Balcaskie House is a 17th century mansion which incorporates a 16th century tower house and was extended in the 18th and 19th centuries.

The lands of Balcaskie were owned by the Anstruther of Anstruther family from the 13th century and there may have been a castle built here at that time. The property passed to the Strange family around 1362 upon the marriage of John Strang and Cecilia Anstruther, daughter of Henry of Anstruther. In 1363 John Strang of Balcaskie and his wife received various lands in Anstruther, next to the lands belonging to Dryburgh Abbey, from Cecilia’s brother, Richard of Anstruther.

In 1528 John Strang, younger of Balcaskie, and John Anstruther of Anstruther acted as sureties for William Anstruther and thirty nine others after David Lindsay was imprisoned in the tower of Dreel.

Balcaskie later passed to the Moncreiff family and in 1631 John Moncreiff of Balcaskie resigned the mill of Pittenweem to Sir William Anstruther of Anstruther.

Sir Robert Anstruther, son of Sir Philip Anstruther of Anstruther, bought Balcaskie in 1698 and was made 1st Lord Anstruther and 1st Baronet of Balcaskie.