In 1354 Waleys relinquished possession of certain lands which, along with rents of £20 a year at Kersey and Hadleigh, he had apparently inherited from his father, and he then moved some ten miles east to Ipswich. There, in 1365 he and his wife, Alice, acquired land at Thurleston on the outskirts of the town and, three years later, shops in the parishes of St. Mary and St. Leonard. To these properties he later added 40 acres in Stoke next Ipswich and tenements in the parishes of St. Lawrence and St. Nicholas. In 1376 he became a feoffee, together with Walter Stratton, of holdings in the area of Westerfield belonging to another man from Ipswich.
Waleys quickly established a prominent place for himself in the merchant community of Ipswich, and built up trading connexions with the ports of the Baltic and the Low Countries, dealing in a variety of commodities which included grain, vetch, cheese, skins, cloth and iron. His fellow burgesses chose him as bailiff at least ten times; and it was by virtue of his office that he was responsible for making several parliamentary returns, recording among these his own election to the assemblies of 1377 (Oct.), 1385, 1386 and 1388.
In 1386 Waleys became a trustee of a manor at Sproughton on behalf of the widow of Sir Thomas Visdelou, and four years later, following her death, he and his co-feoffees granted the reversion of the same to John Slegh, the chief butler. In July 1395 Waleys obtained a royal pardon of outlawry for failing to appear in the courts at Westminster to answer two Salisbury drapers for a debt of £39 2s.8d. He was not so fortunate with regard to another outstanding sum: on 6 Apr. 1400 Sir John Cheyne I informed Henry IV that Waleys was in the Fleet prison as a result of legal action begun in the previous reign by the Exchequer for recovery of £23 10s. he had collected as customs revenue. Thanks to Sir John’s intervention, Waleys was released, and evidently cleared his name for, in July following, he was granted custody of crown property in St. Lawrence’s parish, Ipswich.
