Lying in the shadow of Kittoctin Mountain, the main building of Sleepy Hollow Farm is an evolved two-story stone dwelling, built by Quaker Jacob Janney in 1769, with additions in 1820 and 1890. Janney’s relocation from Pennsylvania in the mid-18th-century is representative of the broader movement of Quakers into the Waterford and Leesburg areas, bringing with them important farming traditions and social tenets that had profound importance for this area of Virginia. The form and plan of the main house is representative of common forms seen in Maryland and Virginia. Its fine interior exhibits the diffusion of stylistic treatments from urban to rural areas that accompanied the accumulation of wealth and prosperous agricultural practices, through details such as mantel and trim motifs. The property also contains a stone springhouse, which still supplies water to the house and one of the barns. Sleepy Hollow, today on 14 acres, is an excellent example of Loudoun County architectural development associated with the migration of an important social and religious movement in Virginia’s history.