Situated atop a low hill, Stottesden seems to have been the nucleus of an extensive Anglo-Saxon estate held by Roger de Montgomery at Domesday, forfeited by Robert de Bellesme, then granted out piecemeal by twelfth-century monarchs. The central manor was granted by Henry III in 1240 to John de Plessetis during pleasure, and the following year the grant was made unconditional. Plessetis had been a knight in the king's service since at least 1227 and had distinguished himself sufficiently to be appointed keeper of Devizes Castle in 1239, sheriff of Oxfordshire the following year, and constable of the Tower of London in 1244. In 1243 he took as his second wife Margaret de Beaumont, daughter and co-heiress of the late Earl of Warwick; a few years later Henry made Plessetis, one of his favourites, Earl of Warwick, by right of his wife, thus temporarily by-passing the blood heir.
It was prior to that elevation that Plessetis obtained, in February 1244, a licence for a Tuesday market and a three-day fair in August for Stottesden. He was already the owner of a market at the manor of Gamlingay (Cambs.) which in 1239 was the subject of a complaint that it was detrimental to a market at Potton (Beds.); no licence is recorded for either, nor any outcome of the complaint, but a market was still operating at Gamlingay in 1279. After becoming earl John acquired, in the name of himself and his wife, licence for a market and fair at Brailes (Warks.), where an earlier earl had built a castle, and in 1275 it was complained that the earl's bailiffs were demanding excessive tolls at the market; Plessetis perhaps founded a short-lived town there, for it was referred to as a borough in 1268. He also obtained grant of a fair for the borough of Warwick in 1261, which he passed along to the burgesses the following year.
From John de Plessetis (d.1263), the manor of Stottesden (though not the title of earl nor any earldom estates) passed to a son Hugh, by John's first wife, and he gave it to John, son of Nicholas Seagrave, as part of a marriage contract (1270); the engaged couple were both children, so it was Nicholas who was the effective lord of the manor. Nicholas in 1292 obtained a market licence for the small Leicestershire town of Mountsorrel, while in the early fourteenth century John would go on to establish markets at his manors of Alconbury and Fen Stanton, both in Huntingdonshire. In 1292 John, who had been in possession of Stottesden for fifteen years, had to defend before the king's justices his claim to administering the assize of bread and ale at Stottesden, which he did by reference to Henry III's grant of the manor to Plessetis and to the market licence. The king's attorney objected that the market licence ought not to be valid, since it was granted to Plessetis and his heirs, and that John Seagrave was not an heir; the matter was referred to the next parliament, where John must have succeeded in asserting his rights, for he died (in 1324, the same year as his father) as lord of the manor.
Stottesden was built around a single axial street, off which ran minor lanes. The marketplace was probably a part of the street, still known as The Square, that opened out into a funnel shape. Stottesden, which has left little documentation from the medieval period, did not formally obtain borough status until 1619 and references to burgages are first encountered later in that century. Post-medieval maps do not give any clear indication of laid-out burgage plots along the axial street, although some may be tentatively identifed around the posited marketplace. It is possible the market licence points to a short-lived attempt to found a new town or a burghal component, which, failing to prosper, had reverted to a village before the close of the Middle Ages.
