371 E Piccadilly St, Winchester, VA 22601
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Property image
OFF MARKET

371 E Piccadilly St
Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 1,449 sqft

$317,800

Trulia Estimate
as of Jul 13, 2026
Est. Refi. Payment $1,783/mo*
Refinance Your Home

$317,800

Trulia Estimate
as of Jul 13, 2026
Est. Refi. Payment $1,783/mo*
Refinance Your Home
3 Beds
1 Bath
1,449 sqft

Local Information

  • Map ViewExplore the area around 371 E Piccadilly St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Priced to sell! This charming home built in 1930 sits on Winchester's next up & coming street! Located within walking distance of Old Town, the home has many improvements while still maintaining it's character. Enjoy evenings on the covered front porch featuring tongue & groove flooring. A quaint vestibule greats visitors at the front door and opens to the living room. The main floor offers two large living spaces, a cozy nook, window seat and wood floors. Circa 2010, the heat was converted to electric heat pump with gas backup, all the plumbing was redone and the first floor was wired for modern 200 amp service. The standing seam metal roof and half round gutters were installed around 2005 and have decades of life left in them. The property features a PHENOMENAL 24x24 garage & conditioned workshop built in 2020. Currently used as a print shop, it could be used as a gym, home office, home school, art studio and more. The possibilities are endless! One wall features vintage glass that allows natural light to flow in. The building has a standing seam metal roof and allows for off street parking. Fenced backyard oasis is a dream come true. Don't miss this opportunity to invest in one of Winchester's best kept secrets - East Piccadilly Street!
371 E Piccadilly St, Winchester, VA 22601 is a 3 bedroom, 1 bathroom, 1,449 sqft single-family home built in 1930. It last sold for $282,000 on Jul 26, 2024 (3% below the $289,900 asking price). It is currently off market. The Trulia Estimate is $317,800, with a rent estimate of $1,937/month.

Home Highlights

Parking
Garage
Outdoor
Porch
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 371 E Piccadilly St

Interior Features

Interior Details
Basement: OtherNumber of Rooms: 9Types of Rooms: Bedroom 1, Bedroom 2, Bedroom 3, Family Room, Full Bath, Kitchen, Laundry, Living Room, Other
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 1449 Square Feet
Appliances & Utilities
Appliances: Electric Water HeaterLaundry: Main Level,Laundry Room
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Window: TransomFlooring: Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: NoneFloors: Wood
View
No View

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: PorchFencing: Back Yard, PrivacyOther Structures: Above Grade, Below Grade, OutbuildingFoundation: PermanentNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 1Parking: Garage Door Opener,Oversized,Detached,On Street
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1449 Square Feet

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Bungalow,Craftsman
Building
Construction Materials: Stucco, Shake SidingNot a New Construction
Property Information
Parcel Number: 19401F 21

Price & Status

Price
List Price: $289,900
Status Change & Dates
Off Market Date: Fri Jul 26 2024Possession Timing: Seller Rent Back, Subject to Home Choice

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: WINCHESTERCommunity: None Available
School Information
Elementary School District: Winchester City Public SchoolsJr High / Middle School District: Winchester City Public SchoolsHigh School: John HandleyHigh School District: Winchester City Public Schools

Building

Building Area
Building Area: 1449 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 4269 sqft

Listing Info

Special Conditions: Standard

Offer

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

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: VAWI2005538Above Grade Unfinished Area: 1449
Last check for updates: about 6 hours ago
Listed by Stephanie Ryall, (540) 535-5653
Realty ONE Group Old Towne
Bought with: Richard Butcher, (540) 336-8270, Coldwell Banker Premier
Source: Bright MLS, MLS#VAWI2005538

Price History for 371 E Piccadilly St

DatePriceEventSource
07/26/2024$282,000Sold
Bright MLS #VAWI2005538
06/27/2024$289,900PendingBright MLS #VAWI2005538
06/20/2024$289,900PriceChange
Bright MLS #VAWI2005538
05/26/2024$298,900PriceChange
Bright MLS #VAWI2005538
05/18/2024$299,900PriceChange
Bright MLS #VAWI2005538
05/02/2024$315,000PriceChange
Bright MLS #VAWI2005538
04/25/2024$329,900Listed For SaleBright MLS #VAWI2005538

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
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Property Tax and Assessment

Year2025
Tax$1,908
Assessment$239,996
Home facts updated by county records

Comparable Sales for 371 E Piccadilly St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
323 Fairview Ave, Winchester, VA
0.13
Single-Family Home
$249,500
07/09/26
2
1
1,472
320 Highland Ave, Winchester, VA
0.20
Single-Family Home
$266,000
11/06/25
3
2
1,313
320 E Piccadilly St, Winchester, VA
0.09
Single-Family Home
$375,000
04/17/26
3
2
1,764
423 Highland Ave, Winchester, VA
0.28
Single-Family Home
$270,000
01/21/26
3
2
1,300
126 S Euclid Ave, Winchester, VA
0.41
Single-Family Home
$299,900
06/29/26
3
1
1,086
318 E Piccadilly St, Winchester, VA
0.10
Single-Family Home
$375,000
02/06/26
4
1.5
1,953
424 Highland Ave, Winchester, VA
0.26
Single-Family Home
$279,000
03/27/26
2
1
759
501 Battle Ave, Winchester, VA
0.41
Single-Family Home
$300,000
03/26/26
3
1
1,789

Nearby homes

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Assigned Schools

These are the assigned schools for 371 E Piccadilly 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 464 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.
  • 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."
    5
    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"
    6
    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!"
    2
    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. "
    2
    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 !"
    2
    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 "
    11
    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 "
    10
    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."
    8
    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 "
    9
    Flag
  • Trulia User
    "Everyone I have ran into has been nice. Definitely a very family friendly neighborhood. Feels very cozy "
    7
    Flag
  • Morganva
    "Dog friendly, plenty of green space, and lots of dog bag dispensers for cleaning up after the pooch. "
    7
    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 "
    8
    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."
    6
    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"
    3
    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 😁 "
    2
    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. "
    4
    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
  • Nellycordon
    "The neighborhood is great plus shopping center are very close. Also. Friendly people. So I feel safe "
    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

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Homes for sale near 371 E Piccadilly St

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Off Market Homes Near 371 E Piccadilly St

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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