Roslin Castle, Trelawny, Jamaica belonged to Henry Wisden, "practitioner of physic and surgery" who acquired it in 1684. Between that date and 1743, he and his five children increased the holding to 4,145 acres. An imposing mansion (long-since demolished) was built about 2 miles inland.
After 1743, Jervis Gallimore (later to gain repute for his hard line during the Second Maroon War) became owner by marrying one of the daughters. By 1769, Jervis had sold all the land to William Virgo, whose wife Rebecca's tomb can still be seen on the hilltop.
From Rebecca, the Estate passed to Samuel Cunningham (as confirmed by the 1840 Jamaica Almanac) and then to his son James. Custos of Trelawny. In 1840, the Estate is listed as consisting of 1262 acres, though there is another property called Mason Gang, 1340 acres, belonging to the same Samuel Cunningham.
In 1817 there were 188 slaves on the property.

The Roslin Castle wharf is now the site of the Trelawny Beach hotel.