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.
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.
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.