During Bacon's Rebellion, Sherwood alienated both sides, and later served as the colony's Attorney General until disbarred for a previous felony.
[1][2] By his death, Sherwood owned most of Jamestown Island, which went to his heirs, including 28.5 acres known as Block House Hill specifically bequeathed to his nephew John Jarrett, who had died by 1710.
[5] During his lifetime, Sherwood also petitioned the king for reimbursement for over 11,000 pounds of tobacco destroyed when Jamestown burned, and another 1000 pounds sterling on behalf of his ward, the orphaned Richard James, because of a house destroyed in the fire set by Richard Lawrence and other Baconites.
In 1696, Sherwood sold two parcels totalling 2770 acres of land in Stafford County Virginia to George Mason.
The property included Dogue's Island, and a further recording was required in 1699 because he had not obtained release of his wife's dower interest.