The original part of this home is believed to have been built by Andrew Mackie after he purchased the lot in 1758. Mackie and his family occupied the house until 1778, when he sold it to Captain John Sinclair. Sinclair occupied the house from 1778-1796. He was a colorful character who was the captain of a blockade runner during the Revolutionary war. As a blockade runner, he would secretly maneuver his ships through the blockade of British warships in order to bring in supplies to the colonists. After the war, he operated as a privateer against British trade ships.