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Winter Garden Single Family Homes For Sale - 732 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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  • 9459 JAYWOOD RD, WINTER GARDEN, FL 34787

    $749,500144 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

    $1,225,00023 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

    $699,99041 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

    $761,49745 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

    $965,00069 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

    $799,99080 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

    $1,849,00038 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

    $2,350,00037 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

    $850,00011 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

    $668,990238 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


  • 1692 HIGHBANKS CIR, WINTER GARDEN, FL 34787

    $749,90067 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


  • 15124 CANOE PL, WINTER GARDEN, FL 34787

    $1,119,00026 Days on yellowkey   MLS ID: O6419984

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

    For Sale O6419984 - 15124 CANOE PL, WINTER GARDEN, FL 34787 50 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3953
       Built: 2019
    Monthly Fee: $360
       Tax: $15,463 (2025)
    Community: Lakeshore Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $7,780 (change assumption)
    Mortgage ($6,131) + Fees ($360) + Taxes in 2025 ($1,289)


    Taxes:$15,463

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17139 INGRAM BLUFF DR, WINTER GARDEN, FL 34787

    $823,30937 Days on yellowkey   MLS ID: G5113974

    For Sale G5113974 - 17139 INGRAM BLUFF DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3412
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,661 (change assumption)
    Mortgage ($4,511) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17127 INGRAM BLUFF DR, WINTER GARDEN, FL 34787

    $721,82037 Days on yellowkey   MLS ID: G5113973

    For Sale G5113973 - 17127 INGRAM BLUFF DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2235
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,105 (change assumption)
    Mortgage ($3,955) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16006 GILDEN WAY, WINTER GARDEN, FL 34787

    $1,024,999119 Days on yellowkey   MLS ID: O6392997

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

    REDUCED by $60,000 (5.5%) on 07/02/2026

    For Sale O6392997 - 16006 GILDEN WAY, WINTER GARDEN, FL 34787 67 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3617
       Built: 2023
    Monthly Fee: $225
       Tax: $12,929 (2025)
    Community: Encore At Ovation
    Single Family


    Estimated Monthly Payment: $6,919 (change assumption)
    Mortgage ($5,616) + Fees ($225) + Taxes in 2025 ($1,077)


    Taxes:$12,929

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13037 SANDCASTLE DR, WINTER GARDEN, FL 34787

    $994,295141 Days on yellowkey   MLS ID: O6387932

    2 Days Off yellowkey (back on 3/26/2026)

    For Sale O6387932 - 13037 SANDCASTLE DR, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2902
       Built: 2022
    Monthly Fee: $534
       Tax: $12,617 (2025)
    Community: Del Webb Oasis
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,033 (change assumption)
    Mortgage ($5,448) + Fees ($534) + Taxes in 2025 ($1,051)


    Taxes:$12,617

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11036 ROBERT FROST DR, WINTER GARDEN, FL 34787

    $634,99056 Days on yellowkey   MLS ID: O6410350

    REDUCED by $15,000 (2.3%) on 07/13/2026

    For Sale O6410350 - 11036 ROBERT FROST DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2136
       Built: 2021
    Monthly Fee: $221
       Tax: $8,394 (2025)
    Community: Storey Grove Ph 3
    Single Family


    Estimated Monthly Payment: $4,400 (change assumption)
    Mortgage ($3,479) + Fees ($221) + Taxes in 2025 ($700)


    Taxes:$8,394

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16707 SANCTUARY DR, WINTER GARDEN, FL 34787

    $712,00029 Days on yellowkey   MLS ID: O6419784

    REDUCED by $5,000 (0.7%) on 07/13/2026

    For Sale O6419784 - 16707 SANCTUARY DR, WINTER GARDEN, FL 34787 22 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2516
       Built: 2020
    Monthly Fee: $165

    Community: Sanctuary/Twin Waters
    Single Family


    Estimated Monthly Payment: $4,066 (change assumption)
    Mortgage ($3,901) + Fees ($165) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14536 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787

    $450,000386 Days on yellowkey   MLS ID: O6320739

    SHORT SALE O6320739 - 14536 GOLDEN HARBOR LN, WINTER GARDEN, FL 34787 23 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1904
       Built: 2016
    Monthly Fee: $159
       Tax: $7,554 (2024)
    Community: Watermark Ph 2C
    Single Family


    Estimated Monthly Payment: $3,254 (change assumption)
    Mortgage ($2,466) + Fees ($159) + Taxes in 2024 ($630)


    Taxes:$7,554

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 15183 BRIDGEWATER CROSSINGS BLVD, WINTER GARDEN, FL 34787

    $520,00032 Days on yellowkey   MLS ID: O6416462

    For Sale O6416462 - 15183 BRIDGEWATER CROSSINGS BLVD, WINTER GARDEN, FL 34787 47 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1998
       Built: 2017
    Monthly Fee: $195
       Tax: $6,636 (2025)
    Community: Signature Lakes Ph 3B-4, 3B-5 &
    Single Family


    Estimated Monthly Payment: $3,597 (change assumption)
    Mortgage ($2,849) + Fees ($195) + Taxes in 2025 ($553)


    Taxes:$6,636

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater 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.