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Winter Garden Homes For Sale & Real Estate - 843 homes

Winter Garden homes for sale are located in Orange County, Florida. Find homes in Winter Garden for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Garden houses.

Location: Winter Garden

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  • 11117 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $520,0001 Day on yellowkey   MLS ID: O6407552

    For Sale O6407552 - 11117 BOSTWICK ALY, WINTER GARDEN, FL 34787 19 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1685
       Built: 2022
    Monthly Fee: $291
       Tax: $6,722 (2025)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $3,700 (change assumption)
    Mortgage ($2,849) + Fees ($291) + Taxes in 2025 ($560)


    Taxes:$6,722

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 7302 TWILIGHT BAY DR, WINTER GARDEN, FL 34787

    $749,0001 Day on yellowkey   MLS ID: O6407453

    For Sale O6407453 - 7302 TWILIGHT BAY DR, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2810
       Built: 2018
    Monthly Fee: $260
       Tax: $5,903 (2025)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $4,856 (change assumption)
    Mortgage ($4,104) + Fees ($260) + Taxes in 2025 ($492)


    Taxes:$5,903

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 3351 HANGING TIDE ST, WINTER GARDEN, FL 34787

    $635,0001 Day on yellowkey   MLS ID: O6407746

    For Sale O6407746 - 3351 HANGING TIDE ST, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2741
       Built: 2021
    Monthly Fee: $152
       Tax: $7,521 (2025)
    Community: Lakeview Preserve Ph 2
    Single Family


    Estimated Monthly Payment: $4,258 (change assumption)
    Mortgage ($3,479) + Fees ($152) + Taxes in 2025 ($627)


    Taxes:$7,521

    Elementary School: Lost Lake Elem

    High School: East Ridge High

    Tax Year: 2025

    Middle School: Windy Hill Middle


  • 13542 SUNSET LAKES CIR, WINTER GARDEN, FL 34787

    $3,799,0001 Day on yellowkey   MLS ID: O6402896

    For Sale O6402896 - 13542 SUNSET LAKES CIR, WINTER GARDEN, FL 34787 78 photos

    Bed: 5   Bath: 5.5   Gar: 3
    Liv Area Sq Ft: 5450
       Built: 1997
    Monthly Fee: $69
       Tax: $25,701 (2025)
    Community: Sunset Lakes
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $23,027 (change assumption)
    Mortgage ($20,816) + Fees ($69) + Taxes in 2025 ($2,142)


    Taxes:$25,701

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 11193 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $819,99065 Days on yellowkey   MLS ID: O6389839

    REDUCED by $15,000 (1.8%) on 05/15/2026

    For Sale O6389839 - 11193 HOLLOW BAY DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3327
       Built: 2025
    Monthly Fee: $250
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,909 (change assumption)
    Mortgage ($4,493) + Fees ($250) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1015 WESTSIDE DR, WINTER GARDEN, FL 34787

    $224,0003 Days on yellowkey   MLS ID: O6407229

    For Sale O6407229 - 1015 WESTSIDE DR, WINTER GARDEN, FL 34787 23 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 938
       Built: 1986
    Monthly Fee: $61
       Tax: $360 (2025)
    Community: Westside Twnhms
    Spa: No

    Townhouse


    Estimated Monthly Payment: $1,318 (change assumption)
    Mortgage ($1,227) + Fees ($61) + Taxes in 2025 ($30)


    Taxes:$360

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5545 BOWMAN DR, WINTER GARDEN, FL 34787

    $485,0002 Days on yellowkey   MLS ID: O6407484

    For Sale O6407484 - 5545 BOWMAN DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1998
       Built: 2016
    Monthly Fee: $339
       Tax: $7,894 (2025)
    Community: Overlook 2/Hamlin Ph 1 & 6
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,654 (change assumption)
    Mortgage ($2,657) + Fees ($339) + Taxes in 2025 ($658)


    Taxes:$7,894

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 107 TRADITIONS DR, WINTER GARDEN, FL 34787

    $474,97559 Days on yellowkey   MLS ID: S5145650

    REDUCED by $25,020 (5.0%) on 04/20/2026

    For Sale S5145650 - 107 TRADITIONS DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1582
       Built: 1999
    Monthly Fee: $45
       Tax: $1,458 (2024)
    Community: Traditions Sub
    Single Family


    Estimated Monthly Payment: $2,769 (change assumption)
    Mortgage ($2,603) + Fees ($45) + Taxes in 2024 ($121)


    Taxes:$1,458

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 15419 UGLIS ALY, WINTER GARDEN, FL 34787

    $595,00015 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


  • 12249 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787

    $725,000241 Days on yellowkey   MLS ID: O6344139

    3 Days Off yellowkey (back on 5/14/2026)

    For Sale O6344139 - 12249 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787 41 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2346
       Built: 2021
    Monthly Fee: $225
       Tax: $492 (2024)
    Community: Encore/Ovation-Ph 2
    Single Family


    Estimated Monthly Payment: $4,239 (change assumption)
    Mortgage ($3,973) + Fees ($225) + Taxes in 2024 ($41)


    Taxes:$492

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 632 DHARMA CIR, WINTER GARDEN, FL 34787

    $380,00042 Days on yellowkey   MLS ID: O6396151

    For Sale O6396151 - 632 DHARMA CIR, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1315
       Built: 2000
    Monthly Fee: $78
       Tax: $5,780 (2025)
    Community: Daniels Crossing Ph 03
    Single Family


    Estimated Monthly Payment: $2,642 (change assumption)
    Mortgage ($2,082) + Fees ($78) + Taxes in 2025 ($482)


    Taxes:$5,780

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13780 FRESH IVY ST, WINTER GARDEN, FL 34787

    $939,9009 Days on yellowkey   MLS ID: O6403387

    REDUCED by $10,000 (1.1%) on 05/14/2026

    For Sale O6403387 - 13780 FRESH IVY ST, WINTER GARDEN, FL 34787 50 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2862
       Built: 2025
    Monthly Fee: $642
       Tax: $2,578 (2025)
    Community: Del Webb Oasis Ph 3
    Single Family


    Estimated Monthly Payment: $6,007 (change assumption)
    Mortgage ($5,150) + Fees ($642) + Taxes in 2025 ($215)


    Taxes:$2,578

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 17425 LAKE INGRAM RD, WINTER GARDEN, FL 34787

    $1,199,99935 Days on yellowkey   MLS ID: O6397109

    For Sale O6397109 - 17425 LAKE INGRAM RD, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 1.5   Gar: 2
    Liv Area Sq Ft: 2246
       Built: 1977   Tax: $9,794 (2025)
    Community: Mt Park Orange Grove
    Single Family


    Estimated Monthly Payment: $7,391 (change assumption)
    Mortgage ($6,575) + Taxes in 2025 ($816)


    Taxes:$9,794

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16776 BROADWATER AVE, WINTER GARDEN, FL 34787

    $1,324,0002 Days on yellowkey   MLS ID: O6407043

    For Sale O6407043 - 16776 BROADWATER AVE, WINTER GARDEN, FL 34787 72 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3713
       Built: 2018
    Monthly Fee: $383
       Tax: $9,438 (2025)
    Community: Waterside/Johns Lk-Ph 1
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,424 (change assumption)
    Mortgage ($7,255) + Fees ($383) + Taxes in 2025 ($787)


    Taxes:$9,438

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16277 HONEY HARVEST ST, WINTER GARDEN, FL 34787

    $670,00025 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


  • 636 S PARK AVE, WINTER GARDEN, FL 34787

    $259,90027 Days on yellowkey   MLS ID: O6400433

    REDUCED by $39,000 (13.0%) on 05/14/2026

    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: $1,737 (change assumption)
    Mortgage ($1,424) + Taxes in 2025 ($313)


    Taxes:$3,751

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14416 TRAVOIS WAY, WINTER GARDEN, FL 34787

    $786,86877 Days on yellowkey   MLS ID: O6382140

    REDUCED by $7,132 (0.9%) on 04/21/2026

    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: $5,012 (change assumption)
    Mortgage ($4,311) + Fees ($70) + Taxes in 2025 ($631)


    Taxes:$7,567

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 833 BENDING OAK TRL, WINTER GARDEN, FL 34787

    $425,0007 Days on yellowkey   MLS ID: O6403683

    REDUCED by $10,000 (2.3%) on 05/13/2026

    For Sale O6403683 - 833 BENDING OAK TRL, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1789
       Built: 2009
    Monthly Fee: $447
       Tax: $4,032 (2025)
    Community: Oaks/Brandy Lake O
    Townhouse


    Estimated Monthly Payment: $3,112 (change assumption)
    Mortgage ($2,329) + Fees ($447) + Taxes in 2025 ($336)


    Taxes:$4,032

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 2621 SHIREHALL LN, WINTER GARDEN, FL 34787

    $475,00070 Days on yellowkey   MLS ID: O6386585

    0 Days Off yellowkey (back on 5/14/2026)

    REDUCED by $25,000 (5.0%) on 04/17/2026

    For Sale O6386585 - 2621 SHIREHALL LN, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1960
       Built: 2003
    Monthly Fee: $243
       Tax: $3,181 (2024)
    Community: Stoneybrook West Ut 04 48 48
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,111 (change assumption)
    Mortgage ($2,603) + Fees ($243) + Taxes in 2024 ($265)


    Taxes:$3,181

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 11072 SILVER SURFER ALY, WINTER GARDEN, FL 34787

    $460,0005 Days on yellowkey   MLS ID: O6406656

    For Sale O6406656 - 11072 SILVER SURFER ALY, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1770
       Built: 2018
    Monthly Fee: $108
       Tax: $3,977 (2025)
    Community: Storey Grove Ph 1B-2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,960 (change assumption)
    Mortgage ($2,520) + Fees ($108) + Taxes in 2025 ($331)


    Taxes:$3,977

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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Winter Garden home, townhome, condo, villa, and other listing sales 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 houses for sale in Winter Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden Real Estate. 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 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.