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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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  • 243 FLORIDA AVE, WINTER GARDEN, FL 34787

    $335,00068 Days on yellowkey   MLS ID: S5149991

    2 Days Off yellowkey (back on 5/28/2026)

    For Sale S5149991 - 243 FLORIDA AVE, WINTER GARDEN, FL 34787 30 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1100
       Built: 1939   Tax: $2,090 (2025)
    Community: Shadow Lawn L/125 Lot 9 Blk F
    Single Family


    Estimated Monthly Payment: $2,010 (change assumption)
    Mortgage ($1,836) + Taxes in 2025 ($174)


    Taxes:$2,090

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 440 TIERRA VERDE LN, WINTER GARDEN, FL 34787

    $980,00051 Days on yellowkey   MLS ID: O6412260

    0 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $220,000 (18.3%) on 06/26/2026

    For Sale O6412260 - 440 TIERRA VERDE LN, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 3.0   Gar: 4
    Liv Area Sq Ft: 3512
       Built: 2004
    Monthly Fee: $94
       Tax: $5,135 (2025)
    Community: Lake Cove Pointe
    Single Family


    Estimated Monthly Payment: $5,892 (change assumption)
    Mortgage ($5,370) + Fees ($94) + Taxes in 2025 ($428)


    Taxes:$5,135

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16736 GULLFLOSS TER, WINTER GARDEN, FL 34787

    $799,00012 Days on yellowkey   MLS ID: O6423968

    For Sale O6423968 - 16736 GULLFLOSS TER, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2806
       Built: 2018
    Monthly Fee: $184
       Tax: $5,991 (2025)
    Community: Twinwaters
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,061 (change assumption)
    Mortgage ($4,378) + Fees ($184) + Taxes in 2025 ($499)


    Taxes:$5,991

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14542 BLACK CHERRY TRL, WINTER GARDEN, FL 34787

    $575,00057 Days on yellowkey   MLS ID: O6410574

    REDUCED by $14,900 (2.5%) on 07/14/2026

    For Sale O6410574 - 14542 BLACK CHERRY TRL, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2234
       Built: 2008
    Monthly Fee: $184
       Tax: $5,498 (2025)
    Community: Signature Lks-Pcl 01D Ph 01
    Single Family


    Estimated Monthly Payment: $3,793 (change assumption)
    Mortgage ($3,151) + Fees ($184) + Taxes in 2025 ($458)


    Taxes:$5,498

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13780 FRESH IVY ST, WINTER GARDEN, FL 34787

    $849,00077 Days on yellowkey   MLS ID: O6403387

    0 Days Off yellowkey (back on 7/13/2026)

    REDUCED by $16,000 (1.8%) on 07/08/2026

    For Sale O6403387 - 13780 FRESH IVY ST, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2862
       Built: 2025
    Monthly Fee: $642
       Tax: $2,578 (2025)
    Community: Del Webb Oasis Ph 3
    Single Family


    Estimated Monthly Payment: $5,509 (change assumption)
    Mortgage ($4,652) + Fees ($642) + Taxes in 2025 ($215)


    Taxes:$2,578

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9717 WATERWAY PASSAGE DR, WINTER GARDEN, FL 34787

    $669,50048 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: $614 (2025)
    Community: Waterleigh Ph 2A
    Single Family


    Estimated Monthly Payment: $3,970 (change assumption)
    Mortgage ($3,668) + Fees ($250) + Taxes in 2025 ($51)


    Taxes:$614

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15149 CANOE PL, WINTER GARDEN, FL 34787

    $794,98950 Days on yellowkey   MLS ID: O6412776

    REDUCED by $3,902 (0.5%) on 07/13/2026

    For Sale O6412776 - 15149 CANOE PL, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3081
       Built: 2019
    Monthly Fee: $385
       Tax: $9,388 (2025)
    Community: Lakeshore Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $5,523 (change assumption)
    Mortgage ($4,356) + Fees ($385) + Taxes in 2025 ($782)


    Taxes:$9,388

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16197 WIND VIEW LN, WINTER GARDEN, FL 34787

    $517,000104 Days on yellowkey   MLS ID: O6397229

    REDUCED by $3,000 (0.6%) on 05/24/2026

    For Sale O6397229 - 16197 WIND VIEW LN, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 2016
    Monthly Fee: $332
       Tax: $7,677 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,805 (change assumption)
    Mortgage ($2,833) + Fees ($332) + Taxes in 2025 ($640)


    Taxes:$7,677

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 9459 JAYWOOD RD, WINTER GARDEN, FL 34787

    $749,500142 Days on yellowkey   MLS ID: O6386488

    0 Days Off yellowkey (back on 6/20/2026)

    REDUCED by $5,500 (0.7%) on 05/28/2026

    For Sale O6386488 - 9459 JAYWOOD RD, WINTER GARDEN, FL 34787 55 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2840
       Built: 2020
    Monthly Fee: $261
       Tax: $6,669 (2025)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $4,923 (change assumption)
    Mortgage ($4,107) + Fees ($261) + Taxes in 2025 ($556)


    Taxes:$6,669

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 844 OAKLAND PARK BLVD, WINTER GARDEN, FL 34787

    $1,225,00021 Days on yellowkey   MLS ID: O6419976

    For Sale O6419976 - 844 OAKLAND PARK BLVD, WINTER GARDEN, FL 34787 74 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3525
       Built: 2012
    Monthly Fee: $208
       Tax: $14,087 (2025)
    Community: Oakland Park Unit 1B-1B
    Single Family


    Estimated Monthly Payment: $8,094 (change assumption)
    Mortgage ($6,712) + Fees ($208) + Taxes in 2025 ($1,174)


    Taxes:$14,087

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13380 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787

    $699,99039 Days on yellowkey   MLS ID: G5113738

    For Sale G5113738 - 13380 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787 26 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2235
       Built: 2026
    Monthly Fee: $160

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $3,995 (change assumption)
    Mortgage ($3,835) + Fees ($160) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 11192 CARDING MILL LN, WINTER GARDEN, FL 34787

    $761,49743 Days on yellowkey   MLS ID: O6415420

    1 Days Off yellowkey (back on 7/14/2026)

    For Sale O6415420 - 11192 CARDING MILL LN, WINTER GARDEN, FL 34787 11 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2306
       Built: 2026
    Monthly Fee: $421

    Community: Esplanade At Mckinnon Groves
    Single Family


    Estimated Monthly Payment: $4,593 (change assumption)
    Mortgage ($4,172) + Fees ($421) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 10103 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787

    $965,00067 Days on yellowkey   MLS ID: O6407394

    REDUCED by $5,000 (0.5%) on 07/14/2026

    For Sale O6407394 - 10103 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787 14 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4305
       Built: 2019
    Monthly Fee: $159
       Tax: $13,406 (2025)
    Community: Watermark Ph 4
    Single Family


    Estimated Monthly Payment: $6,564 (change assumption)
    Mortgage ($5,288) + Fees ($159) + Taxes in 2025 ($1,117)


    Taxes:$13,406

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11253 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $799,99078 Days on yellowkey   MLS ID: O6405126

    2 Days Off yellowkey (back on 7/14/2026)

    REDUCED by $19,116 (2.3%) on 07/02/2026

    For Sale O6405126 - 11253 HOLLOW BAY DR, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,748 (change assumption)
    Mortgage ($4,383) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 8750 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787

    $1,849,00036 Days on yellowkey   MLS ID: O6416046

    REDUCED by $46,000 (2.4%) on 07/13/2026

    For Sale O6416046 - 8750 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787 88 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 4641
       Built: 2017
    Monthly Fee: $380
       Tax: $16,679 (2025)
    Community: Waterleigh Ph 1
    Single Family


    Estimated Monthly Payment: $11,901 (change assumption)
    Mortgage ($10,131) + Fees ($380) + Taxes in 2025 ($1,390)


    Taxes:$16,679

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15592 AVENUE OF THE ARBORS, WINTER GARDEN, FL 34787

    $2,350,00035 Days on yellowkey   MLS ID: A4697264

    1 Days Off yellowkey (back on 6/25/2026)

    For Sale A4697264 - 15592 AVENUE OF THE ARBORS, WINTER GARDEN, FL 34787 61 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4978
       Built: 2015
    Monthly Fee: $195
       Tax: $21,848 (2026)
    Community: Signature Lks-Pcl 01D Ph 02
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $14,892 (change assumption)
    Mortgage ($12,876) + Fees ($195) + Taxes in 2026 ($1,821)


    Taxes:$21,848

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2026

    Middle School: Horizon West Middle School


  • 15784 SWEET LIMETTA DR, WINTER GARDEN, FL 34787

    $850,0009 Days on yellowkey   MLS ID: O6424831

    For Sale O6424831 - 15784 SWEET LIMETTA DR, WINTER GARDEN, FL 34787 61 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3635
       Built: 2019
    Monthly Fee: $130
       Tax: $11,996 (2025)
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $5,787 (change assumption)
    Mortgage ($4,657) + Fees ($130) + Taxes in 2025 ($1,000)


    Taxes:$11,996

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6315 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $668,990236 Days on yellowkey   MLS ID: G5105013

    0 Days Off yellowkey (back on 11/28/2025)

    For Sale G5105013 - 6315 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2102
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,816 (change assumption)
    Mortgage ($3,666) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14902 ARRENA RD, WINTER GARDEN, FL 34787

    $628,000642 Days on yellowkey   MLS ID: O6248982

    REDUCED by $10,000 (1.6%) on 07/14/2026

    For Sale O6248982 - 14902 ARRENA RD, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3392
       Built: 2001   Tax: $7,754 (2023)
    Community: Arrowhead Lakes
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,087 (change assumption)
    Mortgage ($3,441) + Taxes in 2023 ($646)


    Taxes:$7,754

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 1692 HIGHBANKS CIR, WINTER GARDEN, FL 34787

    $749,90065 Days on yellowkey   MLS ID: O6408620

    REDUCED by $10,100 (1.3%) on 07/13/2026

    For Sale O6408620 - 1692 HIGHBANKS CIR, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2848
       Built: 2017
    Monthly Fee: $142
       Tax: $5,936 (2025)
    Community: Roper Reserve
    Single Family


    Estimated Monthly Payment: $4,746 (change assumption)
    Mortgage ($4,109) + Fees ($142) + Taxes in 2025 ($495)


    Taxes:$5,936

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.