159 Ashton Dr, Winchester, VA 22603
Property image
Property image
SOLD
NOV 26, 2025

$270,400

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 2,795 sqft (on 0.50 acres)

159 Ashton Dr, Winchester, VA 22603

Est. Refi. Payment $1,621/mo*
Refinance Your Home
Currently Off Market - Sold Nov 26, 2025 for $260,000 (4% above list price)

Home Value

Trulia Estimate
$270K
Since last month
Decreased$300 (-0.1%)
Since last year
Decreased$22K (-7.5%)
Since last sale
Increased$10K (+3.8%)
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 +19% in the last 10 years
MonthEstimated value
2026
September 2026$270K
August 2026$270K
July 2026$266K
June 2026$265K
May 2026$265K
April 2026$265K
March 2026$264K
February 2026$264K
January 2026$262K
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
139 Bryarly Rd, Winchester, VA
0.63
Single-Family Home
$315,000
09/02/26
3
2
1,585
115 Hickory Ln, Winchester, VA
0.90
Single-Family Home
$295,000
07/07/26
2
1
990
1243 N Frederick Pike, Winchester, VA
1.05
Single-Family Home
$360,000
12/18/25
3
2
1,508
327 Bryarly Rd, Winchester, VA
0.87
Single-Family Home
$460,000
10/01/25
3
2
2,165
1629 Pondview Dr, Winchester, VA
0.84
Single-Family Home
$574,900
10/17/25
4
3.5
2,602
428 Apple Pie Ridge Rd, Winchester, VA
0.61
Single-Family Home
$550,000
06/08/26
3
2
2,216
519 Whitacre St, Winchester, VA
1.00
Single-Family Home
$419,000
03/30/26
4
2
2,408
1317 Caroline St, Winchester, VA
1.18
Single-Family Home
$487,500
07/29/26
4
2
2,837

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
140 Ashton Dr, Winchester, VA 22603
0.04
$305,700
2
1
1,020
Off Market
1667 N Frederick Pike, Winchester, VA 22603
0.27
$1,400,000
-
-
-
For Sale
101 Ridge Ct, Winchester, VA 22603
0.52
$320,500
2
3
1,800
Off Market
111 Ridge Ct, Winchester, VA 22603
0.53
$330,000
3
3
1,920
Recently Sold
547 Apple Pie Ridge Rd, Winchester, VA 22603
0.52
$1,296,900
4
6.5
8,171
Off Market
821-829 839 #851, Winchester, VA 22603
0.61
$1,499,000
-
-
-
For Sale
428 Apple Pie Ridge Rd, Winchester, VA 22603
0.61
$550,000
3
2
2,216
Recently Sold
139 Bryarly Rd, Winchester, VA 22603
0.63
$315,000
3
2
1,585
Recently Sold
LOT Behind 591 Apple Pie Ridge Rd, Winchester, VA 22603
0.64
-
-
-
-
Off Market
792 Fox Dr, Winchester, VA 22603
0.69
$150,000
2
1
644
Recently Sold
792 Fox Ct, Winchester, VA 22603
0.69
$209,300
2
1
644
Off Market

Local Information

  • Map ViewExplore the area around 159 Ashton Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1956
0.5 acre lot
2,795 sqft
$93/sqft
Garage

About this House

Cash only -Sold "AS IS" Great Location! 2-Bedroom, 2-Bath Ranch with Great Potential! Ranch-style home featuring 2 bedrooms and 2 full bathrooms. A large living room with a wood-burning fireplace. Kitchen and separate dining room. Hardwood flooring under carpet. The full basement offers a full bath, ample space for storage, a workshop, or future finished living areas. Outside, you'll find a detached 4-car garage with electric, perfect for car enthusiasts, hobbyists, or extra storage. RV concrete pad. Enjoy morning coffee on the covered front porch or the rear deck. While the home needs some TLC, it has great bones and is ideal for anyone looking for a fixer-upper. Prime location – just minutes from shopping, dining, schools, Winchester Medical Center, and historic Old Town Winchester. Don’t miss out on this diamond in the rough with incredible potential! All sizes are approximate.
159 Ashton Dr, Winchester, VA 22603 is a 2 bedroom, 2 bathroom, 2,795 sqft single-family home built in 1956. It last sold for $260,000 on Nov 26, 2025 (4% above the $250,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $270,400, with a rent estimate of $1,954/month.
Last check for updates: about 10 hours ago
Listed by Roxanna Grimes, (540) 327-2798
RE/MAX Roots
Listing Team: Roxann Grimes Team
Bought with: Chelsea Betah, (703) 477-0119, Century 21 Redwood Realty
Source: Bright MLS, MLS#VAFV2036300

Home Details for 159 Ashton Dr

Interior Features

Interior Details
Basement: Connecting StairwayNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 2Main Level Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2795 Square Feet
Appliances & Utilities
Appliances: Electric Water Heater
Heating & Cooling
Heating: Heat Pump,Electric,WoodHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Flooring: Carpet, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: NoneFloors: Carpet, Hardwood
View
No View

Exterior Features

Exterior Home Features
Other Structures: Above Grade, Below GradeFoundation: BlockNo Private Pool
Parking & Garage
Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 4Parking: Garage Faces Front,Detached,Driveway
Pool
Pool: None
Frontage
Responsible for Road Maintenance: City/CountyNot on Waterfront
Water & Sewer
Sewer: Septic Exists
Finished Area
Finished Area (above surface): 1973 Square FeetFinished Area (below surface): 822 Square Feet

Property Information

Year Built
Year Built: 1956
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Ranch/Rambler
Building
Construction Materials: StoneNot a New Construction
Property Information
Parcel Number: 42A218

Price & Status

Price
List Price: $250,000Price Per Sqft: $93/sqft
Status Change & Dates
Off Market Date: Wed Nov 26 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Media

Location

Direction & Address
City: WINCHESTERCommunity: None Available
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: 3617 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.50 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: VAFV2036300Above Grade Unfinished Area: 1973

Price and Tax history

DateEventPrice
Nov 26, 2025
Source: Bright MLS #VAFV2036300
Sold
$260,000
Nov 13, 2025
Source: Bright MLS #VAFV2036300
Pending
$250,000
Nov 11, 2025
Source: Bright MLS #VAFV2036300
PriceChange
$250,000
Price decreased by 4%
Oct 24, 2025
Source: Bright MLS #VAFV2036300
Listed For Sale
$260,000
Sep 24, 2025
Source: Bright MLS #VAFV2036300
ListingRemoved
$299,000

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! "
    7
    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."
    13
    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

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

Frequently asked questions about 159 Ashton Dr

  • What is 159 Ashton Dr estimated to be worth?
    Trulia's estimated value for 159 Ashton Dr in Winchester, VA is $270,400.
  • What is the price history for 159 Ashton Dr?
    159 Ashton Dr in Winchester, VA last sold for $260,000 in November 2025.
  • 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 159 Ashton Dr have air conditioning?
    Yes, 159 Ashton Dr in Winchester, VA has air conditioning.
  • How big is the lot at 159 Ashton Dr?
    The lot at 159 Ashton Dr in Winchester, VA is about 0.50 acres (21,780 sq ft).

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