123 Grindstone Dr, Winchester, VA 22602
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OFF MARKET

123 Grindstone Dr
Winchester, VA 22602

  • 5 Beds
  • 3.5 Baths
  • 2,864 sqft (on 0.33 acres)

$535,800

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $2,986/mo*
Refinance Your Home

$535,800

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $2,986/mo*
Refinance Your Home
5 Beds
3.5 Baths
2,864 sqft
(on 0.33 acres)

Local Information

  • Map ViewExplore the area around 123 Grindstone Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2002
Lot Size
0.33 acres
Living Area
2,864 sqft
Price/Sqft
$187
Parking
2 Car Garage
HOA
$10/Monthly

About this House

Nestled on a picturesque corner lot, this charming 5-bedroom, 3.5-bathroom colonial home exudes timeless elegance and modern comfort. Its classic architecture was built by a local builder (Walker and Cross). This home is warm and inviting and is being sold by the original owners! As you approach the house, the full front porch welcomes you with ample space! Perfect for sipping your morning cup of coffee overlooking the beautiful pond across the street. Upon entering the foyer, you're greeted by the newly refinished hardwood floors that flow seamlessly throughout the main level, adding an element of sophistication. To your left a spacious office or bonus room and to your right a dining room with crown molding and chair railing that is very inviting. The open-concept kitchen and living room area is truly the heart of the home providing both functionality and style. The living room has a cozy fireplace and a bay window with a large bench seat and plenty of storage space offering a comfortable space for relaxation and entertainment. Step through a set of french doors that open to a lovely TREX deck that was installed in 2019. This is a wonderful area for outdoor dining, grilling, or simply enjoying the serene views of the landscaped yard. The corner lot offers a sense of openness and privacy, creating a serene oasis within a well-established community. Upstairs, the four well-appointed bedrooms provide comfort and privacy for the entire family with freshly cleaned carpets. The primary bedroom features a generous walk-in closet and an ensuite bathroom complete with a soaking tub, a separate shower, and double vanities. The remaining bedrooms are spacious, filled with natural light, and offer ample closet space. The lower level of the home offers a versatile space that can be used as a recreation room, a home gym, or a media room. A full bathroom and a 5th bedroom on this level adds versatility. One of the standout features of this home is its abundance of storage space. From extra shelving in the garage, to spacious closets and a large pantry in the kitchen, you'll have plenty of room to organize your belongings and keep your living spaces clutter-free.
123 Grindstone Dr, Winchester, VA 22602 is a 5 bedroom, 4 bathroom, 2,864 sqft single-family home built in 2002. It last sold for the $495,000 asking price on Oct 18, 2023. More recently, it was listed as a rental in April 2020 with an asking price of $2,000 per month. That rental listing was removed on February 27, 2021. It is currently off market. The Trulia Estimate is $535,800, with a rent estimate of $3,024/month.

Home Details for 123 Grindstone Dr

Interior Features

Interior Details
Basement: Walk-Out Access,Windows,Finished,Interior Entry,Exterior Entry,Rear EntranceNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2864 Square Feet
Appliances & Utilities
Utilities: Cable Available, Natural Gas Available, Water Available, Phone Available, Electricity Available, Sewer AvailableAppliances: Microwave, Dishwasher, Disposal, Dryer, Extra Refrigerator/Freezer, Humidifier, Oven/Range - Gas, Refrigerator, Washer, Gas Water HeaterDishwasherDisposalDryerLaundry: Has Laundry,Main Level,Dryer In Unit,Washer In Unit,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Heat Pump,Natural GasHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,ElectricHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Gas/Propane, Mantel(s)Has a Fireplace
Windows, Doors, Floors & Walls
Door: French DoorsFlooring: Carpet, Ceramic Tile, Hardwood, Wood
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Carpet, Ceramic Tile, Hardwood, Wood
View
No View

Exterior Features

Exterior Home Features
Roof: Shingle AsphaltPatio / Porch: Deck, Patio, PorchOther Structures: Above Grade, Below GradeExterior: Play Equipment, Satellite DishFoundation: Slab, Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Storage,Garage Faces Side,Garage Door Opener,Inside Entrance,Oversized,Asphalt,Attached,Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses
Finished Area
Finished Area (above surface): 2102 Square FeetFinished Area (below surface): 762 Square Feet

Property Information

Year Built
Year Built: 2002
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New Construction
Property Information
Condition: ExcellentParcel Number: 64D 8 1 77

Price & Status

Price
List Price: $495,000
Status Change & Dates
Off Market Date: Wed Oct 18 2023Possession Timing: Immediate, 0-30 Days CD, 31-60 Days CD

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: WINCHESTERCommunity: Red Fox Run
School Information
Elementary School: ArmelElementary School District: Frederick County Public SchoolsJr High / Middle School: Admiral Richard E. ByrdJr High / Middle School District: Frederick County Public SchoolsHigh School: MillbrookHigh School District: Frederick County Public Schools

Building

Building Area
Building Area: 2864 Square Feet

Community

Not Senior Community

HOA

Has an HOAHOA Fee: $125/Annually

Lot Information

Lot Area: 0.33 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: VAFV2014700Above Grade Unfinished Area: 2102
Last check for updates: about 7 hours ago
Listed by Alisa Cole, (540) 931-8979
Century 21 Redwood Realty
Bought with: Angela Duncan, (540) 247-0563, MarketPlace REALTY
Source: Bright MLS, MLS#VAFV2014700

Price History for 123 Grindstone Dr

DatePriceEventSource
10/18/2023$495,000Sold
Bright MLS #VAFV2014700
10/06/2023$495,000PendingBright MLS #VAFV2014700
09/17/2023$495,000ContingentBright MLS #VAFV2014700
09/11/2023$495,000Listed For SaleBright MLS #VAFV2014700
02/27/2021ListingRemovedN/A
04/26/2020$2,200ListingRemovedN/A
04/24/2020$2,200PriceChange
N/A
04/18/2020$2,000Listed For RentN/A
11/01/2017$2,000ListingRemovedN/A
08/16/2017$2,000Listed For RentN/A
06/20/2002$225,000Sold
N/A

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$2,224
Assessment$463,300
Home facts updated by county records

Comparable Sales for 123 Grindstone Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
124 Mcclure Way, Winchester, VA
0.05
Single-Family Home
$570,000
10/01/25
5
3.5
3,526
109 Shelby Ct, Winchester, VA
0.19
Single-Family Home
$475,000
12/12/25
3
2.5
2,412
112 Westwood Cir, Winchester, VA
0.33
Single-Family Home
$510,000
05/15/26
4
3
2,652
121 Travis Ct, Winchester, VA
0.24
Single-Family Home
$468,900
07/07/26
3
2.5
1,770
112 Grindstone Dr, Winchester, VA
0.07
Single-Family Home
$470,000
05/01/26
4
1
2,158
125 Alliance Ct, Winchester, VA
0.33
Single-Family Home
$445,000
12/09/25
4
3.5
2,176
101 Sovereign Ct, Winchester, VA
0.40
Single-Family Home
$595,000
04/27/26
4
3.5
3,462
100 Alliance Ct, Winchester, VA
0.46
Single-Family Home
$515,000
07/15/26
6
3.5
2,539
236 Bentley Ave, Winchester, VA
0.14
Single-Family Home
$419,000
01/30/26
3
2
1,791
224 Vine Ln, Winchester, VA
0.19
Single-Family Home
$585,000
09/15/25
3
2.5
2,268

Nearby homes

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Assigned Schools

These are the assigned schools for 123 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 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! "
    2
    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."
    8
    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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Apartments for Rent

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Explore by feature - Pet Friendly

59 pet-friendly rentals in Winchester, VA

Explore by feature - Garage

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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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Homes for sale near 123 Grindstone Dr

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Off Market Homes Near 123 Grindstone Dr

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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