GARDEN, FL 34787

    $389,0008 Days on yellowkey   MLS ID: O6412643

    0 Days Off yellowkey (back on 6/4/2026)

    For Sale O6412643 - 2123 PORTCASTLE CIR, WINTER GARDEN, FL 34787 39 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1606
       Built: 2006
    Monthly Fee: $46
       Tax: $5,857 (2025)
    Community: Stone Creek Unit 4
    Single Family


    Estimated Monthly Payment: $2,666 (change assumption)
    Mortgage ($2,131) + Fees ($46) + Taxes in 2025 ($488)


    Taxes:$5,857

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 3208 SAILING PIER AVE, WINTER GARDEN, FL 34787

    $1,049,90046 Days on yellowkey   MLS ID: O6402332

    For Sale O6402332 - 3208 SAILING PIER AVE, WINTER GARDEN, FL 34787 50 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3998
       Built: 2023
    Monthly Fee: $208
       Tax: $12,135 (2024)
    Community: Ests/Lakeview Preserve
    Single Family


    Estimated Monthly Payment: $6,972 (change assumption)
    Mortgage ($5,753) + Fees ($208) + Taxes in 2024 ($1,011)


    Taxes:$12,135

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16754 OAKBORO ST, WINTER GARDEN, FL 34787

    $535,00034 Days on yellowkey   MLS ID: O6404652

    REDUCED by $4,000 (0.7%) on 06/05/2026

    For Sale O6404652 - 16754 OAKBORO ST, WINTER GARDEN, FL 34787 85 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $254
       Tax: $8,808 (2025)
    Community: Waterleigh Ph 3B 3C 3D
    Single Family


    Estimated Monthly Payment: $3,919 (change assumption)
    Mortgage ($2,931) + Fees ($254) + Taxes in 2025 ($734)


    Taxes:$8,808

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5139 LAKE HAMLIN TRL, WINTER GARDEN, FL 34787

    $645,00034 Days on yellowkey   MLS ID: O6404614

    REDUCED by $10,000 (1.5%) on 06/05/2026

    For Sale O6404614 - 5139 LAKE HAMLIN TRL, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2742
       Built: 2023
    Monthly Fee: $271
       Tax: $8,755 (2025)
    Community: Lakeside At Hamlin
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,535 (change assumption)
    Mortgage ($3,534) + Fees ($271) + Taxes in 2025 ($730)


    Taxes:$8,755

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9189 BUSACO PARK WAY, WINTER GARDEN, FL 34787

    $1,300,00010 Days on yellowkey   MLS ID: O6410698

    For Sale O6410698 - 9189 BUSACO PARK WAY, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3424
       Built: 2015
    Monthly Fee: $158
       Tax: $7,174 (2025)
    Community: Watermark Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,879 (change assumption)
    Mortgage ($7,123) + Fees ($158) + Taxes in 2025 ($598)


    Taxes:$7,174

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17552 LAKE STAR RD, WINTER GARDEN, FL 34787

    $999,000256 Days on yellowkey   MLS ID: O6344668

    For Sale O6344668 - 17552 LAKE STAR RD, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2605
       Built: 2023
    Monthly Fee: $83
       Tax: $12,990 (2024)
    Community: Northlake/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $6,639 (change assumption)
    Mortgage ($5,474) + Fees ($83) + Taxes in 2024 ($1,083)


    Taxes:$12,990

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 9468 KOMIKA LN, WINTER GARDEN, FL 34787

    $459,90014 Days on yellowkey   MLS ID: S5150415

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

    FORECLOSURE S5150415 - 9468 KOMIKA LN, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2020
    Monthly Fee: $300
       Tax: $7,605 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $3,454 (change assumption)
    Mortgage ($2,520) + Fees ($300) + Taxes in 2025 ($634)


    Taxes:$7,605

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16283 HONEY HARVEST ST, WINTER GARDEN, FL 34787

    $649,00054 Days on yellowkey   MLS ID: O6399528

    REDUCED by $21,000 (3.1%) on 06/04/2026

    For Sale O6399528 - 16283 HONEY HARVEST ST, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2927
       Built: 2024
    Monthly Fee: $229
       Tax: $9,705 (2025)
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $4,594 (change assumption)
    Mortgage ($3,556) + Fees ($229) + Taxes in 2025 ($809)


    Taxes:$9,705

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 241 N DILLARD ST, WINTER GARDEN, FL 34787

    $1,499,999233 Days on yellowkey   MLS ID: O6353975

    REDUCED by $100,001 (6.3%) on 04/13/2026

    For Sale O6353975 - 241 N DILLARD ST, WINTER GARDEN, FL 34787 52 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3507
       Built: 1953   Tax: $2,959 (2024)
    Community: J L Dillard Sub 3
    Single Family


    Estimated Monthly Payment: $8,466 (change assumption)
    Mortgage ($8,219) + Taxes in 2024 ($247)


    Taxes:$2,959

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 9355 TYRELLA PINE TRL, WINTER GARDEN, FL 34787

    $459,00077 Days on yellowkey   MLS ID: O6391856

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

    REDUCED by $8,000 (1.7%) on 05/30/2026

    For Sale O6391856 - 9355 TYRELLA PINE TRL, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1670
       Built: 2016
    Monthly Fee: $148
       Tax: $657 (2025)
    Community: Watermark Ph 1B
    Single Family


    Estimated Monthly Payment: $2,718 (change assumption)
    Mortgage ($2,515) + Fees ($148) + Taxes in 2025 ($55)


    Taxes:$657

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16783 TURTLE HATCH DR, WINTER GARDEN, FL 34787

    $1,199,99933 Days on yellowkey   MLS ID: O6404708

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

    REDUCED by $1 (0.0%) on 05/20/2026

    For Sale O6404708 - 16783 TURTLE HATCH DR, WINTER GARDEN, FL 34787 61 photos

    Bed: 5   Bath: 5.5   Gar: 2
    Liv Area Sq Ft: 3513
       Built: 2019
    Monthly Fee: $240
       Tax: $13,161 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Single Family


    Estimated Monthly Payment: $7,912 (change assumption)
    Mortgage ($6,575) + Fees ($240) + Taxes in 2025 ($1,097)


    Taxes:$13,161

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9717 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787

    $669,5006 Days on yellowkey   MLS ID: O6413773

    For Sale O6413773 - 9717 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787 54 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2117
       Built: 2018
    Monthly Fee: $250
       Tax: $6,258 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $4,440 (change assumption)
    Mortgage ($3,668) + Fees ($250) + Taxes in 2025 ($521)


    Taxes:$6,258

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • WINTER GARDEN, FL 34787

    $855,5206 Days on yellowkey   MLS ID: G5113317

    0 Days Off yellowkey (back on 6/4/2026)

    For Sale G5113317 - WINTER GARDEN, FL 34787 3 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $125

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,813 (change assumption)
    Mortgage ($4,688) + Fees ($125) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • WINTER GARDEN, FL 34787

    $909,9906 Days on yellowkey   MLS ID: G5113315

    0 Days Off yellowkey (back on 6/4/2026)

    For Sale G5113315 - WINTER GARDEN, FL 34787 3 photos

    Bed: 6   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 4236
       Built: 2026
    Monthly Fee: $125

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $5,111 (change assumption)
    Mortgage ($4,986) + Fees ($125) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14451 WINDSOR HALL WAY, WINTER GARDEN, FL 34787

    $510,00023 Days on yellowkey   MLS ID: O6408731

    0 Days Off yellowkey (back on 6/4/2026)

    For Sale O6408731 - 14451 WINDSOR HALL WAY, WINTER GARDEN, FL 34787 39 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1814
       Built: 2016
    Monthly Fee: $192
       Tax: $5,900 (2025)
    Community: Lake Hancock Preserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,478 (change assumption)
    Mortgage ($2,794) + Fees ($192) + Taxes in 2025 ($492)


    Taxes:$5,900

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14359 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787

    $1,008,00025 Days on yellowkey   MLS ID: O6408165

    REDUCED by $10,000 (1.0%) on 06/04/2026

    For Sale O6408165 - 14359 MAGNOLIA RIDGE LOOP, WINTER GARDEN, FL 34787 19 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3881
       Built: 2015
    Monthly Fee: $188
       Tax: $13,774 (2025)
    Community: Orchard Hills Phase 1
    Single Family


    Estimated Monthly Payment: $6,859 (change assumption)
    Mortgage ($5,523) + Fees ($188) + Taxes in 2025 ($1,148)


    Taxes:$13,774

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 11036 ROBERT FROST DR, WINTER GARDEN, FL 34787

    $649,99012 Days on yellowkey   MLS ID: O6410350

    For Sale O6410350 - 11036 ROBERT FROST DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2136
       Built: 2021
    Monthly Fee: $221
       Tax: $8,394 (2025)
    Community: Storey Grove Ph 3
    Single Family


    Estimated Monthly Payment: $4,482 (change assumption)
    Mortgage ($3,562) + Fees ($221) + Taxes in 2025 ($700)


    Taxes:$8,394

    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.