The surname Chestereton was first found in Cambridgeshire, though the actual place of origin of the family is uncertain. The name is a habitational name, meaning that it was taken from a place where they lived, and presumably held some power; many names of this sort allow the family's place of origin to be pinned down very precisely, but Chesterton is a common place name in England; Chestertons exist in Cambridgeshire, Glouchestershire, Huntingdonshire, Oxfordshire, Staffordshire and Warwickshire.
The family could have originated and taken their name from any of these places or, more likely, the surname appeared around the same time in several of these places and there is more than one family Chestereton. The place-name itself comes from Old English and refers to a town or farmstead near an old Roman fort. Even the racial origin of the family is somewhat of a mystery; they crop up mere decades after the arrival of the Normans and the early occurrences of the name use the word "de," which is typically Norman, but some doubt remains; the family may in fact be Anglo-Saxon and predate the Normans.
Alternatively the name could have originated with Adam de Cestreton (d. 1269), "one of the justices itinerant in the reign of Henry III. He is said to have been the king's chaplain, and on 28 Nov. 1265 he received a grant for life of the mastership of the domus conversorum. "