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Winter Garden Homes For Sale & Real Estate - 809 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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  • 14501 GROVE RESORT AVE #3109, WINTER GARDEN, FL 34787

    $314,90068 Days on yellowkey   MLS ID: O6386655

    For Sale O6386655 - 14501 GROVE RESORT AVE #3109, WINTER GARDEN, FL 34787 62 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1434
       Built: 2018
    Monthly Fee: $1,025
       Tax: $4,503 (2025)
    Community: Grove Residence & Spa Hotel Condo 2
    Spa: Yes

    Condo


    Estimated Monthly Payment: $3,126 (change assumption)
    Mortgage ($1,725) + Fees ($1,025) + Taxes in 2025 ($375)


    Taxes:$4,503

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13946 TITLE WAY, WINTER GARDEN, FL 34787

    $438,00081 Days on yellowkey   MLS ID: O6384098

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

    For Sale O6384098 - 13946 TITLE WAY, WINTER GARDEN, FL 34787 44 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1992
       Built: 2023
    Monthly Fee: $270
       Tax: $6,667 (2024)
    Community: Storey Grove Ph 4
    Townhouse


    Estimated Monthly Payment: $3,226 (change assumption)
    Mortgage ($2,400) + Fees ($270) + Taxes in 2024 ($556)


    Taxes:$6,667

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14501 GROVE RESORT AVE #2522, WINTER GARDEN, FL 34787

    $180,000434 Days on yellowkey   MLS ID: O6285998

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

    For Sale O6285998 - 14501 GROVE RESORT AVE #2522, WINTER GARDEN, FL 34787 36 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1265
       Built: 2018
    Monthly Fee: $793
       Tax: $7,635 (2024)
    Community: Grove Resort And Spa Hotel Condominium
    Condo


    Estimated Monthly Payment: $2,416 (change assumption)
    Mortgage ($986) + Fees ($793) + Taxes in 2024 ($636)


    Taxes:$7,635

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16467 OLIVE HILL DR, WINTER GARDEN, FL 34787

    $599,900607 Days on yellowkey   MLS ID: O6240446

    2 Days Off yellowkey (back on 6/27/2025)

    For Sale O6240446 - 16467 OLIVE HILL DR, WINTER GARDEN, FL 34787 67 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2355
       Built: 2019
    Monthly Fee: $115
       Tax: $7,249 (2023)
    Community: Hawksmoor Ph 1
    Single Family


    Estimated Monthly Payment: $4,006 (change assumption)
    Mortgage ($3,287) + Fees ($115) + Taxes in 2023 ($604)


    Taxes:$7,249

    Elementary School: None

    High School: None

    Tax Year: 2023

    Middle School: None


  • 205 SURPRISE DR, WINTER GARDEN, FL 34787

    $1,200,000158 Days on yellowkey   MLS ID: O6365188

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

    For Sale O6365188 - 205 SURPRISE DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2171
       Built: 1950   Tax: $3,406 (2024)
    Community: Winter Garden Shores Rep
    Single Family


    Estimated Monthly Payment: $6,859 (change assumption)
    Mortgage ($6,575) + Taxes in 2024 ($284)


    Taxes:$3,406

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2024

    Middle School: Lakeview Middle


  • 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $580,00082 Days on yellowkey   MLS ID: O6383534

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

    For Sale O6383534 - 15408 LEBEAU LOOP, WINTER GARDEN, FL 34787 43 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2415
       Built: 2022
    Monthly Fee: $101
       Tax: $7,566 (2024)
    Community: Winding Bay Ph 3
    Single Family


    Estimated Monthly Payment: $3,909 (change assumption)
    Mortgage ($3,178) + Fees ($101) + Taxes in 2024 ($630)


    Taxes:$7,566

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15306 LEBEAU LOOP, WINTER GARDEN, FL 34787

    $568,00080 Days on yellowkey   MLS ID: O6384014

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

    For Sale O6384014 - 15306 LEBEAU LOOP, WINTER GARDEN, FL 34787 52 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2482
       Built: 2021
    Monthly Fee: $101
       Tax: $6,339 (2024)
    Community: Winding Bay Ph 3
    Single Family


    Estimated Monthly Payment: $3,741 (change assumption)
    Mortgage ($3,112) + Fees ($101) + Taxes in 2024 ($528)


    Taxes:$6,339

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787

    $634,99019 Days on yellowkey   MLS ID: O6401373

    For Sale O6401373 - 16834 HOBE SOUND CT, WINTER GARDEN, FL 34787 18 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2494
       Built: 2026
    Monthly Fee: $190
       Tax: $1,989 (2025)
    Community: Waterleigh
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,835 (change assumption)
    Mortgage ($3,479) + Fees ($190) + Taxes in 2025 ($166)


    Taxes:$1,989

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13837 LANYARD WAY, WINTER GARDEN, FL 34787

    $490,00063 Days on yellowkey   MLS ID: O6388993

    REDUCED by $5,000 (1.0%) on 04/22/2026

    For Sale O6388993 - 13837 LANYARD WAY, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1994
       Built: 2023
    Monthly Fee: $225
       Tax: $7,647 (2024)
    Community: Encore/Ovation Ph 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,547 (change assumption)
    Mortgage ($2,685) + Fees ($225) + Taxes in 2024 ($637)


    Taxes:$7,647

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14989 APOLLO BOND DR, WINTER GARDEN, FL 34787

    $415,00086 Days on yellowkey   MLS ID: O6378685

    For Sale O6378685 - 14989 APOLLO BOND DR, WINTER GARDEN, FL 34787 35 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1789
       Built: 2019
    Monthly Fee: $241
       Tax: $3,914 (2024)
    Community: Watermark Ph 3
    Townhouse


    Estimated Monthly Payment: $2,841 (change assumption)
    Mortgage ($2,274) + Fees ($241) + Taxes in 2024 ($326)


    Taxes:$3,914

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 64 N PARK AVE, WINTER GARDEN, FL 34787

    $1,095,00076 Days on yellowkey   MLS ID: O6385285

    REDUCED by $54,000 (4.7%) on 04/22/2026

    For Sale O6385285 - 64 N PARK AVE, WINTER GARDEN, FL 34787 38 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2225
       Built: 2023
    Monthly Fee: $325
       Tax: $15,104 (2025)
    Community: 30 North Park
    Townhouse


    Estimated Monthly Payment: $7,584 (change assumption)
    Mortgage ($6,000) + Fees ($325) + Taxes in 2025 ($1,259)


    Taxes:$15,104

    Elementary School: Tildenville Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 7343 TWILIGHT BAY DR, WINTER GARDEN, FL 34787

    $599,99927 Days on yellowkey   MLS ID: S5147747

    0 Days Off yellowkey (back on 4/22/2026)

    For Sale S5147747 - 7343 TWILIGHT BAY DR, WINTER GARDEN, FL 34787 20 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1975
       Built: 2017
    Monthly Fee: $249
       Tax: $5,164 (2025)
    Community: Lakeview Pointe/Horizon West P
    Single Family


    Estimated Monthly Payment: $3,967 (change assumption)
    Mortgage ($3,288) + Fees ($249) + Taxes in 2025 ($430)


    Taxes:$5,164

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14971 APOLLO BOND DR, WINTER GARDEN, FL 34787

    $414,900264 Days on yellowkey   MLS ID: O6337468

    For Sale O6337468 - 14971 APOLLO BOND DR, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1655
       Built: 2019
    Monthly Fee: $253
       Tax: $6,577 (2025)
    Community: Watermark Ph 3
    Townhouse


    Estimated Monthly Payment: $3,074 (change assumption)
    Mortgage ($2,273) + Fees ($253) + Taxes in 2025 ($548)


    Taxes:$6,577

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 2621 SHIREHALL LN, WINTER GARDEN, FL 34787

    $475,00066 Days on yellowkey   MLS ID: O6386585

    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


  • 650 SETTING SUN DR, WINTER GARDEN, FL 34787

    $740,00054 Days on yellowkey   MLS ID: O6390644

    1 Days Off yellowkey (back on 4/22/2026)

    For Sale O6390644 - 650 SETTING SUN DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3605
       Built: 2006
    Monthly Fee: $123
       Tax: $9,067 (2025)
    Community: Black Lake Park Ph 01
    Single Family


    Estimated Monthly Payment: $4,933 (change assumption)
    Mortgage ($4,055) + Fees ($123) + Taxes in 2025 ($756)


    Taxes:$9,067

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 276 SUMMER PINE ST, WINTER GARDEN, FL 34787

    $875,00079 Days on yellowkey   MLS ID: O6384565

    REDUCED by $5,000 (0.6%) on 04/22/2026

    For Sale O6384565 - 276 SUMMER PINE ST, WINTER GARDEN, FL 34787 25 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3147
       Built: 2025
    Monthly Fee: $240
       Tax: $1,914 (2024)
    Community: Winter Grove
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,194 (change assumption)
    Mortgage ($4,794) + Fees ($240) + Taxes in 2024 ($160)


    Taxes:$1,914

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $609,61184 Days on yellowkey   MLS ID: G5108288

    0 Days Off yellowkey (back on 4/7/2026)

    For Sale G5108288 - 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 2 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2520
       Built: 2026
    Monthly Fee: $122

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,462 (change assumption)
    Mortgage ($3,340) + Fees ($122) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14014 LANYARD WAY, WINTER GARDEN, FL 34787

    $778,20620 Days on yellowkey   MLS ID: G5111358

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

    For Sale G5111358 - 14014 LANYARD WAY, WINTER GARDEN, FL 34787 3 photos

    Bed: 5   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3076
       Built: 2026
    Monthly Fee: $160

    Community: Serenade At Ovation
    Single Family


    Estimated Monthly Payment: $4,424 (change assumption)
    Mortgage ($4,264) + Fees ($160) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: None


  • 12036 HOLYSTONE ST, WINTER GARDEN, FL 34787

    $455,000158 Days on yellowkey   MLS ID: S5139531

    For Sale S5139531 - 12036 HOLYSTONE ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1817
       Built: 2022
    Monthly Fee: $256
       Tax: $6,116 (2024)
    Community: Waterleigh Ph 4A
    Townhouse


    Estimated Monthly Payment: $3,259 (change assumption)
    Mortgage ($2,493) + Fees ($256) + Taxes in 2024 ($510)


    Taxes:$6,116

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14645 SCOTT KEY DR, WINTER GARDEN, FL 34787

    $890,000115 Days on yellowkey   MLS ID: G5106818

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

    For Sale G5106818 - 14645 SCOTT KEY DR, WINTER GARDEN, FL 34787 72 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3427
       Built: 2016   Tax: $10,465 (2024)
    Community: Watermark Ph 1B
    Single Family


    Estimated Monthly Payment: $5,749 (change assumption)
    Mortgage ($4,877) + Taxes in 2024 ($872)


    Taxes:$10,465

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle




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.