On October 31, 1808, house carpenter Abner Howard purchased twenty-two square rods of land on Pine Street for $250.00. Two years later he sold the property, with a dwelling house, to mariner David Swain 2nd (1784–1841) for $1,350. Swain became a master mariner and was captain of a number of whaling vessels: Lydia,1808–09 and 1810–12; John Jay, 1815–17; States, 1818–20; Constitution, 1821–23; and Lydia again on two more voyages, 1825–28 and 1830–33. His first wife, Phebe Ellis (1791–1831), spent most of her married life managing the household and four young children while David was at sea; she died while he was away on his last whaling voyage in the Lydia. In 1834, shortly after his marriage to second wife Eliza Bunker (1799–1868), Swain sold the house at 43 Pine to another master mariner, Seth Coffin Jr.