After farmer John Gregory moved from Mecklenburg County to Lunenburg County, he purchased land and constructed the earliest portion of the current Woodburn dwelling around 1815. The 168-plus-acre Woodburn property, straddling Meherrin River Road in southwestern Lunenburg, has remained in the Gregory family ever since. A fine example of an Early National-period vernacular dwelling with Federal-style detailing, the original house was a one-and-one-half-story frame building on a raised basement, reflecting the large residence of a middle-upper-income farmer. As the family and living standards grew, so too did the house. The family made additions likely around 1838 and 1890, and in 1938 and 1997, all of which complement the scale, form, and design of the original vernacular house. In 1937, the Works Progress Administration surveyed Woodburn as part of its Virginia Historical Inventory. The WPA surveyor noted the interior hinges and woodwork, particularly in the dining room, located then in the basement level. In 1971, when the Virginia Historic Landmarks Commission (now the Virginia Department of Historic Resources) re-documented the property, a surveyor again noted the hinges and woodwork, including “lovely mantelpieces,” and that it had been “beautifully restored.” The Woodburn property also includes two contributing sites–the Gregory family cemetery and the site of two collapsed stone chimneys–and an affiliated building of unknown purpose.