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Winter Garden Single Family Homes For Sale - 697 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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  • 1105 LINCOLN TER, WINTER GARDEN, FL 34787

    $255,00021 Days on yellowkey   MLS ID: O6416937

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

    For Sale O6416937 - 1105 LINCOLN TER, WINTER GARDEN, FL 34787 25 photos

    Bed: 3   Bath: 1.0
    Liv Area Sq Ft: 814
       Built: 1961   Tax: $1,586 (2025)
    Community: Bay St Park
    Single Family


    Estimated Monthly Payment: $1,529 (change assumption)
    Mortgage ($1,397) + Taxes in 2025 ($132)


    Taxes:$1,586

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 17126 ARROWHEAD BLVD, WINTER GARDEN, FL 34787

    $565,00048 Days on yellowkey   MLS ID: O6409499

    4 Days Off yellowkey (back on 5/27/2026)

    For Sale O6409499 - 17126 ARROWHEAD BLVD, WINTER GARDEN, FL 34787 6 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2114
       Built: 1984   Tax: $2,608 (2025)
    Community: Arrowhead Lakes
    Single Family


    Estimated Monthly Payment: $3,313 (change assumption)
    Mortgage ($3,096) + Taxes in 2025 ($217)


    Taxes:$2,608

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787

    $1,495,00029 Days on yellowkey   MLS ID: O6414639

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

    For Sale O6414639 - 16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787 69 photos

    Bed: 6   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4882
       Built: 2016
    Monthly Fee: $168
       Tax: $11,216 (2025)
    Community: Waterside/Johns Lake Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,294 (change assumption)
    Mortgage ($8,192) + Fees ($168) + Taxes in 2025 ($935)


    Taxes:$11,216

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 2022 BOSS HEWETT ST, WINTER GARDEN, FL 34787

    $679,00019 Days on yellowkey   MLS ID: O6417697

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

    For Sale O6417697 - 2022 BOSS HEWETT ST, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2281
       Built: 2022
    Monthly Fee: $171
       Tax: $7,948 (2025)
    Community: Hull Island/Oakland Ph 2
    Single Family


    Estimated Monthly Payment: $4,554 (change assumption)
    Mortgage ($3,720) + Fees ($171) + Taxes in 2025 ($662)


    Taxes:$7,948

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 1711 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787

    $1,046,0006 Days on yellowkey   MLS ID: G5114517

    For Sale G5114517 - 1711 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787 72 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3863
       Built: 2017
    Monthly Fee: $187
       Tax: $10,792 (2024)
    Community: Twinwaters
    Single Family


    Estimated Monthly Payment: $6,818 (change assumption)
    Mortgage ($5,731) + Fees ($187) + Taxes in 2024 ($899)


    Taxes:$10,792

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 120 BLUE STONE CIR, WINTER GARDEN, FL 34787

    $747,90047 Days on yellowkey   MLS ID: O6409811

    REDUCED by $2,000 (0.3%) on 06/05/2026

    For Sale O6409811 - 120 BLUE STONE CIR, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2529
       Built: 1998
    Monthly Fee: $68
       Tax: $4,291 (2025)
    Community: Westfield Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,524 (change assumption)
    Mortgage ($4,098) + Fees ($68) + Taxes in 2025 ($358)


    Taxes:$4,291

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1642 CHANDELLE LN, WINTER GARDEN, FL 34787

    $709,9006 Days on yellowkey   MLS ID: G5114093

    For Sale G5114093 - 1642 CHANDELLE LN, WINTER GARDEN, FL 34787 5 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2918
       Built: 2006
    Monthly Fee: $167
       Tax: $8,474 (2025)
    Community: Belle Meade-Ph I B D & G
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,763 (change assumption)
    Mortgage ($3,890) + Fees ($167) + Taxes in 2025 ($706)


    Taxes:$8,474

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 2496 BARONSMEDE CT, WINTER GARDEN, FL 34787

    $875,00011 Days on yellowkey   MLS ID: G5114233

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

    For Sale G5114233 - 2496 BARONSMEDE CT, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4184
       Built: 2002
    Monthly Fee: $210
       Tax: $8,903 (2025)
    Community: Stoneybrook West 47/78
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,746 (change assumption)
    Mortgage ($4,794) + Fees ($210) + Taxes in 2025 ($742)


    Taxes:$8,903

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 729 MEADOW GLADE DR, WINTER GARDEN, FL 34787

    $515,00054 Days on yellowkey   MLS ID: O6407943

    REDUCED by $14,000 (2.6%) on 06/16/2026

    For Sale O6407943 - 729 MEADOW GLADE DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2011
    Monthly Fee: $72
       Tax: $3,138 (2025)
    Community: Covington Park A B D E F G & J
    Single Family


    Estimated Monthly Payment: $3,155 (change assumption)
    Mortgage ($2,822) + Fees ($72) + Taxes in 2025 ($262)


    Taxes:$3,138

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11277 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,99012 Days on yellowkey   MLS ID: O6419923

    REDUCED by $15,000 (1.6%) on 07/02/2026

    For Sale O6419923 - 11277 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: $208
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,305 (change assumption)
    Mortgage ($4,931) + Fees ($208) + 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

    $539,990228 Days on yellowkey   MLS ID: O6362478

    REDUCED by $7,000 (1.3%) on 07/02/2026

    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: $3,315 (change assumption)
    Mortgage ($2,959) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16827 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $594,990162 Days on yellowkey   MLS ID: O6376919

    REDUCED by $5,000 (0.8%) on 07/02/2026

    For Sale O6376919 - 16827 HOBE SOUND CT, WINTER GARDEN, FL 34787 21 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $248
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,674 (change assumption)
    Mortgage ($3,260) + Fees ($248) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $539,990207 Days on yellowkey   MLS ID: O6367156

    REDUCED by $7,000 (1.3%) on 07/02/2026

    For Sale O6367156 - 16821 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 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: $3,315 (change assumption)
    Mortgage ($2,959) + Fees ($190) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14790 TULLAMORE LOOP, WINTER GARDEN, FL 34787

    $675,00097 Days on yellowkey   MLS ID: O6395287

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

    REDUCED by $14,999 (2.2%) on 06/13/2026

    For Sale O6395287 - 14790 TULLAMORE LOOP, WINTER GARDEN, FL 34787 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3410
       Built: 2005
    Monthly Fee: $100
       Tax: $3,503 (2025)
    Community: Emerald Ridge
    Single Family


    Estimated Monthly Payment: $4,090 (change assumption)
    Mortgage ($3,699) + Fees ($100) + Taxes in 2025 ($292)


    Taxes:$3,503

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16827 SANCTUARY DR, WINTER GARDEN, FL 34787

    $918,00073 Days on yellowkey   MLS ID: S5148416

    REDUCED by $80,000 (8.0%) on 07/02/2026

    For Sale S5148416 - 16827 SANCTUARY DR, WINTER GARDEN, FL 34787 64 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2281
       Built: 2020
    Monthly Fee: $165
       Tax: $6,024 (2025)
    Community: Sanctuary/Twin Waters
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,697 (change assumption)
    Mortgage ($5,030) + Fees ($165) + Taxes in 2025 ($502)


    Taxes:$6,024

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5330 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787

    $579,0006 Days on yellowkey   MLS ID: O6420269

    For Sale O6420269 - 5330 LAKE VIRGINIA ST, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2022
    Monthly Fee: $160
       Tax: $7,489 (2025)
    Community: Lakeside At Hamlin
    Single Family


    Estimated Monthly Payment: $3,957 (change assumption)
    Mortgage ($3,173) + Fees ($160) + Taxes in 2025 ($624)


    Taxes:$7,489

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 6137 WATERSIDE ISLAND LN, WINTER GARDEN, FL 34787

    $599,9005 Days on yellowkey   MLS ID: O6418786

    For Sale O6418786 - 6137 WATERSIDE ISLAND LN, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2607
       Built: 2014
    Monthly Fee: $184
       Tax: $8,719 (2025)
    Community: Signature Lakes Ph 3B-1
    Single Family


    Estimated Monthly Payment: $4,198 (change assumption)
    Mortgage ($3,287) + Fees ($184) + Taxes in 2025 ($727)


    Taxes:$8,719

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14006 FRASIER STREET, WINTER GARDEN, FL 34787

    $658,00085 Days on yellowkey   MLS ID: O6398760

    REDUCED by $1,000 (0.2%) on 07/01/2026

    For Sale O6398760 - 14006 FRASIER STREET, WINTER GARDEN, FL 34787 79 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2098
       Built: 2023
    Monthly Fee: $100
       Tax: $8,274 (2025)
    Community: Highland Ridge
    Single Family


    Estimated Monthly Payment: $4,395 (change assumption)
    Mortgage ($3,605) + Fees ($100) + Taxes in 2025 ($689)


    Taxes:$8,274

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 12541 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787

    $809,99035 Days on yellowkey   MLS ID: O6412476

    REDUCED by $10,000 (1.2%) on 07/01/2026

    For Sale O6412476 - 12541 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2636
       Built: 2026
    Monthly Fee: $96
       Tax: $10,790 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $5,433 (change assumption)
    Mortgage ($4,438) + Fees ($96) + Taxes in 2026 ($899)


    Taxes:$10,790

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Water Spring Middle


  • 12570 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787

    $932,89232 Days on yellowkey   MLS ID: O6414289

    REDUCED by $30,000 (3.1%) on 07/01/2026

    For Sale O6414289 - 12570 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3636
       Built: 2026
    Monthly Fee: $96
       Tax: $15,480 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $6,498 (change assumption)
    Mortgage ($5,112) + Fees ($96) + Taxes in 2026 ($1,290)


    Taxes:$15,480

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None




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.