Living in Winchester, VA | Community Info | Long & Foster

Living in Winchester, VA

Winchester, Virginia, used to be a hidden gem in the Shenandoah Valley. However, as the population of the Washington, D.C., metro area expands, more and more people are finding Winchester and making it home. Winchester offers a laid-back, small-town atmosphere that provides a nice contrast to the nation's capital, located about 75 miles to the east. What's more, the city of Winchester, Virginia, is steeped in history, especially due to the many Civil War battles fought in the region.

Pedestrian mall in Winchester, VA

More Than the 'Apple Capital'

Winchester, Virginia, earned the nickname the "Apple Capital" because of the large of swaths of orchards surrounding it. In fact, this small city is one of the largest U.S. apple export markets. Every year, around the end of April and beginning of May, hundreds of thousands of folks flock to Winchester, VA, for the Shenandoah Apple Blossom Festival. Celebrities such as Mario Lopez (2012) and Val Kilmer (2010) have served as grand marshals at the festival.

The downtown area is one place where Winchester really shines. It offers history among restaurants and shops galore. Popular historic sites in the city include Civil War-era cemeteries and barracks, and the headquarters of George Washington, Stonewall Jackson, and Philip Sheridan, a Union general. Shenandoah University, a private liberal arts school, also calls Winchester home, and its conservatory is downtown.

People walking on Pedestrian mall in Winchester, VA

Where Patsy Cline Lived

Singer Patsy Cline is one of the people who called a Winchester neighborhood home. She lived in the house from ages 16 to 21, but moved after her marriage to Gerald Cline. While the house is in a working-class area, it is not among the homes for sale in Winchester, and it is a popular tourist spot and on the National Register of Historic Places.

Museum of the Shenandoah Valley in Winchester, VA

Housing and Recreation in Winchester

Winchester, Virginia, real estate is a fun mix of old homes, townhouses, and new development. Whatever your needs and budget, chances are good that you'll find a match to help you live in Winchester. The city provides plenty of opportunities for getting out and about. There are the many festivals, of course, and also sites such as the 3-acre Wilkins Lake, a dog park, and a disc-golf course. Nature's playground awaits not far off in the forms of the George Washington and Jefferson National Forests, Shenandoah National Park, and Monongahela National Forest. Hiking and horseback riding are just two of the activities that Winchester residents enjoy at these places.

There's no question that Winchester, Virginia, appeals to a diverse mix of people, from those who commute to work in Northern Virginia to those who are retired. With its housing options, small-town charm, and proximity to D.C., there's much to love about Winchester.


Getting There & Around


What Locals Love

Don't Miss It

  • The highlight event of the year, the Shenandoah Apple Blossom Festival is a family-friendly event that features parades, carnival rides, music competitions, dances, and the coronation of Queen Shenandoah.
  • Downtown Winchester features a walking mall that shares space with modern day amenities, historic buildings, and artifacts from the past.
  • Locals and tourists alike love to pay a visit to the house that Patsy Cline grew up in, a modest home located in the center of town, which also features walking tours.


Winchester Real Estate at a Glance

  • 294 Homes Sold*
  • 93 Avg. Days on Market*
  • $445,000 Median Price*

*over last 3 months

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