The son of Staffordshire’s junior county Member in 1604, Littleton was knighted and appointed to the Staffordshire bench in his father’s lifetime. In 1610 he inherited a substantial estate centred on Pillaton Hall, in the parish of Penkridge, six miles south of Stafford. He kept a ‘bountiful and liberal house’,
It was probably not long after his return to Staffordshire that Littleton became embroiled in a feud between John Bowen, the minister of Penkridge, and his parishioners. Bowen, who had been installed by Littleton in 1617, may have been a puritan, as one of the charges against him was that of nonconformity, but he was also accused of having fathered an illegitimate child. High Commission dismissed the case, but Littleton was then sued in Star Chamber for exerting undue influence on Bowen’s behalf. It is unclear how much these cases reveal about Littleton’s own religious leanings, although it may be significant that he admitted to failing to investigate rumours that Bowen had criticized the Book of Sports.
Elected knight of the shire for Staffordshire in 1624, Littleton was almost certainly the candidate of the Devereux affinity. His father had been a supporter of the 2nd earl of Essex in the 1590s, and he owed his appointment as captain of Staffordshire’s horse militia to the 3rd earl, the county’s lord lieutenant. However, as the Devereux candidate he had to take second place in the return to Sir William Bowyer II*, his inferior in the county hierarchy.
In 1625 Littleton’s finances were bolstered when his eldest son Edward married the daughter of the wealthy Anglo-Dutch merchant, Sir William Courteen. The match brought him a portion of £5,000, part of which was probably used to purchase from a courtier the baronetcy conferred on his heir two years later.
Littleton died on 25 July 1629 at Pillaton Hall and was buried the following day in Penkeridge church where, in accordance with his request, a monument was erected to himself, his wife, his father and mother. In his will, dated 1 June 1629, he left his wife 200 sheep plus cattle and ‘implements of husbandry’.
