217 Gloucester Dr, Winchester, VA 22603
Property image
Property image
OFF MARKET

$797,200

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 4,317 sqft (on 2.33 acres)

217 Gloucester Dr, Winchester, VA 22603

Est. Refi. Payment $4,623/mo*
Refinance Your Home
Currently Off Market - Sold Apr 29, 2024 for $755,000

Home Value

Trulia Estimate
$797K
Since last month
Decreased$6K (-0.7%)
Since last year
Increased$22K (+2.8%)
Since last sale
Increased$44K (+5.9%)
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 +80% in the last 10 years
MonthEstimated value
2026
September 2026$799K
August 2026$799K
July 2026$805K
June 2026$811K
May 2026$808K
April 2026$798K
March 2026$801K
February 2026$790K
January 2026$781K
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
138 Gloucester Dr, Winchester, VA
0.19
Single-Family Home
$500,000
03/27/26
3
2.5
1,963
274 Woodside Ln, Winchester, VA
0.34
Single-Family Home
$735,000
08/21/26
5
4
4,075
247 McGuire Rd, Winchester, VA
0.49
Single-Family Home
$900,000
05/20/26
4
2.5
2,894
731 Apple Pie Ridge Rd, Winchester, VA
0.38
Single-Family Home
$1,500,000
10/28/25
4
3.5
4,304
505 Glendobbin Rd, Winchester, VA
0.82
Single-Family Home
$760,000
10/31/25
4
2.5
2,786
428 Apple Pie Ridge Rd, Winchester, VA
0.40
Single-Family Home
$550,000
06/08/26
3
2
2,216
240 Glendobbin Rd, Winchester, VA
0.72
Single-Family Home
$929,200
03/27/26
6
3.5
3,848
160 Wilton Dr, Winchester, VA
0.99
Single-Family Home
$840,000
09/03/26
4
4.5
4,059
105 Salvo Cir, Winchester, VA
0.81
Single-Family Home
$515,000
09/26/25
4
3.5
4,123
821 Apple Pie Ridge Rd, Winchester, VA
0.55
Single-Family Home
$2,000,000
01/22/26
5
5
5,590

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
Lot 24 Handley Dr, Winchester, VA 22603
0.14
$265,000
-
-
-
Recently Sold
Lot-27A Handley Dr, Winchester, VA 22603
0.16
$250,000
-
-
-
Recently Sold
138 Gloucester Dr, Winchester, VA 22603
0.19
$500,000
3
2.5
1,963
Recently Sold
Lot 4 Handley Dr, Winchester, VA 22603
0.23
$265,000
-
-
-
Recently Sold
Lot 23 Greenfield Dr, Winchester, VA 22603
0.32
$270,000
-
-
-
Recently Sold
274 Woodside Ln, Winchester, VA 22603
0.34
$735,000
5
4
4,075
Recently Sold
LOT Behind 591 Apple Pie Ridge Rd, Winchester, VA 22603
0.36
-
-
-
-
Off Market
210 McGuire Rd, Winchester, VA 22603
0.37
$1,024,000
5
4.5
4,524
Off Market
428 Apple Pie Ridge Rd, Winchester, VA 22603
0.40
$550,000
3
2
2,216
Recently Sold
731 Apple Pie Ridge Rd, Winchester, VA 22603
0.38
$1,151,900
4
3.5
4,304
Off Market
547 Apple Pie Ridge Rd, Winchester, VA 22603
0.40
$1,330,900
4
6.5
8,171
Off Market

Local Information

  • Map ViewExplore the area around 217 Gloucester Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1986
2.33 acre lot
4,317 sqft
$185/sqft
2 Car Garage

About this House

Welcome to 217 Gloucester Drive. A well-maintained cape cod with Tudor details, located just off Apple Pie Ridge Road right near James Wood High School, this home features a 2+ acre lot, 4 Bedrooms and 4.5 baths, 3000+ square feet above grade, and a fully finished basement, for a total of 4300 finished square feet. Other features include: a formal dining room, 2 working wood Fireplaces, very nice landscaping, and nice hardwood floors on the main level. The current owner has lived here for 9+ years, and has done a great job of maintaining and improving the property. Come and see this comfortable family home,
217 Gloucester Dr, Winchester, VA 22603 is a 4 bedroom, 4 bathroom, 4,317 sqft single-family home built in 1986. It last sold for $755,000 on Apr 29, 2024 (3% below the $778,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $797,200, with a rent estimate of $3,698/month.
Last check for updates: about 3 hours ago
Listed by Chip Schutte, (540) 323-0732
RE/MAX Roots
Bought with: Bradley Comstock, (540) 631-4913, ERA Oakcrest Realty, Inc.
Source: Bright MLS, MLS#VAFV2017376

Home Details for 217 Gloucester Dr

Interior Features

Interior Details
Basement: Partial,Full,Finished,Exterior EntryNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 4317 Square Feet
Appliances & Utilities
Utilities: Cable ConnectedAppliances: Microwave, Dishwasher, Disposal, Dryer, Ice Maker, Double Oven, Oven, Oven/Range - Electric, Range Hood, Refrigerator, Washer, Electric Water HeaterDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Heat Pump,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Windows, Doors, Floors & Walls
Flooring: Ceramic Tile, Carpet, Hardwood, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: NoneFloors: Ceramic Tile, Carpet, Hardwood, Wood
View
No View

Exterior Features

Exterior Home Features
Roof: AsphaltOther Structures: Above Grade, Below GradeFoundation: Block, Active Radon Mitigation, Crawl SpaceNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Storage,Garage Faces Side,Garage Door Opener,Inside Entrance,Oversized,Driveway,Paved,Attached
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: On Site Septic
Finished Area
Finished Area (above surface): 3039 Square FeetFinished Area (below surface): 1278 Square Feet

Property Information

Year Built
Year Built: 1986
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial,Tudor
Building
Construction Materials: Frame, BrickNot a New Construction
Property Information
Condition: Very GoodIncluded in Sale: All AppliancesParcel Number: 42 16 14

Price & Status

Price
List Price: $778,000
Status Change & Dates
Off Market Date: Mon Apr 29 2024Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: WINCHESTERCommunity: Fox Lair
School Information
Elementary School: Call School BoardElementary School District: Frederick County Public SchoolsJr High / Middle School: Frederick CountyJr High / Middle School District: Frederick County Public SchoolsHigh School: James WoodHigh School District: Frederick County Public Schools

Building

Building Area
Building Area: 4317 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 2.33 Acres

Listing Info

Special Conditions: Standard

Offer

Contingencies: Appraisal, Home Inspection, Financing ApprovalListing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, Farm Credit Service

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: VAFV2017376Above Grade Unfinished Area: 3039

Price and Tax history

DateEventPrice
Apr 29, 2024
Source: Bright MLS #VAFV2017376
Sold
$755,000
Mar 14, 2024
Source: Bright MLS #VAFV2017376
Contingent
$778,000
Mar 1, 2024
Source: Bright MLS #VAFV2017376
Listed For Sale
$778,000
Sep 20, 2014
Source: Agent Provided
ListingRemoved
$499,900
May 1, 2014
Source: Agent Provided
PriceChange
$499,900
Price decreased by 5%

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! "
    6
    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."
    12
    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 217 Gloucester Dr

  • What is 217 Gloucester Dr estimated to be worth?
    Trulia's estimated value for 217 Gloucester Dr in Winchester, VA is $797,200.
  • What is the price history for 217 Gloucester Dr?
    217 Gloucester Dr in Winchester, VA last sold for $755,000 in April 2024.
  • 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 217 Gloucester Dr have air conditioning?
    Yes, 217 Gloucester Dr in Winchester, VA has air conditioning.
  • Does 217 Gloucester Dr have laundry facilities?
    Yes, 217 Gloucester Dr in Winchester, VA has in-unit laundry.

Explore by feature - Pet Friendly

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