Perhaps a descendant of John Harry, who lived in Romney in the 1370S, Stephen paid maltolts in Bocherye ward from 1406 to 1428, and traded in the town as a butcher. He and his first wife held land at Peasmarsh in Sussex, which they conveyed to Thomas Oxenbridge in 1409.1Reg. Daniel Rough (Kent Rec. Ser. xvi), 154, 190; assmt. bk. 2, ff. 64-105; Suss. Feet of Fines, no. 2800.
In 1406 Harry became a feoffee of property at Wittersham, Kent, for Thomas atte Grove of Appledore. A few years later he and Henry atte Stone became involved in a dispute with the parson of Old Romney, which in 1419 they submitted to arbitration, each party entering into bonds of £40. On occasion Harry travelled out of Romney on the town’s business, as when in 1423-4 he went to Dover to represent his fellow jurats in a lawsuit.2CP25(1)113/290/294; CCR, 1419-22, pp. 45-46; assmt. bk. 2, f. 100.
Harry died shortly before March 1428, when his widow accounted for the rent for some land he had leased from the commonalty. She was still living in 1433.3Assmt. bk. 2, ff. 106-7, 114.