Robert’s father, John, represented their county in the Commons on at least six occasions in the reigns of the first three Lancastrians, and his elder brother Thomas did likewise in 1435 after their father’s death. Robert, a younger son, was first returned for the county town of Guildford in 1429, undoubtedly with the support of his father, who was then serving as sheriff of Surrey and presided over the parliamentary elections.
Robert’s father died while they were attending the Parliament of 1433, and his elder brother Thomas succeeded to the family lands,
Robert assumed his family’s traditional place in county society. In November 1441 he took office as escheator, and thereafter was sporadically appointed to ad hoc commissions of local government. His standing in the locality appears to have been high, and although he was never returned to Parliament for the county, he did attest the election of the shire knights, conducted at Guildford, on no fewer than nine occasions between September 1435 (when his elder brother was returned) and September 1472.
In spite of his membership of Henry VI’s household, Wintershall may have been an early convert to the Yorkist cause. In late 1460, after the duke of York and his allies had taken over the government, he was appointed to deliver the royal gaol of Guildford, and he received further such appointments after Edward IV’s accession, when he was also added to the county bench. It is not certain whether he continued in his household office throughout this period, but the terms of its grant to his younger son Thomas in June 1464 may suggest that he did.
Little else is known of Wintershall’s career. He was well connected among the county gentry, at various times serving or employing as a feoffee men like Thomas Slyfield* and William Redstone*.
