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Winter Garden Single Family Homes For Sale - 730 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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  • 4863 LACEWING DR, WINTER GARDEN, FL 34787

    $540,000104 Days on yellowkey   MLS ID: O6397857

    For Sale O6397857 - 4863 LACEWING DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1788
       Built: 2023
    Monthly Fee: $171
       Tax: $6,905 (2025)
    Community: Silverleaf Reserve Bungalows
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,705 (change assumption)
    Mortgage ($2,959) + Fees ($171) + Taxes in 2025 ($575)


    Taxes:$6,905

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 2230 ROMANUM DR, WINTER GARDEN, FL 34787

    $565,000132 Days on yellowkey   MLS ID: O6389947

    1 Days Off yellowkey (back on 5/17/2026)

    For Sale O6389947 - 2230 ROMANUM DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2562
       Built: 2014
    Monthly Fee: $207
       Tax: $8,425 (2025)
    Community: Alexander Rdg
    Single Family


    Estimated Monthly Payment: $4,005 (change assumption)
    Mortgage ($3,096) + Fees ($207) + Taxes in 2025 ($702)


    Taxes:$8,425

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 33 TIMBERCREEK PINES CIR, WINTER GARDEN, FL 34787

    $535,00062 Days on yellowkey   MLS ID: O6408941

    REDUCED by $10,000 (1.8%) on 07/03/2026

    For Sale O6408941 - 33 TIMBERCREEK PINES CIR, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1584
       Built: 2004
    Monthly Fee: $46
       Tax: $7,326 (2025)
    Community: Timbercreek Pines A B C & D
    Single Family


    Estimated Monthly Payment: $3,588 (change assumption)
    Mortgage ($2,931) + Fees ($46) + Taxes in 2025 ($610)


    Taxes:$7,326

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 689 BETHUNE AVE, WINTER GARDEN, FL 34787

    $434,00020 Days on yellowkey   MLS ID: O6421715

    For Sale O6421715 - 689 BETHUNE AVE, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1434
       Built: 1950   Tax: $2,330 (2025)
    Community: Joe Louis Park Q162
    Single Family


    Estimated Monthly Payment: $2,572 (change assumption)
    Mortgage ($2,378) + Taxes in 2025 ($194)


    Taxes:$2,330

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16330 BRISK BREEZE ALY, WINTER GARDEN, FL 34787

    $525,000202 Days on yellowkey   MLS ID: G5106012

    REDUCED by $15,000 (2.8%) on 06/19/2026

    For Sale G5106012 - 16330 BRISK BREEZE ALY, WINTER GARDEN, FL 34787 54 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2018
    Monthly Fee: $245
       Tax: $7,556 (2024)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $3,751 (change assumption)
    Mortgage ($2,877) + Fees ($245) + Taxes in 2024 ($630)


    Taxes:$7,556

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787

    $650,000475 Days on yellowkey   MLS ID: O6280496

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

    REDUCED by $98,000 (13.1%) on 06/10/2026

    SHORT SALE O6280496 - 18339 OLIVER TWIST WAY, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2023
    Monthly Fee: $250
       Tax: $9,777 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,626 (change assumption)
    Mortgage ($3,562) + Fees ($250) + Taxes in 2024 ($815)


    Taxes:$9,777

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15073 VALVERSE ALY, WINTER GARDEN, FL 34787

    $499,99941 Days on yellowkey   MLS ID: O6416182

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

    REDUCED by $15,001 (2.9%) on 06/24/2026

    For Sale O6416182 - 15073 VALVERSE ALY, WINTER GARDEN, FL 34787 38 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1892
       Built: 2017
    Monthly Fee: $339
       Tax: $4,172 (2025)
    Community: Overlook 2/Hamlin Ph 2 & 5
    Single Family


    Estimated Monthly Payment: $3,426 (change assumption)
    Mortgage ($2,740) + Fees ($339) + Taxes in 2025 ($348)


    Taxes:$4,172

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15648 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $699,00040 Days on yellowkey   MLS ID: G5113473

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

    REDUCED by $30,000 (4.1%) on 06/28/2026

    For Sale G5113473 - 15648 SHOREBIRD LN, WINTER GARDEN, FL 34787 93 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2018
    Monthly Fee: $360
       Tax: $7,052 (2025)
    Community: Lakeshore Preserve Ph 1
    Single Family


    Estimated Monthly Payment: $4,778 (change assumption)
    Mortgage ($3,830) + Fees ($360) + Taxes in 2025 ($588)


    Taxes:$7,052

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15456 GILLIGAN CT, WINTER GARDEN, FL 34787

    $550,000356 Days on yellowkey   MLS ID: A4660262

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

    REDUCED by $25,000 (4.3%) on 06/12/2026

    For Sale A4660262 - 15456 GILLIGAN CT, WINTER GARDEN, FL 34787 45 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2571
       Built: 2020
    Monthly Fee: $102
       Tax: $8,702 (2024)
    Community: Winding Bay Ph 1B
    Single Family


    Estimated Monthly Payment: $3,841 (change assumption)
    Mortgage ($3,014) + Fees ($102) + Taxes in 2024 ($725)


    Taxes:$8,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2022 BOSS HEWETT ST, WINTER GARDEN, FL 34787

    $679,00034 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


  • 2496 BARONSMEDE CT, WINTER GARDEN, FL 34787

    $875,00026 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


  • 11277 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,99027 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

    $539,990243 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

    $594,990177 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

    $539,990222 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

    $675,000112 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


  • 14006 FRASIER STREET, WINTER GARDEN, FL 34787

    $658,000100 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


  • 12570 GOLD HONEYSUCKLE ST, WINTER GARDEN, FL 34787

    $932,89247 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


  • 12731 GROVEHURST AVE, WINTER GARDEN, FL 34787

    $580,000168 Days on yellowkey   MLS ID: O6379203

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

    REDUCED by $19,900 (3.3%) on 06/18/2026

    For Sale O6379203 - 12731 GROVEHURST AVE, WINTER GARDEN, FL 34787 59 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3474
       Built: 2006
    Monthly Fee: $111
       Tax: $8,378 (2025)
    Community: Grovehurst A-D
    Single Family


    Estimated Monthly Payment: $3,987 (change assumption)
    Mortgage ($3,178) + Fees ($111) + Taxes in 2025 ($698)


    Taxes:$8,378

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16031 SCARPETTA ST, WINTER GARDEN, FL 34787

    $595,000190 Days on yellowkey   MLS ID: O6373345

    REDUCED by $10,500 (1.7%) on 07/01/2026

    For Sale O6373345 - 16031 SCARPETTA ST, WINTER GARDEN, FL 34787 16 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2023
    Monthly Fee: $268
       Tax: $8,487 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,235 (change assumption)
    Mortgage ($3,260) + Fees ($268) + Taxes in 2024 ($707)


    Taxes:$8,487

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    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.