Charlottesville is not where Cassie and Carrington Guy expected to end up. The couple first hired architect Thomas Ryan in 2013—like them, he was then based in New York, just starting his own firm—to renovate a brownstone in Brooklyn they were looking to buy. When that didn’t materialize, they thought about building a small weekend retreat on Long Island instead. But again their plans changed. With their two young children craving the country life they experienced visiting their grandparents, and a work-from-home scenario becoming more feasible with Carrington’s new business venture, the Guys, both originally from northern Virginia, decided to plant roots near the hometown of Thomas Jefferson, founding father and self-taught architect. Ryan, now in San Francisco and designing residences and art galleries on both coasts, was thrilled at the expanded scope of the project, and helped his clients find the 45-acre rolling property on which they would build their 5,800-square-foot house.