In 1406 Edmund Ford of Swainswick leased to Ashley and others various lands in the hundred of Berkeley, Gloucestershire. Ashley’s home, however, was across the border near Bradford in Wiltshire, he having inherited through his mother several properties in Trowbridge and elsewhere in that region, as well as in Salisbury. From 1414 he was joint lessee of the duchy of Lancaster lordship of Trowbridge and a fishery at Staverton on the River Avon. Ashley witnessed several local deeds, and attended the Wiltshire elections to the Parliaments of 1407, 1413 (May), 1414, 1417, 1421, 1422 and 1426.
Meanwhile, in 1418, the year before his own return to Parliament, Ashley had been fined 12 marks for marrying without licence Gillian Plecy, the widow of a tenant-in-chief. Besides dower lands in Dorset, Surrey and Northamptonshire, Gillian held, in her own right, the manor of Wimbourne St. Giles in Dorset, and stood to inherit, after her mother’s death, the manors of Cranbourne and Eastrop in Hampshire.
Ashley died shortly before 20 Apr. 1433. His widow married, thirdly, Thomas Thame, and lived on until 1476, when the heir to her estates was Ashley’s son, Edmund.