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Winter Garden Homes For Sale & Real Estate - 764 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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  • 5531 CYPRESS HILL RD, WINTER GARDEN, FL 34787

    $610,00087 Days on yellowkey   MLS ID: O6378167

    1 Days Off yellowkey (back on 4/24/2026)

    For Sale O6378167 - 5531 CYPRESS HILL RD, WINTER GARDEN, FL 34787 62 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2204
       Built: 2016
    Monthly Fee: $188
       Tax: $8,644 (2025)
    Community: Orchard Hills Ph 2 Signature Lakes
    Single Family


    Estimated Monthly Payment: $4,251 (change assumption)
    Mortgage ($3,342) + Fees ($188) + Taxes in 2025 ($720)


    Taxes:$8,644

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787

    $470,00032 Days on yellowkey   MLS ID: O6393056

    REDUCED by $4,900 (1.0%) on 04/15/2026

    For Sale O6393056 - 16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1705
       Built: 2020
    Monthly Fee: $257
       Tax: $4,805 (2025)
    Community: Waterleigh
    Single Family


    Estimated Monthly Payment: $3,233 (change assumption)
    Mortgage ($2,575) + Fees ($257) + Taxes in 2025 ($400)


    Taxes:$4,805

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 5413 NEW INDEPENDENCE PKWY, WINTER GARDEN, FL 34787

    $488,00025 Days on yellowkey   MLS ID: S5146601

    For Sale S5146601 - 5413 NEW INDEPENDENCE PKWY, WINTER GARDEN, FL 34787 28 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2131
       Built: 2012
    Monthly Fee: $264
       Tax: $5,449 (2025)
    Community: Signature Lakes Ph 02 A B H I J
    Townhouse


    Estimated Monthly Payment: $3,392 (change assumption)
    Mortgage ($2,674) + Fees ($264) + Taxes in 2025 ($454)


    Taxes:$5,449

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2217 RICKOVER PL, WINTER GARDEN, FL 34787

    $1,059,00047 Days on yellowkey   MLS ID: O6388647

    REDUCED by $16,000 (1.5%) on 04/20/2026

    For Sale O6388647 - 2217 RICKOVER PL, WINTER GARDEN, FL 34787 49 photos

    Bed: 5   Bath: 5.0   Gar: 3
    Liv Area Sq Ft: 4324
       Built: 2008
    Monthly Fee: $260
       Tax: $8,547 (2025)
    Community: Bronsons Lndgs F & M
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $6,775 (change assumption)
    Mortgage ($5,803) + Fees ($260) + Taxes in 2025 ($712)


    Taxes:$8,547

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 306 DANIELS POINTE DR, WINTER GARDEN, FL 34787

    $310,000107 Days on yellowkey   MLS ID: O6371413

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

    For Sale O6371413 - 306 DANIELS POINTE DR, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1326
       Built: 1999
    Monthly Fee: $78
       Tax: $4,120 (2024)
    Community: Daniels Crossing
    Single Family


    Estimated Monthly Payment: $2,120 (change assumption)
    Mortgage ($1,699) + Fees ($78) + Taxes in 2024 ($343)


    Taxes:$4,120

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


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

    $2,000,00097 Days on yellowkey   MLS ID: O6371664

    REDUCED by $45,000 (2.2%) on 04/21/2026

    For Sale O6371664 - 15532 AVENUE OF THE ARBORS, WINTER GARDEN, FL 34787 54 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3837
       Built: 2016   Tax: $16,503 (2024)
    Community: Independence
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $12,334 (change assumption)
    Mortgage ($10,959) + Taxes in 2024 ($1,375)


    Taxes:$16,503

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 7526 SPRING VALLEY ST, WINTER GARDEN, FL 34787

    $676,2453 Days on yellowkey   MLS ID: G5111448

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

    For Sale G5111448 - 7526 SPRING VALLEY ST, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2680
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,855 (change assumption)
    Mortgage ($3,705) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 7036 BOLANZO ALY, WINTER GARDEN, FL 34787

    $475,0003 Days on yellowkey   MLS ID: O6401429

    For Sale O6401429 - 7036 BOLANZO ALY, WINTER GARDEN, FL 34787 20 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 1920
       Built: 2024
    Monthly Fee: $188
       Tax: $6,919 (2025)
    Community: Mezzano
    Townhouse


    Estimated Monthly Payment: $3,367 (change assumption)
    Mortgage ($2,603) + Fees ($188) + Taxes in 2025 ($577)


    Taxes:$6,919

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 776 RAINFALL DR, WINTER GARDEN, FL 34787

    $550,0003 Days on yellowkey   MLS ID: O6400904

    For Sale O6400904 - 776 RAINFALL DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2238
       Built: 2007
    Monthly Fee: $92
       Tax: $7,884 (2025)
    Community: Black Lake Park Ph 02
    Single Family


    Estimated Monthly Payment: $3,763 (change assumption)
    Mortgage ($3,014) + Fees ($92) + Taxes in 2025 ($657)


    Taxes:$7,884

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 3430 TURNINGWIND LN, WINTER GARDEN, FL 34787

    $825,0003 Days on yellowkey   MLS ID: G5111151

    For Sale G5111151 - 3430 TURNINGWIND LN, WINTER GARDEN, FL 34787 56 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3358
       Built: 2002
    Monthly Fee: $115
       Tax: $6,001 (2024)
    Community: Windward Cay 48 125
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,135 (change assumption)
    Mortgage ($4,520) + Fees ($115) + Taxes in 2024 ($500)


    Taxes:$6,001

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 837 GRANDE REGAL PT, WINTER GARDEN, FL 34787

    $479,0003 Days on yellowkey   MLS ID: O6400571

    For Sale O6400571 - 837 GRANDE REGAL PT, WINTER GARDEN, FL 34787 28 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1874
       Built: 2002
    Monthly Fee: $60
       Tax: $1,662 (2025)
    Community: Regal Pointe Ph 02 47/133
    Single Family


    Estimated Monthly Payment: $2,823 (change assumption)
    Mortgage ($2,625) + Fees ($60) + Taxes in 2025 ($138)


    Taxes:$1,662

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 14501 GROVE RESORT AVE #2534, WINTER GARDEN, FL 34787

    $225,000124 Days on yellowkey   MLS ID: O6369252

    REDUCED by $10,000 (4.3%) on 04/23/2026

    For Sale O6369252 - 14501 GROVE RESORT AVE #2534, WINTER GARDEN, FL 34787 22 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1396
       Built: 2018   Tax: $8,154 (2024)
    Community: Grove Residence & Spa Hotel Condo Ii
    Condo


    Estimated Monthly Payment: $1,912 (change assumption)
    Mortgage ($1,233) + Taxes in 2024 ($680)


    Taxes:$8,154

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 14766 ELLINGSWORTH LN, WINTER GARDEN, FL 34787

    $1,099,00041 Days on yellowkey   MLS ID: O6390518

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

    For Sale O6390518 - 14766 ELLINGSWORTH LN, WINTER GARDEN, FL 34787 42 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 4661
       Built: 2018
    Monthly Fee: $210
       Tax: $14,115 (2025)
    Community: Oxford Chase
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,408 (change assumption)
    Mortgage ($6,022) + Fees ($210) + Taxes in 2025 ($1,176)


    Taxes:$14,115

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15306 GILLIGAN CT, WINTER GARDEN, FL 34787

    $925,0009 Days on yellowkey   MLS ID: O6399653

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

    For Sale O6399653 - 15306 GILLIGAN CT, WINTER GARDEN, FL 34787 49 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3127
       Built: 2020
    Monthly Fee: $102
       Tax: $8,308 (2025)
    Community: Winding Bay Ph 1B
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,863 (change assumption)
    Mortgage ($5,068) + Fees ($102) + Taxes in 2025 ($692)


    Taxes:$8,308

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 1075 CHASE DR, WINTER GARDEN, FL 34787

    $625,00055 Days on yellowkey   MLS ID: O6386607

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

    For Sale O6386607 - 1075 CHASE DR, WINTER GARDEN, FL 34787 63 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2125
       Built: 2015
    Monthly Fee: $41
       Tax: $2,734 (2024)
    Community: Island Pointe Sub
    Single Family


    Estimated Monthly Payment: $3,693 (change assumption)
    Mortgage ($3,425) + Fees ($41) + Taxes in 2024 ($228)


    Taxes:$2,734

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 17005 ARROWHEAD BLVD, WINTER GARDEN, FL 34787

    $615,0005 Days on yellowkey   MLS ID: O6401039

    For Sale O6401039 - 17005 ARROWHEAD BLVD, WINTER GARDEN, FL 34787 53 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1655
       Built: 1983   Tax: $5,400 (2025)
    Community: Arrowhead Lakes
    Single Family


    Estimated Monthly Payment: $3,820 (change assumption)
    Mortgage ($3,370) + Taxes in 2025 ($450)


    Taxes:$5,400

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 15659 JUNGLE ALY, WINTER GARDEN, FL 34787

    $435,00036 Days on yellowkey   MLS ID: S5143684

    INCREASED by $75,000 (20.8%) on 04/23/2026

    For Sale S5143684 - 15659 JUNGLE ALY, WINTER GARDEN, FL 34787 16 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1732
       Built: 2021
    Monthly Fee: $203
       Tax: $6,265 (2024)
    Community: Winding Bay Ph 2
    Townhouse


    Estimated Monthly Payment: $3,109 (change assumption)
    Mortgage ($2,384) + Fees ($203) + Taxes in 2024 ($522)


    Taxes:$6,265

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787

    $645,900555 Days on yellowkey   MLS ID: O6250356

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

    REDUCED by $3,900 (0.6%) on 04/17/2026

    For Sale O6250356 - 15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3359
       Built: 2001
    Monthly Fee: $233
       Tax: $8,538 (2023)
    Community: Stoneybrook West
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,484 (change assumption)
    Mortgage ($3,539) + Fees ($233) + Taxes in 2023 ($712)


    Taxes:$8,538

    Elementary School: Whispering Oak Elem

    High School: West Orange High

    Tax Year: 2023

    Middle School: SunRidge Middle


  • 328 BAYSIDE AVE, WINTER GARDEN, FL 34787

    $445,0009 Days on yellowkey   MLS ID: O6396654

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

    For Sale O6396654 - 328 BAYSIDE AVE, WINTER GARDEN, FL 34787 26 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1235
       Built: 1986
    Monthly Fee: $7
       Tax: $5,354 (2025)
    Community: Kings Bay
    Single Family


    Estimated Monthly Payment: $2,891 (change assumption)
    Mortgage ($2,438) + Fees ($7) + Taxes in 2025 ($446)


    Taxes:$5,354

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14501 GROVE RESORT AVE #2438, WINTER GARDEN, FL 34787

    $224,000346 Days on yellowkey   MLS ID: O6306977

    For Sale O6306977 - 14501 GROVE RESORT AVE #2438, WINTER GARDEN, FL 34787 37 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1396
       Built: 2018   Tax: $8,035 (2024)
    Community: Grove Residence Y Spa Hotel Condo Ii
    Condo


    Estimated Monthly Payment: $1,897 (change assumption)
    Mortgage ($1,227) + Taxes in 2024 ($670)


    Taxes:$8,035

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring 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.