Bailieborough Castle was located in Bailieborough, County Cavan, Ireland. It was built in an enclosed demesne by 1629. Also known as Castle House, Lisgar House, or simply 'The Castle', the country house was located just to the south-west of Castle Lough in what is now known as Bailieborough Demesne, on the north-western edge of the town. It is now totally demolished.
Castle Lake loop is a 3-kilometre (1.9 mi) hiking trail around part of the former castle's property.
William Bailie, a Scottish "undertaker" or Planter, was granted the lands of Tonergie (Tandragee) in East Breffnie by James I in 1610 on condition he enclosed a demesne, built a fortified house and settled on the estate a number of Scottish or English families. This he did by 1629. During the rising of 1641 the house was attacked and occupied for a month by a troop of Irish soldiers under Colonel Hugh O’Reilly.
William died c.1648 and the estate passed to his son, William, the Bishop of Clonfert and Kilmacduagh. On the bishop's death in 1664 the estate was inherited by his only daughter, who had married James Hamilton. James was succeeded by his son Henry, the M.P. for Cavan who was killed at the siege of Limerick during the Jacobite war. His successor was his son, another James Hamilton, who sold the property in 1724 to Major Charles Stewart - nephew and co-heir of General William Steuart - and left the area.
Charles Stewart died in 1740 and left the estate to his son, William Stewart, who was High Sheriff of Cavan for 1749 and MP for Cavan county (1766–1768). He was followed by his son Charles, who was also MP for Cavan (1783–1793). He was killed in an accident in 1795, when the estate passed to a nephew, Thomas Charles Stewart Corry, who sold it to Colonel William Young in 1814.