During the lifetime of his elder brother John, the fourth lord, and very soon after her husband's death in Ireland (20 July 1398), Edward married the widowed Countess of March.
About this time Charlton showed his personal severity and the extent of the franchises of a lord marcher by condemning to death the seneschal of Usk for an intrigue with his natural sister, probable prioress of that town.
In 1406 his new charter to Welshpool shows in its minute and curious provisions the extreme care taken to preserve that town as a centre of English influence, and exclude the 'foreign Welsh' from its government, its courts, and even its soil.
In January 1414 Sir John Oldcastle, after his great failure, escaped to those Welsh marches, where he had first won fame as a warrior, and ultimately took refuge in the Powys estates of Charlton.
There he lurked for some time until the promise of a great reward and the exhortations of the bishops to capture the common enemy of religion and society induced Charlton to take active steps for his apprehension.