296 Chickadee Ln, Winchester, VA 22603
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OFF MARKET

296 Chickadee Ln
Winchester, VA 22603

  • 2 Beds
  • 2 Baths
  • 2,086 sqft (on 5 acres)

$303,800

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $1,706/mo*
Refinance Your Home

$303,800

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $1,706/mo*
Refinance Your Home
2 Beds
2 Baths
2,086 sqft
(on 5 acres)

Local Information

  • Map ViewExplore the area around 296 Chickadee Ln.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1992
Lot Size
5 acres
Living Area
2,086 sqft
Price/Sqft
$146
Parking
2 Car Garage

Description

If you're looking for privacy in the woods, look no further! This contemporary-style home offers great potential and sits on 5 wooded acres just minutes from Rt 522/Rt 37. The great room offers a beautiful stone 2-sided fireplace, an open and spacious dining room area. There are lots of large windows for natural lighting throughout. The kitchen is just off the dining area. The main level bedroom and bath complete the first floor. The upper level is your spacious Primary Suite. Walk out onto the breezeway from the primary bedroom to the spacious bonus room above the 2-car garage! Perfect space for your game room, gym or office! Full unfinished basement to finish to your liking! This home will not qualify for government loans and is being sold in AS IS condition. Please see the documents and agent remarks for more information. Agents must accompany their buyers for all showings.
296 Chickadee Ln, Winchester, VA 22603 is a 2 bedroom, 2 bathroom, 2,086 sqft single-family home built in 1992. It last sold for $290,000 on May 14, 2025 (5% below the $304,900 asking price). It is currently off market. The Trulia Estimate is $303,800, with a rent estimate of $2,280/month.

Home Details for 296 Chickadee Ln

Interior Features

Interior Details
Basement: Full,UnfinishedNumber of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 2, Primary Bathroom, Bathroom 2, Bonus Room, Dining Room, Great Room, Kitchen
Beds & Baths
Number of Bedrooms: 2Main Level Bedrooms: 1Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2086 Square Feet
Heating & Cooling
Heating: NoneNo CoolingAir Conditioning: NoneHas Heating
Fireplace & Spa
Number of Fireplaces: 1Fireplace: StoneHas a Fireplace
Windows, Doors, Floors & Walls
Flooring: Wood
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Wood
View
No View

Exterior Features

Exterior Home Features
Other Structures: Above Grade, Below GradeFoundation: BlockNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Faces Front,Attached,Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: On Site Septic
Finished Area
Finished Area (above surface): 2086 Square Feet

Property Information

Year Built
Year Built: 1992
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Contemporary
Building
Construction Materials: FrameNot a New Construction
Property Information
Parcel Number: 31 3 7

Price & Status

Price
List Price: $304,900
Status Change & Dates
Off Market Date: Wed May 14 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: WINCHESTERCommunity: Grouse Hollow Estates
School Information
Elementary School District: Frederick County Public SchoolsJr High / Middle School District: Frederick County Public SchoolsHigh School District: Frederick County Public Schools

Building

Building Area
Building Area: 2086 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 5 Acres

Listing Info

Special Conditions: Real Estate Owned

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, FHA 203(k)

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: VAFV2023412Above Grade Unfinished Area: 2086
Last check for updates: about 4 hours ago
Listed by Sandra Brookman, (540) 671-0020
RE/MAX Real Estate Connections
Co-Listing Agent: Crystal D Elliott, (540) 671-5850
RE/MAX Real Estate Connections
Bought with: Chris Roszko, (703) 943-7585, Colony Realty
Source: Bright MLS, MLS#VAFV2023412

Price History for 296 Chickadee Ln

DatePriceEventSource
05/14/2025$290,000Sold
Bright MLS #VAFV2023412
03/07/2025$304,900Listed For SaleBright MLS #VAFV2023412
10/20/2023$352,270Sold
N/A
01/11/2020$0ListingRemovedAgent Provided
12/31/2019$0Listed For SaleAgent Provided

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$2,059
Assessment$429,000
Home facts updated by county records

Comparable Sales for 296 Chickadee Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
321 Cedar Grove Rd, Winchester, VA
0.70
Single-Family Home
$420,000
09/22/25
3
2
1,728
474 Cedar Grove Rd, Winchester, VA
0.50
Single-Family Home
$465,000
08/05/25
3
2
2,934
1576 Old Bethel Church Rd, Winchester, VA
1.09
Single-Family Home
$400,000
10/24/25
3
2
1,721
1239 Cedar Grove Rd, Winchester, VA
1.14
Single-Family Home
$525,000
06/17/26
3
2
1,793
3339 N Frederick Pike, Winchester, VA
1.27
Single-Family Home
$280,000
03/06/26
5
2
3,378
191 Chapman Ln, Winchester, VA
1.28
Single-Family Home
$345,000
12/08/25
3
2
1,674
405 Spring Valley Dr, Winchester, VA
0.69
Single-Family Home
$700,000
12/05/25
4
2.5
4,050
620 Lake Serene Dr, Winchester, VA
0.40
Single-Family Home
$850,000
07/17/26
4
4
4,545

Nearby homes

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Assigned Schools

These are the assigned schools for 296 Chickadee Ln.
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 296 Chickadee Ln

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Off Market Homes Near 296 Chickadee Ln

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information