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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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  • 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $635,50012 Days on yellowkey   MLS ID: O6403063

    For Sale O6403063 - 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787 36 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2692
       Built: 2017
    Monthly Fee: $215
       Tax: $8,922 (2025)
    Community: Waterside/Johns Lake Ph 2A
    Single Family


    Estimated Monthly Payment: $4,441 (change assumption)
    Mortgage ($3,482) + Fees ($215) + Taxes in 2025 ($744)


    Taxes:$8,922

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 12025 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $1,275,00037 Days on yellowkey   MLS ID: O6395850

    REDUCED by $50,000 (3.8%) on 05/01/2026

    For Sale O6395850 - 12025 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 98 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 4321
       Built: 2020
    Monthly Fee: $192
       Tax: $15,050 (2025)
    Community: Encore/Ovation Ph 1
    Single Family


    Estimated Monthly Payment: $8,432 (change assumption)
    Mortgage ($6,986) + Fees ($192) + Taxes in 2025 ($1,254)


    Taxes:$15,050

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15813 SWEET LEMON WAY, WINTER GARDEN, FL 34787

    $575,00065 Days on yellowkey   MLS ID: O6386264

    For Sale O6386264 - 15813 SWEET LEMON WAY, WINTER GARDEN, FL 34787 60 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2119
       Built: 2018
    Monthly Fee: $58
       Tax: $8,371 (2025)
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $3,906 (change assumption)
    Mortgage ($3,151) + Fees ($58) + Taxes in 2025 ($698)


    Taxes:$8,371

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13526 FOX GLOVE ST, WINTER GARDEN, FL 34787

    $845,00047 Days on yellowkey   MLS ID: O6388630

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

    For Sale O6388630 - 13526 FOX GLOVE ST, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3866
       Built: 2005
    Monthly Fee: $243
       Tax: $11,960 (2025)
    Community: Stoneybrook West
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,870 (change assumption)
    Mortgage ($4,630) + Fees ($243) + Taxes in 2025 ($997)


    Taxes:$11,960

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 14039 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787

    $819,900471 Days on yellowkey   MLS ID: O6274785

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

    For Sale O6274785 - 14039 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787 86 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3801
       Built: 2006
    Monthly Fee: $141
       Tax: $11,068 (2024)
    Community: Bay Isle 48 17
    Single Family


    Estimated Monthly Payment: $5,556 (change assumption)
    Mortgage ($4,492) + Fees ($141) + Taxes in 2024 ($922)


    Taxes:$11,068

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7212 DESERT MANDARIN ST, WINTER GARDEN, FL 34787

    $650,00017 Days on yellowkey   MLS ID: O6401040

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

    For Sale O6401040 - 7212 DESERT MANDARIN ST, WINTER GARDEN, FL 34787 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2605
       Built: 2018
    Monthly Fee: $64
       Tax: $5,661 (2025)
    Community: Highlands/Summerlake Grvs Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,097 (change assumption)
    Mortgage ($3,562) + Fees ($64) + Taxes in 2025 ($472)


    Taxes:$5,661

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16828 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $581,19018 Days on yellowkey   MLS ID: O6401359

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

    For Sale O6401359 - 16828 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2026
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,540 (change assumption)
    Mortgage ($3,185) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 18029 CIDER MILL LN, WINTER GARDEN, FL 34787

    $724,99086 Days on yellowkey   MLS ID: O6382363

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

    REDUCED by $6,876 (0.9%) on 04/22/2026

    For Sale O6382363 - 18029 CIDER MILL LN, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2113
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,388 (change assumption)
    Mortgage ($3,972) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9354 MEADOW HUNT WAY, WINTER GARDEN, FL 34787

    $525,00015 Days on yellowkey   MLS ID: O6400695

    For Sale O6400695 - 9354 MEADOW HUNT WAY, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2079
       Built: 2017
    Monthly Fee: $164
       Tax: $4,974 (2025)
    Community: Watermark
    Single Family


    Estimated Monthly Payment: $3,455 (change assumption)
    Mortgage ($2,877) + Fees ($164) + Taxes in 2025 ($415)


    Taxes:$4,974

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 10291 ATWATER BAY DR, WINTER GARDEN, FL 34787

    $1,274,500300 Days on yellowkey   MLS ID: O6326819

    REDUCED by $25,000 (1.9%) on 04/01/2026

    For Sale O6326819 - 10291 ATWATER BAY DR, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2019
    Monthly Fee: $250
       Tax: $15,141 (2024)
    Community: Waterleigh Ph 2B
    Single Family


    Estimated Monthly Payment: $8,495 (change assumption)
    Mortgage ($6,983) + Fees ($250) + Taxes in 2024 ($1,262)


    Taxes:$15,141

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 15419 UGLIS ALY, WINTER GARDEN, FL 34787

    $595,00010 Days on yellowkey   MLS ID: O6403047

    For Sale O6403047 - 15419 UGLIS ALY, WINTER GARDEN, FL 34787 51 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2270
       Built: 2018
    Monthly Fee: $60
       Tax: $8,121 (2025)
    Community: Highlands/Summerlake Grvs Ph 2
    Single Family


    Estimated Monthly Payment: $3,997 (change assumption)
    Mortgage ($3,260) + Fees ($60) + Taxes in 2025 ($677)


    Taxes:$8,121

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12790 BRODLOVE LN, WINTER GARDEN, FL 34787

    $574,90010 Days on yellowkey   MLS ID: O6403539

    For Sale O6403539 - 12790 BRODLOVE LN, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2322
       Built: 2022
    Monthly Fee: $225
       Tax: $8,775 (2025)
    Community: Encore/Ovation-Ph 3
    Single Family


    Estimated Monthly Payment: $4,106 (change assumption)
    Mortgage ($3,150) + Fees ($225) + Taxes in 2025 ($731)


    Taxes:$8,775

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 650 MEDORA WAY, WINTER GARDEN, FL 34787

    $1,152,19010 Days on yellowkey   MLS ID: O6403543

    For Sale O6403543 - 650 MEDORA WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2902
       Built: 2026
    Monthly Fee: $155
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Single Family


    Estimated Monthly Payment: $6,551 (change assumption)
    Mortgage ($6,313) + Fees ($155) + Taxes in 2025 ($83)


    Taxes:$993

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 642 MEDORA WAY, WINTER GARDEN, FL 34787

    $1,140,15010 Days on yellowkey   MLS ID: O6403542

    For Sale O6403542 - 642 MEDORA WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3109
       Built: 2026
    Monthly Fee: $155
       Tax: $993 (2025)
    Community: Lakeview Village Estates
    Single Family


    Estimated Monthly Payment: $6,485 (change assumption)
    Mortgage ($6,247) + Fees ($155) + Taxes in 2025 ($83)


    Taxes:$993

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 6165 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $745,13015 Days on yellowkey   MLS ID: G5111538

    0 Days Off yellowkey (back on 4/25/2026)

    For Sale G5111538 - 6165 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3038
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,233 (change assumption)
    Mortgage ($4,083) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17434 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $749,36016 Days on yellowkey   MLS ID: G5111523

    0 Days Off yellowkey (back on 4/24/2026)

    For Sale G5111523 - 17434 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 6   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3412
       Built: 2026
    Monthly Fee: $140

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,246 (change assumption)
    Mortgage ($4,106) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 3430 TURNINGWIND LN, WINTER GARDEN, FL 34787

    $825,00017 Days on yellowkey   MLS ID: G5111151

    0 Days Off yellowkey (back on 4/28/2026)

    For Sale G5111151 - 3430 TURNINGWIND LN, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3358
       Built: 2002
    Monthly Fee: $115
       Tax: $6,001 (2024)
    Community: Windward Cay 48 125
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,135 (change assumption)
    Mortgage ($4,520) + Fees ($115) + Taxes in 2024 ($500)


    Taxes:$6,001

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 13259 SERENE GLADE RD, WINTER GARDEN, FL 34787

    $778,53122 Days on yellowkey   MLS ID: G5111211

    0 Days Off yellowkey (back on 4/18/2026)

    For Sale G5111211 - 13259 SERENE GLADE RD, WINTER GARDEN, FL 34787 19 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2689
       Built: 2026
    Monthly Fee: $160

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $4,426 (change assumption)
    Mortgage ($4,266) + Fees ($160) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: None


  • 17416 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $784,49054 Days on yellowkey   MLS ID: G5109744

    0 Days Off yellowkey (back on 3/17/2026)

    For Sale G5109744 - 17416 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2688
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $4,448 (change assumption)
    Mortgage ($4,298) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13067 TOLLCROSS WAY, WINTER GARDEN, FL 34787

    $599,000118 Days on yellowkey   MLS ID: O6367311

    For Sale O6367311 - 13067 TOLLCROSS WAY, WINTER GARDEN, FL 34787 64 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1906
       Built: 2024
    Monthly Fee: $96
       Tax: $2,239 (2024)
    Community: Westhaven At Ovation
    Single Family


    Estimated Monthly Payment: $3,565 (change assumption)
    Mortgage ($3,282) + Fees ($96) + Taxes in 2024 ($187)


    Taxes:$2,239

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    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.