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$535,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,774 Sq. Ft.
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Discover this beautifully maintained 4-bedroom, 2-bath home nestled in the heart of historic Winter Garden. Featuring a spacious open floor plan with approximately 1,774 square feet of living space, this home offers generous living and dining areas ideal for everyday living and entertaining. The kitchen provides ample cabinet and counter space and opens seamlessly to the main living area. The split-bedroom layout offers privacy for the primary suite, while the additional bedrooms provide flexibility for family, guests, or a home office. Enjoy the convenience of an attached two-car garage, central air conditioning, and a large fenced backyard with plenty of room for outdoor entertaining, gardening, or pets. Located just minutes from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning restaurants, boutique shopping, the West Orange Trail, the Winter Garden Farmers Market, and numerous community events throughout the year. Conveniently located near SR-429, the Florida Turnpike, Downtown Orlando, major employers, and world-renowned theme parks. No HOA makes this an outstanding opportunity for homeowners and investors alike.

Full Property Details for 300 S Woodland St

General

  • Price: $535,000
  • Taxes: $6,538 (2025)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6431568
  • Updated: 9/23/2026
  • Added to Site: 54 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 4
  • Interior Features: Ceiling Fan(s)
  • Appliances: Dishwasher, Microwave, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Carpet, Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room

Exterior

  • Exterior Features: Sidewalk, Sliding Doors

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: VININGS ADD WINTER GARDEN
  • Driving Directions: From FL-429, take Exit 24 for Plant Street (FL-438) and head east toward Downtown Winter Garden. Continue on Plant Street, turn right onto South Woodland Street, and the property will be on the left
  • Direction Faces: East

School Information

  • Elementary School: Dillard Street Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Electricity Connected, Sewer Connected, Water Connected

Structural Information

  • Exterior Const.: Stucco
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,774
  • Sq. Ft. Source: Public Records
  • Year Built: 2003

Lot Features

  • Lot Size (Acres): 0.22
  • Lot Size (Sq. Ft.): 9,640
  • Lot Size: 9640
  • Street/Road Desc.: Paved

Financial Considerations

  • Tax Amount: $6,538.81
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: FRIES SURVEY OF WINTER GARDEN VININGS ADDITION E/16 N 31.66 FT OF LOT 120 & S 31.66 FT OF LOT 123
  • Flood Zone Info: X
  • APN: 232227890001201
  • Property ID: 232227890001201
  • Block/Lot/Section: 1

Listed by Houwzer Inc

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Listing agent

— 300 S Woodland St —

  • Houwzer Inc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 300 S Woodland St

School District:Orange County School District
NameGradesDistance
Dillard Street Elementary School
311 North Dillard Street, Winter Garden, FL 34787
PK-50.6 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-81.2 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-121.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 300 S Woodland St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/10/2026
Price Reduced
$535,000
-1.83%
MLS
8/20/2026
Listed
$545,000
228.51%
MLS
12/12/2003
Sold
$165,900
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 300 S Woodland St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,539
8%
$376,729
-21%
2024
$6,051
2%
$479,104
-6%
2023
$5,957
56%
$509,432
117%
2021
$3,814
-7%
$234,463
-9%
2022
$4,109
8%
$257,311
11%
2021
$3,814
-5%
$230,931
-4%
2019
$3,994
2%
$239,740
3%
2018
$3,920
17%
$232,425
6%
2017
$3,350
17%
$220,193
32%
2016
$2,861
8%
$167,403
11%
2015
$2,655
53%
$151,038
12%
2014
$1,732
3%
$135,140
1%
2013
$1,685
—
$133,143
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Houwzer Inc

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300 S Woodland Street, Winter Garden, FL 34787 (MLS# O6431568) is a Single Family property with 3 bedrooms and 2 full bathrooms. 300 S Woodland Street is currently listed for $535,000 and was received on August 20, 2026. Want to learn more about 300 S Woodland Street? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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