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Winter Garden Single Family Homes For Sale - 644 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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  • 46 W VINING ST, WINTER GARDEN, FL 34787

    $569,9004 Days on yellowkey   MLS ID: O6408720

    For Sale O6408720 - 46 W VINING ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1273
       Built: 1938   Tax: $6,287 (2025)
    Community: Ellman Park
    Single Family


    Estimated Monthly Payment: $3,647 (change assumption)
    Mortgage ($3,123) + Taxes in 2025 ($524)


    Taxes:$6,287

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14531 CEDAR HILL DR, WINTER GARDEN, FL 34787

    $799,0007 Days on yellowkey   MLS ID: O6408070

    For Sale O6408070 - 14531 CEDAR HILL DR, WINTER GARDEN, FL 34787 51 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 3510
       Built: 2014
    Monthly Fee: $187
       Tax: $6,330 (2025)
    Community: Orchard Hills Ph 1
    Single Family


    Estimated Monthly Payment: $5,092 (change assumption)
    Mortgage ($4,378) + Fees ($187) + Taxes in 2025 ($528)


    Taxes:$6,330

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 16294 HONEY HARVEST ST, WINTER GARDEN, FL 34787

    $685,00021 Days on yellowkey   MLS ID: O6403794

    REDUCED by $25,000 (3.5%) on 05/15/2026

    For Sale O6403794 - 16294 HONEY HARVEST ST, WINTER GARDEN, FL 34787 37 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2812
       Built: 2024
    Monthly Fee: $229
       Tax: $9,329 (2025)
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $4,760 (change assumption)
    Mortgage ($3,753) + Fees ($229) + Taxes in 2025 ($777)


    Taxes:$9,329

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 16004 OLLIVETT ST, WINTER GARDEN, FL 34787

    $859,000325 Days on yellowkey   MLS ID: S5130060

    For Sale S5130060 - 16004 OLLIVETT ST, WINTER GARDEN, FL 34787 33 photos

    Bed: 7   Bath: 4.0   Gar: 4
    Liv Area Sq Ft: 4704
       Built: 2014
    Monthly Fee: $110
       Tax: $9,493 (2024)
    Community: Verde Park Ph 1
    Single Family


    Estimated Monthly Payment: $5,608 (change assumption)
    Mortgage ($4,707) + Fees ($110) + Taxes in 2024 ($791)


    Taxes:$9,493

    Elementary School: Grassy Lake Elementary

    High School: Lake Minneola High

    Tax Year: 2024

    Middle School: East Ridge Middle


  • 241 N DILLARD ST, WINTER GARDEN, FL 34787

    $1,499,999214 Days on yellowkey   MLS ID: O6353975

    REDUCED by $100,001 (6.3%) on 04/13/2026

    For Sale O6353975 - 241 N DILLARD ST, WINTER GARDEN, FL 34787 52 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3507
       Built: 1953   Tax: $2,959 (2024)
    Community: J L Dillard Sub 3
    Single Family


    Estimated Monthly Payment: $8,466 (change assumption)
    Mortgage ($8,219) + Taxes in 2024 ($247)


    Taxes:$2,959

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 636 S PARK AVE, WINTER GARDEN, FL 34787

    $249,90034 Days on yellowkey   MLS ID: O6400433

    0 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $10,000 (3.8%) on 05/19/2026

    For Sale O6400433 - 636 S PARK AVE, WINTER GARDEN, FL 34787 14 photos

    Bed: 4   Bath: 1.5   Gar: 2
    Liv Area Sq Ft: 1272
       Built: 1953   Tax: $3,751 (2025)
    Community: Burchshire
    Single Family


    Estimated Monthly Payment: $1,682 (change assumption)
    Mortgage ($1,369) + Taxes in 2025 ($313)


    Taxes:$3,751

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 345 WINTER ST, WINTER GARDEN, FL 34787

    $285,00028 Days on yellowkey   MLS ID: O6402105

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

    INCREASED by $5,100 (1.8%) on 04/26/2026

    For Sale O6402105 - 345 WINTER ST, WINTER GARDEN, FL 34787 18 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 700
       Built: 1951   Tax: $211 (2025)
    Community: Shadow Lawn
    Single Family


    Estimated Monthly Payment: $1,579 (change assumption)
    Mortgage ($1,562) + Taxes in 2025 ($18)


    Taxes:$211

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16749 HARPER COVE DR, WINTER GARDEN, FL 34787

    $499,99933 Days on yellowkey   MLS ID: O6400511

    REDUCED by $15,001 (2.9%) on 05/19/2026

    For Sale O6400511 - 16749 HARPER COVE DR, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2014
       Built: 2019
    Monthly Fee: $257
       Tax: $7,287 (2024)
    Community: Waterleigh Ph 2C-1
    Single Family


    Estimated Monthly Payment: $3,604 (change assumption)
    Mortgage ($2,740) + Fees ($257) + Taxes in 2024 ($607)


    Taxes:$7,287

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 3306 HANGING TIDE ST, WINTER GARDEN, FL 34787

    $585,000260 Days on yellowkey   MLS ID: G5101402

    4 Days Off yellowkey (back on 3/23/2026)

    SHORT SALE G5101402 - 3306 HANGING TIDE ST, WINTER GARDEN, FL 34787 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2894
       Built: 2022
    Monthly Fee: $138
       Tax: $9,355 (2024)
    Community: Lakeview Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $4,123 (change assumption)
    Mortgage ($3,205) + Fees ($138) + Taxes in 2024 ($780)


    Taxes:$9,355

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2024

    Middle School: Windy Hill Middle


  • 11265 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $870,33116 Days on yellowkey   MLS ID: O6405351

    2 Days Off yellowkey (back on 5/19/2026)

    For Sale O6405351 - 11265 HOLLOW BAY DR, WINTER GARDEN, FL 34787 7 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3225
       Built: 2025
    Monthly Fee: $200
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,135 (change assumption)
    Mortgage ($4,769) + Fees ($200) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16809 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $559,990134 Days on yellowkey   MLS ID: O6372242

    2 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $10,000 (1.8%) on 05/14/2026

    For Sale O6372242 - 16809 HOBE SOUND CT, WINTER GARDEN, FL 34787 7 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2216
       Built: 2025
    Monthly Fee: $248
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,482 (change assumption)
    Mortgage ($3,068) + Fees ($248) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11217 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $849,99038 Days on yellowkey   MLS ID: O6399115

    2 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $16,821 (1.9%) on 04/22/2026

    For Sale O6399115 - 11217 HOLLOW BAY DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $199
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,022 (change assumption)
    Mortgage ($4,657) + Fees ($199) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14784 FIELD DAISY DR, WINTER GARDEN, FL 34787

    $690,0007 Days on yellowkey   MLS ID: O6408277

    For Sale O6408277 - 14784 FIELD DAISY DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2841
       Built: 2026
    Monthly Fee: $229

    Community: Harvest At Ovation
    Single Family


    Estimated Monthly Payment: $4,010 (change assumption)
    Mortgage ($3,781) + Fees ($229) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1101 EAGLES PASS WAY, WINTER GARDEN, FL 34787

    $1,725,0004 Days on yellowkey   MLS ID: O6408835

    For Sale O6408835 - 1101 EAGLES PASS WAY, WINTER GARDEN, FL 34787 62 photos

    Bed: 6   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4104
       Built: 2023
    Monthly Fee: $203
       Tax: $19,016 (2024)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $11,239 (change assumption)
    Mortgage ($9,452) + Fees ($203) + Taxes in 2024 ($1,585)


    Taxes:$19,016

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 1692 HIGHBANKS CIR, WINTER GARDEN, FL 34787

    $760,0004 Days on yellowkey   MLS ID: O6408620

    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: $4,801 (change assumption)
    Mortgage ($4,164) + Fees ($142) + Taxes in 2025 ($495)


    Taxes:$5,936

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17124 BEACHGRASS ALY, WINTER GARDEN, FL 34787

    $559,9904 Days on yellowkey   MLS ID: O6408024

    For Sale O6408024 - 17124 BEACHGRASS ALY, WINTER GARDEN, FL 34787 4 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1983
       Built: 2026
    Monthly Fee: $112
       Tax: $6,874 (2025)
    Community: Lake Star At Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,753 (change assumption)
    Mortgage ($3,068) + Fees ($112) + Taxes in 2025 ($573)


    Taxes:$6,874

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17106 BEACHGRASS ALY, WINTER GARDEN, FL 34787

    $799,9904 Days on yellowkey   MLS ID: O6407735

    For Sale O6407735 - 17106 BEACHGRASS ALY, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1983
       Built: 2025
    Monthly Fee: $172
       Tax: $10,166 (2025)
    Community: Lake Star At Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,403 (change assumption)
    Mortgage ($4,383) + Fees ($172) + Taxes in 2025 ($847)


    Taxes:$10,166

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787

    $1,287,00053 Days on yellowkey   MLS ID: O6394059

    REDUCED by $30,000 (2.3%) on 05/09/2026

    For Sale O6394059 - 706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 5   Bath: 6.0   Gar: 3
    Liv Area Sq Ft: 4019
       Built: 2018
    Monthly Fee: $298
       Tax: $17,895 (2025)
    Community: Canopy Oaks Ph 1
    Single Family


    Estimated Monthly Payment: $8,841 (change assumption)
    Mortgage ($7,052) + Fees ($298) + Taxes in 2025 ($1,491)


    Taxes:$17,895

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 16277 HONEY HARVEST ST, WINTER GARDEN, FL 34787

    $670,00032 Days on yellowkey   MLS ID: O6400235

    For Sale O6400235 - 16277 HONEY HARVEST ST, WINTER GARDEN, FL 34787 35 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2930
       Built: 2024
    Monthly Fee: $229
       Tax: $9,784 (2025)
    Community: Harvest/Ovation
    Single Family


    Estimated Monthly Payment: $4,715 (change assumption)
    Mortgage ($3,671) + Fees ($229) + Taxes in 2025 ($815)


    Taxes:$9,784

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17100 BEACHGRASS, WINTER GARDEN, FL 34787

    $834,9907 Days on yellowkey   MLS ID: O6407707

    For Sale O6407707 - 17100 BEACHGRASS, WINTER GARDEN, FL 34787 33 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2781
       Built: 2025
    Monthly Fee: $172
       Tax: $10,646 (2025)
    Community: Lake Star At Ovation
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,634 (change assumption)
    Mortgage ($4,575) + Fees ($172) + Taxes in 2025 ($887)


    Taxes:$10,646

    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.