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$225,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,526 Sq. Ft.
  • Updated 8 hours ago
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This two-story home offers classic charm with a covered front porch, fenced backyard, and upper-level balcony. Located just minutes from downtown, 369 Charles Street features a recently updated kitchen with modern cabinetry, granite countertops, and stainless steel appliances. The main level features updated flooring, while the upstairs level provides access to a private, covered balcony. Two full bathrooms have been recently renovated with a tiled walk-in shower and new fixtures. Alley access and a spacious backyard offer potential for off-street parking or additional improvements. Sold as-is. Ideal for investors or buyers seeking to complete mostly cosmetic work and build equity. The property was built before 1978, and Lead-Based Paint Potentially Exists.

Full Property Details for 369 Charles St

General

  • Price: $225,000
  • Taxes: $2,005 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAWI2008716
  • Updated: 1/15/2026
  • Added to Site: 185 day(s) ago

Interior

  • Number of Rooms: 8
  • Rooms/Areas: Living Room, Dining Room, Bedroom 2, Bedroom 3, Kitchen, Bedroom 1, Bathroom 1, Bathroom 2
  • Interior Features: Attic, Window Treatments, Other, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Combination Dining/Living, Floor Plan - Open
  • Flooring: Ceramic Tile, Laminated

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 1
  • Main - Full Baths: 1

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 3

Other Rooms

  • Laundry: Main Floor

Additional Information

  • Security/Safety: Main Entrance Lock, Smoke Detector

Exterior

  • Exterior Features: Outbuilding(s), Sidewalks, Street Lights
  • Porch/Patio/Deck: Balcony, Deck(s), Porch(es)

Parking

  • Total Spaces: 2
  • Parking Features: Gravel Driveway
  • Parking Type: Driveway, Off Street

Location

  • County: WINCHESTER CITY
  • Subdivision: WINCHESTER CITY
  • Driving Directions: National Avenue, turn onto Smithfield, turn onto Charles St. Property is on the right side. There is a gravel alley.
  • City Limits: Yes

School Information

  • School District: Winchester City Public Schools
  • Elementary School: Virginia Avenue Charlotte Dehart
  • Middle School: Daniel Morgan
  • High School: John Handley

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Central, Heat Pump(s), Forced Air
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Above Ground

Structural Information

  • Architectural Style: Traditional
  • Structure Type: Detached
  • Construction: Wood Siding, Other
  • Basement: Yes
  • Basement Desc.: Unfinished
  • Foundation: Other
  • Roof: Metal
  • Walls/Ceilings: Dry Wall
  • Windows: Double Hung
  • Stories Description: Main, Upper 1
  • Square Feet: 1,526
  • Sq. Ft. Source: Estimated
  • Living Area: 1,526 Sq. Ft.
  • Finished Above Grnd: 1,526 Sq. Ft.
  • Year Built: 1930
  • Year Built Source: Estimated
  • Property Condition: Average

Lot Features

  • Lot Size (Acres): 0.09
  • Lot Size (Sq. Ft.): 3,741
  • Lot Size Source: Estimated
  • Street/Road Desc.: Paved
  • Zoning: HR1

Financial Considerations

  • Price Per Sq. Ft.: $147.44
  • Assessment Year: 2025
  • City/TownTax: $2,005
  • City/TownTax Freq: Semi-Annually
  • County Tax Freq: Annually
  • Tax w/Assessment: $252,200
  • Tax Amount: $2,005
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Bank-owned: Yes

Listed by ERA Oakcrest Realty, Inc., Marisa L Varley

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Listing agent

— 369 Charles St —

  • Marisa L Varley

    ERA Oakcrest Realty, 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 369 Charles St

School District:Winchester City Public Schools
NameGradesDistance
Virginia Ave. Charlotte Dehart Elementary School
550 Virginia Avenue, Winchester, VA 22601
PK-40.2 mi
Daniel Morgan Middle School
48 South Purcell Avenue, Winchester, VA 22601
7-80.6 mi
John Handley High School
425 Handley Boulevard, Winchester, VA 22601
9-121.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 369 Charles St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/06/2025
Price Reduced
$225,000
-8.16%
MLS
11/15/2025
Price Reduced
$245,000
-7.55%
MLS
10/28/2025
Price Reduced
$265,000
-7.02%
MLS
9/23/2025
Price Reduced
$285,000
-6.56%
MLS
8/19/2025
Price Reduced
$305,000
-4.39%
MLS
7/15/2025
Listed
$319,000
—
MLS
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 369 Charles St

Year
Property Taxes
Change
Tax Assessment
Change
2024
100%
$252,200
14%
2024
-100%
$221,300
—
2023
$1,837
20%
$221,300
35%
2022
$1,527
41%
$164,200
41%
2021
$1,085
34%
$116,700
34%
2020
$811
—
$87,200
—
2018
$811
9%
$87,200
6%
2018
$747
13%
$82,100
—
2016
$662
—
$82,100
13%
2016
$662
—
$72,700
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 369 Charles St

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Listed by ERA Oakcrest Realty, Inc., Marisa L Varley

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369 Charles Street, Winchester, VA 22601 (MLS# VAWI2008716) is a Single Family property with 3 bedrooms and 2 full bathrooms. 369 Charles Street is currently listed for $225,000 and was received on July 15, 2025. Want to learn more about 369 Charles Street? Do you have questions about finding other Single Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

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