Winchester

Background Image

Winchester, VA

Area Guide

Share Guide

A dream city in the Shenandoah Valley

Picturesque Unique Historic Shopping College Festivals Mountains

If you could design your dream city, would it include treasured historic sites, great shopping, an excellent location, beautiful parks, a popular university, and cozy neighborhoods tucked among rolling green hills? If so, then Winchester is a dream-come-true. Winchester was settled around 1729, and the town was officially chartered in 1752. The city played a role in three major wars: the French and Indian War, the American Revolution, and the Civil War. The Kernstown Battlefield, located on the Pritchard-Grim Farm, includes the 1854 Pritchard House. The Civil War battlefield park covers 350 acres and offers guided tours.

Old Town Winchester is a fantastic location to have as your backyard. This area features a brick-paved pedestrian mall lined with historic architecture, courtyards, and terrific shops and restaurants. It is the site of community events, including outdoor movies, the Haunted Pub Crawl, food and wine tours, a seasonal farmers market, Oktoberfest, and the Old Town Holiday Parade. The Shenandoah Apple Blossom Festival is held annually in Winchester, a huge event that attracts nearly 250,000 visitors a year and includes parades, a carnival, a wine festival, live music, and a 10K race.

The oldest house in Winchester, Abram's Delight, was built in 1754. This historic house museum is a state landmark and is listed on the National Register of Historic Places. It is located near Shenandoah University, a private liberal arts university that was established in 1875. Hikers can access the Appalachian Trail from Winchester, and Jim Barnett Park features a disc golf course, a fitness trail, indoor and outdoor swimming pools, a playground, the Winchester BMX, and ball fields. Shopping destinations include Winchester Station and the Apple Blossom Mall.

Explore the City

The historic Handley Library was built in 1913

A sunny day at Wilkins Lake

Rent Trends

As of January 2025, the average apartment rent in Winchester, VA is $1,169 for a studio, $1,326 for one bedroom, $1,506 for two bedrooms, and $1,801 for three bedrooms. Apartment rent in Winchester has increased by 3.3% in the past year.

Property Type
Average Rent
Average Sq Ft
Apartment
$1,326/month
714 Sq Ft
House
$2,298/month
1,658 Sq Ft
Townhome
$2,021/month
1,294 Sq Ft
See Rental Market Trends in Winchester, VA

Transportation

48

Car-Dependent

out of 100 WalkScore® Rating

This area is considered a car-dependent area and most errands will require a car.

39

Somewhat Bikeable

out of 100 BikeScore® Rating

You might be able to find places to ride your bike in this area, but you’ll most likely want your car for most errands.

Schools

Evendale Elementary

Public

Grades PK-5

530 Students

5
out of 10

Indian Hollow Elementary

Public

Grades PK-5

393 Students

5
out of 10

Frederick Douglass Elementary

Public

Grades PK-4

325 Students

5
out of 10

Armel Elementary

Public

Grades PK-5

615 Students

4
out of 10

John Kerr Elementary

Public

Grades PK-4

526 Students

4
out of 10

Daniel Morgan Middle

Public

Grades 7-8

613 Students

5
out of 10

Admiral Richard E. Byrd Middle

Public

Grades 6-8

804 Students

3
out of 10

James Wood Middle

Public

Grades 6-8

803 Students

3
out of 10

Frederick County Middle

Public

Grades 6-8

751 Students

2
out of 10

James Wood High

Public

Grades 9-12

1,437 Students

5
out of 10

Millbrook High

Public

Grades 9-12

1,516 Students

4
out of 10

John Handley High

Public

Grades 9-12

1,384 Students

3
out of 10

Points of Interest

Parks and Recreation

  • Shenandoah Valley Discovery Museum
  • Museum of the Shenandoah Valley
  • Hedgebrook Farms
  • State Arboretum of Virginia and Blandy Experimental Farm

Top Apartments in Winchester

Houses for Rent in Winchester

Property Management Companies in Winchester, VA

Search Nearby Rentals