2721 Middle Rd, Winchester, VA 22601
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OFF MARKET

2721 Middle Rd
Winchester, VA 22601

  • 6 Beds
  • 3 Baths
  • 3,452 sqft (on 0.37 acres)

$528,100

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $2,911/mo*
Refinance Your Home

$528,100

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $2,911/mo*
Refinance Your Home
6 Beds
3 Baths
3,452 sqft
(on 0.37 acres)

Local Information

  • Map ViewExplore the area around 2721 Middle Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2002
Lot Size
0.37 acres
Living Area
3,452 sqft
Price/Sqft
$153
Parking
2 Car Garage

Description

Move-in ready with endless possibilities! This large home is just minutes from downtown Winchester. Enjoy hardwood floors on the main level which includes 4 bedrooms, 2 full baths, and laundry. The lower level offers over 1000 square feet of living space that includes 2 additional bedrooms and 1 full bath. The lower level has a separate entrance and a sink and wiring in place to complete a full kitchen if desired. This space could easily become a small separate rental to provide additional income, or an in-law suite! Other details: -new HVAC installed 2023 -new hot water heater installed 2021 -no HOA
2721 Middle Rd, Winchester, VA 22601 is a 6 bedroom, 3 bathroom, 3,452 sqft single-family home built in 2002. It last sold for $508,000 on Mar 14, 2025 (1% below the $515,000 asking price). It is currently off market. The Trulia Estimate is $528,100, with a rent estimate of $3,487/month.

Home Details for 2721 Middle Rd

Interior Features

Interior Details
Basement: Connecting Stairway,Partially Finished,Rear Entrance,Windows,Space For Rooms,Exterior Entry,Interior Entry,HeatedNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 6Main Level Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 3452 Square Feet
Appliances & Utilities
Utilities: CableAppliances: Microwave, Oven/Range - Electric, Dishwasher, Disposal, Dryer, Ice Maker, Refrigerator, Washer, Water Heater, Gas Water HeaterDishwasherDisposalDryerLaundry: Main LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Programmable Thermostat,Natural GasHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Gas/Propane, Mantel(s)Has a Fireplace
Gas & Electric
Electric: Underground
Windows, Doors, Floors & Walls
Window: Double Pane Windows, Window TreatmentsFlooring: Carpet, Hardwood, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: Stair LiftFloors: Carpet, Hardwood, Wood
View
Has a ViewView: Trees/Woods, Street

Exterior Features

Exterior Home Features
Roof: Architectural ShingleOther Structures: Above Grade, Below GradeFoundation: PermanentNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Faces Front,Inside Entrance,Asphalt,Attached
Pool
Pool: None
Frontage
Responsible for Road Maintenance: City/CountyRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2052 Square FeetFinished Area (below surface): 1400 Square Feet

Property Information

Year Built
Year Built: 2002
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Ranch/Rambler
Building
Construction Materials: Vinyl SidingNot a New ConstructionNo Additional Parcels
Property Information
Condition: GoodParcel Number: 28904C 85

Price & Status

Price
List Price: $515,000
Status Change & Dates
Off Market Date: Fri Mar 14 2025Possession Timing: Immediate

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: WINCHESTERCommunity: Westridge
School Information
Elementary School District: Winchester City Public SchoolsJr High / Middle School: Daniel MorganJr High / Middle School District: Winchester City Public SchoolsHigh School: John HandleyHigh School District: Winchester City Public Schools

Building

Building Details
Builder Name: Butler Builders
Building Area
Building Area: 4104 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.37 acres

Listing Info

Special Conditions: Standard

Offer

Contingencies: Appraisal, Financing Approval, Home Inspection, Home SaleListing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, VA Loan, VHDA

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: VAWI2006284Above Grade Unfinished Area: 2052
Last check for updates: about 4 hours ago
Listed by Chad Lesman, (540) 539-8362
RE/MAX Roots
Bought with: Teresa Strohmeyer, (540) 664-2000, ERA Oakcrest Realty, Inc.
Source: Bright MLS, MLS#VAWI2006284

Price History for 2721 Middle Rd

DatePriceEventSource
03/14/2025$508,000Sold
Bright MLS #VAWI2006284
03/12/2025$515,000PendingBright MLS #VAWI2006284
12/18/2024$515,000ContingentBright MLS #VAWI2006284
12/06/2024$515,000PriceChange
Bright MLS #VAWI2006284
09/18/2024$525,000Listed For SaleBright MLS #VAWI2006284

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$4,936
Assessment$620,900
Home facts updated by county records

Comparable Sales for 2721 Middle Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2723 Windwood Dr, Winchester, VA
0.07
Single-Family Home
$525,000
11/14/25
3
3
2,726
2708 Cassidy Ct, Winchester, VA
0.23
Single-Family Home
$650,000
01/21/26
5
3.5
3,552
2812 Ridgetop Ct, Winchester, VA
0.14
Single-Family Home
$525,000
12/23/25
4
3.5
2,976
800 Kennedy Dr, Winchester, VA
0.14
Single-Family Home
$635,000
08/01/25
5
4
2,639
800 Lake Dr, Winchester, VA
0.19
Single-Family Home
$675,000
02/12/26
5
4
4,576
921 Kennedy Dr, Winchester, VA
0.18
Single-Family Home
$739,000
08/13/25
5
4.5
4,625
609 Crystal Ct, Winchester, VA
0.25
Single-Family Home
$450,000
11/21/25
4
2.5
2,868
407 Mikey Ct, Winchester, VA
0.14
Single-Family Home
$690,000
07/09/26
3
3
3,280
2321 Stoneridge Rd, Winchester, VA
0.47
Single-Family Home
$625,900
11/12/25
4
2.5
3,512

Nearby homes

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Assigned Schools

These are the assigned schools for 2721 Middle Rd.
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! "
    1
    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."
    7
    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

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Explore by feature - Garage

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Explore by feature - Outdoor Space

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Homes for sale near 2721 Middle Rd

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Off Market Homes Near 2721 Middle Rd

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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