Winchester VA : Virginia


What It Is Like to Retire in Winchester VA

Winchester is a growing town of just over 25,000 in extreme northern Virginia.  Winchester has a long history going back to the French and Indian War, the Revolution, and the Civil War.  The nearby mountains and Shenandoah National Park are quite beautiful, yet it is not that far from Washington D.C. A college town, Winchester is home to the 3,400 students of Shenandoah University (a Methodist affiliated university). Winchester was listed as one of the most affordable cities by AARP. Photo of Glen Bournie Museum courtesy of Wikpedia and GustaveCourbet in the public domain.

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Where to Retire in Winchester VA and Home Prices

You can live in town or in one of the nearby active adult communities. Nearby towns and places like Lake Frederick also have 55+ communities (see link at top left to Shenandoah and others). Zillow reports the median home value was $341,084 in mid-2022.


What Is Special about Winchester VA

The rich history and beautiful Shenandoah Valley are 2 good reasons to consider Winchester. Old Town Winchester features interesting shopping and restaurants, along with a pedestrian mall. Colonel George Washington designed and began constructing Fort Loudoun in 1756 on the site of present-day Winchester.  There are at least a dozen places listed on the National Register of Historic Plans, including the Winchester Historic District.

What Is Not Special about Winchester VA

Some people might find the pace too slow.

Who Will Like Retirement in Winchester VA

People who want to retire to a little more of a rural area that still has a nice town might like it in Winchester. Civil War and history buffs will like it too.

Local Economy Is Driven by

Tourism, government, education, and health care dominate the local economy.

Climate and Physical Environment

Winchester is in north central Virgina, perched just above the Shenandoah Valley. The average July high temperature is 85 and the average January high is 39 (the average low is 22). The wettest month is May (4").

Restaurants & Cultural Scene

The annual Shenandoah Apple Blossom Festival has existed since 1924 and draws approximately 250,000 visitors to the area. The Museum of the Shenandoah Valley has gardens, museum, and a home to visit.


The crime rate is slightly below the U.S. average.

Medical Facilities

Winchester Medical Center serves the town.


I 81 goes through town. There is a small airport.

Valuable Links

Old Town Winchester

Winchester Virginia


What people are saying about Winchester VA

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