Southeast Winchester: homes, schools, parks and commute

Last checked Oct. 19, 2026. The area and its boundaries are the City of Winchester’s Southeast 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).

Southeast Winchester is the city’s main shopping district, with Apple Blossom Mall and the big stores along South Pleasant Valley Road and Legge Boulevard, plus homes in a range of densities and types. The city’s 2022 Comprehensive Plan also lists three grocery stores, one neighborhood park and industrial land in the area. It holds about 760 of the city’s 16,729 address points, though it is the second-largest planning area by land.

What this means for you

• High school: John Handley High School, 425 Handley Blvd., rated Distinguished
• Elementary: Frederick Douglass Elementary for most addresses; part of the area is in the Quarles zone
• 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 1.9 miles by road

Where it is

The plan draws the Southeast area east of the CSX railroad and south of Millwood Avenue and Jubal Early Drive, down to the city’s southern tip. South Pleasant Valley Road runs through it from north to south. The plan’s redevelopment ideas for the area are the Apple Blossom Mall site, with new homes, shops and offices around the mall, and the land near South Pleasant Valley Road and Battaile Drive.

Every address is in ZIP code 22601 and in City Council Ward 3, on the city’s voting wards map.

Schools

Every city student goes to the same intermediate, middle and high school. Only the elementary school depends on the address. On the city’s School Districts map layer:

All seven city schools are Fully Accredited. Frederick Douglass Elementary has the highest framework score of the city’s four elementary schools, 88.34. The map layer is undated, so check one address with the division’s WebQuery lookup or call Winchester Public Schools at 540-667-4253. 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, 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. Our home prices guide has the trend.

Parks and trails

• Weaver Park, 167 Bruce Drive, about 6.5 acres, on the city’s parks map
• Green Circle Trail: the loop starts and ends at Millwood Avenue and East Jubal Early Drive, on the area’s northern edge, according to our parks and trails guide

Jim Barnett Park, the city’s largest, is just north of Jubal Early Drive in East Central.

Getting around

• Interstate 81: Exit 313 (U.S. 17, U.S. 50 and U.S. 522) is about 1.9 miles by road from the middle of the area’s homes; Exit 310 (U.S. 11 and Route 37, Kernstown) is about 2.7 miles.
• Downtown: the Loudoun Street Mall is about 2.9 miles by road.
• Washington Dulles International Airport: about 55 miles by road.
• Buses: the Loop Route stops on South Pleasant Valley Road at the shopping centers, at Adams Drive and Legge Boulevard, at Walmart on Legge Boulevard and on Crossover Boulevard at Winchester Station, according to the city’s bus stop map. The Laurel Ridge Route stops on Jubal Early Drive at Walgreens.
• On demand: WinReady rides cover the whole city.

Distances are measured on the road network with OSRM routing on OpenStreetMap data. They are distances, not drive times. More in our getting around guide.

Groceries and everyday stores

From OpenStreetMap:

• Apple Blossom Mall, with Belk, 1850 Apple Blossom Drive, and JCPenney
• Martin’s, 1950 S. Pleasant Valley Road, with a pharmacy
• Walmart Supercenter, 2350 S. Pleasant Valley Road, with a pharmacy
• Target, 2340 Legge Blvd., and TJ Maxx, 2330 Legge Blvd.
• Kohl’s, 2194 S. Pleasant Valley Road, and Ross, 2460 S. Pleasant Valley Road
• Walgreens, 645 E. Jubal Early Drive
• CVS Pharmacy, near Legge Boulevard

For holiday hours and new openings, see our Black Friday and holiday shopping guide and new businesses.

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 Southeast Winchester?

About 74% of addresses in the Southeast planning area are in the Frederick Douglass Elementary zone and about 26% in the Garland R. Quarles Elementary zone, on the city’s School Districts map layer. Check one address with the division’s WebQuery lookup.

What stores are in Southeast Winchester?

OpenStreetMap lists Apple Blossom Mall, Martin’s at 1950 S. Pleasant Valley Road, Walmart Supercenter at 2350 S. Pleasant Valley Road, Target at 2340 Legge Blvd. and Walgreens at 645 E. Jubal Early Drive, among others.

Is there a park in Southeast Winchester?

Weaver Park, 167 Bruce Drive, about 6.5 acres, is the city park inside the Southeast planning area.

What is the typical home value in Southeast Winchester?

The area is in ZIP 22601, where the Zillow Home Value Index was $349,952 in September 2026, up 1.1% from a year earlier. It is a modeled value, not a sale price.