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Winter Garden Single Family Homes For Sale - 569 homes

Winter Garden Single Family Homes for Sale are located in Orange County, Florida. Find single family homes for sale in Winter Garden with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Garden single family houses.

Location: Winter Garden

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  • 9062 SONOMA COAST DR, WINTER GARDEN, FL 34787

    $785,000193 Days on yellowkey   MLS ID: O6352763

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

    For Sale O6352763 - 9062 SONOMA COAST DR, WINTER GARDEN, FL 34787 69 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2909
       Built: 2021
    Monthly Fee: $261
       Tax: $10,736 (2024)
    Community: Waterleigh Ph 3B 3C & 3D
    Single Family


    Estimated Monthly Payment: $5,457 (change assumption)
    Mortgage ($4,301) + Fees ($261) + Taxes in 2024 ($895)


    Taxes:$10,736

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 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


  • 17326 BAL HARBOUR DR, WINTER GARDEN, FL 34787

    $769,00031 Days on yellowkey   MLS ID: O6393857

    REDUCED by $5,000 (0.6%) on 04/24/2026

    For Sale O6393857 - 17326 BAL HARBOUR DR, WINTER GARDEN, FL 34787 81 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3196
       Built: 2018
    Monthly Fee: $215
       Tax: $11,210 (2025)
    Community: Waterside/Johns Lk-Ph 2B
    Single Family


    Estimated Monthly Payment: $5,363 (change assumption)
    Mortgage ($4,214) + Fees ($215) + Taxes in 2025 ($934)


    Taxes:$11,210

    Elementary School: Hamlin Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 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


  • 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


  • 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


  • 17224 OLD COUNTRY LN, WINTER GARDEN, FL 34787

    $2,099,00060 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


  • 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


  • 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


  • 4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787

    $554,990114 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

    $445,0009 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


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $590,000241 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 Single Family Homes for Sale?

Winter Garden home, townhome, and condo, villa, and other listing sale 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 single family homes for sale in Winter Garden . You can use our website to view Multiple Listing Service (MLS) data on Winter Garden single family homes. 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 single family home 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.