Sir John Montgomerie of Hessilhead and Corsecraigs inherited the estate from his father, Hugh Montgomerie of Bawgraw (Balgray). John was slain at the battle of Flodden in 1513 and the estate passed to his son Hugh, who died on 23 January 1556. Hugh's heir was his son John who was appointed one of the tutors to Hugh, third Earl of Eglintoun. John married Margaret Fraser of Knock and was succeed in 1558 by his son Hugh. This "young Hugh" was a member of the Convention Parliament of 1560, at which the Protestant Confession of Faith was established.