Little is known of Medford’s origins or early career, although a John Medford, very likely the MP, was involved in transactions regarding property at Bromley and Hayes in Kent in 1443, and five years later, as an ‘esquire’ of the diocese of Canterbury, he obtained a papal indult for himself and his wife Sibyl enabling them to have a portable altar.
More is known of Medford’s career after what was almost certainly his second marriage, to Blanche, the widow of a London grocer, John Bolle. In his will, enrolled in October 1461, Bolle had left Blanche a life interest in properties in several places in Kent, together with buildings in the London parish of All Hallows Barking. These last Medford and Blanche made over in February 1466 to a group of feoffees including Thomas Mauncell† and John Young†. Other premises, in three different parishes in the city, were acquired by Medford from Juliana Whapshote of Horsell in Surrey, the heiress of a London draper, Walter Chertsey.
In spite of his post in London, Medford maintained his connexion with Surrey throughout his career, and in May 1467 he was among those who attested the county election at Guildford (at which his feoffee John Young was returned for the borough). Five years later he was asked to witness a quitclaim by (Sir) Robert Fiennes* of lands formerly belonging to Sir Robert’s late father-in-law William Massy.
In his will, dated 19 Oct. and proved on 7 Dec. 1487, Medford left a gold chain to his grand-daughter Bridget Weston (daughter of Margaret) for her marriage and gowns to his ‘cosyns’, John, Richard and William Medford. These and other bequests, including a gold chain inset with two pearls and a diamond given to Elizabeth, the child of another daughter, Isabell Castell, suggest that he had acquired a certain amount of wealth by the time of his death. He left his lands and tenements in Surrey to his widow for her lifetime, after which they were to pass to his son-in-law and executor John Castell, a London mercer. Medford asked to be buried in his parish church of All Hallows Barking, next to the stone erected, in advance, for Blanche.
