In the mid-fourteenth century, the nucleus of what became the Woolley estate belonged to Sir William de Notton, a man of local origin who achieved wealth and fame as a lawyer, and was later appointed Lord Chief Justice of Ireland. He derived his name from Notton, the village to the east of Woolley. His lands in Woolley and Notton passed in 1365 to Sir William Fyncheden, by whose executor they were sold in 1377 to John Woodrove (or Woodroffe / Woodruffe) of Normanton. Despite owning these extensive lands, however, John Woodrove was not Lord of the Manor of Woolley, although his descendants would be.