320 E Piccadilly St, Winchester, VA 22601
Property image
Property image
SOLD
APR 17, 2026

$404,900

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,764 sqft

320 E Piccadilly St, Winchester, VA 22601

Est. Refi. Payment $2,389/mo*
Refinance Your Home
Currently Off Market - Sold Apr 17, 2026 for $375,000 (9% below list price)

Home Value

Trulia Estimate
$405K
Since last month
Decreased$500 (-0.1%)
Since last year
Increased$86K (+27.1%)
Since last sale
Increased$30K (+7.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +241% in the last 10 years
MonthEstimated value
2026
September 2026$405K
August 2026$405K
July 2026$406K
June 2026$406K
May 2026$406K
April 2026$376K
March 2026$406K
February 2026$410K
January 2026$317K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
318 E Piccadilly St, Winchester, VA
0.01
Single-Family Home
$375,000
02/06/26
4
1.5
1,953
320 Highland Ave, Winchester, VA
0.13
Single-Family Home
$266,000
11/06/25
3
2
1,313
322 E Piccadilly St, Winchester, VA
0.01
Single-Family Home
$300,000
07/09/26
4
1
1,768
501 National Ave, Winchester, VA
0.24
Single-Family Home
$335,000
01/02/26
4
1.5
1,820
423 Highland Ave, Winchester, VA
0.21
Single-Family Home
$270,000
01/21/26
3
2
1,300
317 Fairview Ave, Winchester, VA
0.16
Single-Family Home
$255,000
08/26/26
3
1.5
1,222
317 N Kent St, Winchester, VA
0.18
Single-Family Home
$302,000
08/14/26
4
3
1,916
320 Virginia Ave, Winchester, VA
0.19
Single-Family Home
$450,000
07/15/26
3
2.5
1,549
419 Van Fossen St, Winchester, VA
0.29
Single-Family Home
$385,000
08/18/26
4
2
1,785

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
326 E Piccadilly St, Winchester, VA 22601
0.02
$272,200
2
1.5
1,066
Off Market
322 E Piccadilly St, Winchester, VA 22601
0.01
$409,000
4
1
1,768
For Sale
315 E Piccadilly St, Winchester, VA 22601
0.03
$426,400
3
2.5
1,409
Off Market
318 E Piccadilly St, Winchester, VA 22601
0.01
$375,000
4
1.5
1,953
Recently Sold
307 E Piccadilly 1/2 St, Winchester, VA 22601
0.03
$329,000
3
1.5
1,600
For Sale
315 National Ave, Winchester, VA 22601
0.03
$432,700
2
2
1,678
Off Market
311 National Ave, Winchester, VA 22601
0.04
$212,900
2
2
1,536
Off Market
344 National Ave, Winchester, VA 22601
0.06
$295,300
3
2
1,386
Off Market
371 E Piccadilly St, Winchester, VA 22601
0.09
$311,800
3
1
1,449
Off Market
301 National Ave #303, Winchester, VA 22601
0.06
$283,600
2
-
2,282
Off Market
313 Gray Ave, Winchester, VA 22601
0.08
$288,300
3
1
1,531
Off Market

Local Information

  • Map ViewExplore the area around 320 E Piccadilly St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1940
1,764 sqft
$213/sqft
Garage

About this House

What's unique:Detached rear garageRefinished floorsPrivate drivewayCrisp clean aestheticNew flooringThree generous bedrooms
Discover the perfect blend of historic charm and modern convenience at 320 E Piccadilly Street. This classic brick residence is situated in a premier Winchester location, offering a lifestyle of effortless connectivity just moments from local boutiques, restaurants, parks, schools, and the vibrant downtown pedestrian mall. Commuters will appreciate the easy access to major routes, while the rare inclusion of a private driveway and a detached rear garage provides highly coveted off-street parking in the heart of the city. Inside, the home radiates timeless character, beginning with a bright foyer that showcases rich hardwood floors and an elegant wooden staircase. The main level offers a fluid layout with a sizable living room and a formal dining room, perfect for hosting gatherings. The updated kitchen is a modern standout, boasting new flooring, countertops, contemporary paint tones, and new stainless steel appliances, all complemented by a convenient main-floor full bath. The upper level continues to impress with three generous bedrooms and a beautifully renovated full bath that serves as a bright and modern sanctuary. This luxurious space was designed with both style and functionality in mind, featuring high-end finishes and a crisp, clean aesthetic. The primary suite offers a serene atmosphere with direct access to a fabulous, sun-drenched sunroom. This versatile space, wrapped in windows, offers a peaceful vantage point overlooking the property and serves as an ideal setting for a morning coffee lounge, a tranquil reading nook, or an inspiring home office. For added organization, a large walk-in closet is conveniently located just adjacent to the primary bedroom. The lower level provides an unfinished basement, ideal for additional storage and housing the home’s laundry facilities. To finish the interior, a set of convenient walk-up stairs leads to a sizable unfinished attic affording incredible storage capacity or future possibilities. Outside, the rear of the home features a large covered porch overlooking a level backyard, creating a private outdoor oasis next to the detached garage. Featuring new windows, new HVAC, paint, refinished floors and more. Combining a thoughtfully cared for interior with a premier downtown location, this home offers an unparalleled opportunity to enjoy the very best of Winchester living.
320 E Piccadilly St, Winchester, VA 22601 is a 3 bedroom, 2 bathroom, 1,764 sqft single-family home built in 1940. It last sold for $375,000 on Apr 17, 2026 (9% below the $409,900 asking price). More recently, it was listed as a rental in June 2021 with an asking price of $1,350 per month. That rental listing was removed on June 10, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $404,900, with a rent estimate of $1,937/month.
Last check for updates: about 18 hours ago
Listed by Dan Whitacre, (540) 327-6718
Colony Realty
Bought with: Richard Bell, (540) 247-6501, Adams-Nelson & Associates Inc
Source: Bright MLS, MLS#VAWI2010018

Home Details for 320 E Piccadilly St

Interior Features

Interior Details
Basement: Unfinished,Connecting Stairway,Interior EntryNumber of Rooms: 11Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Attic, Basement, Dining Room, Full Bath, Kitchen, Living Room, Sun Florida Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1764 Square Feet
Appliances & Utilities
Appliances: Oven/Range - Electric, Washer, Dryer, Refrigerator, Stainless Steel Appliance(s), Electric Water HeaterDryerLaundry: Lower LevelRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,Zoned,ElectricHas CoolingAir Conditioning: Central Air,Zoned,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Flooring: Hardwood, Wood
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Hardwood, Wood
View
No View

Exterior Features

Exterior Home Features
Patio / Porch: PorchOther Structures: Above Grade, Below GradeFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 1Parking: Garage Faces Rear,Detached,Off Street,Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1764 Square Feet

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Traditional
Building
Construction Materials: BrickNot a New Construction
Property Information
Parcel Number: 17401K8

Price & Status

Price
List Price: $409,900Price Per Sqft: $213/sqft
Status Change & Dates
Off Market Date: Fri Apr 17 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: WINCHESTERCommunity: None Available
School Information
Elementary School: John KerrElementary 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

Building

Building Area
Building Area: 2646 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 4861 sqft

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: VAWI2010018Above Grade Unfinished Area: 1764

Additional Information

Source Internet Entire Listing Display: Y

Price and Tax history

DateEventPrice
Apr 17, 2026
Source: Bright MLS #VAWI2010018
Sold
$375,000
Mar 31, 2026
Source: Bright MLS #VAWI2010018
Pending
$409,900
Mar 13, 2026
Source: Bright MLS #VAWI2010018
PendingToActive
$409,900
Mar 6, 2026
Source: Bright MLS #VAWI2010018
Pending
$409,900
Feb 24, 2026
Source: Bright MLS #VAWI2010018
Listed For Sale
$409,900

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$393K
$3.33KMoM
Sale-to-List Price
99.9%
0.1%MoM
Price per sq ft
$221
$1MoM
Available listings
346
37MoM

Around this home

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! "
    7
    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."
    4
    Flag
  • George
    "I’ve only lived here several weeks but am impressed by the people in our neighborhood. Polite and friendly."
    13
    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. "
    2
    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"
    10
    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!"
    4
    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. "
    5
    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 !"
    6
    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

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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

Frequently asked questions about 320 E Piccadilly St

  • What is 320 E Piccadilly St estimated to be worth?
    Trulia's estimated value for 320 E Piccadilly St in Winchester, VA is $404,900.
  • What is the price history for 320 E Piccadilly St?
    320 E Piccadilly St in Winchester, VA last sold for $375,000 in April 2026.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $393K. That is up $3.33K from the prior month.
  • Does 320 E Piccadilly St have air conditioning?
    Yes, 320 E Piccadilly St in Winchester, VA has air conditioning.
  • Does 320 E Piccadilly St have laundry facilities?
    Yes, 320 E Piccadilly St in Winchester, VA has in-unit laundry.

Explore by feature - Pet Friendly

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Off Market Homes Near 320 E Piccadilly St

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