102 Gregory Pl, Winchester, VA 22603
OFF MARKET

102 Gregory Pl
Winchester, VA 22603

  • 3 Beds
  • 2 Baths
  • 1,400 sqft

$208,600

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $1,180/mo*
Refinance Your Home

$208,600

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $1,180/mo*
Refinance Your Home
3 Beds
2 Baths
1,400 sqft

Local Information

Map showing home location
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Description

Winchester/Frederick County, 3 bedrooms/2 full baths single family home, 1995 Oakwood, 1,400 sq. ft. Selling for only $27,000. wood fireplace, garden tub in master bathroom. Storage shed. Frederick County Public Schools, personal parking for two cars, pool, fitness center, clubhouse, lakes, playground and volleyball court.Clubhouse address is 216 Regency Lakes Drive, Winchester, VA 22603.Home physical address is 102 Gregory Place, Winchester, VA 22603. Call 540-662-1999Must be able to pass a criminal and credit check.AVAILABLE NOW.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 102 Gregory Pl

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: Single Family Home

Price History for 102 Gregory Pl

DatePriceEventSource
05/24/2015$27,000ListingRemovedAgent Provided
04/25/2015$27,000PriceChange
Agent Provided
04/07/2015$29,000PriceChange
Agent Provided
04/03/2015$37,900Listed For SaleAgent Provided

Market trends in Winchester

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$385K
$14.17KMoM
Sale-to-List Price
99.4%
0.3%MoM
Price per sq ft
$218
$0MoM
Available listings
242
39MoM
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Property Tax and Assessment

Year2025
Tax$302
Assessment$63,000
Home facts updated by county records

Comparable Sales for 102 Gregory Pl

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
109 Lake Sever Dr, Winchester, VA
0.45
Single-Family Home
$296,574
08/20/25
3
2
1,232
102 Winnepeg Pl, Winchester, VA
0.53
Single-Family Home
$415,000
07/17/25
3
2
1,344
163 Denny Ln, Winchester, VA
0.49
Single-Family Home
$315,000
02/13/26
3
2
1,152
153 Denny Ln, Winchester, VA
0.44
Single-Family Home
$359,641
11/14/25
3
3
1,644
331 Dogwood Rd, Winchester, VA
0.71
Single-Family Home
$275,000
11/20/25
3
1.5
1,353
109 Ash Hollow Dr, Winchester, VA
0.69
Single-Family Home
$259,000
03/27/26
3
1.5
1,160
104 McNeil Pl, Winchester, VA
0.75
Single-Family Home
$299,000
05/05/26
3
2
1,064
111 Berkshire Cir, Winchester, VA
0.52
Single-Family Home
$20,000
03/11/26
4
3
1,988
226 Muse Dr, Winchester, VA
0.75
Single-Family Home
$285,000
10/31/25
3
1.5
1,064
200 Dogwood Rd, Winchester, VA
0.77
Single-Family Home
$385,000
06/09/25
3
1.5
1,104

Nearby homes

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Assigned Schools

These are the assigned schools for 102 Gregory Pl.
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

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Off Market Homes Near 102 Gregory Pl

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102 Gregory Pl, Winchester, VA 22603 is a 3 bedroom, 2 bathroom, 1,400 sqft single-family home built in 1995. This property is not currently available for sale. The current Trulia Estimate for 102 Gregory Pl is $208,600.