At fourteen his grandfather sent him back to Oldtown, were Raymound would studied at the Citadel for a number of years forge ten links of a maesters chain. He became a page at the court of his grandfather Lord Caswell, were he then became a page, though he never became a squire, as he read all the books and scrolls in his grandfathers library. In his early years Raymound read and write early then most of his other pears. He had a younger sister born three years after his birth, Maellery Hightower and a brother born five years after, Quentyn Hightower. Raymound was the first born of Lord Aldore Hightower and Lady Elen Caswell in 3265 VC. He wears simply grey, white, or black clothing. His once blond hair has all gone to greyish dark or white.
Raymound has a plain face, with wrinkles all around it. He has three sons, Theodore, Eon, Anderson and a daughter Fiyona. Raymound Hightower was Lord of the Hightower and head of House Hightower during the Wars for the Reach.