The lands of Petcarlings originally formed part of the Barony of Abernethy. In 1312, the lands passed into the ownership of the Leslie family, Earls of Rothes, when Sir Andrew Leslie married the daughter of Sir Alexander Abernethy. Sir Alexander had been a supporter of Robert the Bruce, but had later espoused the cause of Edward I and commanded the English garrison at Dundee.

Pitcairlie House dates from the early 16th century and may have been the original home of the Leslies of Pitcairlie. The tower was probably built around 1550 by George Leslie, 3rd Earl of Rothes. The strength of the ground floor vaulting and the thickness of the walls, together with the position of the house on an elevated ridge protected on two sides by the loch and on the other two sides by the burn and glen to form a moat, suggest it was created in a defensive role. The 4th Earl of Rothes granted Pitcairlie to his second son, Sir Patrick Leslie, who afterwards became 1st Lord of Lindores in 1600.

The most famous person connected with the house was a son of Sir Patrick Leslie, namely Major General David Leslie, who was born at Pitcairlie. Having served in the army of Gustavaus Adolphus, he commanded the Scottish forces in the days of the Covenant. During the Civil War, he fought on both sides, at one time leading a dashing cavalry charge which was prominent in deciding the Battle of Marston Moor for Cromwell in 1644.

Later in the conflict, he rose to the rank of Commander-in-Chief of the royalist forces and shared in Charles I’s defeat at Worcester in 1651. He was imprisoned thereafter, but was created Lord Newark at the Restoration.

Another son of Sir Patrick Leslie became 2nd Lord of Lindores, but his death in 1649 left the estate in financial disarray. This led to the Court of Session granting Pitcairlie to a creditor, John Bayne, in 1667, thus ending 355 years of ownership by the Leslie family.

In the mid-18th century, Pitcairlie was acquired by Colonel James Cathcart of Carbiston, whose family retained the estate until the mid-1960s. There were several notable members of this family, including Major James Cathcart, who had a distinguished miltary career in India; Captain Robert Cathcart, who served with distinction under Nelson at the Battle of the Nile and in the Baltic; and Robert Cathcart, who was appointed Vice-Lieutenant of Fife in 1886.