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Winter Garden Single Family Homes For Sale - 695 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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  • 15456 GILLIGAN CT, WINTER GARDEN, FL 34787

    $550,000318 Days on yellowkey   MLS ID: A4660262

    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


  • 15121 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787

    $874,9003 Days on yellowkey   MLS ID: O6416065

    For Sale O6416065 - 15121 EVERGREEN OAK LOOP, WINTER GARDEN, FL 34787 43 photos

    Bed: 6   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4042
       Built: 2016
    Monthly Fee: $180
       Tax: $552 (2024)
    Community: Signature Lakes Ph 3B-4
    Single Family


    Estimated Monthly Payment: $5,020 (change assumption)
    Mortgage ($4,794) + Fees ($180) + Taxes in 2024 ($46)


    Taxes:$552

    Elementary School: Independence Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 16893 BROADWATER AVE, WINTER GARDEN, FL 34787

    $2,795,9003 Days on yellowkey   MLS ID: O6415972

    For Sale O6415972 - 16893 BROADWATER AVE, WINTER GARDEN, FL 34787 76 photos

    Bed: 7   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 6289
       Built: 2019
    Monthly Fee: $383
       Tax: $25,448 (2025)
    Community: Waterside 90'S
    Single Family


    Estimated Monthly Payment: $17,823 (change assumption)
    Mortgage ($15,320) + Fees ($383) + Taxes in 2025 ($2,121)


    Taxes:$25,448

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • WINTER GARDEN, FL 34787

    $558,9903 Days on yellowkey   MLS ID: G5113611

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale G5113611 - WINTER GARDEN, FL 34787 1 photos

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

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,213 (change assumption)
    Mortgage ($3,063) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6171 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $792,8053 Days on yellowkey   MLS ID: G5113609

    0 Days Off yellowkey (back on 6/11/2026)

    For Sale G5113609 - 6171 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 1 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: $4,494 (change assumption)
    Mortgage ($4,344) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 11221 CARDING MILL LN, WINTER GARDEN, FL 34787

    $758,1884 Days on yellowkey   MLS ID: O6415572

    For Sale O6415572 - 11221 CARDING MILL LN, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2085
       Built: 2026
    Monthly Fee: $140

    Community: Esplanade At Mckinnon Groves
    Single Family


    Estimated Monthly Payment: $4,294 (change assumption)
    Mortgage ($4,154) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 1343 CASTLEPORT RD, WINTER GARDEN, FL 34787

    $535,0003 Days on yellowkey   MLS ID: O6414756

    For Sale O6414756 - 1343 CASTLEPORT RD, WINTER GARDEN, FL 34787 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2170
       Built: 2001
    Monthly Fee: $243
       Tax: $4,191 (2025)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,524 (change assumption)
    Mortgage ($2,931) + Fees ($243) + Taxes in 2025 ($349)


    Taxes:$4,191

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9481 EMERALD BERRY DR, WINTER GARDEN, FL 34787

    $789,9903 Days on yellowkey   MLS ID: O6414779

    For Sale O6414779 - 9481 EMERALD BERRY DR, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2569
       Built: 2023
    Monthly Fee: $99
       Tax: $9,756 (2025)
    Community: Summerlake Reserve
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,241 (change assumption)
    Mortgage ($4,329) + Fees ($99) + Taxes in 2025 ($813)


    Taxes:$9,756

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12391 SILK MIMOSA ALY #258, WINTER GARDEN, FL 34787

    $607,6799 Days on yellowkey   MLS ID: O6414276

    For Sale O6414276 - 12391 SILK MIMOSA ALY #258, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2026
    Monthly Fee: $96
       Tax: $9,115 (2026)
    Community: Osprey Ranch
    Single Family


    Estimated Monthly Payment: $4,185 (change assumption)
    Mortgage ($3,330) + Fees ($96) + Taxes in 2026 ($760)


    Taxes:$9,115

    Elementary School: None

    High School: None

    Tax Year: 2026

    Middle School: None


  • 4863 LACEWING DR, WINTER GARDEN, FL 34787

    $540,00066 Days on yellowkey   MLS ID: O6397857

    0 Days Off yellowkey (back on 5/23/2026)

    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


  • 13343 SUNNY RETREAT LN, WINTER GARDEN, FL 34787

    $799,900130 Days on yellowkey   MLS ID: O6379591

    REDUCED by $49,100 (5.8%) on 06/11/2026

    For Sale O6379591 - 13343 SUNNY RETREAT LN, WINTER GARDEN, FL 34787 49 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2214
       Built: 2023
    Monthly Fee: $544
       Tax: $10,256 (2024)
    Community: Del Webb Oasis
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,782 (change assumption)
    Mortgage ($4,383) + Fees ($544) + Taxes in 2024 ($855)


    Taxes:$10,256

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16104 SANDHILL RD, WINTER GARDEN, FL 34787

    $1,020,00017 Days on yellowkey   MLS ID: O6411589

    For Sale O6411589 - 16104 SANDHILL RD, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1364
       Built: 1988
    Monthly Fee: $3
       Tax: $2,191 (2025)
    Community: Lake Avalon Groves
    Single Family


    Estimated Monthly Payment: $5,774 (change assumption)
    Mortgage ($5,589) + Fees ($3) + Taxes in 2025 ($183)


    Taxes:$2,191

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14280 BRAEMAR ST, WINTER GARDEN, FL 34787

    $499,00053 Days on yellowkey   MLS ID: TB8500322

    REDUCED by $40,000 (7.4%) on 06/12/2026

    For Sale TB8500322 - 14280 BRAEMAR ST, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1964
       Built: 2023
    Monthly Fee: $100
       Tax: $7,928 (2025)
    Community: Highland Rdg
    Single Family


    Estimated Monthly Payment: $3,495 (change assumption)
    Mortgage ($2,734) + Fees ($100) + Taxes in 2025 ($661)


    Taxes:$7,928

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • WINTER GARDEN, FL 34787

    $599,00059 Days on yellowkey   MLS ID: O6399369

    REDUCED by $20,000 (3.2%) on 05/22/2026

    For Sale O6399369 - WINTER GARDEN, FL 34787 18 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1827
       Built: 2001
    Monthly Fee: $320
       Tax: $4,811 (2025)
    Community: Woodbridge On Green
    Single Family


    Estimated Monthly Payment: $4,003 (change assumption)
    Mortgage ($3,282) + Fees ($320) + Taxes in 2025 ($401)


    Taxes:$4,811

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 9827 BEACH PORT DR, WINTER GARDEN, FL 34787

    $1,399,99038 Days on yellowkey   MLS ID: O6405480

    INCREASED by $25,000 (1.8%) on 06/11/2026

    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: $8,857 (change assumption)
    Mortgage ($7,671) + 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


  • 15336 FIRELIGHT DR, WINTER GARDEN, FL 34787

    $585,0004 Days on yellowkey   MLS ID: G5113550

    For Sale G5113550 - 15336 FIRELIGHT DR, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2242
       Built: 2007
    Monthly Fee: $167
       Tax: $4,649 (2025)
    Community: Belle Meade Ph 2
    Single Family


    Estimated Monthly Payment: $3,760 (change assumption)
    Mortgage ($3,205) + Fees ($167) + Taxes in 2025 ($387)


    Taxes:$4,649

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 398 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787

    $1,498,44040 Days on yellowkey   MLS ID: O6405194

    1 Days Off yellowkey (back on 6/11/2026)

    For Sale O6405194 - 398 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4442
       Built: 2024
    Monthly Fee: $240
       Tax: $14,707 (2025)
    Community: Winter Grove
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,676 (change assumption)
    Mortgage ($8,210) + Fees ($240) + Taxes in 2025 ($1,226)


    Taxes:$14,707

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 936 KYLEE ALY, WINTER GARDEN, FL 34787

    $675,00080 Days on yellowkey   MLS ID: O6393910

    4 Days Off yellowkey (back on 6/11/2026)

    For Sale O6393910 - 936 KYLEE ALY, WINTER GARDEN, FL 34787 60 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1772
       Built: 2022
    Monthly Fee: $356
       Tax: $6,058 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $4,559 (change assumption)
    Mortgage ($3,699) + Fees ($356) + Taxes in 2025 ($505)


    Taxes:$6,058

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Legacy Middle


  • 13062 SUNSET GARDEN LN, WINTER GARDEN, FL 34787

    $693,27057 Days on yellowkey   MLS ID: O6400441

    INCREASED by $3,000 (0.4%) on 04/30/2026

    For Sale O6400441 - 13062 SUNSET GARDEN LN, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2686
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $4,069 (change assumption)
    Mortgage ($3,799) + Fees ($77) + Taxes in 2025 ($194)


    Taxes:$2,326

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 13026 SUNSET GARDEN LN, WINTER GARDEN, FL 34787

    $547,16058 Days on yellowkey   MLS ID: O6400188

    INCREASED by $3,000 (0.6%) on 04/30/2026

    For Sale O6400188 - 13026 SUNSET GARDEN LN, WINTER GARDEN, FL 34787 6 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1908
       Built: 2026
    Monthly Fee: $77
       Tax: $2,326 (2025)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,269 (change assumption)
    Mortgage ($2,998) + Fees ($77) + Taxes in 2025 ($194)


    Taxes:$2,326

    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.