342 Gray Ave, Winchester, VA 22601
OFF MARKET

$203,300

Trulia Estimate
as of Sep 2, 2026
  • 3 Beds
  • 1 Bath
  • 1,178 sqft
  • 3 Beds
  • 1 Bath
  • 1,178 sqft

342 Gray Ave, Winchester, VA 22601

Home Highlights

Property Type
Single-Family Home
Year Built
1930
Living Area
1,178 sqft
Price/Sqft
$173

Local Information

  • Map ViewExplore the area around 342 Gray Ave.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Built in 1930
3 Bedroom / 1 bath Duplex just a few blocks from downtown Winchester. Convenient to shopping and grocery stores. 1 Mile to I-81 and Rt. 7.
Newly remodeled Kitchen with Refrigerator, Stove and Microwave.
Hardwood and Vinyl Plank Flooring.
Gas Heat Tenant would provide window AC units
Walk-up Attic for Storage
Dirt Floor Cellar
Fenced Back Yard Front and Back Porch
Street Parking
Water/Sewer Included Tenant pays Electric & Gas
There are no laundry hookups in this home
Small Pets Considered - Under 30lbs ($400 Pet Deposit Required If Approved)
No Smoking
Application fee is $45 per adult
Credit report should show more positive than negative accounts
No Criminal History of Violence or Drugs
No Prior Evictions
Monthly Income Should Be 3 Times The Monthly Rent
3 Bdr. 1 bath Duplex
Refrigerator / Elec. Stove / Microwave
Hardwood / Vinyl
Street Parking
342 Gray Ave, Winchester, VA 22601 is a 3 bedroom, 1 bathroom, 1,178 sqft single-family home built in 1930. More recently, it was listed as a rental in January 2025 with an asking price of $1,500 per month. That rental listing was removed on January 27, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $203,300, with a rent estimate of $1,548/month.

Home Details for 342 Gray Ave

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For DetailsAvailable: now

Comparable Sales for 342 Gray Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
376 Charles St, Winchester, VA
0.08
Single-Family Home
$175,000
03/02/26
3
1
1,232 sqft
322 E Piccadilly St, Winchester, VA
0.12
Single-Family Home
$300,000
07/09/26
3
1
1,764 sqft
323 Fairview Ave, Winchester, VA
0.12
Single-Family Home
$249,500
07/09/26
2
1
1,472 sqft
320 Highland Ave, Winchester, VA
0.08
Single-Family Home
$266,000
11/06/25
3
2
1,313 sqft
317 Fairview Ave, Winchester, VA
0.13
Single-Family Home
$255,000
08/26/26
3
1.5
1,222 sqft
423 Highland Ave, Winchester, VA
0.12
Single-Family Home
$270,000
01/21/26
3
2
1,300 sqft
406 Highland Ave, Winchester, VA
0.08
Single-Family Home
$305,000
08/24/26
3
2
1,474 sqft
424 Highland Ave, Winchester, VA
0.10
Single-Family Home
$279,000
03/27/26
2
1
759 sqft
410 N Pleasant Valley Rd, Winchester, VA
0.28
Single-Family Home
$305,000
06/17/26
3
1
1,558 sqft
45 Race St #1/2, Winchester, VA
0.26
Single-Family Home
$226,000
08/28/26
2
1
1,249 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Winchester

Last updated Sep 2026
Trulia Rent Estimate$1,548/mo
Average rent
$1.7K
Available listings
161
View rental market trends in Winchester, VA

Around this home

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! "
    4
    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."
    10
    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 !"
    5
    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

Price and Tax history

DateEventPrice
Jan 27, 2025
Source: Zillow Rentals
ListingRemoved
$1,500
Jan 23, 2025
Source: Zillow Rentals
Listed For Rent
$1,500

Frequently asked questions about 342 Gray Ave

  • What is 342 Gray Ave estimated to be worth?
    Trulia's estimated value for 342 Gray Ave in Winchester, VA is $203,300.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $390K. That is up $10K from the prior month.
  • What do residents say about Winchester?
    Residents describe Winchester, VA as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Winchester, VA.

Homes for rent near 342 Gray Ave

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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