For much of its recent history, Upton Cressett has been a farmhouse, partially demolished and forsaken by its landed family, the Cressetts – later Cressett Pelhams and Thursby-Pelhams. They left the remote house and its deserted medieval village high on the hill above Bridgnorth, for a newly built and fashionable house at Cound (q.v.) in the early eighteenth century. Sat besides the little Norman church of St Michael and All Angels, Upton Cressett was probably originally a great south-facing H-plan house and still has traces of a former moat. Its most important architectural entity – the late sixteenth-century turreted brick gatehouse – remains and stands to the south of the former Cressett mansion.

Upton Cressett came to the Cressett family through the marriage of Constance, the daughter and heiress of Royal verderer, John de Upton, with Thomas Cressett. Cressett’s family had previously lived at Garmston, near Leighton on the north side of the River Severn and the couple’s grandson, Hugh Cressett (1398–1449), styled himself as ‘of Upton’. The family’s name eventually came to be associated with the place, distinguishing it from other Uptons, such as that close to Haughmond. Hugh served as Constable of Mortimer Castle, was a Royal Commissioner of the Welsh March, and was Sheriff of Shropshire in 1435.

Hugh Cressett was almost certainly responsible for a significant box-framed timber rebuilding of the family’s home, of which major elements still remain encased in the surviving part of the house. Dendrochronological dating has given a felling date of 1428/30 for the south-eastern end of the house (the present drawing room), which was seemingly intended as a solar cross-wing for the family’s private occupation. Interestingly this appears to have been built first, providing accommodation whilst the grander part of the house was undergoing construction. This, the great hall, was adjacent to the solar to its west (the present hall). Following eighteenth-century demolition, though, only the eastern remnant end of the hall remains and yet even in its truncated state it is an impressive survival. Dendrochronologically dated as having been felled in 1431, the timbers were used to create a hall that was originally open to the roof and what can still be seen – even though divided by a later floor – represents what appears to be the aisled end.