By the 1570s, Henslowe had moved to London, becoming a member of the Dyers' Company. Henslowe is recorded working as assistant to Henry Woodward, reputed to be the bailiff for Anthony Browne, 1st Viscount Montagu, owner of Cowdray House and Battle Abbey in Sussex. Henslowe married Woodward's widow, Agnes, and from 1577 lived in Southwark, opposite the Clink prison. His elder brother Edmund, a merchant, also owned property in Southwark. It was at one time assumed that his wife's inheritance gave Henslowe his start in business, but there is no evidence.