Landowner
Littleton consolidated and enlarge his family's holdings of land, taking advantage wherever possible of the revolution in land ownership carried through by the Tudor dynasty – in particular the Dissolution of the monasteries and of the chantries, which changed many relationships and created many opportunities. He was frequently involved in litigation and other disputes in his pursuit of these ends.
Pillaton itself, with the manor house, actually belonged to Burton Abbey, probably since about, when Wulfric Spot donated land in the area. Dissolution placed overlordship in the hands of the king, and Henry VIII gave it to Sir William Paget in 1546: it was to rest in the Paget family's hands for at least two centuries. However, the Littletons, as terre tenants, were secure in possession of Pillaton. When Edward Littleton died in 1558, the rent they paid to the overlord amounted to just 16 shillings, while the estate was valued at £15 3s. 9d.
Black Ladies Priory, Brewood, was one of the very small houses swept away in the first round of dissolutions in 1536. Littleton and Thomas Giffard both petitioned the King for the right to buy the site and property. Both apparently received his consent. Littleton won the support of Rowland Lee, the bishop of Coventry and Lichfield. The issue went to Thomas Cromwell who decided to sell to Giffard, who, after some negotiation, bought the site, mill and demesne lands, worth £7 9s. 1d. a year, for £134 1s. 8d. The competition for the priory does not seem to have affected relationship between Giffard and Littleton adversely. Haughmond Abbey in Shropshire was a much larger property, put on the market after the Suppression of Religious Houses Act 1539. Bishop Lee supported Littleton in his bid to buy the Abbey, and he acquired it in 1540. Two years later, he sold it, presumably at a profit, to Rowland Hill, a Shropshire-born businessman who was to become Lord Mayor of London seven years later.
In 1543 Littleton leased the deanery manor of Penkridge from the collegiate church of St. Michael and All Angels. This included everything from the site of the church itself and the canons' residential buildings, to paddocks in the town and areas of arable land and pasture, most of it farmed by tenants, around the town. The deanery manor had existed since the 13th century, when Henry de Loundres, Archbishop of Dublin and dean of Penkridge, had acquired the manor of Penkridge at the instigation of King John and divided it into two. The smaller part, conferred on the church was known as the deanery manor, while the remainder was placed in lay hands – in the 16th century the Grevilles, who were Barons Willoughby de Broke. The church was a Royal Peculiar which had survived since the Anglo-Saxon period. However, the deanery and college were soon abolished by the dissolution of the chantries under Edward VI in 1547. The Crown conferred the deanery manor on John Dudley, Earl of Warwick, an immensely ambitious member of Edward's government. Dudley had also recently acquired Penkridge manor itself by foreclosing on a loan from his father to the cash-strapped Grevilles.
Warwick, soon to become Duke of Northumberland, inherited the deanery's legal obligations. The lease still stood and Littleton was able to continue exploiting the estate in return for annual rent. The assessment carried out at the dissolution in 1547 valued the college's property at £82 6s. 8d. annually. It was because of his attempts to maximise the value of the deanery manor that Littleton got into dispute with Stafford. The latter believed that Northumberland was used as a buckler in the dispute, i.e. that his great power shielded Littleton when he was in the wrong. The downfall of Northumberland at the beginning of Mary's reign returned the deanery manor to the Crown, but the Littletons continued to lease it until, in the 1580s Littleton's grandson was able to buy the estate.
Another acquisition, hugely important in the future to Littleton's family, was Teddesley Hay. This sparsely populated area was part of the royal forest of Cannock, sometimes (not quite accurately) called Cannock Chase: Cannock Chase originally referred to the bishop's hunting grounds, which were contiguous with the king's. The Hay was granted to Dudley in 1550. After his execution in 1553 it reverted to the Crown, but Dudley's widow, Jane Dudley, Duchess of Northumberland was granted a life's interest in it from 1554. However, she died only a year later and Littleton was able to buy the Hay. Two hundred years later it would become the site of a new home for the Littletons: Teddesley Hall.
Littleton clearly became both rich and locally powerful through his numerous dealings. Both Pillaton Hall and the parish church of St. Michael were greatly altered in the early to mid-16th century. The hall was rebuilt in typical Tudor style. The church acquired a Littleton family chapel in its south aisle and was partly rebuilt in Perpendicular style, with impressive square tower and east windows of local sandstone. Littleton must have played a significant part in all of these changes, although some may have continued in his son's time.