The Oliver family held property in Dartmouth in Devon from early in the fourteenth century,
Exactly how long Oliver remained in the duke’s service or stayed with him in France is not known, but it must have been soon after his return to England that he acquired property in Dorchester through marriage to the widow of a former bailiff of the town. In October 1423 he and his wife Alice leased out a house called ‘La Pentys’ in High West Street, which she held by her late husband’s bequest, and in her will of 6 May 1425 Alice bequeathed to Oliver this same property together with a burgage in the lane leading from South Street towards Durnegate.
Oliver continued to add to his landed holdings in Devon,
