The early history of the Orleton estate is not clear, although it is suggested that there might have been a Dark Ages council building on the present house’s site. Orleton first appeared as a manor in 1295, when William of Orleton was described as the tenant in chief. The Orleton or de Erleton family, however, may have been living there much earlier, since records indicate a Ralph de Orleton, or d’Erleton, in 1141– 55, with further members of the family continuing his succession. In the fourteenth century, on the death of Richard d’Erleton (d. 1388), Orleton passed to his cousin Giles d’Erleton who, for a financial consideration, in 1392, sold the estate to Joan, Richard’s widow.

On Joan’s death, she left Orleton to her cousin, William Cludde of Cluddley, the son of Margaret de Orleton. William – a wool-monger – was later described as of both Cluddley and Orleton and he appears to have been the estate’s owner in 1382–1431. The Cluddes were a family with an ancient lineage, being recorded at Wrockwardine in the twelfth century, and John Blakeway suggested that Edward IV’s Yeoman of the Pantry, William Cludde, might have been one of their number.

Orleton remained Cludde property in the male line until the late eighteenth century, when the estate passed through the female line, although the Cludde name was adopted. The core of the house, as it stands, represents an evolution of an early building and it has, in its cellars, stonework that appears to be pre-Medieval. This is said to be part of a structure that was perhaps built by Ralph d’Erleton in the twelfth century. Within the house above, a medieval truss and carved boss, apparently dating from circa 1400 survive in the structure of two rooms on the south-east front. The truss’s arch itself is sixteen feet across, with cross-beams that extend, to form an apex, into what is now the second floor. This extraordinarily high space would have formed the medieval great hall and probably is indebted to William Cludde for its construction.

There was a square moat round the house until at least 1728, of which one arm still remains.