108 Cannon Cir, Winchester, VA 22602
Master bedroom
Bedroom 3
OFF MARKET

$554,100

Trulia Estimate
as of Sep 14, 2026
  • 5 Beds
  • 3.5 Baths
  • 2,826 sqft

108 Cannon Cir, Winchester, VA 22602

Home Highlights

Single-Family Home
2,826 sqft
$196/sqft
Attached Garage

Local Information

  • Map ViewExplore the area around 108 Cannon Cir.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Lovely 5 BR 3.5 BA SFH with 2 car attached garage, fenced yard, on quiet cul-de-sac. Master on main floor with walk in closet. Finished walk out basement with full bath. Top floor has four bedrooms (one with walk in closet) 1 full bath and a small office space. New roof, new HVAC, new deck, new carpet, new washer and dryer, updated Master bath.

Owner pays HOA fees. Tenants responsible for water, gas, electric and yard maintenance
108 Cannon Cir, Winchester, VA 22602 is a 5 bedroom, 4 bathroom, 2,826 sqft single-family home. More recently, it was listed as a rental in September 2025 with an asking price of $2,900 per month. That rental listing was removed on October 7, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $554,100, with a rent estimate of $2,999/month.

Home Details for 108 Cannon Cir

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: Central AirHeating Fuel: Heat Pump
Appliances & Utilities
DishwasherDryerWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Parking & Garage
Parking: Attached, On Site

Comparable Sales for 108 Cannon Cir

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
111 Asbury Rd, Winchester, VA
0.16
Single-Family Home
$429,250
05/12/26
4
2.5
2,353 sqft
100 Winns Cir, Winchester, VA
0.24
Single-Family Home
$405,000
03/27/26
4
2.5
2,636 sqft
107 Tucks Cir, Winchester, VA
0.11
Single-Family Home
$489,000
02/12/26
4
2
2,401 sqft
102 Settlers Cir, Winchester, VA
0.14
Single-Family Home
$497,000
07/15/26
3
2.5
2,268 sqft
234 Asbury Rd, Winchester, VA
0.32
Single-Family Home
$549,000
11/03/25
4
3
2,772 sqft
111 Old Wagon Rd, Winchester, VA
0.32
Single-Family Home
$553,847
06/18/26
4
2.5
2,400 sqft
237 Asbury Rd, Winchester, VA
0.35
Single-Family Home
$475,000
06/23/26
4
2.5
2,330 sqft
275 Greenwood Rd, Winchester, VA
0.20
Single-Family Home
$439,900
11/20/25
3
3
1,732 sqft
116 Camden Dr, Winchester, VA
0.13
Single-Family Home
$430,000
11/21/25
3
2.5
1,313 sqft
223 Cavalry Dr, Winchester, VA
0.50
Single-Family Home
$515,000
11/20/25
5
4
2,529 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$2,999/mo
Average rent
$1.7K
$100MoM
Available listings
160
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! "
    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

Price and Tax history

DateEventPrice
Oct 7, 2025
Source: Zillow Rentals
ListingRemoved
$2,900
Sep 22, 2025
Source: Zillow Rentals
Listed For Rent
$2,900
Jan 23, 2024
Source: Zillow Rentals
ListingRemoved
Jan 9, 2024
Source: Zillow Rentals
Listed For Rent
$2,900
Feb 22, 2018
Source: Agent Provided
ListingRemoved
$1,850

Frequently asked questions about 108 Cannon Cir

  • What is 108 Cannon Cir estimated to be worth?
    Trulia's estimated value for 108 Cannon Cir in Winchester, VA is $554,100.
  • 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.
  • 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.
  • Does 108 Cannon Cir have air conditioning?
    Yes, 108 Cannon Cir in Winchester, VA has air conditioning.
  • Does 108 Cannon Cir have laundry facilities?
    Yes, 108 Cannon Cir in Winchester, VA has in-unit laundry.

Homes for rent near 108 Cannon Cir

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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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