those four 18th century houses
It seems pretty difficult to find coherent information about the four houses (some sources only refer to three houses), apart from Headquarters House, but I will try to string together what I can find. I shall be most grateful for references and information that anyone can help with!
from Historic Jamaica, by Frank Cundall, 1915
With the destruction of "Jasper Hall" in the earthquake of 1907, Headquarters House, as it is still called, in Duke street, became possessor of the undisputed title of the finest old house in Kingston. Its history is of interest.
The story goes that in the latter half of the eighteenth century four Kingston merchants with great wealth and equally great ambition as to appearance — Jasper Hall, Thomas Hibbert, John Bull and another, made a heavy bet amongst themselves as to who should build the most magnificent dwelling. This resulted in Jasper Hall, till recently standing in High Holborn street; Headquarters House; Bull House, in North street; and the house to the north of the old "Mico" in Hanover street, once called "Harmony Hall." The name of the winner of the bet is not recorded. It should have been Jasper Hall.
Jasper Hall, who was receiver-general and speaker of the house of Assembly, died in 1778. As mentioned above, he was in 1774 one of the commissioners for purchasing a pen for an official residence for the admiral on the station. His house, which he named "Constantine House," bore the date "June 1, 1756"; and not many years ago possessed what was probably the best collection of paintings, engravings and books ever got together by a private individual in Jamaica. Unfortunately at the sale many bibliographical treasures were allowed to leave the colony.
Thomas Hibbert, who arrived in Jamaica in 1734, soon became one of the principal and most opulent merchants in Jamaica. He was member of Assembly for St. George and for Portland, and speaker of the Assembly in 1756. He died in 1780, and was buried at "Agualta Vale" pen in St. Mary. His house was long known as Hibbert's House.
In November 1755, when the Assembly was sitting in Kingston, it on the 12th adjourned "to the dwelling house of Thomas Hibbert, Esquire, a member of this House, where he and Colonel Lawrence, another member of this House, are indisposed, there to proceed to business," and the House met there for several days. In December 1814 it was purchased by the War Office of the widow of Dr. Solomon Deleon, of Kingston, and was thenceforward known as General's House or Headquarters House. Although the governor of the colony has ever held the rank of captain-general of the forces, there has always been a general officer in actual command of the troops; and in former days, and as late as 1895, such general held, ex officio, a commission as lieutenant-governor of the colony, and succeeded to the control of affairs when occasion arose. The house still retains the name of Headquarters House, though it has been the colonial secretary's office since the government was removed from Spanish Town to Kingston. It was purchased by the Government in 1872 for £5000. It also contains the chamber in which the legislative council sits. The "Hibbert Trust" was founded by a member of this family.
John Bull was the owner of Sheldon coffee estate in the Blue mountains. The name of the builder of the house to the north of the Mico has not been recorded.
Vale Royal, the House and the People
Jamaican Historical Society, 1983
'Three rich merchants had placed a bet as to who could build the finest house. Colonel Jasper Hall built Jasper Hall in High Holborn Street . . . . [Eliphalet] Fitch built a house on Hanover Street and Hibbert built Hibbert Hall on Duke Street.'
Daily Gleaner, January 15, 1913