What is considered the oldest family-owned business in America is located a scenic drive down Route 5 in Charles City and home to Lauren and Charles Carter.
Shirley Plantation, Virginia’s very first plantation, was founded in 1613 as a result of a land grant to Sir Thomas West. In 1638, the land changed hands to Edward Hill I, whose descendants – eleven generations – have been taking care of the land ever since.
Currently, the property is open to the public daily for tours and events, including the main floor of the “Great House.” Lauren and Charles Carter live in the second and third floors of the home.
The “Great House” was built in 1738 when Elizabeth Hill married to John Carter. Though it’s considered a Queen Anne, the home has a number of elements that Charles imagines Elizabeth and John saw on their travels in Europe and incorporated into their own home, like the unique “Flying Staircase.”
Visitors can view original family artifacts and hear family stories on the guided tour. The Carters have a pretty good understanding of the family history since family records were kept safe in the home over the years.
“That’s one special thing about Shirley that you won’t find at other places,” Lauren said. “Because we’re now on the twelfth generation and the family never left, all those documents stayed with the family.”
Since before Charles was born, the home had been open for tours.
“Charles certainly grew up knowing the expectation of him being the next patriarch of the family, but really we consider ourselves not so much the owners of Shirley but rather the stewards,” Lauren said.
One of the reasons that the property is still in the family is because of who was chosen to inherit the house over the years. Rather than automatically handing the property to the oldest son, the Hill-Carter descendants sometimes strayed from tradition and elected the family member they thought was most likely to keep the house in the family and care for it.
“They made the best choices for preserving the place,” Charles said. “Shirley has been run by women almost forty percent of the time in its history.”
Over the years, Charles said, the owners showed adaptability, another reason he credits for its longevity. When the tobacco industry stopped booming, they instead planted a variety of crops, ran a lumber mill at times, and were even ice merchants following the Civil War.
Charles continues farming crops like soybeans and wheat on the land, and has the same entrepreneurial spirit of his descendants. He recently planted pecan trees, which he hopes will grow for another hundred years and provide for his children.
Today, the Carters say that while it can feel like living in a fishbowl at times having their home in such a public display, they are happy to accept the responsibility to continue running the property for the next generation.
“Sometimes when I am giving a tour I say that I live here with my family and they go ‘You live here? Why are you letting us in your house?’” Lauren said. “Because it’s too special not to share. That’s our contribution.”
To learn more about this home, click here.
Where We Live is a weekly feature looking at homes in the Historic Triangle. Do you have a home, on or off the market, that our readers may be interested in seeing? Let us know at [email protected].

