MacDuff’s Castle is a ruined 14th century tower which was built by the Wemyss family.

In the 11th century there may have been a castle here belonging to the MacDuff Thanes of Fife which is said to have been destroyed by Edward I of England.

In 1294 or 1295 David de Lochor was Chamberlain and he is said to have been the last of the main line of the Lochore family having two daughters who were his co-heiresses. The barony of Lochoreshire was split into the baronies of East Lochoreshire or simply Lochoreshire, annexed to the barony of East Wemyss, and of Westerlochorshire or Inchgall. The younger daughter, Agnes, married Sir Michael Wemyss of Wemyss and the eastern half of the barony went to them.

The Wemyss family from nearby Wemyss built a new castle in the 14th century.

The castle later passed to the Livingstone family and in the mid-15th century Sir Andrew Livingstone of Drumray and East Wemyss was married to the third daughter and co-heiress of James de Valognes of Lochore. Upon her father’s death they received half the parish of Auchterderran.