369 Gray Ave, Winchester, VA 22601
OFF MARKET

369 Gray Ave
Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 2,228 sqft

$291,200

Trulia Estimate
as of May 12, 2026
Est. Refi. Payment $1,601/mo*
Refinance Your Home

$291,200

Trulia Estimate
as of May 12, 2026
Est. Refi. Payment $1,601/mo*
Refinance Your Home
3 Beds
1 Bath
2,228 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

3 bedroom/1 Bath home in Winchester City. Inviting front porch. Hardwoods throughout home.Built ins. Kitchen w/ss appliances & huge pantry w/built in shelving. Claw foot tub. 25 x 25 insulated, detached garage. Laundry in Basement, W/D convey. Approx. 1516 sq ft. Fenced rear yard. Off street parking. New roof in 2000. Garage built in 2007. Lot acreage approximate.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 369 Gray Ave

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: BaseboardHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DryerRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: CompositionExterior: OtherFoundation Type: Concrete
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1923
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 7405 sqft

Price History for 369 Gray Ave

DatePriceEventSource
11/02/2020$170,000Sold
N/A
06/15/2018$134,000Sold
N/A
06/02/2018$134,000PendingAgent Provided
05/24/2018$134,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$2,029
Assessment$255,200
Home facts updated by county records

Comparable Sales for 369 Gray Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
323 Fairview Ave, Winchester, VA
0.15
Single-Family Home
$105,000
10/07/25
2
1
1,472
245 E Fairfax Ln, Winchester, VA
0.13
Single-Family Home
$286,000
08/01/25
3
1
1,284
501 Battle Ave, Winchester, VA
0.40
Single-Family Home
$300,000
03/26/26
3
1
1,789
304 Virginia Ave, Winchester, VA
0.07
Single-Family Home
$322,900
05/21/25
3
2.5
1,839
320 Highland Ave, Winchester, VA
0.04
Single-Family Home
$266,000
11/06/25
3
2
1,313
320 E Piccadilly St, Winchester, VA
0.12
Single-Family Home
$375,000
04/17/26
3
2
1,764
430 Virginia Ave, Winchester, VA
0.19
Single-Family Home
$359,000
05/23/25
3
2.5
1,956
412 Fairview Ave, Winchester, VA
0.18
Single-Family Home
$325,000
07/25/25
3
3
1,900
423 Highland Ave, Winchester, VA
0.10
Single-Family Home
$270,000
01/21/26
3
2
1,300
501 National Ave, Winchester, VA
0.26
Single-Family Home
$335,000
01/02/26
4
1.5
1,820

Assigned Schools

These are the assigned schools for 369 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 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

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."
    1
    Flag
  • George
    "I’ve only lived here several weeks but am impressed by the people in our neighborhood. Polite and friendly."
    1
    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"
    2
    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!"
    1
    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. "
    1
    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 !"
    1
    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 "
    10
    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."
    7
    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 "
    8
    Flag
  • Trulia User
    "Everyone I have ran into has been nice. Definitely a very family friendly neighborhood. Feels very cozy "
    6
    Flag
  • Morganva
    "Dog friendly, plenty of green space, and lots of dog bag dispensers for cleaning up after the pooch. "
    6
    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 "
    7
    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."
    5
    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"
    2
    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. "
    3
    Flag
  • Rob R.
    "My commute to downtown is usually fairly quick, not too much traffic. Public transportation is not very popular."
    2
    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. "
    1
    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. "
    2
    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"
    2
    Flag
  • Nellycordon
    "The neighborhood is great plus shopping center are very close. Also. Friendly people. So I feel safe "
    2
    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"
    50
    Flag
  • Brock M.
    "Great area to live and raise a family. Good earnings potential. Great university. Awesome private and public school system."
    1
    Flag
  • Coach_ramos
    "You must drive or carpool. There is a local bus/trolley, but only locally within the city. No rail or subway."
    1
    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. "
    1
    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."
    1
    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."
    0
    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."
    0
    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"
    1
    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!"
    0
    Flag
  • Island4tj
    "The city is relatively safe and the schools are very good. Nice, clean town to live in that’s family-oriented. "
    0
    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. "
    0
    Flag

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369 Gray Ave, Winchester, VA 22601 is a 3 bedroom, 1 bathroom, 2,228 sqft single-family home built in 1923. This property is not currently available for sale. 369 Gray Ave was last sold on Nov 2, 2020 for $170,000. The current Trulia Estimate for 369 Gray Ave is $291,200.