Old Town, Winchester: homes, schools, parks and commute

Last checked Oct. 19, 2026. The area and its boundaries are the City of Winchester’s Old Town/North Central planning area from its 2022 Comprehensive Plan (Chapter 11). School zones, parks and bus stops come from the city’s open GIS data; ratings from Virginia’s School Quality Profiles; home values from the Zillow Home Value Index (Zillow Research); stores and road distances from OpenStreetMap (© OpenStreetMap contributors).

Old Town/North Central is the historic center of Winchester: the Loudoun Street Mall, the courthouse blocks and the streets of row houses and older homes around them. It is one of the 10 planning areas the city uses in its Comprehensive Plan, and its 2,860 or so address points, out of 16,729 in the city, are second only to the Northeast area.

What this means for you

• High school: John Handley High School, 425 Handley Blvd., rated Distinguished
• Typical home value, ZIP 22601: $349,952 in September 2026, according to Zillow
• Nearest I-81 exit: Exit 313 (U.S. 17, U.S. 50 and U.S. 522), about 1.8 miles by road
• School zone check: the division’s WebQuery address lookup or Winchester Public Schools, 540-667-4253

Where it is

The plan draws Old Town/North Central west of the CSX railroad, south of Wyck Street, east of the abandoned rail line and Stewart Street, and north of Gerrard Street, Handley Boulevard and Millwood Avenue. U.S. 11 runs through it as Loudoun and Cameron streets, and U.S. 50 as Amherst Street to the west. The plan describes the area’s clear hub as the historic downtown, with traditional architecture, many civic buildings and a mix of uses.

Every address in the area is in ZIP code 22601, the ZIP for the whole city. Most of the area falls in City Council Ward 1, with the eastern third in Ward 2, on the city’s voting wards map.

Old Town is also one of the city’s four Neighborhood Design Districts, a city effort to plan redevelopment and rezone land in advance. The city has posted an Old Town plan for public comment. For shops, restaurants and events downtown, see our Old Town Winchester guide.

Schools

Winchester Public Schools sends every city student to the same intermediate, middle and high school. Only the elementary school depends on the address. On the city’s School Districts map layer, the area is split:

All seven city schools are Fully Accredited. The map layer is undated, so confirm one address with the division’s WebQuery lookup before you rely on it. Our schools guide has every rating and how to register.

Home values

The Zillow Home Value Index for ZIP 22601 was $349,952 in September 2026, up 1.1% from $346,046 in September 2025. Zillow’s index for Winchester as a whole was $398,946 in September 2026, up 1%. The index is a modeled typical value for the middle third of homes, not a sale price, and one ZIP covers the whole city, so it does not separate Old Town from other areas. See our home prices guide for the trend.

Parks and trails

The city’s parks map places two small parks in or at the edge of the area:

• Ruth Jackson Memorial Park, 128 E. Cecil St.
• Mellon Park, 220 E. Pall Mall St., about 1.5 acres, on the area’s southern edge

The Green Circle Trail runs through Old Town as a marked walking and biking route, linking downtown with Jim Barnett Park to the east and Glen Burnie and the Museum of the Shenandoah Valley to the west, according to the city’s trail map. Our parks and trails guide has the full loop.

Getting around

• Interstate 81: Exit 313 (U.S. 17, U.S. 50 and U.S. 522) is about 1.8 miles by road from the middle of the area; Exit 315 (Route 7) is about 2.1 miles.
• Washington Dulles International Airport: about 52 miles by road.
• Buses: Winchester Transit’s Loop Route stops on Piccadilly Street at the walking mall and on Braddock Street at Clifford and Amherst streets, and the Boscawen Street hub serves every route, according to the city’s bus stop map. The Laurel Ridge Route to the community college starts there in the fall and spring semesters.
• On demand: WinReady rides cover the whole city.

Distances are measured on the road network with OSRM routing on OpenStreetMap data, from the middle of the area’s homes. They are distances, not drive times. More in our getting around guide.

Groceries and everyday stores

OpenStreetMap lists no full supermarket inside Old Town/North Central; the 2022 plan asks the city to recruit a grocery store downtown. The nearest are on Berryville Avenue in the Northeast area. Inside the area:

• Handley Library (listed in OpenStreetMap as Handley Public Library)
• Winchester Post Office, 132 N. Loudoun St.

How we built this

The boundary is the one the 2022 Comprehensive Plan gives in words; we drew it on the city’s own street and rail lines. School shares count the city’s address points inside each elementary zone on the city’s map layer. We do not name individual subdivisions or describe who lives in an area.

Related guides: all Winchester neighborhoods, moving to Winchester and property taxes.

Frequently asked questions

What elementary school serves Old Town Winchester?

It depends on the street. About two-thirds of Old Town/North Central addresses are in the John Kerr Elementary zone and about one-third in the Virginia Avenue Charlotte DeHart Elementary zone on the city’s School Districts map layer. Check one address with the division’s WebQuery lookup.

What high school serves Old Town Winchester?

John Handley High School, 425 Handley Blvd. Every city address goes to Handley, which is rated Distinguished on Virginia’s School Quality Profiles.

What is the typical home value in Old Town Winchester?

All of Old Town is in ZIP 22601, where the Zillow Home Value Index was $349,952 in September 2026, up 1.1% from a year earlier. That is a modeled value, not a sale price.

Is Old Town Winchester close to I-81?

Exit 313 (U.S. 17, U.S. 50 and U.S. 522) is about 1.8 miles by road from the middle of the area, and Exit 315 (Route 7) is about 2.1 miles.