A native of Romsey, Wichford is first noted in 1395 when he became a scholar at Winchester college, it being perhaps intended that he should enter the Church. However, he chose the legal profession instead, and completed his training by 1408, then standing bail in Chancery for a litigant from Ogbourne St. George in Wiltshire. Two years later, as the right heir of William Wichford, he inherited lands in ‘Bathampton Wyly’ in the parish of Steeple Langford, also in Wiltshire, from a distant relative, Christine atte Mulle. Yet despite his new role as a landowner, by 1414 he had decided to settle in Southampton, where through marriage to the widow of a former mayor he was able to take over her lease of a site in Bugle Street. This he conveyed in January 1415 to the vicar of Holy Rood church and other trustees, saving to himself and his wife a messuage in St. Michael’s parish (probably the house which they afterwards occupied on the west side of French Street). Ten years later Wichford sold two dwellings and a garden in English Street. In April 1429 his second wife’s mother settled on him all her lands and property in Winchester, Petersfield and elsewhere in Hampshire, probably including the tenement in Tanner Street, Winchester, for which he subsequently paid rent to St. John’s hospital.
Wichford’s main business as a lawyer was transacted in the local courts, or else concerned the transfer of ownership of property. But, as one of the attorneys officially appointed by the borough of Southampton, he went up to Westminster in 1414, 1415 (using the opportunity presented by his first election to Parliament) and 1417, on each occasion in order to pay the fee farm at the Exchequer.