110 Grindstone Dr, Winchester, VA 22602
COMING SOON 5/28
0.53 ACRES

110 Grindstone Dr
Winchester, VA 22602

  • 4 Beds
  • 4 Baths
  • 4,055 sqft (on 0.53 acres)

$539,900

Est. Mortgage $2,984/mo*
Get Pre-Qualified

$539,900

Est. Mortgage $2,984/mo*
Get Pre-Qualified
4 Beds
4 Baths
4,055 sqft
(on 0.53 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Rare offerings demand attention, and this property delivers a combination seldom found in Winchester. Originally established before Red Fox Run was developed, this .53-acre property offers the privacy, space, and flexibility that newer subdivision homes simply cannot replicate. A fully fenced concrete pool, expansive outdoor entertaining space, mature setting, and oversized homesite create a standout opportunity for buyers seeking multigenerational living, income-producing potential, or a high-functioning primary residence with amazing flexibility. The main level offers one-level living with three spacious bedrooms and three full bathrooms, including a private ensuite primary bedroom thoughtfully positioned opposite the secondary bedrooms for separation and privacy. Recently refinished hardwood floors, fresh interior paint, freshly painted pool decking, and refreshed exterior elements create a move-in ready presentation with immediate appeal. Natural light pours through the oversized picture window into the large family room, while the dining room and dedicated laundry room are conveniently situated. The fully finished basement dramatically expands the home's value proposition with a separate entrance, full kitchen, full bath, bedroom, family room, and additional flex space ideal for short-term rental opportunities, college event lodging, in-law accommodations, extended guest stays, or supplemental income potential. Few properties in Winchester offer this level of versatility combined with a private pool and oversized lot within an established neighborhood setting. Positioned approximately $60,000 below assessment value, this property presents a compelling opportunity for buyers searching for house hacking potential, multigenerational layouts, STR flexibility, pool homes, finished basements with kitchens, or homes suited for Shenandoah University events and regional festivals. Properties with this combination of land, flexibility, privacy, pool amenities, and income-producing capability rarely reach the market.

Home Highlights

Parking
2 Car Garage
Outdoor
Pool
A/C
Heating & Cooling
HOA
$15/Monthly
Price/Sqft
$133
Listed
3 days ago

Home Details for 110 Grindstone Dr

Interior Features

Interior Details
Basement: Common Basement,Full,FinishedNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Family Room, Full Bath, Kitchen, Laundry, Office, Recreation
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 4055 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Electric Water Heater, Disposal, Microwave, Oven, Refrigerator, WasherDishwasherDisposalMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Electric,Heat Pump,Natural Gas,Wood,Wood StoveHas CoolingAir Conditioning: Central Air,Heat PumpHas HeatingHeating Fuel: Electric
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Masonry, Wood BurningHas a Fireplace
Windows, Doors, Floors & Walls
Flooring: Carpet, Ceramic Tile, Vinyl
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneFloors: Carpet, Ceramic Tile, Vinyl
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: StoopFencing: Back Yard, Fenced, PartialExterior: Paved DrivewayHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Attached,Driveway,Garage,Oversized,Paved,Garage Faces Rear,Garage Faces Side
Pool
Pool: Concrete, In Ground, Pool, PrivatePool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Surface & Elevation
Topography: Level
Finished Area
Finished Area (above surface): 2253 Square FeetFinished Area (below surface): 1802 Square Feet

Days on Market

Days on Market: 3

Property Information

Year Built
Year Built: 1963
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Brick, DrywallNot a New ConstructionNot Attached Property
Property Information
Condition: ResaleParcel Number: 64D815

Price & Status

Price
List Price: $539,900Price Per Sqft: $133
Status Change & Dates
Possession Timing: Close Of Escrow

Active Status

MLS Status: Coming Soon

Media

Location

Direction & Address
City: WinchesterCommunity: None
School Information
Elementary School: ArmelJr High / Middle School: Admiral Richard E ByrdHigh School: Millbrook

Agent Information

Listing Agent
Listing ID: 2614019

Community

Community Features: Home Owners Association

HOA

HOA Fee Includes: Common AreasAssociation for this Listing: Central Virginia Regional MLSHas an HOAHOA Fee: $175/Annually

Lot Information

Lot Area: 0.53 acres

Business

Business Information
Ownership: Individuals

Miscellaneous

BasementMls Number: 2614019Living Area Range Units: Square FeetAttic: Pull Down StairsAbove Grade Unfinished Area: 2253Above Grade Unfinished Area Units: Square FeetActivation Date: Thu May 28 2026Below Grade Unfinished Area: 451Below Grade Unfinished Area Units: Square FeetUniversal Property Id: US-51069-N-64D815-R-N

Additional Information

Home Owners Association
Last check for updates: about 2 hours ago
Listing courtesy of Daune Zook, (804) 852-6454
Samson Properties
Originating MLS: Central Virginia Regional MLS
Source: CVRMLS, MLS#2614019
Also Listed on CVRMLS, Bright MLS, Bright MLS.

Price History for 110 Grindstone Dr

DatePriceEventSource
08/13/2021$380,000Sold
Bright MLS #VAFV2000642
06/09/2018$290,500Sold
N/A
05/25/2018$294,500PendingAgent Provided
04/16/2018$294,500Listed For SaleAgent Provided
05/18/2012$235,000Sold
N/A
01/21/2012$249,900Listed For SaleAgent Provided
08/19/2003$255,000Sold
N/A
10/23/2001$48,000Sold
N/A
03/16/2001$47,000Sold
N/A

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Property Tax and Assessment

Year2024
Tax$2,493
Assessment$488,800
Home facts updated by county records

Comparable Sales for 110 Grindstone Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
124 Mcclure Way, Winchester, VA
0.12
Single-Family Home
$570,000
10/01/25
5
3.5
3,526
112 Westwood Cir, Winchester, VA
0.27
Single-Family Home
$510,000
05/15/26
4
3
2,652
100 Melissa Ave, Winchester, VA
0.27
Single-Family Home
$520,000
05/30/25
4
3.5
3,030
101 Sovereign Ct, Winchester, VA
0.33
Single-Family Home
$595,000
04/27/26
4
3.5
3,462
125 Alliance Ct, Winchester, VA
0.25
Single-Family Home
$445,000
12/09/25
4
3.5
2,176
104 Quigley Ct, Winchester, VA
0.40
Single-Family Home
$585,000
06/06/25
4
2.5
3,078
109 Shelby Ct, Winchester, VA
0.26
Single-Family Home
$475,000
12/12/25
3
2.5
2,412
212 Bentley Ave, Winchester, VA
0.18
Single-Family Home
$449,950
07/07/25
3
2
1,782
128 Longcroft Rd, Winchester, VA
0.39
Single-Family Home
$365,000
12/22/25
3
2
2,108

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 110 Grindstone Dr.
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 464 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.
  • 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."
    1
    Flag
  • George
    "I’ve only lived here several weeks but am impressed by the people in our neighborhood. Polite and friendly."
    1
    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"
    2
    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!"
    1
    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. "
    1
    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 !"
    1
    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 "
    10
    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 "
    10
    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."
    7
    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 "
    8
    Flag
  • Trulia User
    "Everyone I have ran into has been nice. Definitely a very family friendly neighborhood. Feels very cozy "
    6
    Flag
  • Morganva
    "Dog friendly, plenty of green space, and lots of dog bag dispensers for cleaning up after the pooch. "
    6
    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 "
    7
    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."
    5
    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"
    2
    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 😁 "
    2
    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. "
    3
    Flag
  • Rob R.
    "My commute to downtown is usually fairly quick, not too much traffic. Public transportation is not very popular."
    2
    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. "
    1
    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. "
    2
    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"
    2
    Flag
  • Nellycordon
    "The neighborhood is great plus shopping center are very close. Also. Friendly people. So I feel safe "
    2
    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"
    50
    Flag
  • Brock M.
    "Great area to live and raise a family. Good earnings potential. Great university. Awesome private and public school system."
    1
    Flag
  • Coach_ramos
    "You must drive or carpool. There is a local bus/trolley, but only locally within the city. No rail or subway."
    1
    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. "
    1
    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."
    1
    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."
    0
    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."
    0
    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"
    1
    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!"
    0
    Flag
  • Island4tj
    "The city is relatively safe and the schools are very good. Nice, clean town to live in that’s family-oriented. "
    0
    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. "
    0
    Flag

LGBTQ Local Legal Protections

Daune Zook, Samson Properties
Agent Phone: (804) 852-6454
All or a portion of the multiple Listing information is provided by the Central Virginia Regional Multiple Listing Service, LLC, from a copyrighted compilation of Listing s. All CVR MLS information provided is deemed reliable but is not guaranteed accurate. The compilation of Listings and each individual Listing are ©2026 Central Virginia Regional Multiple Listing Service, LLC. All rights reserved.
110 Grindstone Dr, Winchester, VA 22602 is a 4 bedroom, 4 bathroom, 4,055 sqft single-family home built in 1963. This property is currently available for sale and was listed by CVRMLS on May 24, 2026. The MLS # for this home is MLS# 2614019.