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Winter Garden Homes For Sale & Real Estate - 665 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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  • 17054 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $688,32434 Days on yellowkey   MLS ID: G5109477

    For Sale G5109477 - 17054 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2235
       Built: 2026
    Monthly Fee: $150

    Community: Hamlin Meadows At Hamlin
    Single Family


    Estimated Monthly Payment: $3,922 (change assumption)
    Mortgage ($3,772) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 17037 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787

    $609,61158 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


  • 15672 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $859,90082 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


  • 1005 CHASE DR, WINTER GARDEN, FL 34787

    $649,000131 Days on yellowkey   MLS ID: A4674195

    For Sale A4674195 - 1005 CHASE DR, WINTER GARDEN, FL 34787 30 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2319
       Built: 2005
    Monthly Fee: $68
       Tax: $7,086 (2024)
    Community: Island Pointe Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,215 (change assumption)
    Mortgage ($3,556) + Fees ($68) + Taxes in 2024 ($591)


    Taxes:$7,086

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 15831 GEM VIEW ST, WINTER GARDEN, FL 34787

    $399,590154 Days on yellowkey   MLS ID: O6360251

    3 Days Off yellowkey (back on 4/6/2026)

    For Sale O6360251 - 15831 GEM VIEW ST, WINTER GARDEN, FL 34787 31 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1579
       Built: 2026
    Monthly Fee: $596
       Tax: $1,614 (2025)
    Community: Del Webb Oasis
    Spa: No

    Villa


    Estimated Monthly Payment: $2,920 (change assumption)
    Mortgage ($2,189) + Fees ($596) + Taxes in 2025 ($134)


    Taxes:$1,614

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 5983 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787

    $858,014209 Days on yellowkey   MLS ID: G5102280

    For Sale G5102280 - 5983 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787 1 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2879
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,851 (change assumption)
    Mortgage ($4,701) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6345 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787

    $581,285209 Days on yellowkey   MLS ID: G5102273

    For Sale G5102273 - 6345 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787 2 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1772
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $3,335 (change assumption)
    Mortgage ($3,185) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 15075 TEA TREE DR, WINTER GARDEN, FL 34787

    $829,347211 Days on yellowkey   MLS ID: G5102184

    For Sale G5102184 - 15075 TEA TREE DR, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3038
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,694 (change assumption)
    Mortgage ($4,544) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $590,000230 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


  • 632 DHARMA CIR, WINTER GARDEN, FL 34787

    $380,00012 Days on yellowkey   MLS ID: O6396151

    For Sale O6396151 - 632 DHARMA CIR, WINTER GARDEN, FL 34787 24 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1315
       Built: 2000
    Monthly Fee: $78
       Tax: $5,780 (2025)
    Community: Daniels Crossing Ph 03
    Single Family


    Estimated Monthly Payment: $2,642 (change assumption)
    Mortgage ($2,082) + Fees ($78) + Taxes in 2025 ($482)


    Taxes:$5,780

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13836 DANIELS LANDING CIR, WINTER GARDEN, FL 34787

    $300,00025 Days on yellowkey   MLS ID: O6392319

    REDUCED by $5,000 (1.6%) on 04/12/2026

    For Sale O6392319 - 13836 DANIELS LANDING CIR, WINTER GARDEN, FL 34787 62 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1234
       Built: 2005
    Monthly Fee: $320
       Tax: $4,243 (2025)
    Community: Daniels Lndg A-J
    Townhouse


    Estimated Monthly Payment: $2,317 (change assumption)
    Mortgage ($1,644) + Fees ($320) + Taxes in 2025 ($354)


    Taxes:$4,243

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 13750 DANIELS LANDING CIR, WINTER GARDEN, FL 34787

    $319,50034 Days on yellowkey   MLS ID: O6390396

    For Sale O6390396 - 13750 DANIELS LANDING CIR, WINTER GARDEN, FL 34787 40 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1293
       Built: 2005
    Monthly Fee: $320
       Tax: $3,091 (2025)
    Community: Daniels Landing A-J
    Townhouse


    Estimated Monthly Payment: $2,328 (change assumption)
    Mortgage ($1,751) + Fees ($320) + Taxes in 2025 ($258)


    Taxes:$3,091

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 15098 WINDFLOWER ALY, WINTER GARDEN, FL 34787

    $365,00041 Days on yellowkey   MLS ID: O6386823

    For Sale O6386823 - 15098 WINDFLOWER ALY, WINTER GARDEN, FL 34787 30 photos

    Bed: 2   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1276
       Built: 2024
    Monthly Fee: $200
       Tax: $5,492 (2025)
    Community: Osprey Ranch - Phase 1
    Townhouse


    Estimated Monthly Payment: $2,658 (change assumption)
    Mortgage ($2,000) + Fees ($200) + Taxes in 2025 ($458)


    Taxes:$5,492

    Elementary School: Water Spring Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Water Spring Middle


  • 15351 HAMLIN PARK DRIVE, WINTER GARDEN, FL 34787

    $489,99096 Days on yellowkey   MLS ID: TB8462966

    3 Days Off yellowkey (back on 4/6/2026)

    For Sale TB8462966 - 15351 HAMLIN PARK DRIVE, WINTER GARDEN, FL 34787 42 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2072
       Built: 2025
    Monthly Fee: $248
       Tax: $1,371 (2025)
    Community: Parkview At Hamlin
    Townhouse


    Estimated Monthly Payment: $3,047 (change assumption)
    Mortgage ($2,685) + Fees ($248) + Taxes in 2025 ($114)


    Taxes:$1,371

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 13412 FOX GLOVE ST, WINTER GARDEN, FL 34787

    $892,90016 Days on yellowkey   MLS ID: G5110319

    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: $5,626 (change assumption)
    Mortgage ($4,892) + 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


  • 14790 TULLAMORE LOOP, WINTER GARDEN, FL 34787

    $699,99914 Days on yellowkey   MLS ID: O6395287

    For Sale O6395287 - 14790 TULLAMORE LOOP, WINTER GARDEN, FL 34787 42 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 3410
       Built: 2005
    Monthly Fee: $100
       Tax: $3,503 (2025)
    Community: Emerald Ridge
    Single Family


    Estimated Monthly Payment: $4,227 (change assumption)
    Mortgage ($3,836) + Fees ($100) + Taxes in 2025 ($292)


    Taxes:$3,503

    Elementary School: Lake Whitney Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 408 S BOYD ST, WINTER GARDEN, FL 34787

    $835,00015 Days on yellowkey   MLS ID: O6394810

    For Sale O6394810 - 408 S BOYD ST, WINTER GARDEN, FL 34787 40 photos

    Bed: 3   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2295
       Built: 1939   Tax: $2,572 (2025)
    Community: G T Smith Sub 3
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,790 (change assumption)
    Mortgage ($4,575) + Taxes in 2025 ($214)


    Taxes:$2,572

    Elementary School: Dillard Street Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 838 BETHUNE AVE, WINTER GARDEN, FL 34787

    $275,00039 Days on yellowkey   MLS ID: O6388596

    REDUCED by $2,000 (0.7%) on 04/02/2026

    For Sale O6388596 - 838 BETHUNE AVE, WINTER GARDEN, FL 34787 8 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 985
       Built: 1961   Tax: $1,340 (2025)
    Community: Overstreet Crate
    Single Family


    Estimated Monthly Payment: $1,618 (change assumption)
    Mortgage ($1,507) + Taxes in 2025 ($112)


    Taxes:$1,340

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14416 TRAVOIS WAY, WINTER GARDEN, FL 34787

    $794,00047 Days on yellowkey   MLS ID: O6382140

    For Sale O6382140 - 14416 TRAVOIS WAY, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 4.5   Gar: 3
    Liv Area Sq Ft: 3324
       Built: 2022
    Monthly Fee: $70
       Tax: $7,567 (2025)
    Community: Lake Apopka Sound
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,051 (change assumption)
    Mortgage ($4,351) + Fees ($70) + Taxes in 2025 ($631)


    Taxes:$7,567

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 9354 LAKE HICKORY NUT DR, WINTER GARDEN, FL 34787

    $1,049,00047 Days on yellowkey   MLS ID: O6385808

    REDUCED by $50,000 (4.5%) on 04/07/2026

    For Sale O6385808 - 9354 LAKE HICKORY NUT DR, WINTER GARDEN, FL 34787 47 photos

    Bed: 3   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2278
       Built: 1983   Tax: $3,375 (2025)
    Community: Hickory Lake Estates
    Single Family


    Estimated Monthly Payment: $6,029 (change assumption)
    Mortgage ($5,748) + Taxes in 2025 ($281)


    Taxes:$3,375

    Elementary School: Panther Lake Elementary

    High School: None

    Tax Year: 2025

    Middle School: Water Spring Middle




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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.