In 1447 he migrated to Italy, where Cardinal Bessarion gave him his patronage. He became famous as a teacher of Greek letters and the Platonic philosophy; in 1463 he was made professor at Padua, and in 1479 he was summoned by Lorenzo de Medici to Florence to fill the professorship vacated by John Argyropoulos. In 1492 he removed to Milan.
He was associated with Marsilius Ficinus, Angelus Politianus, and Theodorus Gaza, in the revival of letters in the western world. One of his pupils at Florence was the famous Johann Reuchlin. Demetrius Chalcondyles published the editio princeps of Homer, Isocrates, and Suidas, and a Greek grammar (Erotemata) in the form of question and answer.
He wrote a history, in ten books, of the period from 1298-1463, describing the fall of the Greek empire and the rise of the Ottoman Turks, which forms the centre of the narrative, down to the conquest of the Venetians and Mathias, king of Hungary, by Mahommed II.
His brother, DemetriusChalcondyles (1424-1511), was born in Athens.
DemetriusChalcondyles published the editio princeps of Homer, Isocrates, and Suidas, and a Greek grammar (Erotemata) in the form of question and answer.