In 1363 Maisterman and his wife rented from the nunnery of St. Radegund a vacant site in the parish of Barnwell, a suburb of Cambridge. Nothing more is heard of him, however, until January 1380, when he attended the county court at Cambridge for the shire elections to Parliament, there offering mainprise for Roger Harleston, a prominent figure in the town.
Notwithstanding his unpopularity with certain sections of the community, Maisterman continued to hold the mayoral office until 1391 with only one interruption (1386-8), a length of service extremely unusual in the borough. He was also returned to a remarkably long succession of Parliaments, from his first in 1381 to his seventh in 1385, the sole exception being the Salisbury Parliament of April 1384, to which the town returned the man, John Marshall, whom he had displaced as mayor in 1381. It was during a further term as mayor that Maisterman was elected to his last Parliament, that of January 1390. In the meantime he had retained his connexion with the Hospitallers, in whose place he had exercised the right of presentation to the church of Sawston near Duxford in 1383. A few years later he was named as one of the six brethren of the religious guild attached to the church of the Holy Trinity at Cambridge.
