272 Homes For Sale in Winchester, VA

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Winchester is located in the Shenandoah Valley region of Virginia. This suburb boasts a rich history, as while working as a land surveyor, George Washington made his first trip here at age 16. With a population just over 27,000, the suburb offers a blend of historic charm, modern-day amenities and family-friendly events. There’s a home for you here, whether it’s located in the historic Clifford neighborhood, sits on three acres of land or is within walking distance of Winchester’s Old Town Mall.

Downtown Winchester (aka Old Town Winchester) values its heritage. This Virginia Main Street community is an important marketplace with a 250-year history and features a 45-block pedestrian walking mall. You will experience an eclectic mixture of antique shops, upscale furnishings, gift items, local and regional artwork, and fine clothing stores. The restaurants include indoor and outdoor café dining. Instead of strolling through downtown, you can use the city’s public transit system Monday through Friday. You have the option of travelling by bus or trolley. For travels outside of Winchester, there’s the Winchester Regional Airport, which is 70 miles from Dulles International Airport, and seven major roadways to get you where you need to go.

The signature Winchester event is the annual Shenandoah Apple Blossom Festival. Started in 1924, the festival has expanded into a ten-day extravaganza. Every year, hundreds of thousands of folks celebrate the arrival of apple blossoms while adorning the city in green and pink. There are over 30 events, including concerts, dances, a 10k race, golf tournament, wine festival, two massive parades, and more. Speaking of apples, the local farm market is a family favorite where residents pick fruit, take wagon rides or hang out at the playground. The Jim Barnett Park is the spot where you can enjoy a picnic lunch, chill by the swimming pool, play golf, basketball or tennis, hike, fish or go horseback riding. The other major events include Rockin’ Independence Eve, October Fest, KidzFest and Family Movies on the Mall, just to name a few. Winchester is a hard-working community in which 71 percent of its residents hold blue-collar jobs. There are four elementary schools, a middle school and high school serving the children of these hard-working families. In addition, there are two institutions of higher learning - Lord Fairfax Community College and Shenandoah University. If you work hard, play harder and relish a family atmosphere, then browse our selection of homes for sale in Winchester. Filter the listings and find your ideal property.