The Dudley Diggs house occupies Lot 77 on the land originally purchased in November 1691 by David Stoner, the planter. He failed to build within the one year requirement and forfeited the land. He may have headed back to England according to his public notice of May 24, 1692. A few years later, Miles and Emanuel Wills in 1706 likely built a structure and remained there until 1721. From archaeological evidence, the Wills structure with cellar (38 by 18 foot) was closer to Main Street than the current building indicating the older house was likely occupied while the newer one was under construction. A merchant, William Stark, purchased the property in 1721 and remained until January 1731. Cole Diggs, grandson of Governor Edward Diggs, purchased the property and in 1744 at his death, his son Dudley this lot and others to include Lots 39, 42, 76, and 77. Dudley Diggs, then 16, continued to live at his residence at the Cole Diggs House (now the Carrot Tree Restaurant) on Lot 42 on Main and Read Street. In 1755 he added Lot 79, which then provided three adjacent lots (76, 77, and 79) for an excellent setting for his new home. An insurance policy of 1796 shows the new house on outline with a number of outbuildings shown as a granary, kitchen, smokehouse, well house, and stable.
Dudley Diggs was a close friend of Patrick Henry, and very influential in the American Revolution. He moved to Williamsburg after the Revolution. In 1787 he gave to house to his daughter, Elizabeth, who married Robert Nicholson. Dudley Diggs passed away in 1790, at age 62. In June 1821 the house was sold to Major John R. West whose wife was Elizabeth, daughter of Governor Thomas Nelson. This house was known as the “West House.”
In 1866 when Benson J. Lossing visited Yorktown, the town appeared desolate and the house, owned by Mrs. Robert Anderson, of Williamsburg, in which McClellan and all the Union commanders were quartered was not ravaged by the war.
Today the house owned by the National Park Service, having restored the home in 1960. The home is now leased by the Superintendent of Colonial National Historic Park (CNHP).