Winchester, VA has been rated by Reader’s Digest as 1 of the Best Small Towns in America to Retire. Reader’s Digest describes Winchester in their article; If having room to roam, clean air to breath, and a quiet space to reflect and relax come to mind, retire to this Virginia town that’s only 65 miles west of Washington, D.C. Not only is this city budget-friendly, but 14.5 percent of its population is above the age of 65, meaning you have a high chance of making new pals. This is especially true if you’re active! In addition to golf courses for the birdie-seeking crowd, there are also opportunities for equestrian lovers and bicycle road warriors. Your friends and family will be keen to visit you, too since Winchester is home to the popular Shenandoah Apple Blossom Festival and plenty of parades, concerts, a circus, and more.

As real estate agents living in Winchester, VA, we can only agree with them. Winchester is a quaint area with so much to offer. Winchester is rich in history, dating back to the Revolutionary and Civil Wars. There are at least a dozen places listed on the National Register of Historic Places. Nestled in the beautiful Shenandoah Valley area, Winchester offers beautiful year-round weather boasting many local activities. You will never lack a nearby adventure. Whether you like shopping, dining, festivals (the annual Apple Blossom Festival!) or day trip car rides, you will find everything you need at your fingertips. Saturdays from May through October, the Old Town Farmers Market offers produce and baked goods from area farms.

Winchester is a playground for outdoor enthusiasts: From kayaking and fishing on the Shenandoah River or hiking in the nearby Shenandoah National Park in the warmer months, to being only minutes away from great skiing in the winter months. Many local farms feature pick your own produce and fruit, including strawberries, apples and pumpkins. Winchester and surrounding towns in Frederick County and the Shenandoah Valley offer many local wineries and breweries as well.

Winchester is rated below the U.S. average for crime rates.

Home prices are also below the U.S. median average home cost, boasting a median sold price in June of 2017 for Winchester and surrounding counties of $242,000. With such a large percentage of the population being over 65, many nearby towns and communities, such as Lake Frederick, offer 55+ only communities. Winchester offers a small-town feel, with a lot of Southern charm.

Active Adult Communities

Retirement Communities:

  • Willow Lawn Cottages

  • Harvest Ridge

  • Cross Creek Village

  • Cedar Meadows

  • Shenandoah at Lake Frederick

  • Cottage Glen

  • Woodbrook Village

  • The Highlands at Blue Ridge Shadows

  • Trilogy at Lake Frederick

  • Autumn Glen

  • The Village at Harvest Ridge