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Winter Garden Single Family Homes For Sale - 569 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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  • 15359 MARITIME PINE DR, WINTER GARDEN, FL 34787

    $828,10511 Days on yellowkey   MLS ID: G5110994

    0 Days Off yellowkey (back on 4/14/2026)

    For Sale G5110994 - 15359 MARITIME PINE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,687 (change assumption)
    Mortgage ($4,537) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5685 SURPRISE LILY DR, WINTER GARDEN, FL 34787

    $685,000190 Days on yellowkey   MLS ID: O6353593

    1 Days Off yellowkey (back on 2/4/2026)

    SHORT SALE O6353593 - 5685 SURPRISE LILY DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2902
       Built: 2021
    Monthly Fee: $80
       Tax: $513 (2024)
    Community: Hamilton Gardens Ph 2A & 2B
    Single Family


    Estimated Monthly Payment: $3,876 (change assumption)
    Mortgage ($3,753) + Fees ($80) + Taxes in 2024 ($43)


    Taxes:$513

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 14050 FAIRWAY WILLOW LN, WINTER GARDEN, FL 34787

    $749,00032 Days on yellowkey   MLS ID: O6392994

    REDUCED by $46,000 (5.8%) on 04/15/2026

    For Sale O6392994 - 14050 FAIRWAY WILLOW LN, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 1989
    Monthly Fee: $322
       Tax: $4,924 (2025)
    Community: Woodbridge On Green
    Single Family


    Estimated Monthly Payment: $4,836 (change assumption)
    Mortgage ($4,104) + Fees ($322) + Taxes in 2025 ($410)


    Taxes:$4,924

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1035 CHASE DR, WINTER GARDEN, FL 34787

    $465,00015 Days on yellowkey   MLS ID: O6396474

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6396474 - 1035 CHASE DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1793
       Built: 1995
    Monthly Fee: $44
       Tax: $3,337 (2025)
    Community: Island Pointe Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,870 (change assumption)
    Mortgage ($2,548) + Fees ($44) + Taxes in 2025 ($278)


    Taxes:$3,337

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14423 WABASSO LOOP, WINTER GARDEN, FL 34787

    $899,999108 Days on yellowkey   MLS ID: O6368408

    1 Days Off yellowkey (back on 4/15/2026)

    For Sale O6368408 - 14423 WABASSO LOOP, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3630
       Built: 2023
    Monthly Fee: $217
       Tax: $12,742 (2024)
    Community: Tilden Place/Winter Garden
    Single Family


    Estimated Monthly Payment: $6,210 (change assumption)
    Mortgage ($4,931) + Fees ($217) + Taxes in 2024 ($1,062)


    Taxes:$12,742

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 1923 JEAN MARIE DR, WINTER GARDEN, FL 34787

    $580,00098 Days on yellowkey   MLS ID: G5106903

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale G5106903 - 1923 JEAN MARIE DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2916
       Built: 2007
    Monthly Fee: $90
       Tax: $4,275 (2024)
    Community: Carriage Pointe A-I & L
    Single Family


    Estimated Monthly Payment: $3,624 (change assumption)
    Mortgage ($3,178) + Fees ($90) + Taxes in 2024 ($356)


    Taxes:$4,275

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 9107 GRAND ISLAND WAY, WINTER GARDEN, FL 34787

    $505,00040 Days on yellowkey   MLS ID: O6391117

    For Sale O6391117 - 9107 GRAND ISLAND WAY, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2082
       Built: 2017
    Monthly Fee: $159
       Tax: $7,996 (2025)
    Community: Watermark Ph 2C
    Single Family


    Estimated Monthly Payment: $3,592 (change assumption)
    Mortgage ($2,767) + Fees ($159) + Taxes in 2025 ($666)


    Taxes:$7,996

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6226 MANUSCRIPT ST, WINTER GARDEN, FL 34787

    $627,900168 Days on yellowkey   MLS ID: O6359078

    1 Days Off yellowkey (back on 4/15/2026)

    REDUCED by $8,000 (1.3%) on 04/02/2026

    For Sale O6359078 - 6226 MANUSCRIPT ST, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2849
       Built: 2012
    Monthly Fee: $168
       Tax: $7,134 (2024)
    Community: Signature Lakes Ph 02 A B H I J
    Single Family


    Estimated Monthly Payment: $4,203 (change assumption)
    Mortgage ($3,440) + Fees ($168) + Taxes in 2024 ($595)


    Taxes:$7,134

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 626 DUFF DR, WINTER GARDEN, FL 34787

    $900,00066 Days on yellowkey   MLS ID: O6382820

    For Sale O6382820 - 626 DUFF DR, WINTER GARDEN, FL 34787 95 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3335
       Built: 2004
    Monthly Fee: $185
       Tax: $11,715 (2024)
    Community: Lake Forest Sec 10A
    Single Family


    Estimated Monthly Payment: $6,093 (change assumption)
    Mortgage ($4,931) + Fees ($185) + Taxes in 2024 ($976)


    Taxes:$11,715

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 1710 E BAY ST, WINTER GARDEN, FL 34787

    $249,99053 Days on yellowkey   MLS ID: O6376343

    0 Days Off yellowkey (back on 4/15/2026)

    REDUCED by $5,005 (2.0%) on 04/15/2026

    For Sale O6376343 - 1710 E BAY ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 972
       Built: 1957   Tax: $958 (2025)
    Community: Joe Louis Park First Add
    Single Family


    Estimated Monthly Payment: $1,450 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($80)


    Taxes:$958

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787

    $339,90011 Days on yellowkey   MLS ID: O6398208

    For Sale O6398208 - 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787 4 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1988   Tax: $2,702 (2025)
    Community: East Garden Manor Add 03
    Single Family


    Estimated Monthly Payment: $2,088 (change assumption)
    Mortgage ($1,862) + Taxes in 2025 ($225)


    Taxes:$2,702

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 15852 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $779,000157 Days on yellowkey   MLS ID: O6361580

    REDUCED by $20,000 (2.5%) on 04/15/2026

    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: $5,564 (change assumption)
    Mortgage ($4,268) + 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


  • 17222 DANCY ORANGE CT, WINTER GARDEN, FL 34787

    $965,00064 Days on yellowkey   MLS ID: O6383910

    REDUCED by $25,000 (2.5%) on 04/06/2026

    For Sale O6383910 - 17222 DANCY ORANGE CT, WINTER GARDEN, FL 34787 56 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3787
       Built: 2023
    Monthly Fee: $83
       Tax: $11,862 (2024)
    Community: Northlake/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $6,359 (change assumption)
    Mortgage ($5,288) + Fees ($83) + Taxes in 2024 ($989)


    Taxes:$11,862

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 14571 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787

    $519,900128 Days on yellowkey   MLS ID: O6368387

    For Sale O6368387 - 14571 BAHAMA SWALLOW BLVD, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2063
       Built: 2012
    Monthly Fee: $251
       Tax: $7,507 (2024)
    Community: Summerlake Pd Ph 01A
    Single Family


    Estimated Monthly Payment: $3,725 (change assumption)
    Mortgage ($2,849) + Fees ($251) + Taxes in 2024 ($626)


    Taxes:$7,507

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • WINTER GARDEN, FL 34787

    $1,695,00012 Days on yellowkey   MLS ID: O6396808

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6396808 - WINTER GARDEN, FL 34787 61 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2957
       Built: 2015
    Monthly Fee: $235
       Tax: $11,222 (2025)
    Community: Hlckory Hammock Ph 1D
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $10,458 (change assumption)
    Mortgage ($9,287) + Fees ($235) + Taxes in 2025 ($935)


    Taxes:$11,222

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15161 CANOE PL, WINTER GARDEN, FL 34787

    $1,200,00011 Days on yellowkey   MLS ID: O6398949

    For Sale O6398949 - 15161 CANOE PL, WINTER GARDEN, FL 34787 63 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: $8,063 (change assumption)
    Mortgage ($6,575) + 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


  • 17162 INGRAM BLUFF DR, WINTER GARDEN, FL 34787

    $699,97011 Days on yellowkey   MLS ID: G5110993

    0 Days Off yellowkey (back on 4/14/2026)

    For Sale G5110993 - 17162 INGRAM BLUFF DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3122
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,957 (change assumption)
    Mortgage ($3,835) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7550 SPRING VALLEY ST, WINTER GARDEN, FL 34787

    $701,34011 Days on yellowkey   MLS ID: G5110990

    0 Days Off yellowkey (back on 4/14/2026)

    For Sale G5110990 - 7550 SPRING VALLEY ST, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,965 (change assumption)
    Mortgage ($3,843) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9355 TYRELLA PINE TRL, WINTER GARDEN, FL 34787

    $475,00031 Days on yellowkey   MLS ID: O6391856

    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: $2,805 (change assumption)
    Mortgage ($2,603) + 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


  • 8685 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $555,00020 Days on yellowkey   MLS ID: O6394975

    1 Days Off yellowkey (back on 4/14/2026)

    For Sale O6394975 - 8685 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2015
    Monthly Fee: $332
       Tax: $8,849 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $4,110 (change assumption)
    Mortgage ($3,041) + Fees ($332) + Taxes in 2025 ($737)


    Taxes:$8,849

    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.