Originally owned by Jefferson's father-in-law, John Wayles, Lewis was brought to Monticello in 1774 following Wayles's death. Lewis met his wife, Jenny, and the couple had six children by 1800. But while “Jenny… [and the] children of the said Jenny,” were leased to tenant farmer John H. Craven “for the term of 5. years” at adjacent Tufton, Lewis remained at Monticello.
In 1798, “Davy, Lewis & Abram … [did] the carpenter’s work of Bagwell’s house,” likely near the Rivanna River. Later, Lewis worked on the renovation of the main house under joiners James Dinsmore and John Oldham. Though in 1801 “Luis went of[f] from me [Oldham] twice,” Lewis continued to work on the mountaintop. In 1807, Jefferson wrote Dinsmore that Lewis should “be constantly engaged in getting ready those ballusters,” for Monticello II (1796–1809). After the hired white joiners left Monticello, Lewis continued to work in the Joiner’s Shop with John Hemmings, making furniture, including a dressing table, and “a set of Venetian blinds.”