The City of Winchester was founded in 1744, and it's the oldest Virginia city west of the Blue Ridge Mountains. The City is located at the northern entrance of the Shenandoah Valley; the City encompasses 9.3 sq. miles and is the medical, industrial, commercial and agricultural center for the surrounding areas. The City has a population of approximately 27,000 with 6,600 single family homes and over 3,500 multi-family dwellings.