311 Gray Ave, Winchester, VA 22601
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OFF MARKET

311 Gray Ave
Winchester, VA 22601

  • 4 Beds
  • 1.5 Baths
  • 1,868 sqft

$348,800

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $1,959/mo*
Refinance Your Home

$348,800

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $1,959/mo*
Refinance Your Home
4 Beds
1.5 Baths
1,868 sqft

Local Information

  • Map ViewExplore the area around 311 Gray Ave.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1927
Living Area
1,868 sqft
Price/Sqft
$187
Parking
Garage

About this House

**OPEN HOUSE SUNDAY JAN 24, 2021 FROM 12-4 PM**

This four bedroom, two bath single family home is just blocks from Historic Downtown Winchester and features updated fixtures, appliances, paint, finished hardwood floors. The original charm has been well maintained from when it was built in 1927 with built-in cabinets, dining room hutch, columns, large baseboards, and crown molding make this home a beauty. You'll walk in through the front door to a gorgeous archway leading you into the living room which connects to a relaxing sunroom on the front of the house and connects to the dining room on the other end. It's a great open floor plan for a house of this age. The kitchen offers all the amenities and storage of today's most modern kitchens, and off the back of it is a combination half bath and laundry room. The back door off the kitchen opens to a screened porch looking into the fenced backyard. The second floor provides ample living space with four bedrooms and a fifth room attached to the back bedroom that can be used for another bedroom, an office, a playroom, etc. From the second floor you can walk up stairs into a finished attic providing great storage space. Below the first floor is a basement which has a utility shower, toilet, and sink. It's a great room for storage and has been occupied by previous residents. Dual zone central air and heating keeps the house comfortable all year and every room has a ceiling fan. Detached garage and large driveway offer ample storage and off street parking.

Pets considered on a case by case basis.

Rental applications will be available at the Open House this Sunday. $50 application fee. Please reach out with any questions even if you can’t make the Open House.
311 Gray Ave, Winchester, VA 22601 is a 4 bedroom, 2 bathroom, 1,868 sqft single-family home built in 1927. It last sold for $260,000 on Feb 1, 2022. More recently, it was listed as a rental in January 2021 with an asking price of $1,550 per month. That rental listing was removed on January 25, 2021. It is currently off market. The Trulia Estimate is $348,800, with a rent estimate of $2,299/month.

Home Details for 311 Gray Ave

Interior Features

Interior Details
BasementNumber of Rooms: 11Types of Rooms: Dining Room, Family Room, Laundry Room, Recreation Room, Sun Room
Heating & Cooling
Heating: Forced Air, Electric, OilCooling System: OtherHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood
Appliances & Utilities
DryerWasher

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Stucco, BrickFoundation Type: Concrete
Parking & Garage
GarageParking: Off Street, Garage

Property Information

Year Built
Year Built: 1927
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Price History for 311 Gray Ave

DatePriceEventSource
02/01/2022$260,000Sold
N/A
01/25/2021ListingRemovedZillow Rental Manager
01/20/2021$1,550Listed For RentZillow Rental Manager
06/24/2015$160,000Sold
N/A
01/19/2012$139,900Sold
N/A
12/16/2011$139,900Listed For SaleAgent Provided
11/10/2011$60,000Sold
N/A

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$2,627
Assessment$330,400
Home facts updated by county records

Comparable Sales for 311 Gray Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
318 E Piccadilly St, Winchester, VA
0.08
Single-Family Home
$375,000
02/06/26
4
1.5
1,953
322 E Piccadilly St, Winchester, VA
0.07
Single-Family Home
$300,000
07/09/26
3
1
1,764
320 Highland Ave, Winchester, VA
0.07
Single-Family Home
$266,000
11/06/25
3
2
1,313
320 E Piccadilly St, Winchester, VA
0.08
Single-Family Home
$375,000
04/17/26
3
2
1,764
317 Gray Ave, Winchester, VA
0.02
Single-Family Home
$374,900
07/17/26
4
2.5
1,536
501 National Ave, Winchester, VA
0.23
Single-Family Home
$335,000
01/02/26
4
1.5
1,820
423 Highland Ave, Winchester, VA
0.14
Single-Family Home
$270,000
01/21/26
3
2
1,300
245 E Fairfax Ln, Winchester, VA
0.11
Single-Family Home
$286,000
08/01/25
3
1
1,284
621 Butler Ave, Winchester, VA
0.37
Single-Family Home
$300,000
12/15/25
4
2
1,803
311 National Ave, Winchester, VA
0.06
Single-Family Home
$176,000
09/12/25
2
2
1,536

Nearby homes

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Assigned Schools

These are the assigned schools for 311 Gray Ave.
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

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Homes for sale near 311 Gray Ave

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Off Market Homes Near 311 Gray Ave

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