This limestone rubble house was constructed for Isaac Hollingsworth on land he inherited from his father, Abraham, an early Quaker settler. Built by master stonemason Taylor, the two-story center-passage gable-roofed house also served as a Quaker meetinghouse. The diminutive two-story west wing was added c. 1800. In the mid-nineteenth century the house was remodeled in Greek Revival by Isaac's grandson, David Hollingsworth, who also constructed the adjacent mill, a two-story, gable-roofed stone building. In 1943, the City of Winchester purchased the then-deteriorated house, renovated it, and opened it in 1961 as a house museum. The building now houses historical exhibits sponsored by the Winchester-Frederick County Historical Society.
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