[5] By May 1656, Drummond owned a town lot in Jamestown, which he sold to John Barber in December 1664, not long after the Virginia General Assembly decided to subsidize the construction of brick houses in the colony's capital.
Drummond also acquired 1,200 acres on the east side of the Chickahominy River in Virginia (near its confluence with Warrany Creek), and expanded that parcel in 1674.
Drummond failed to respond to a summons issued by sheriff Francis Kirkman, a friend of Virginia Governor William Berkeley.
[6] Following his daughter's marriage to Samuel Swann, the eldest son of tavernkeeper and powerful planter Thomas Swann, Drummond held local offices in Jamestown and surrounding James City County, including as a Justice of the Peace, High Sheriff of James City County, bailiff of the Quarter Court and sergeant at arms of the Virginia General Assembly (which met at designated times in Jamestown).
[9] 19th century historian John W. Moore characterized Drummond as a man who deserved respect and confidence, based on his plain and prudent lifestyle and concern for the people he governed.
Bacon may have half expected Drummond to convince people in the Albemarle colony to also rise against Governor Berkeley, but the Carolinians had no interest in the Virginia conflict and even if they did, could have provided negligible help to that rebellion.
[9] On September 19, 1676, as Bacon's followers burned Jamestown, Drummond set his own house ablaze, although he also rescued government records by moving them from the statehouse.
However, Drummond's widow (and executor of his estate) Sarah, initially supported (with her five children) by Bacon's allies, demanded that Lady Berkeley returned the property.