Nestled among the rolling hills of Apple Pie Ridge north of Winchester, Cherry Row is an unusually large and sophisticated house that combines Georgian and Federal elements. The two-story brick house was constructed by David Lupton, one of several Quakers who lived in this area. Jack arches, a belt course, and a water table articulate the exterior. Cherry Row contains fine interior woodwork, some of which is based on designs in William Pain's popular pattern books. Innovative features are the basement with a vaulted brick wine cellar, a water trough fed by gravity from a spring a quarter of a mile away, and windows operated by cords and weights, believed to be the first such use in the Shenandoah Valley. The bucolic setting is enhanced by a collection of outbuildings of various dates, including a bank barn, a corncrib, chicken coops, and a stone meat house with a revolving rack for smoking meat.