Winchester 55+ Active Adult Retirement Communities

6 Communities near Winchester

Select one...
# Homes (High-Low)

55+ active adults will enjoy Winchester’s abundant natural recreation areas and its many historical sites.  Financially Winchester is appealing to seniors looking for retirement communities due to its low sales tax rate and because social security income is not taxed.

Climate & Geography

Winchester is in a humid subtropical zone with humid warm summers and cold winters. The area sees about 30 inches of rain per year, much of it falling during the month of May. Winter temperatures average from 23° to 40° and snow accumulations average over 17 inches. Summer in Winchester is hot and humid with summer temperatures averaging 64° to 86° and 79% humidity.

Located 10 miles south of the Virginia/West Virginia state line Winchester is in the Shenandoah Valley nestled between the Blue Ridge and Allegheny Mountains.

Recreation, Culture & Entertainment

There are a variety of leisure options for active adults in the Winchester area, including:

Historical sites and museums

    • Museum of the Shenandoah Valley
    • Stonewall Jackson’s Headquarters
    • Shenandoah Valley Civil War Museum
    • Kernstown Battlefield and Pritchard House
    • Washington’s Office Museum
    • Old Town Winchester
    • Stonewall Confederate Cemetery

Outdoor activities

    • Rocking S Ranch horseback riding
    • Abrams Creek Wetlands Preserve
    • Shawnee Springs Preserve
    • The Wagon Wheel Ranch horseback riding
    • Magic Mountain Farms horseback riding
    • Rock Harbor Golf Course

Other activities

    • Briede Family Vineyards
    • James Charles Winery & Vineyard
    • Ravenwood Faire

Cost of Living & Taxes

Virginia collects a personal income tax, sales tax, and food tax. The property tax is set and collected at a local level, which varies throughout Virginia. Social Security benefits are not taxed, and real estate is assessed at 100 percent of fair market value. The combined state, county and city taxes equals to a 5.3% sales tax on purchases in Winchester.

Health Care

Winchester Medical Center is the only hospital that is close to Winchester, the hospital has 495 beds and is a Level II trauma center. Warren Memorial Hospital and Jefferson Medical Center in Ranson, WV are both about 20 miles from Winchester. Warren Memorial Hospital has earned a grade A from the Leapfrog Group.

Take me back to the top
Scroll to Top