In November 1691 the town trustees deeded Lot 36, on the corner of Main and Church Street, to William Digges of Bellfield Plantation, but he failed to build on it and hence forfeited it. After eight year with no construction, it was reassigned to Robert Lightenhouse, a school teacher. He too failed to build and his widow, Elizabeth who married Mungo Somerwell began to build on the lot. He to dies and Elizabeth successfully in May 1707 obtains title to the lot and buildings. She married Edward Powers, then she dies. The property was willed to Joseph Mountfort “as heir at Law.” Next Mountfort sells the property in 1716, now a rental property, to Philip Lightfoot. The property was rented by Mary Smith who operated it as an ordinary starting in 1715. Philip Lightfoot dies in 1748 passing the property to his son, William, including a storehouse which he had bought from Joseph Mountfort. Lightfoot in 1783 sells the property to John Moss. The Bertier plan of 1781, showed three small structures on Lot 36 – the T-shaped Somerwell house, a small structure to the east, and a large one beyond that one.
John Moss built a store on the eastern half of the lot. The entire property was sold to Peyton Southall in July 1804 having split the property up in 1798. A number of fire insurance properties in the first half of the 19th century, with the earliest in 1817, provided the following description: Dwelling of brick covered with wood (39 by 42 ft), a kitchen wood covered with wood one story (18 by 24 ft), stable wood covered with wood one story (16 by 16 ft), dairy, and smoke house. The policies continued through 1853 as did a store wood covered with wood (25 by 44 ft) one and a half stories). This was likely the store Moss built in the southwest corner. The policy of 1823 indicated the east and west sides of the rear wing of the Somerwell House had porches.
During the Civil War, the stable was moved behind and the structure was enlarged and served as a hospital for Union troops. Following the war, the entire structure was made into a hotel. There was a sizeable addition here in 1881 at the centennial observance and known as “Dawson’s Hotel.” This was a long and low dormered extension with a porch behind it. There was already of porch on the front side as noted in a postal card of 1903. In the winter of 1917-18, a sailor photographed the building showing the extension had been raised to two stories.
Also at the centennial celebration, a large two-story framed building was constructed parallel to the Somerwell House. The Somerwell House however continued to be the principle hotel known as the “Old English Tavern” and next as the “Yorktown Hotel.” Many a sailor in 1918 frequented the hotel as the Atlantic Fleet anchored in sight of Yorktown.
By the 1930’s when the National Park Service acquired the Somerwell House, still a hotel, all traces of the dependencies had disappeared. The Park Service initially used the house as an administration building as well as housing for staff until the Swan Tavern was completed in 1934. There were initial repairs in 1932. The full restoration proceeded from 1935-36. After restoration it became the Park Headquarters for some 20 years. In the extreme north corner, the Park Service constructed a period type stable which would house the Yorktown telephone exchange. The stable according to insurance records was 16 square feet. According to Peyton Southhall who occupied the house from 1804 until 1812, the stable held 3 horses, 2 cows, a carriage, and a cart. Using insurance data, investigative excavations beginning on July 8, 1935 was able to find the chimney for the kitchen, foundations for the smokehouse, floor for the stable and stable yard.