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Winter Garden Homes For Sale & Real Estate - 758 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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  • 7036 BOLANZO ALY, WINTER GARDEN, FL 34787

    $475,000Listed 04/23/2026 10:13PM   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

    $550,0001 Day 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

    $825,000Listed 04/23/2026 9:47PM   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

    $479,0001 Day 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

    $225,000122 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


  • 16329 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787

    $490,000187 Days on yellowkey   MLS ID: O6353551

    For Sale O6353551 - 16329 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787 76 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2070
       Built: 2021
    Monthly Fee: $284
       Tax: $5,869 (2024)
    Community: Hawksmoor Ph 3
    Townhouse


    Estimated Monthly Payment: $3,458 (change assumption)
    Mortgage ($2,685) + Fees ($284) + Taxes in 2024 ($489)


    Taxes:$5,869

    Elementary School: None

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Water Spring Middle


  • 14766 ELLINGSWORTH LN, WINTER GARDEN, FL 34787

    $1,099,00039 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


  • 13813 PEACH ORCHARD WAY, WINTER GARDEN, FL 34787

    $850,00017 Days on yellowkey   MLS ID: O6392351

    For Sale O6392351 - 13813 PEACH ORCHARD WAY, WINTER GARDEN, FL 34787 40 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3793
       Built: 2018
    Monthly Fee: $190
       Tax: $7,249 (2025)
    Community: Orchard Pk/Stillwater Xing Ph
    Single Family


    Estimated Monthly Payment: $5,452 (change assumption)
    Mortgage ($4,657) + Fees ($190) + Taxes in 2025 ($604)


    Taxes:$7,249

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 15306 GILLIGAN CT, WINTER GARDEN, FL 34787

    $925,0007 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


  • 17224 OLD COUNTRY LN, WINTER GARDEN, FL 34787

    $2,099,00058 Days on yellowkey   MLS ID: O6384075

    REDUCED by $101,000 (4.6%) on 04/16/2026

    For Sale O6384075 - 17224 OLD COUNTRY LN, WINTER GARDEN, FL 34787 41 photos

    Bed: 6   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 3629
       Built: 1980   Tax: $9,822 (2024)
    Community: Lake Avalon Groves Rep
    Single Family


    Estimated Monthly Payment: $12,320 (change assumption)
    Mortgage ($11,501) + Taxes in 2024 ($819)


    Taxes:$9,822

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787

    $700,00028 Days on yellowkey   MLS ID: O6394429

    For Sale O6394429 - 15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787 38 photos

    Bed: 3   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 2383
       Built: 2017
    Monthly Fee: $118
       Tax: $5,959 (2025)
    Community: Highlands/Summerlake Grvs Ph 1
    Single Family


    Estimated Monthly Payment: $4,450 (change assumption)
    Mortgage ($3,836) + Fees ($118) + Taxes in 2025 ($497)


    Taxes:$5,959

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 12731 GROVEHURST AVE, WINTER GARDEN, FL 34787

    $620,00079 Days on yellowkey   MLS ID: O6379203

    REDUCED by $24,900 (3.9%) on 04/20/2026

    For Sale O6379203 - 12731 GROVEHURST AVE, WINTER GARDEN, FL 34787 59 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3474
       Built: 2006
    Monthly Fee: $111
       Tax: $8,378 (2025)
    Community: Grovehurst A-D
    Single Family


    Estimated Monthly Payment: $4,206 (change assumption)
    Mortgage ($3,397) + Fees ($111) + Taxes in 2025 ($698)


    Taxes:$8,378

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 8031 NAVEL ORANGE LN, WINTER GARDEN, FL 34787

    $675,0009 Days on yellowkey   MLS ID: O6399594

    For Sale O6399594 - 8031 NAVEL ORANGE LN, WINTER GARDEN, FL 34787 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2298
       Built: 2015
    Monthly Fee: $82
       Tax: $8,090 (2025)
    Community: Summerlake Grvs
    Single Family


    Estimated Monthly Payment: $4,455 (change assumption)
    Mortgage ($3,699) + Fees ($82) + Taxes in 2025 ($674)


    Taxes:$8,090

    Elementary School: Summerlake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 1075 CHASE DR, WINTER GARDEN, FL 34787

    $625,00053 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

    $615,0003 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

    $435,00034 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

    $645,900553 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


  • 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787

    $554,990112 Days on yellowkey   MLS ID: O6370363

    For Sale O6370363 - 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787 44 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2459
       Built: 2021
    Monthly Fee: $281
       Tax: $8,150 (2024)
    Community: Enclave/Hamlin
    Single Family


    Estimated Monthly Payment: $4,001 (change assumption)
    Mortgage ($3,041) + Fees ($281) + Taxes in 2024 ($679)


    Taxes:$8,150

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 328 BAYSIDE AVE, WINTER GARDEN, FL 34787

    $445,0007 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


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $590,000239 Days on yellowkey   MLS ID: O6337436

    For Sale O6337436 - 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787 89 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2292
       Built: 2023
    Monthly Fee: $245
       Tax: $9,031 (2024)
    Community: Waterleigh Ph 4A
    Single Family


    Estimated Monthly Payment: $4,230 (change assumption)
    Mortgage ($3,233) + Fees ($245) + Taxes in 2024 ($753)


    Taxes:$9,031

    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.