106 Jackson Ave, Winchester, VA 22601
Property image
Property image
OFF MARKET

$385,900

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,456 sqft

106 Jackson Ave, Winchester, VA 22601

Est. Refi. Payment $2,256/mo*
Refinance Your Home
Currently Off Market - Sold Jun 27, 2016 for $191,000

Home Value

Trulia Estimate
$386K
Since last month
Decreased$9K (-2.4%)
Since last year
Decreased$2K (-0.4%)
Since last sale
Increased$196K (+102.4%)
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 +101% in the last 10 years
MonthEstimated value
2026
August 2026$387K
August 2026$385K
July 2026$396K
June 2026$406K
May 2026$406K
April 2026$398K
March 2026$388K
February 2026$387K
January 2026$377K
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
1005 Pennsylvania Ave, Winchester, VA
0.13
Single-Family Home
$340,000
11/12/25
3
2
2,302
112 Star Fort Dr, Winchester, VA
0.14
Single-Family Home
$240,000
05/11/26
3
2
1,072
807 Pennsylvania Ave, Winchester, VA
0.20
Single-Family Home
$200,000
03/31/26
3
1
1,160
27 Jackson Ave, Winchester, VA
0.08
Single-Family Home
$181,000
11/14/25
2
1
1,134
105 W Oates Ave, Winchester, VA
0.35
Single-Family Home
$345,000
03/03/26
3
2
1,066
566 N Loudoun St, Winchester, VA
0.54
Single-Family Home
$277,000
09/17/25
4
2
2,058
632 Watson Ave, Winchester, VA
0.52
Single-Family Home
$325,000
08/25/26
3
2
1,465
415 Fortress Dr, Winchester, VA
0.52
Single-Family Home
$430,000
03/05/26
3
2
1,710
117 W Oates Ave, Winchester, VA
0.34
Single-Family Home
$320,000
05/05/26
3
1
1,237
580 N Braddock St, Winchester, VA
0.58
Single-Family Home
$418,000
12/05/25
4
2
2,200

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
101 Locust Ave, Winchester, VA 22601
0.06
$330,000
3
2.5
1,566
For Sale
27 Jackson Ave, Winchester, VA 22601
0.08
$181,000
2
1
1,134
Recently Sold
909 Pennsylvania Ave, Winchester, VA 22601
0.11
$364,600
3
2
1,176
Off Market
1005 Pennsylvania Ave, Winchester, VA 22601
0.13
$347,000
3
2
2,302
Off Market
112 Star Fort Dr, Winchester, VA 22601
0.14
$240,000
3
2
1,072
Recently Sold
118 Star Fort Dr, Winchester, VA 22601
0.14
$339,600
3
2
1,130
Off Market
102 Star Fort Dr, Winchester, VA 22601
0.15
$306,700
3
1
1,026
Off Market
821 Pennsylvania Ave #823, Winchester, VA 22601
0.16
$527,400
3
-
2,072
Off Market
911 Martinsburg Pike, Winchester, VA 22601
0.19
$360,200
4
2
2,304
Off Market
16 Richards Ave, Winchester, VA 22601
0.20
$402,500
5
2
1,766
Off Market
805 Pennsylvania Ave, Winchester, VA 22601
0.20
$359,000
3
1
1,474
For Sale
10 Richards Ave, Winchester, VA 22601
0.21
$319,200
3
1.5
1,704
Off Market

Local Information

  • Map ViewExplore the area around 106 Jackson Ave.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1954
2,456 sqft
$157/sqft
Garage

About this House

This single-family home is located at 106 Jackson Ave, Winchester, VA. 106 Jackson Ave is in Winchester, VA and in ZIP code 22601. This property has 3 bedrooms, 2 bathrooms and approximately 2,456 sqft of floor space. This property was built in 1954.
106 Jackson Ave, Winchester, VA 22601 is a 3 bedroom, 2 bathroom, 2,456 sqft single-family home built in 1954. It last sold for $191,000 on Jun 27, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $385,900, with a rent estimate of $2,499/month.

Home Details for 106 Jackson Ave

Interior Features

Interior Details
BasementNumber of Rooms: 5Ceiling Fan
Heating & Cooling
Heating: Baseboard, Forced AirAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherExterior: BrickFoundation Type: Concrete Block
Parking & Garage
GarageParking: Carport, Garage

Property Information

Year Built
Year Built: 1954
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Price and Tax history

DateEventPrice
Jun 27, 2016
Source: N/A
Sold
$191,000
May 17, 2016
Source: Agent Provided
Pending
$199,000
Mar 16, 2016
Source: Agent Provided
PendingToActive
$199,000
Mar 2, 2016
Source: Agent Provided
Pending
$199,000
Dec 8, 2015
Source: Agent Provided
Listed For Sale
$199,000

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

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! "
    5
    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."
    11
    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

LGBTQ Local Legal Protections

Frequently asked questions about 106 Jackson Ave

  • What is 106 Jackson Ave estimated to be worth?
    Trulia's estimated value for 106 Jackson Ave in Winchester, VA is $385,900.
  • What is the price history for 106 Jackson Ave?
    106 Jackson Ave in Winchester, VA last sold for $191,000 in June 2016.
  • 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 106 Jackson Ave have air conditioning?
    Yes, 106 Jackson Ave in Winchester, VA has air conditioning.
  • Does 106 Jackson Ave have laundry facilities?
    Yes, 106 Jackson Ave in Winchester, VA has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Outdoor Space

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Off Market Homes Near 106 Jackson Ave

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