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Winter Garden Homes For Sale & Real Estate - 827 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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  • 16827 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $624,990108 Days on yellowkey   MLS ID: O6376919

    REDUCED by $5,000 (0.8%) on 05/14/2026

    For Sale O6376919 - 16827 HOBE SOUND CT, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2489
       Built: 2025
    Monthly Fee: $248
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,838 (change assumption)
    Mortgage ($3,425) + Fees ($248) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $875,990150 Days on yellowkey   MLS ID: O6367437

    REDUCED by $19,000 (2.1%) on 05/14/2026

    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: $5,166 (change assumption)
    Mortgage ($4,800) + Fees ($200) + Taxes in 2024 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 7302 TWILIGHT BAY DR, WINTER GARDEN, FL 34787

    $749,000Listed 05/14/2026 8:47AM   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


  • 18167 CIDER MILL LN, WINTER GARDEN, FL 34787

    $469,99076 Days on yellowkey   MLS ID: O6386278

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

    REDUCED by $5,000 (1.1%) on 04/22/2026

    For Sale O6386278 - 18167 CIDER MILL LN, WINTER GARDEN, FL 34787 15 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2025
    Monthly Fee: $205
       Tax: $1,424 (2025)
    Community: Waterleigh
    Spa: No

    Townhouse


    Estimated Monthly Payment: $2,899 (change assumption)
    Mortgage ($2,575) + Fees ($205) + Taxes in 2025 ($119)


    Taxes:$1,424

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6166 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787

    $664,90030 Days on yellowkey   MLS ID: O6399123

    REDUCED by $10,100 (1.5%) on 04/20/2026

    For Sale O6399123 - 6166 HAMLIN RESERVE BLVD, WINTER GARDEN, FL 34787 54 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2818
       Built: 2018
    Monthly Fee: $142
       Tax: $6,366 (2025)
    Community: Hamlin Reserve
    Single Family


    Estimated Monthly Payment: $4,316 (change assumption)
    Mortgage ($3,643) + Fees ($142) + Taxes in 2025 ($531)


    Taxes:$6,366

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 907 EASLEY AVE, WINTER GARDEN, FL 34787

    $865,0002 Days on yellowkey   MLS ID: O6406147

    For Sale O6406147 - 907 EASLEY AVE, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2252
       Built: 2017
    Monthly Fee: $208
       Tax: $4,712 (2025)
    Community: Oakland Park
    Single Family


    Estimated Monthly Payment: $5,340 (change assumption)
    Mortgage ($4,740) + Fees ($208) + Taxes in 2025 ($393)


    Taxes:$4,712

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3351 HANGING TIDE ST, WINTER GARDEN, FL 34787

    $635,000Listed 05/14/2026 7:05AM   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


  • 6174 WHISPERING GLEN, WINTER GARDEN, FL 34787

    $546,290Listed 05/13/2026 11:53PM   MLS ID: O6407807

    For Sale O6407807 - 6174 WHISPERING GLEN, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1628
       Built: 2026
    Monthly Fee: $147
       Tax: $1,373 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,255 (change assumption)
    Mortgage ($2,993) + Fees ($147) + Taxes in 2024 ($114)


    Taxes:$1,373

    Elementary School: Vista Lakes Elem

    High School: Colonial High

    Tax Year: 2024

    Middle School: Odyssey Middle


  • 1431 VISCAYA COVE BLVD, WINTER GARDEN, FL 34787

    $535,000Listed 05/13/2026 11:30PM   MLS ID: O6407306

    For Sale O6407306 - 1431 VISCAYA COVE BLVD, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2030
       Built: 2022
    Monthly Fee: $215
       Tax: $7,429 (2025)
    Community: Waterside/Johns Lake Ph 2C
    Single Family


    Estimated Monthly Payment: $3,766 (change assumption)
    Mortgage ($2,931) + Fees ($215) + Taxes in 2025 ($619)


    Taxes:$7,429

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6102 WHISPERING GLEN, WINTER GARDEN, FL 34787

    $576,890Listed 05/13/2026 10:42PM   MLS ID: O6407803

    For Sale O6407803 - 6102 WHISPERING GLEN, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1913
       Built: 2024
    Monthly Fee: $147
       Tax: $1,372 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,422 (change assumption)
    Mortgage ($3,161) + Fees ($147) + Taxes in 2024 ($114)


    Taxes:$1,372

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 15532 AVENUE OF THE ARBORS, WINTER GARDEN, FL 34787

    $1,999,950Listed 05/13/2026 8:28PM   MLS ID: O6405850

    For Sale O6405850 - 15532 AVENUE OF THE ARBORS, WINTER GARDEN, FL 34787 84 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3837
       Built: 2016
    Monthly Fee: $195
       Tax: $17,089 (2025)
    Community: Signature Lakes Ph 02 A B H I J
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,577 (change assumption)
    Mortgage ($10,958) + Fees ($195) + Taxes in 2025 ($1,424)


    Taxes:$17,089

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Horizon West Middle School


  • 14002 AVENUE OF THE GRVS, WINTER GARDEN, FL 34787

    $345,000Listed 05/13/2026 6:43PM   MLS ID: S5149866

    For Sale S5149866 - 14002 AVENUE OF THE GRVS, WINTER GARDEN, FL 34787 32 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1271
       Built: 2012
    Monthly Fee: $429
       Tax: $5,146 (2025)
    Community: Signature Lks-Pcl 01D Ph 01
    Townhouse


    Estimated Monthly Payment: $2,748 (change assumption)
    Mortgage ($1,890) + Fees ($429) + Taxes in 2025 ($429)


    Taxes:$5,146

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 342 WINDFORD CT, WINTER GARDEN, FL 34787

    $349,900Listed 05/13/2026 4:01PM   MLS ID: O6407632

    For Sale O6407632 - 342 WINDFORD CT, WINTER GARDEN, FL 34787 17 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1194
       Built: 1996
    Monthly Fee: $40
       Tax: $4,266 (2025)
    Community: Park Ave Estates
    Single Family


    Estimated Monthly Payment: $2,313 (change assumption)
    Mortgage ($1,917) + Fees ($40) + Taxes in 2025 ($356)


    Taxes:$4,266

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 6044 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $579,820Listed 05/13/2026 2:42PM   MLS ID: G5112346

    0 Days Off yellowkey (back on 5/13/2026)

    For Sale G5112346 - 6044 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 1 photos

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

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,327 (change assumption)
    Mortgage ($3,177) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 5545 BOWMAN DR, WINTER GARDEN, FL 34787

    $485,0001 Day 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


  • 16776 BROADWATER AVE, WINTER GARDEN, FL 34787

    $1,324,0001 Day on yellowkey   MLS ID: O6407043

    For Sale O6407043 - 16776 BROADWATER AVE, WINTER GARDEN, FL 34787 71 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


  • 17055 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $580,68263 Days on yellowkey   MLS ID: G5109480

    0 Days Off yellowkey (back on 4/29/2026)

    For Sale G5109480 - 17055 HAGGERTY HOLLOW DR, 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: $3,332 (change assumption)
    Mortgage ($3,182) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12055 BRACCO ST, WINTER GARDEN, FL 34787

    $429,000155 Days on yellowkey   MLS ID: O6366675

    3 Days Off yellowkey (back on 4/21/2026)

    REDUCED by $11,000 (2.5%) on 04/14/2026

    For Sale O6366675 - 12055 BRACCO ST, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1668
       Built: 2023
    Monthly Fee: $105
       Tax: $6,881 (2024)
    Community: Highland Ridge
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,029 (change assumption)
    Mortgage ($2,351) + Fees ($105) + Taxes in 2024 ($573)


    Taxes:$6,881

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 6309 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $709,990238 Days on yellowkey   MLS ID: G5102289

    0 Days Off yellowkey (back on 9/18/2025)

    For Sale G5102289 - 6309 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2515
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,040 (change assumption)
    Mortgage ($3,890) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 16425 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787

    $460,00078 Days on yellowkey   MLS ID: O6383709

    INCREASED by $25,000 (5.7%) on 05/14/2026

    For Sale O6383709 - 16425 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787 41 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1662
       Built: 2021
    Monthly Fee: $284
       Tax: $6,683 (2024)
    Community: Hawksmoor-Ph 3
    Townhouse


    Estimated Monthly Payment: $3,361 (change assumption)
    Mortgage ($2,520) + Fees ($284) + Taxes in 2024 ($557)


    Taxes:$6,683

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None




Why Bother Searching Elsewhere for Winter Garden Homes for Sale and Other Real Estate?

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.