Shenandoah Valley’s Scenic City Is Becoming a Tranquil, Low-Stress Destination for Retirees

If history intrigues you and you’d rather not spend your retirement years hustling along busy city streets with the crowds, then this “Apple Capital” in Virginia might be the perfect home for you in retirement.

Winchester is known for its sprawling orchards and boasts an intriguing history that dates back several centuries, with relics scattered about town to prove it. Nestled in the Shenandoah Valley, Winchester was named one of Investopedia’s 100 best places to retire in the U.S.

How Much Will It Cost You to Live Here?

Winchester is reasonably affordable. A mix of single-family homes, townhomes, condos, and downsizing-friendly neighborhoods is available, and housing costs are kinder here than in many Northern Virginia locations. The median home sale price was $390,391 at the close of 2025. Half of all local homes sold for more than this, and half sold for less. You’ll also face a 0.795% property tax rate as a Winchester homeowner.

Maybe you don’t want to deal with all the responsibilities of homeownership in your golden years. Rentals averaged $1,629 here as of February 2026, according to Zillow. That’s $366 less than the national average.

The gasoline tax will cost you an extra, wince-worthy 41.6 cents per gallon in Winchester, and utilities run about 3% more than the national average, but groceries average about 1% less.

The state’s income tax rate is progressive. You’ll pay a greater percentage as your income rises. The rates in Virginia range from 2% to 5.75%. Virginia does not impose an estate or an inheritance tax.

Winchester’s Great Outdoors

Winchester’s great outdoors will take your breath away with its spectacular views of rolling hills, farmland, and mountains. The Museum of the Shenandoah Valley covers 90 acres and offers three miles of scenic trails if you want to take in the beauty on foot. Or you might prefer to stroll through the seven acres of formal gardens at the Glen Burnie House, built in 1794.

Skyline Drive awaits you with 75 breathtaking overlooks if you’d prefer to drive rather than walk. It stretches from Winchester to Front Royal across Shenandoah National Park. Of course, you can walk in the park’s 500 miles of trails if you want to.

You’ll find yet another 20 acres of trails across the Abrams Creek Wetlands Preserve, known for its rare plant species and birdwatching.

Winchester’s climate can get hotter and humid from late June through mid-August and at its coldest from the middle of December until early February, along with averaging the most rain in May (3.5 inches) and the most snow in February (6.7 inches).

The Pace of Daily Life

Winchester is the oldest Virginia city west of the Blue Ridge Mountains. It was founded in 1744. Home to about 27,800 residents, it’s a calm, friendly, medium-sized town community where you’ll find plenty of interesting things to do across its historic Old Town streets in your free time.

It’s a 72-mile drive southeast to the District of Columbia, so you have the option of visiting there if you find yourself craving a little of that urban life edge.

Walking and Enjoying Winchester’s Scenic Downtown

Walk Score has tagged the town as “very walkable” and says most of your errands can be done on foot. It’s a 16-minute walk to downtown Winchester from the outskirts, and just two minutes if you decide to drive. Winchester doesn’t rank highly for bikeability, though Walk Score indicates it offers little in the way of bikeable infrastructure.

You’ll find a lot to take in here. Old Town Winchester is a 250-plus-year-old market area. Eat, drink, and shop at the Loudon Street Pedestrian Mall as you take in more of the town’s history. Savor some apple cider donuts at the Marker-Miller Orchards Farm Market, or just buy a few of an impressive variety of apples and make your own treats when you get back home. Or visit the Bright Box Theater in the evening for some live entertainment spanning music, plays, and comedy shows by both national and regional artists, along with a full-service bar and mini-menu.

The Abram’s Delight house is Winchester’s oldest home. It was built in 1754 and is now a museum. It’s composed of two residences: the house and a historic log cabin. You can take in more of Winchester’s history across the 45 blocks of cobblestone streets lined with 18th- and 19th-century homes and architecture.

Winchester’s Culture and History

Winchester was the site of several Civil War skirmishes. General Stonewall Jackson’s headquarters is here, which he occupied across the winter months of 1861 and 1862. Winchester was claimed back and forth between the North and the South 70 times during the war. The Old Courthouse Civil War Museum showcases some 3,000 relics of Civil War history on North Loudoun Street, including weaponry and uniforms.

George Washington spent time here from 1748 through 1758 during his younger years before he became the first president of the United States. He first visited as a land surveyor at the age of 16. The George Washington Office Museum is a preserved log cabin you can visit on West Cork Street.

Country Music Hall of Fame singer Patsy Cline was born here in modern times. She was a soda fountain waitress in her early years, and she married here. The Patsy Cline Historic House is a must-visit for guided tours. Cline lived in this home from age 16 to 21. It displays personal memorabilia and its original furniture.

What if history doesn’t fascinate you? Take in the Shenandoah Apple Blossom Festival across 10 days in late April through early May each year. It includes more than 40 events, including a carnival, parades, an arts and crafts show, live music, and local food offerings.

Healthcare in the Winchester Area

Access to quality healthcare is a major factor in deciding where you want to retire. Winchester ranks high in this area as well. It’s home to the highly ranked Winchester Medical Center, located right in town, and a good number of primary care physicians call Winchester home as well.

Winchester Medical Center was named to America’s 50 Best Hospitals for Cardiac Surgery list in 2025, and there are 23 additional hospitals within 50 miles of town.

At the state level, the Virginia Insurance Counseling and Assistance Program (VICAP) stands ready to help you with individual counseling on any Medicare issues or problems you might encounter.

For retirees with military service, the U.S. Department of Veterans Affairs offers an outpatient clinic in Winchester.

Healthcare in Winchester will cost you about 2% more than the national average.

The Bottom Line

Winchester is a historic town in Virginia’s Shenandoah Valley. The oldest Virginia city west of the Blue Ridge Mountains, it’s a calm, friendly, medium-sized community that offers spectacular scenery and views. The cost of living here is reasonably affordable, and it’s served by the award-winning Winchester Medical Center. If retiring in Virginia is your goal, you could do far worse.