369 Charles St, Winchester, VA 22601
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Property image
UNDER CONTRACT
FORECLOSURE
BANK OWNED

369 Charles St
Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,526 sqft

$225,000

Est. Mortgage $1,299/mo*
Get Pre-Qualified

$225,000

Est. Mortgage $1,299/mo*
Get Pre-Qualified
3 Beds
2 Baths
1,526 sqft

Home Highlights

Parking
2 Open Spaces
Outdoor
Porch, Deck
Climate Control
Heating & Cooling
Price/Sqft
$147
Listed
180+ days ago

Local Information

  • Map ViewExplore the area around 369 Charles St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Back on the market because the buyer could not secure financing. 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. The property was built before 1978, and Lead-Based Paint Potentially Exists.
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Home Details for 369 Charles St

Interior Features

Interior Details
Basement: UnfinishedNumber of Rooms: 8Types of Rooms: Bedroom 1, Bedroom 2, Bedroom 3, Bathroom 1, Bathroom 2, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1526 Square Feet
Appliances & Utilities
Utilities: Above GroundAppliances: Electric Water HeaterLaundry: Main Level
Heating & Cooling
Heating: Central,Heat Pump,Forced Air,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Central
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Double Hung, Window TreatmentsFlooring: Ceramic Tile, Laminate
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Ceramic Tile, Laminate
View
No View
Security
Security: Main Entrance Lock, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Deck, PorchOther Structures: Above Grade, Below Grade, OutbuildingExterior: Sidewalks, Street Lights, BalconyFoundation: OtherNo Private Pool
Parking & Garage
Open Parking Spaces: 2No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Gravel,Driveway,Off Street
Pool
Pool: None
Frontage
Responsible for Road Maintenance: City/CountyRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses
Finished Area
Finished Area (above surface): 1526 Square Feet

Days on Market

Days on Market: 180+

Property Information

Year Built
Year Built: 1930Year Renovated: 2021
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Traditional
Building
Construction Materials: Wood Siding, OtherNot a New ConstructionNo Additional Parcels
Property Information
Condition: AverageParcel Number: 17401R24

Price & Status

Price
List Price: $225,000Price Per Sqft: $147
Status Change & Dates
Possession Timing: Close Of Escrow

Active Status

MLS Status: ACTIVE UNDER CONTRACT

Location

Direction & Address
City: WINCHESTERCommunity: Winchester City
School Information
Elementary School: Virginia Avenue Charlotte DehartElementary School District: Winchester City Public SchoolsJr High / Middle School: Daniel MorganJr High / Middle School District: Winchester City Public SchoolsHigh School: John HandleyHigh School District: Winchester City Public Schools

Agent Information

Listing Agent
Listing ID: VAWI2008716

Building

Building Area
Building Area: 1526 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 3741 sqft

Listing Info

Special Conditions: Real Estate Owned

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: VAWI2008716Zillow Contingency Status: Under ContractAbove Grade Unfinished Area: 1526

Additional Information

Source Internet Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y
Last check for updates: about 14 hours ago
Listing courtesy of Marisa Varley, (540) 931-1810
ERA Oakcrest Realty, Inc., (540) 665-0360
Source: Bright MLS, MLS#VAWI2008716

Market trends in Winchester

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$380K
$10.67KMoM
Sale-to-List Price
100.0%
0.2%MoM
Price per sq ft
$216
$1MoM
Available listings
302
31MoM

Price History for 369 Charles St

DatePriceEventSource
08/28/2025$305,000ListingRemovedWMLS #BMTVAWI2008716
08/20/2025$305,000Listed For SaleWMLS #BMTVAWI2008716
04/29/2025$267,000Sold
N/A
03/14/2025$275,000PriceChange
Bright MLS #VAWI2007150
03/08/2025$325,000PriceChange
Bright MLS #VAWI2007150
02/17/2025$345,000Listed For SaleBright MLS #VAWI2007150
10/28/2022$267,000Sold
Bright MLS #VAWI2002566
10/02/2022$255,000ContingentBright MLS #VAWI2002566
09/30/2022$255,000Listed For SaleBright MLS #VAWI2002566
02/21/2022ListingRemovedZillow Rental Network Premium
02/03/2022$1,650PriceChange
Zillow Rental Network Premium
02/01/2022$1,750PriceChange
Zillow Rental Network Premium
01/11/2022$1,850Listed For RentZillow Rental Network Premium
12/30/2021$255,000Sold
Bright MLS #VAWI2000160
10/18/2021$254,000PendingWeichert Pro #VAWI2000160
10/18/2021$254,000ContingentBright MLS #VAWI2000160
10/14/2021$254,000PriceChange
Bright MLS #VAWI2000160
10/05/2021$265,000PriceChange
Bright MLS #VAWI2000160
09/24/2021$270,000PriceChange
Bright MLS #VAWI2000160
08/27/2021$275,000PriceChange
Bright MLS #VAWI2000160
08/16/2021$287,999PriceChange
Bright MLS #VAWI2000160
07/23/2021$289,999PriceChange
Bright MLS #VAWI2000160
07/08/2021$300,000Listed For SaleBright MLS #VAWI2000160
08/24/2020$120,000Sold
N/A
11/22/2019$74,000Sold
N/A
11/01/2019$78,000Listed For SaleAgent Provided

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Property Tax and Assessment

Year2025
Tax$2,005
Assessment$252,200
Home facts updated by county records

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 369 Charles St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winchester

At least 465 Trulia users voted on each feature.

  • 84 % Say car is needed

  • 81 % Say it's dog friendly

  • 81 % Say parking is easy

  • 77 % Say yards are well-kept

  • 73 % Say there's holiday spirit

  • 69 % Say kids play outside

  • 64 % Say people would walk alone at night

  • 64 % Say there are sidewalks

  • 59 % Say streets are well-lit

  • 55 % Say it's quiet

  • 52 % Say neighbors are friendly

  • 49 % Say it's walkable to restaurants

  • 49 % Say there's wildlife

  • 48 % Say they plan to stay for at least 5 years

  • 36 % Say it's walkable to grocery stores

  • 28 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • 7seymours
    "It’s quiet, owners take care of their homes, and it’s safe! And pretty! "
    1
    Flag
  • Hmrtgptw2c
    "I drive to and from work. The city has public transportation with WinReady I think it’s called. There is ride share in the area as well."
    3
    Flag
  • George
    "I’ve only lived here several weeks but am impressed by the people in our neighborhood. Polite and friendly."
    7
    Flag
  • Jessica J Contreras
    "There are no sidewalks or safe areas to walk with pets. Cars go by fast. It would be unsafe to walk. "
    1
    Flag
  • 7seymours
    "We live in a beautiful, safe area with an excellent county school system. Our neighbors have pride and take care of their properties in the Green Spring area"
    8
    Flag
  • Izzy874
    "Apple blossom every single year I love it! The food is amazing, the games, the carnival, and especially the parades and events to go too!"
    3
    Flag
  • Singsongone
    "Lived in this quiet neighborhood little over ten years. Convenient to major highways and bypasses, hospital, doctors, grocery and retail stores, restaurants. Lovely mature trees throughout, some wildlife and one can easily hear morning/evening birds. Residents take pride in the appearance of their homes and yards and look out for one another. "
    3
    Flag
  • Smlrws
    "I’ve lived here for a year and my street is much quieter than I ever expected since I live with a mile of the downtown area. It’s safe. There are many restaurants, coffe shops, hair salons, etc. within walking distance !"
    3
    Flag
  • Kelrendon83
    "Great community for live , safe and good for raise kids and the family can have a good place to visit , some good festivals "
    12
    Flag
  • 7seymours
    "Lived here for 22 yrs. Beautiful, spacious, quiet and good neighbors! We feel safe here with a lot of privacy. Neighbors look out for each other & help each other "
    11
    Flag
  • Gfbzc98z9n
    "It is Quiet and safe while still being just a short trip to the big city. Beautiful downtown walking mall. Great outdoors all around in the Blue Ridge Mountains."
    9
    Flag
  • 7seymours
    "Apple Blossom Festival which is held annually with parades, celebrities, dances, music & arts & crafts. A beautiful weekend during Apple Blossom time with over 250,000 visitors attending this special event in the Shenandoah Valley "
    10
    Flag
  • Trulia User
    "Everyone I have ran into has been nice. Definitely a very family friendly neighborhood. Feels very cozy "
    8
    Flag
  • Morganva
    "Dog friendly, plenty of green space, and lots of dog bag dispensers for cleaning up after the pooch. "
    8
    Flag
  • Bridgetdefoe
    "It’s easy to get around Winchester. Roads are well maintained. Traffic is minimal. You can get about anywhere in Winchester is less than 20 minutes. Rt 7 has become busy as an exception due to people commuting to Loudoun County "
    9
    Flag
  • Isabelle M.
    "Is a nice ride and no traffic in the area, many shopping centers, great area to visit, one of the great hospital in the nation."
    7
    Flag
  • Alliav11%40gmail.com
    "A lot of people have dogs here and they are always waking them. There are a lot of stray cats so if dogs don’t like them beware"
    0
    Flag
  • Gina A.
    "It's just a nice neighborhood to walk. People are always waving and stopping to chat. And they clean up after their dogs"
    4
    Flag
  • Cooda K.
    "It’s a lot It’s a lot I can say I honestly feel like it’s a beautiful place I mean the cabs suck But other than that I feel like it’s a nice expensive place to live 😁 "
    3
    Flag
  • Topeye
    "Very good schools, low crime rate, good jobs. Civic pride. Great long-running annual community festival. Many churches and civic organizations are active. Historic preservation. "
    5
    Flag
  • Rob R.
    "My commute to downtown is usually fairly quick, not too much traffic. Public transportation is not very popular."
    3
    Flag
  • Nickruiz270
    "The commute into Winchester is fairly light but around 5pm it’s when it gets heavy. I would try to avoid all small roads as much as possible and use the highway as much as possible. "
    2
    Flag
  • Careliza81
    "We are just walking distance to the walking mall which has tons of activities throughout the year. There are festivals for most major holidays and apple blossom. "
    3
    Flag
  • Nick A.
    "There is a great community of people here and it’s very welcoming. Living here is home for me and I would recommend moving here if you want to be close to major metropolis and still be near countryside"
    3
    Flag
  • Chels J.
    "Great safe place for kids no strange people more of a older group of people live here. It’s out of the way of the city but seconds from town"
    51
    Flag
  • Brock M.
    "Great area to live and raise a family. Good earnings potential. Great university. Awesome private and public school system."
    2
    Flag
  • Coach_ramos
    "You must drive or carpool. There is a local bus/trolley, but only locally within the city. No rail or subway."
    2
    Flag
  • Leslie H.
    "I commute to Northern Va and Loudoun Co. it’s more brutal each year, especially the return commute. "
    0
    Flag
  • Brad M.
    "Old town feel and downtown is lively. We enjoy being able to walk in a safe environment and walk to restaurants and shops. A great place to live in a historic town. "
    2
    Flag
  • Yesenia R.
    "The community center provides events for all. From all the holidays to special events for fundraisers along with also assisting the community with school supplies. There’s also playgrounds and pools."
    2
    Flag
  • Danielle M.
    "There are no community events in my neighborhood...everyone mostly keeps to themselves with the exception of those of us who have lived here for over thirty years. "
    0
    Flag
  • Erin G. .
    "Nothing special, just a nice neighborhood. Nice and quiet. Friendly folks. Safe for kids to play. Convenient to shopping."
    1
    Flag
  • Samantha F.
    "There is a large park just a few blocks away. Enough room to let a we trained dog off the leash. Walking distance to downtown dog friendly restaurants. "
    0
    Flag
  • Topeye
    "The public library across the street and the pedestrian mall 2 blocks away frequently hold community events."
    1
    Flag
  • Juanita e
    "dog owners would love this area great place to live great county sitting quite schools stores dr.s hospital close malls shopping casinos horse racing car raises movies drive in s close tons restaurants parks city county parks swimming snow skiing within hour"
    0
    Flag
  • Andrea
    "Nothing. Nice area not much for kid s to do no playgrounds or nearby parks but nice for adults "
    0
    Flag
  • Destiny W.
    "There's a big Park perfect for taking your dog. Plus you'll see all kinds of dogs being walked downtown on the waking mall. A few businesses even put a water bowl out for the dogs that walk by"
    2
    Flag
  • Debra T.
    "There is a bus stop only a few minutes from my front door. I know you can take the bus down town! I am not sure about long distance travel!"
    1
    Flag
  • Island4tj
    "The city is relatively safe and the schools are very good. Nice, clean town to live in that’s family-oriented. "
    1
    Flag
  • Ruizy8329
    "The neighborhood provides many sidewalks and grassy areas for peaceful and well lit dog walking. People in the area mostly have pets and those who don’t are usually very good about it. "
    1
    Flag

LGBTQ Local Legal Protections

Marisa Varley, ERA Oakcrest Realty, Inc., (540) 665-0360
Agent Phone: (540) 931-1810
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information
369 Charles St, Winchester, VA 22601 is a 3 bedroom, 2 bathroom, 1,526 sqft single-family home built in 1930. This property is currently available for sale and was listed by Bright MLS on Jul 15, 2025. The MLS # for this home is MLS# VAWI2008716.