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Winter Garden Single Family Homes For Sale - 596 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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  • 15665 CITRUS HARVEST RD, WINTER GARDEN, FL 34787

    $769,9009 Days on yellowkey   MLS ID: O6400896

    For Sale O6400896 - 15665 CITRUS HARVEST RD, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2931
       Built: 2016
    Monthly Fee: $235
       Tax: $5,441 (2025)
    Community: Hickory Hammock Ph 2A
    Single Family


    Estimated Monthly Payment: $4,907 (change assumption)
    Mortgage ($4,219) + Fees ($235) + Taxes in 2025 ($453)


    Taxes:$5,441

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17865 ADRIFT RD, WINTER GARDEN, FL 34787

    $599,000292 Days on yellowkey   MLS ID: O6329586

    For Sale O6329586 - 17865 ADRIFT RD, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2484
       Built: 2023
    Monthly Fee: $277
       Tax: $9,155 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $4,322 (change assumption)
    Mortgage ($3,282) + Fees ($277) + Taxes in 2024 ($763)


    Taxes:$9,155

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15456 GILLIGAN CT, WINTER GARDEN, FL 34787

    $575,000284 Days on yellowkey   MLS ID: A4660262

    REDUCED by $25,000 (4.2%) on 05/08/2026

    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: $3,978 (change assumption)
    Mortgage ($3,151) + Fees ($102) + Taxes in 2024 ($725)


    Taxes:$8,702

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15852 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $799,000173 Days on yellowkey   MLS ID: O6361580

    INCREASED by $20,000 (2.6%) on 05/08/2026

    For Sale O6361580 - 15852 SHOREBIRD LN, WINTER GARDEN, FL 34787 71 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2766
       Built: 2019
    Monthly Fee: $385
       Tax: $10,928 (2024)
    Community: Lakeshore Preserve Ph 5
    Single Family


    Estimated Monthly Payment: $5,674 (change assumption)
    Mortgage ($4,378) + Fees ($385) + Taxes in 2024 ($911)


    Taxes:$10,928

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 15686 PANTHER LAKE DR, WINTER GARDEN, FL 34787

    $1,220,00059 Days on yellowkey   MLS ID: O6390015

    REDUCED by $80,000 (6.2%) on 05/08/2026

    For Sale O6390015 - 15686 PANTHER LAKE DR, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3094
       Built: 2019
    Monthly Fee: $456
       Tax: $11,351 (2025)
    Community: Lakeshore Preserve Ph 2
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,087 (change assumption)
    Mortgage ($6,685) + Fees ($456) + Taxes in 2025 ($946)


    Taxes:$11,351

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787

    $549,990129 Days on yellowkey   MLS ID: O6370363

    1 Days Off yellowkey (back on 5/8/2026)

    REDUCED by $5,000 (0.9%) on 05/04/2026

    For Sale O6370363 - 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2021
    Monthly Fee: $281
       Tax: $8,150 (2024)
    Community: Enclave/Hamlin
    Single Family


    Estimated Monthly Payment: $3,974 (change assumption)
    Mortgage ($3,014) + Fees ($281) + Taxes in 2024 ($679)


    Taxes:$8,150

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 1966 PANTHEON DR, WINTER GARDEN, FL 34787

    $525,00066 Days on yellowkey   MLS ID: O6386961

    REDUCED by $25,000 (4.5%) on 04/09/2026

    For Sale O6386961 - 1966 PANTHEON DR, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2076
       Built: 2015
    Monthly Fee: $211
       Tax: $5,734 (2024)
    Community: Alexander Ridge
    Single Family


    Estimated Monthly Payment: $3,565 (change assumption)
    Mortgage ($2,877) + Fees ($211) + Taxes in 2024 ($478)


    Taxes:$5,734

    Elementary School: Hamlin Elementary

    High School: None

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 849 SHADOWMOSS DR, WINTER GARDEN, FL 34787

    $750,00014 Days on yellowkey   MLS ID: O6402463

    For Sale O6402463 - 849 SHADOWMOSS DR, WINTER GARDEN, FL 34787 11 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2620
       Built: 2003
    Monthly Fee: $64
       Tax: $5,153 (2025)
    Community: Westfield 03 Ph-B A-M
    Single Family


    Estimated Monthly Payment: $4,603 (change assumption)
    Mortgage ($4,109) + Fees ($64) + Taxes in 2025 ($429)


    Taxes:$5,153

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787

    $765,00046 Days on yellowkey   MLS ID: O6393987

    REDUCED by $30,000 (3.8%) on 05/08/2026

    For Sale O6393987 - 15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 4307
       Built: 2014
    Monthly Fee: $114
       Tax: $5,670 (2025)
    Community: Reserve/Carriage Pointe Ph 1
    Single Family


    Estimated Monthly Payment: $4,778 (change assumption)
    Mortgage ($4,192) + Fees ($114) + Taxes in 2025 ($472)


    Taxes:$5,670

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9849 LOST CREEK DR, WINTER GARDEN, FL 34787

    $990,000536 Days on yellowkey   MLS ID: O6258009

    For Sale O6258009 - 9849 LOST CREEK DR, WINTER GARDEN, FL 34787 57 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2021
    Monthly Fee: $250
       Tax: $10,950 (2023)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $6,587 (change assumption)
    Mortgage ($5,425) + Fees ($250) + Taxes in 2023 ($913)


    Taxes:$10,950

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 16256 MISTY HILLS AVE, WINTER GARDEN, FL 34787

    $629,000131 Days on yellowkey   MLS ID: O6369818

    REDUCED by $19,000 (2.9%) on 05/08/2026

    For Sale O6369818 - 16256 MISTY HILLS AVE, WINTER GARDEN, FL 34787 55 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2240
       Built: 2020
    Monthly Fee: $115
       Tax: $9,333 (2024)
    Community: Wincey Grvs Ph 1
    Single Family


    Estimated Monthly Payment: $4,339 (change assumption)
    Mortgage ($3,446) + Fees ($115) + Taxes in 2024 ($778)


    Taxes:$9,333

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 18041 CIDER MILL LN, WINTER GARDEN, FL 34787

    $833,19187 Days on yellowkey   MLS ID: O6382386

    1 Days Off yellowkey (back on 5/8/2026)

    For Sale O6382386 - 18041 CIDER MILL LN, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,981 (change assumption)
    Mortgage ($4,565) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9231 GRAND ISLAND WAY, WINTER GARDEN, FL 34787

    $495,0004 Days on yellowkey   MLS ID: O6405710

    For Sale O6405710 - 9231 GRAND ISLAND WAY, WINTER GARDEN, FL 34787 37 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2060
       Built: 2017
    Monthly Fee: $154
       Tax: $6,732 (2025)
    Community: Lakeside
    Single Family


    Estimated Monthly Payment: $3,427 (change assumption)
    Mortgage ($2,712) + Fees ($154) + Taxes in 2025 ($561)


    Taxes:$6,732

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9827 BEACH PORT DR, WINTER GARDEN, FL 34787

    $1,374,9904 Days on yellowkey   MLS ID: O6405480

    For Sale O6405480 - 9827 BEACH PORT DR, WINTER GARDEN, FL 34787 68 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2020
    Monthly Fee: $259
       Tax: $11,122 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,720 (change assumption)
    Mortgage ($7,534) + Fees ($259) + Taxes in 2025 ($927)


    Taxes:$11,122

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5139 LAKE HAMLIN TRL, WINTER GARDEN, FL 34787

    $699,0004 Days on yellowkey   MLS ID: O6404614

    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: $4,831 (change assumption)
    Mortgage ($3,830) + 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


  • 16754 OAKBORO ST, WINTER GARDEN, FL 34787

    $558,0004 Days on yellowkey   MLS ID: O6404652

    For Sale O6404652 - 16754 OAKBORO ST, WINTER GARDEN, FL 34787 86 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: $4,045 (change assumption)
    Mortgage ($3,057) + 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


  • 10187 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787

    $689,0004 Days on yellowkey   MLS ID: O6404599

    For Sale O6404599 - 10187 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787 83 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2020
    Monthly Fee: $250
       Tax: $9,595 (2025)
    Community: Waterleigh Ph 2C-2 & 2C-3
    Single Family


    Estimated Monthly Payment: $4,825 (change assumption)
    Mortgage ($3,775) + Fees ($250) + Taxes in 2025 ($800)


    Taxes:$9,595

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 897 LANDRUM DR, WINTER GARDEN, FL 34787

    $899,9004 Days on yellowkey   MLS ID: O6404632

    For Sale O6404632 - 897 LANDRUM DR, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3012
       Built: 2013
    Monthly Fee: $208
       Tax: $6,263 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $5,661 (change assumption)
    Mortgage ($4,931) + Fees ($208) + Taxes in 2025 ($522)


    Taxes:$6,263

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • WINTER GARDEN, FL 34787

    $688,78940 Days on yellowkey   MLS ID: G5110452

    0 Days Off yellowkey (back on 4/1/2026)

    For Sale G5110452 - WINTER GARDEN, FL 34787 2 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3117
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,924 (change assumption)
    Mortgage ($3,774) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5931 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $829,965235 Days on yellowkey   MLS ID: G5102265

    0 Days Off yellowkey (back on 9/18/2025)

    For Sale G5102265 - 5931 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2688
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,698 (change assumption)
    Mortgage ($4,548) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin 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.