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. Ultimately, the Drummonds owned one of the finest brick houses in Jamestown. During the 1660s, while in Carolina as discussed below, Drummond also patented 4,750 acres in
Westmoreland County, Virginia, as well as bought 600 acres and laid claim to an additional 500 acres in that northern section of Tidewater Virginia. 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. He also bought from Mathew Edloe 700 acres in James City County in 1668 and patented 960 acres in Lower Norfolk County (which became
Norfolk County) in 1672. However, Drummond also clashed with several powerful planters, including
Theodorick Bland and Bryan Smith. During Drummond's time as governor, he and several others went hunting in the
Great Dismal Swamp and became lost; Drummond was the expedition's only survivor. In 1665 Drummond discovered the water source for the Great Dismal Swamp, which lies at its center and is now called
Lake Drummond in his honor. 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's Rebellion, execution and litigation==