In 1655 Hersey Barrett, an officer in the expedition commanded by Admiral Penn and General Venables, was sent by Cromwell's parliament to capture Hispaniola from the Spanish. It proved to be too strongly held so they took the easier prize of Jamaica. Hersey Barrett was granted lands in Jamaica and settled on the island.
Unlike many of the original settlers the Barretts prospered and by the middle of the eighteenth century had become immensely wealthy, owning over 84,000 acres of land and over 2,000 slaves. The family also had a London house, the site of which is still known as Barrett Street, just north of the present day Selfridges.
The head of the family and Elizabeth Barrett Browning's father, Edward Barrett's income was in excess of 60,000 pounds a year. When Edward went to live in England in 1795 accompanied by his brother Samuel and his sister Sarah (Pinkie), his cousin Richard Barrett remained firmly attached to Jamaica, becoming Speaker of the House of Assembly, Custos of the parish of St. James, a judge, among other things.
Construction on Greenwood Great House commenced in 1780 and the house was completed by 1800 -- it was mainly used for entertainment.