The estate of Eyreville, located within the Eastern Shore county of Northampton, sits on a flat neck of land that extends into Cherrystone Inlet, which opens onto the Chesapeake Bay. The property includes the main historic dwelling, several outbuildings, an ornamental garden, and a multi-component archaeological site, which experts in Virginia believe is the oldest colonial site to be excavated on the Delaware/Maryland/Virginia (DELMARVA) peninsula to date. The Eyreville estate revolves around a two-and-a-half-story brick mansion featuring three distinct sections built in 1800, 1806, and 1839. While the dwelling was initially completed in 1800 in the Federal architectural style for one of its owners, William L. Eyre, Greek Revival- and Colonial Revival-style additions and alterations were incorporated in later decades. Documentary and archaeological evidence reveals English colonists may have settled at Eyreville as early as ca. 1623, but the first recorded occupation dates to 1637, when the first English colonist associated with the property, John Howe (ca. 1594 – ca. 1638), patented the land. From the 17th and 18th centuries to the turn of the 20th century, Eyreville was owned by families of high social, economic, and political standing, including the Kendalls and the Eyres. In 1942, Eyreville was acquired by Guy L. Webster, who owned one of the largest canning businesses in the nation during the mid-20th century. Webster, who used Eyreville as a private home and social space for entertaining guests, made upgrades to the mansion, including a rear colonnade that connected to an indoor swimming pool, and added many surrounding outbuildings as well as a formal garden. By 1945, construction of all architectural resources on the property had been completed.  Since 2017, DHR field schools at Eyreville have revealed the remains of two possible post-in-ground structures from ca. 1620 to 1630, two brick foundations dating to the 1650s, and numerous artifacts related to 17th-century trade with Native Americans and English and Dutch interests. Eyreville possesses the potential to yield additional sites, features, and artifacts that could further inform the study of early Chesapeake society, trade relations between the colonies and Europe, and other research topics related to the areas of exploration, settlement, and architecture.