Middleton's father had immigrated from Barbados and had established a plantation in the area which is now part of the cities of Goose Creek - North Charleston. Henry's older brother, William, built the Crowfield plantation in the 1730s, but eventually moved to England, leaving Henry in charge of the family's affairs in South Carolina. Henry continued acquiring land, eventually becoming one of South Carolina's wealthiest planters.
Middleton's father emigrated from Barbados and established a plantation in the area that is now part of Goose Creek - North Charleston. Henry's older brother, William, built the Crowfield plantation in the 1730s but moved to England eventually, leaving Henry in charge of their family's South Carolina business affairs. Henry continued acquiring land, ultimately becoming one of South Carolina's wealthiest planters.