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Winter Garden Homes For Sale & Real Estate - 708 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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  • 5685 SURPRISE LILY DR, WINTER GARDEN, FL 34787

    $685,000184 Days on yellowkey   MLS ID: O6353593

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

    SHORT SALE O6353593 - 5685 SURPRISE LILY DR, WINTER GARDEN, FL 34787 32 photos

    Bed: 5   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2902
       Built: 2021
    Monthly Fee: $80
       Tax: $513 (2024)
    Community: Hamilton Gardens Ph 2A & 2B
    Single Family


    Estimated Monthly Payment: $3,876 (change assumption)
    Mortgage ($3,753) + Fees ($80) + Taxes in 2024 ($43)


    Taxes:$513

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Hamlin Middle


  • 14050 FAIRWAY WILLOW LN, WINTER GARDEN, FL 34787

    $749,00026 Days on yellowkey   MLS ID: O6392994

    REDUCED by $46,000 (5.8%) on 04/15/2026

    For Sale O6392994 - 14050 FAIRWAY WILLOW LN, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2027
       Built: 1989
    Monthly Fee: $322
       Tax: $4,924 (2025)
    Community: Woodbridge On Green
    Single Family


    Estimated Monthly Payment: $4,836 (change assumption)
    Mortgage ($4,104) + Fees ($322) + Taxes in 2025 ($410)


    Taxes:$4,924

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1035 CHASE DR, WINTER GARDEN, FL 34787

    $465,0009 Days on yellowkey   MLS ID: O6396474

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6396474 - 1035 CHASE DR, WINTER GARDEN, FL 34787 52 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1793
       Built: 1995
    Monthly Fee: $44
       Tax: $3,337 (2025)
    Community: Island Pointe Sub
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,870 (change assumption)
    Mortgage ($2,548) + Fees ($44) + Taxes in 2025 ($278)


    Taxes:$3,337

    Elementary School: Dillard Street Elem

    High School: Ocoee High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 14267 AVENUE OF THE GRVS, WINTER GARDEN, FL 34787

    $350,00033 Days on yellowkey   MLS ID: O6390455

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale O6390455 - 14267 AVENUE OF THE GRVS, WINTER GARDEN, FL 34787 29 photos

    Bed: 2   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1289
       Built: 2008
    Monthly Fee: $139
       Tax: $3,450 (2025)
    Community: Signature Lks-Pcl 01D Ph 01
    Townhouse


    Estimated Monthly Payment: $2,344 (change assumption)
    Mortgage ($1,918) + Fees ($139) + Taxes in 2025 ($287)


    Taxes:$3,450

    Elementary School: Independence Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Bridgewater Middle


  • 14423 WABASSO LOOP, WINTER GARDEN, FL 34787

    $899,999102 Days on yellowkey   MLS ID: O6368408

    1 Days Off yellowkey (back on 4/15/2026)

    For Sale O6368408 - 14423 WABASSO LOOP, WINTER GARDEN, FL 34787 63 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3630
       Built: 2023
    Monthly Fee: $217
       Tax: $12,742 (2024)
    Community: Tilden Place/Winter Garden
    Single Family


    Estimated Monthly Payment: $6,210 (change assumption)
    Mortgage ($4,931) + Fees ($217) + Taxes in 2024 ($1,062)


    Taxes:$12,742

    Elementary School: Keene Crossing Elementary

    High School: Windermere High School

    Tax Year: 2024

    Middle School: Bridgewater Middle


  • 13881 EASDALE ALY, WINTER GARDEN, FL 34787

    $460,000258 Days on yellowkey   MLS ID: O6332674

    REDUCED by $10,000 (2.1%) on 04/08/2026

    For Sale O6332674 - 13881 EASDALE ALY, WINTER GARDEN, FL 34787 29 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1996
       Built: 2024
    Monthly Fee: $165
       Tax: $1,535 (2024)
    Community: Westhaven/Ovation
    Townhouse


    Estimated Monthly Payment: $2,813 (change assumption)
    Mortgage ($2,520) + Fees ($165) + Taxes in 2024 ($128)


    Taxes:$1,535

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 13750 DANIELS LANDING CIR, WINTER GARDEN, FL 34787

    $319,50038 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


  • 1923 JEAN MARIE DR, WINTER GARDEN, FL 34787

    $580,00092 Days on yellowkey   MLS ID: G5106903

    0 Days Off yellowkey (back on 4/15/2026)

    For Sale G5106903 - 1923 JEAN MARIE DR, WINTER GARDEN, FL 34787 46 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2916
       Built: 2007
    Monthly Fee: $90
       Tax: $4,275 (2024)
    Community: Carriage Pointe A-I & L
    Single Family


    Estimated Monthly Payment: $3,624 (change assumption)
    Mortgage ($3,178) + Fees ($90) + Taxes in 2024 ($356)


    Taxes:$4,275

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 940 MARSH REED DR, WINTER GARDEN, FL 34787

    $799,9906 Days on yellowkey   MLS ID: O6397274

    For Sale O6397274 - 940 MARSH REED DR, WINTER GARDEN, FL 34787 60 photos

    Bed: 5   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3493
       Built: 2015
    Monthly Fee: $128
       Tax: $10,543 (2025)
    Community: Johns Lake Pointe
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,390 (change assumption)
    Mortgage ($4,383) + Fees ($128) + Taxes in 2025 ($879)


    Taxes:$10,543

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2025

    Middle School: SunRidge Middle


  • 9107 GRAND ISLAND WAY, WINTER GARDEN, FL 34787

    $505,00034 Days on yellowkey   MLS ID: O6391117

    For Sale O6391117 - 9107 GRAND ISLAND WAY, WINTER GARDEN, FL 34787 33 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2082
       Built: 2017
    Monthly Fee: $159
       Tax: $7,996 (2025)
    Community: Watermark Ph 2C
    Single Family


    Estimated Monthly Payment: $3,592 (change assumption)
    Mortgage ($2,767) + Fees ($159) + Taxes in 2025 ($666)


    Taxes:$7,996

    Elementary School: Panther Lake Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 6226 MANUSCRIPT ST, WINTER GARDEN, FL 34787

    $627,900162 Days on yellowkey   MLS ID: O6359078

    1 Days Off yellowkey (back on 4/15/2026)

    REDUCED by $8,000 (1.3%) on 04/02/2026

    For Sale O6359078 - 6226 MANUSCRIPT ST, WINTER GARDEN, FL 34787 74 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2849
       Built: 2012
    Monthly Fee: $168
       Tax: $7,134 (2024)
    Community: Signature Lakes Ph 02 A B H I J
    Single Family


    Estimated Monthly Payment: $4,203 (change assumption)
    Mortgage ($3,440) + Fees ($168) + Taxes in 2024 ($595)


    Taxes:$7,134

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1689 CRANLEIGH DR, WINTER GARDEN, FL 34787

    $888,80046 Days on yellowkey   MLS ID: O6387674

    For Sale O6387674 - 1689 CRANLEIGH DR, WINTER GARDEN, FL 34787 48 photos

    Bed: 4   Bath: 4.0   Gar: 2
    Liv Area Sq Ft: 2937
       Built: 2020
    Monthly Fee: $165
       Tax: $7,225 (2025)
    Community: Sanctuary / Twin Waters
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,637 (change assumption)
    Mortgage ($4,870) + Fees ($165) + Taxes in 2025 ($602)


    Taxes:$7,225

    Elementary School: None

    High School: West Orange High

    Tax Year: 2025

    Middle School: None


  • 626 DUFF DR, WINTER GARDEN, FL 34787

    $900,00060 Days on yellowkey   MLS ID: O6382820

    For Sale O6382820 - 626 DUFF DR, WINTER GARDEN, FL 34787 95 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3335
       Built: 2004
    Monthly Fee: $185
       Tax: $11,715 (2024)
    Community: Lake Forest Sec 10A
    Single Family


    Estimated Monthly Payment: $6,093 (change assumption)
    Mortgage ($4,931) + Fees ($185) + Taxes in 2024 ($976)


    Taxes:$11,715

    Elementary School: SunRidge Elementary

    High School: West Orange High

    Tax Year: 2024

    Middle School: SunRidge Middle


  • 1710 E BAY ST, WINTER GARDEN, FL 34787

    $249,99047 Days on yellowkey   MLS ID: O6376343

    0 Days Off yellowkey (back on 4/15/2026)

    REDUCED by $5,005 (2.0%) on 04/15/2026

    For Sale O6376343 - 1710 E BAY ST, WINTER GARDEN, FL 34787 43 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 972
       Built: 1957   Tax: $958 (2025)
    Community: Joe Louis Park First Add
    Single Family


    Estimated Monthly Payment: $1,450 (change assumption)
    Mortgage ($1,370) + Taxes in 2025 ($80)


    Taxes:$958

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787

    $339,9005 Days on yellowkey   MLS ID: O6398208

    For Sale O6398208 - 483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787 4 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1008
       Built: 1988   Tax: $2,702 (2025)
    Community: East Garden Manor Add 03
    Single Family


    Estimated Monthly Payment: $2,088 (change assumption)
    Mortgage ($1,862) + Taxes in 2025 ($225)


    Taxes:$2,702

    Elementary School: Maxey Elem

    High School: West Orange High

    Tax Year: 2025

    Middle School: Lakeview Middle


  • 11045 BOSTWICK ALY, WINTER GARDEN, FL 34787

    $590,000234 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


  • 15852 SHOREBIRD LN, WINTER GARDEN, FL 34787

    $779,000151 Days on yellowkey   MLS ID: O6361580

    REDUCED by $20,000 (2.5%) on 04/15/2026

    For Sale O6361580 - 15852 SHOREBIRD LN, WINTER GARDEN, FL 34787 71 photos

    Bed: 4   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 2766
       Built: 2019
    Monthly Fee: $385
       Tax: $10,928 (2024)
    Community: Lakeshore Preserve Ph 5
    Single Family


    Estimated Monthly Payment: $5,564 (change assumption)
    Mortgage ($4,268) + Fees ($385) + Taxes in 2024 ($911)


    Taxes:$10,928

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2024

    Middle School: Horizon West Middle School


  • 17458 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787

    $625,58010 Days on yellowkey   MLS ID: G5110835

    0 Days Off yellowkey (back on 4/9/2026)

    For Sale G5110835 - 17458 SUNSET PRAIRIE 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: $3,578 (change assumption)
    Mortgage ($3,428) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    Middle School: Hamlin Middle


  • 14200 AVALON RD #227, WINTER GARDEN, FL 34787

    $259,900231 Days on yellowkey   MLS ID: G5100807

    For Sale G5100807 - 14200 AVALON RD #227, WINTER GARDEN, FL 34787 50 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1288
       Built: 2008
    Monthly Fee: $747
       Tax: $2,851 (2024)
    Community: Palisades Condo
    Condo


    Estimated Monthly Payment: $2,409 (change assumption)
    Mortgage ($1,424) + Fees ($747) + Taxes in 2024 ($238)


    Taxes:$2,851

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 16143 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787

    $875,59583 Days on yellowkey   MLS ID: G5107301

    0 Days Off yellowkey (back on 1/26/2026)

    For Sale G5107301 - 16143 LEYLAND CYPRESS LN, WINTER GARDEN, FL 34787 1 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2740
       Built: 2026
    Monthly Fee: $150

    Community: Avalon Woods
    Single Family


    Estimated Monthly Payment: $4,948 (change assumption)
    Mortgage ($4,798) + Fees ($150) + Taxes in 2025 ($0)


    Taxes:$0

    Elementary School: Hamlin Elementary

    High School: Horizon High School

    Tax Year: 2025

    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.