Sherard was the son of a namesake, who before 1407 held a burgage in Dorchester situated on the lane leading to Durnegate. Perhaps this was the same property that he himself was to occupy later.
The status of ‘gentleman’ implies that Sherard had received a legal training, so it may well have been he who was enfeoffed in 1412 by Robert Quarell of lands in Winterborne Strickland for the purposes of effecting an entail.
Sherard claimed to be the direct descendant and heir of one Alice Rosel, who had lived in the early fourteenth century, as such asserting his right to the Dorset manor of Colway in 1428. On this occasion he was defeated on a technicality after one of the defendants, William, Lord Botreaux, said that it rightly belonged to Thomas Carminowe*, but undeterred, he brought other suits in the court of common pleas as Alice’s heir in Hilary term 1435.
