Hidden behind the Georgian facade is the original chantry college of priests founded by Sir John de Wingfield in 1362. Inside are the medieval great hall, part of the 14th century cloister and Tudor and Georgian interiors. Sir John was a soldier of high reputation in the reign of Edward III, and Chief Counsellor of the Black Prince. In 1355 he accompanied him to Languedoc, and some of Sir John's letters still survive as important records of the war. He fought at the Battle of Poitiers in 1356 and made a fortune by ransoming captured members of the French aristocracy. When he died of the plague in 1361 he left in his will the request for the establishment of a chantry college, next to the church at Wingfield.

The remaining wings were remodelled in provincial Palladian style in the later 18th century. The Georgian appearance concealed the 14th century building and its medieval origin was largely forgotten. It was not until 1971 that careful restoration by the then owner Ian Chance finally revealed the hidden 14th century structure and proved that the lost college had amazingly survived.