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Winter Garden Single Family Homes For Sale - 455 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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  • 12983 HARVEST RAIN AVE, WINTER GARDEN, FL 34787

    $750,000Listed 04/08/2026 9:39PM   MLS ID: O6397592

    For Sale O6397592 - 12983 HARVEST RAIN AVE, WINTER GARDEN, FL 34787 53 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2858
       Built: 2026
    Monthly Fee: $140

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,249 (change assumption)
    Mortgage ($4,109) + Fees ($140) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 743 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,499,99915 Days on yellowkey   MLS ID: O6392705

    0 Days Off yellowkey (back on 4/8/2026)

    For Sale O6392705 - 743 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 71 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4283
       Built: 2018
    Monthly Fee: $298
       Tax: $10,715 (2025)
    Community: Canopy Oaks Ph I
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,410 (change assumption)
    Mortgage ($8,219) + Fees ($298) + Taxes in 2025 ($893)


    Taxes:$10,715

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 5679 ORANGE ORCHARD DR, WINTER GARDEN, FL 34787

    $649,90027 Days on yellowkey   MLS ID: O6389469

    For Sale O6389469 - 5679 ORANGE ORCHARD DR, WINTER GARDEN, FL 34787 51 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2235
       Built: 2021
    Monthly Fee: $117
       Tax: $7,176 (2025)
    Community: Wincey Groves
    Single Family


    Estimated Monthly Payment: $4,276 (change assumption)
    Mortgage ($3,561) + Fees ($117) + Taxes in 2025 ($598)


    Taxes:$7,176

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14282 CREEKBED CIR, WINTER GARDEN, FL 34787

    $924,500116 Days on yellowkey   MLS ID: O6365928

    REDUCED by $5,000 (0.5%) on 04/08/2026

    For Sale O6365928 - 14282 CREEKBED CIR, WINTER GARDEN, FL 34787 25 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3479
       Built: 2015
    Monthly Fee: $180
       Tax: $7,163 (2025)
    Community: Bradford Creek
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,843 (change assumption)
    Mortgage ($5,066) + Fees ($180) + Taxes in 2025 ($597)


    Taxes:$7,163

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15672 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $859,90075 Days on yellowkey   MLS ID: O6375411

    REDUCED by $10,000 (1.1%) on 04/08/2026

    For Sale O6375411 - 15672 SHOREBIRD LN, WINTER GARDEN, FL 34787 79 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2800
       Built: 2017
    Monthly Fee: $360
       Tax: $6,887 (2025)
    Community: Lakeshore Preserve
    Single Family


    Estimated Monthly Payment: $5,646 (change assumption)
    Mortgage ($4,712) + Fees ($360) + Taxes in 2025 ($574)


    Taxes:$6,887

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16006 GILDEN WAY, WINTER GARDEN, FL 34787

    $1,150,00012 Days on yellowkey   MLS ID: O6392997

    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: $7,604 (change assumption)
    Mortgage ($6,301) + 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


  • 14416 TRAVOIS WAY, WINTER GARDEN, FL 34787

    $794,00040 Days on yellowkey   MLS ID: O6382140

    For Sale O6382140 - 14416 TRAVOIS WAY, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3324
       Built: 2022
    Monthly Fee: $70
       Tax: $7,567 (2025)
    Community: Lake Apopka Sound
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,051 (change assumption)
    Mortgage ($4,351) + Fees ($70) + Taxes in 2025 ($631)


    Taxes:$7,567

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 408 S BOYD ST, WINTER GARDEN, FL 34787

    $835,0008 Days on yellowkey   MLS ID: O6394810

    For Sale O6394810 - 408 S BOYD ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2295
       Built: 1939   Tax: $2,572 (2025)
    Community: G T Smith Sub 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,790 (change assumption)
    Mortgage ($4,575) + Taxes in 2025 ($214)


    Taxes:$2,572

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 238 N MAIN ST, WINTER GARDEN, FL 34787

    $600,000Listed 04/08/2026 5:13PM   MLS ID: O6397340

    For Sale O6397340 - 238 N MAIN ST, WINTER GARDEN, FL 34787 22 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1005
       Built: 1950   Tax: $5,389 (2025)
    Community: Orange Grove Sub
    Single Family


    Estimated Monthly Payment: $3,737 (change assumption)
    Mortgage ($3,288) + Taxes in 2025 ($449)


    Taxes:$5,389

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 10031 BEDTIME STORY DR, WINTER GARDEN, FL 34787

    $669,000257 Days on yellowkey   MLS ID: O6329801

    REDUCED by $6,000 (0.9%) on 04/08/2026

    For Sale O6329801 - 10031 BEDTIME STORY DR, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2722
       Built: 2018
    Monthly Fee: $209
       Tax: $912 (2023)
    Community: Storey Grove 50
    Single Family


    Estimated Monthly Payment: $3,951 (change assumption)
    Mortgage ($3,666) + Fees ($209) + Taxes in 2023 ($76)


    Taxes:$912

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2023

    Middle School: Water Spring Middle


  • 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $899,990114 Days on yellowkey   MLS ID: O6367437

    For Sale O6367437 - 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $200
       Tax: $1,989 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,297 (change assumption)
    Mortgage ($4,931) + Fees ($200) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787

    $1,199,90034 Days on yellowkey   MLS ID: O6385964

    INCREASED by $80,900 (7.2%) on 04/02/2026

    For Sale O6385964 - 441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4001
       Built: 2000
    Monthly Fee: $83
       Tax: $5,551 (2024)
    Community: Courtlea Oaks
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,120 (change assumption)
    Mortgage ($6,575) + Fees ($83) + Taxes in 2024 ($463)


    Taxes:$5,551

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 813 MARSH REED DR, WINTER GARDEN, FL 34787

    $609,000288 Days on yellowkey   MLS ID: O6321149

    For Sale O6321149 - 813 MARSH REED DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3148
       Built: 2015
    Monthly Fee: $128
       Tax: $8,220 (2024)
    Community: Johns Lake Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,150 (change assumption)
    Mortgage ($3,337) + Fees ($128) + Taxes in 2024 ($685)


    Taxes:$8,220

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 16391 ADMIRALS COVE LN, WINTER GARDEN, FL 34787

    $540,000321 Days on yellowkey   MLS ID: O6311344

    For Sale O6311344 - 16391 ADMIRALS COVE LN, WINTER GARDEN, FL 34787 27 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2200
       Built: 2020
    Monthly Fee: $254
       Tax: $8,126 (2024)
    Community: Waterleigh Ph 3B & 3C
    Single Family


    Estimated Monthly Payment: $3,890 (change assumption)
    Mortgage ($2,959) + Fees ($254) + Taxes in 2024 ($677)


    Taxes:$8,126

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787

    $570,0001 Day on yellowkey   MLS ID: O6396757

    For Sale O6396757 - 6408 FLAT LEMON DR, WINTER GARDEN, FL 34787 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1979
       Built: 2019
    Monthly Fee: $142
       Tax: $8,155 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $3,945 (change assumption)
    Mortgage ($3,123) + Fees ($142) + Taxes in 2025 ($680)


    Taxes:$8,155

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 720 LAKE BRIM DR, WINTER GARDEN, FL 34787

    $1,850,00033 Days on yellowkey   MLS ID: O6387519

    REDUCED by $49,000 (2.6%) on 04/01/2026

    For Sale O6387519 - 720 LAKE BRIM DR, WINTER GARDEN, FL 34787 88 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3781
       Built: 2020
    Monthly Fee: $203
       Tax: $14,831 (2025)
    Community: Oakland Park
    Spa: No

    Single Family


    Estimated Monthly Payment: $11,576 (change assumption)
    Mortgage ($10,137) + Fees ($203) + Taxes in 2025 ($1,236)


    Taxes:$14,831

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787

    $573,00072 Days on yellowkey   MLS ID: NS1087076

    For Sale NS1087076 - 16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787 27 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2474
       Built: 2024
    Monthly Fee: $291
       Tax: $2,273 (2024)
    Community: Waterleigh Ph 4B & 4C
    Single Family


    Estimated Monthly Payment: $3,620 (change assumption)
    Mortgage ($3,140) + Fees ($291) + Taxes in 2024 ($189)


    Taxes:$2,273

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16736 OAKBORO ST, WINTER GARDEN, FL 34787

    $585,00020 Days on yellowkey   MLS ID: O6388784

    For Sale O6388784 - 16736 OAKBORO ST, WINTER GARDEN, FL 34787 65 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2477
       Built: 2020
    Monthly Fee: $257
       Tax: $6,967 (2024)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,043 (change assumption)
    Mortgage ($3,205) + Fees ($257) + Taxes in 2024 ($581)


    Taxes:$6,967

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2439 BALFORN TOWER WAY, WINTER GARDEN, FL 34787

    $570,00040 Days on yellowkey   MLS ID: O6386373

    For Sale O6386373 - 2439 BALFORN TOWER WAY, WINTER GARDEN, FL 34787 82 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2508
       Built: 2008
    Monthly Fee: $243
       Tax: $3,490 (2025)
    Community: Stoneybrook West D
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,657 (change assumption)
    Mortgage ($3,123) + Fees ($243) + Taxes in 2025 ($291)


    Taxes:$3,490

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9107 GRAND ISLAND WAY, WINTER GARDEN, FL 34787

    $505,00023 Days on yellowkey   MLS ID: O6391117

    For Sale O6391117 - 9107 GRAND ISLAND WAY, WINTER GARDEN, FL 34787 44 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




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.