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Winter Garden Homes For Sale & Real Estate - 947 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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  • 170 WINDTREE LN, WINTER GARDEN, FL 34787

    $204,90040 Days on yellowkey   MLS ID: S5150050

    For Sale S5150050 - 170 WINDTREE LN, WINTER GARDEN, FL 34787 14 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 918
       Built: 1985   Tax: $2,782 (2025)
    Community: Windtree Gardens Condo Ph 06
    Condo


    Estimated Monthly Payment: $1,355 (change assumption)
    Mortgage ($1,123) + Taxes in 2025 ($232)


    Taxes:$2,782

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787

    $630,00058 Days on yellowkey   MLS ID: O6403063

    REDUCED by $5,500 (0.9%) on 05/19/2026

    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: $4,410 (change assumption)
    Mortgage ($3,452) + Fees ($215) + Taxes in 2025 ($744)


    Taxes:$8,922

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3518 TURNINGWIND LN, WINTER GARDEN, FL 34787

    $810,00071 Days on yellowkey   MLS ID: S5147067

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

    REDUCED by $15,000 (1.8%) on 04/30/2026

    For Sale S5147067 - 3518 TURNINGWIND LN, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2744
       Built: 2003
    Monthly Fee: $115
       Tax: $10,313 (2025)
    Community: Windward Cay 48 125
    Single Family


    Estimated Monthly Payment: $5,413 (change assumption)
    Mortgage ($4,438) + Fees ($115) + Taxes in 2025 ($859)


    Taxes:$10,313

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14501 GROVE RESORT AVE #3611, WINTER GARDEN, FL 34787

    $220,000118 Days on yellowkey   MLS ID: TB8481342

    For Sale TB8481342 - 14501 GROVE RESORT AVE #3611, WINTER GARDEN, FL 34787 1 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1396
       Built: 2018
    Monthly Fee: $998
       Tax: $7,177 (2024)
    Community: Grove Residence & Spa Hotel Condo 3
    Condo


    Estimated Monthly Payment: $2,802 (change assumption)
    Mortgage ($1,205) + Fees ($998) + Taxes in 2024 ($598)


    Taxes:$7,177

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787

    $874,99084 Days on yellowkey   MLS ID: O6395693

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

    For Sale O6395693 - 419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787 35 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2650
       Built: 2026
    Monthly Fee: $240
       Tax: $1,955 (2025)
    Community: Winter Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,197 (change assumption)
    Mortgage ($4,794) + Fees ($240) + Taxes in 2025 ($163)


    Taxes:$1,955

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 11265 HOLLOW BAY DR, WINTER GARDEN, FL 34787

    $870,33150 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

    $559,990168 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


  • 1692 HIGHBANKS CIR, WINTER GARDEN, FL 34787

    $760,00038 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


  • 17106 BEACHGRASS ALY, WINTER GARDEN, FL 34787

    $799,99038 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


  • 6102 WHISPERING GLEN, WINTER GARDEN, FL 34787

    $576,89043 Days on yellowkey   MLS ID: O6407803

    3 Days Off yellowkey (back on 5/18/2026)

    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: $152
       Tax: $1,372 (2024)
    Community: Silverleaf Oaks
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,427 (change assumption)
    Mortgage ($3,161) + Fees ($152) + Taxes in 2024 ($114)


    Taxes:$1,372

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 17013 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $455,75239 Days on yellowkey   MLS ID: G5112484

    0 Days Off yellowkey (back on 5/17/2026)

    For Sale G5112484 - 17013 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 5 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1772
       Built: 2026
    Monthly Fee: $225

    Community: Hamlin Meadows
    Townhouse


    Estimated Monthly Payment: $2,722 (change assumption)
    Mortgage ($2,497) + Fees ($225) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15111 DRIFTWOOD BEND ST, WINTER GARDEN, FL 34787

    $628,00039 Days on yellowkey   MLS ID: O6408574

    For Sale O6408574 - 15111 DRIFTWOOD BEND ST, WINTER GARDEN, FL 34787 57 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2573
       Built: 2017
    Monthly Fee: $195
       Tax: $9,620 (2025)
    Community: Signature Lakes Ph 3B-4, 3B-5
    Single Family


    Estimated Monthly Payment: $4,438 (change assumption)
    Mortgage ($3,441) + Fees ($195) + Taxes in 2025 ($802)


    Taxes:$9,620

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 16396 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787

    $474,99076 Days on yellowkey   MLS ID: O6396532

    REDUCED by $10,000 (2.1%) on 04/30/2026

    For Sale O6396532 - 16396 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2021
    Monthly Fee: $286
       Tax: $7,102 (2025)
    Community: Hawksmoor Ph 3
    Townhouse


    Estimated Monthly Payment: $3,480 (change assumption)
    Mortgage ($2,603) + Fees ($286) + Taxes in 2025 ($592)


    Taxes:$7,102

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15672 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $859,900153 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


  • 13412 FOX GLOVE ST, WINTER GARDEN, FL 34787

    $849,90087 Days on yellowkey   MLS ID: G5110319

    REDUCED by $43,000 (4.8%) on 04/16/2026

    For Sale G5110319 - 13412 FOX GLOVE ST, WINTER GARDEN, FL 34787 31 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3954
       Built: 2005
    Monthly Fee: $243
       Tax: $5,889 (2025)
    Community: Stoneybrook West Un 06
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,391 (change assumption)
    Mortgage ($4,657) + Fees ($243) + Taxes in 2025 ($491)


    Taxes:$5,889

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 5138 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787

    $745,00062 Days on yellowkey   MLS ID: O6401856

    0 Days Off yellowkey (back on 5/17/2026)

    For Sale O6401856 - 5138 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787 47 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2468
       Built: 2023
    Monthly Fee: $165
       Tax: $9,407 (2025)
    Community: Silverleaf Reserve/Hamlin Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,031 (change assumption)
    Mortgage ($4,082) + Fees ($165) + Taxes in 2025 ($784)


    Taxes:$9,407

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14501 GROVE RESORT AVE #1439, WINTER GARDEN, FL 34787

    $180,00039 Days on yellowkey   MLS ID: O6407410

    For Sale O6407410 - 14501 GROVE RESORT AVE #1439, WINTER GARDEN, FL 34787 39 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1265
       Built: 2009
    Monthly Fee: $904
       Tax: $6,553 (2025)
    Community: Grove Resort And Spa Hotel Condominium
    Spa: Yes

    Condo


    Estimated Monthly Payment: $2,436 (change assumption)
    Mortgage ($986) + Fees ($904) + Taxes in 2025 ($546)


    Taxes:$6,553

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2230 ROMANUM DR, WINTER GARDEN, FL 34787

    $565,000105 Days on yellowkey   MLS ID: O6389947

    1 Days Off yellowkey (back on 5/17/2026)

    For Sale O6389947 - 2230 ROMANUM DR, WINTER GARDEN, FL 34787 29 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2562
       Built: 2014
    Monthly Fee: $207
       Tax: $8,425 (2025)
    Community: Alexander Rdg
    Single Family


    Estimated Monthly Payment: $4,005 (change assumption)
    Mortgage ($3,096) + Fees ($207) + Taxes in 2025 ($702)


    Taxes:$8,425

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 9549 BOLERO RD, WINTER GARDEN, FL 34787

    $997,000296 Days on yellowkey   MLS ID: O6340193

    2 Days Off yellowkey (back on 5/17/2026)

    For Sale O6340193 - 9549 BOLERO RD, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3910
       Built: 2021
    Monthly Fee: $271
       Tax: $13,484 (2024)
    Community: Waterleigh Ph 3A
    Single Family


    Estimated Monthly Payment: $6,858 (change assumption)
    Mortgage ($5,463) + Fees ($271) + Taxes in 2024 ($1,124)


    Taxes:$13,484

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 10103 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787

    $970,00040 Days on yellowkey   MLS ID: O6407394

    For Sale O6407394 - 10103 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787 14 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4305
       Built: 2019
    Monthly Fee: $159
       Tax: $13,406 (2025)
    Community: Watermark Ph 4
    Single Family


    Estimated Monthly Payment: $6,591 (change assumption)
    Mortgage ($5,315) + Fees ($159) + Taxes in 2025 ($1,117)


    Taxes:$13,406

    Elementary School: None

    High School: None

    Tax Year: 2025

    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.