Henry Street was mentioned in the 4 September 1783 will of his father Henry Street. After the death of his mother Catherine, the younger Henry was to receive 250 acres of land on which the testator lived, with part of the Dragon Swamp and one Negroe Girl Daphney, one bed and Furniture, one Cow and Calf, and one Colt. The will was presented in court on 17 May 1784. [Essex County, Virginia, Will Book 13, page 427.]

A List of Guardians, Orphans and of whom in Essex County from January 1781 to August 1788 includes Henry Street, Eliza Street and Ruth Street, orphans of Henry Street. Richard Street was assigned guardian to Henry Street; Catharine Street was guardian to Eliza and Ruth Street. [Essex County, Virginia, Box Chancery 3-A-83.]

On 16 May 1805, Richard Street and Betsy his wife of Essex County sold to Baylor Carlton of the same. For Sixty one pounds Sixteen shillings, a tract of land containing 40 acres be the same more or less, bordered by George Hundley legatee of Josiah McTyre deceased, William Montague, the said Baylor Carlton, Henry Street, “from thence a Steight line Northward which divides Essex & Middlesex”. Signed Henry Street. Witnesses: Peter Broocke, Robert Dobbyns, Thomas Clarke. On 15 July 1805 ordered to record. [Essex County, Virginia, Deed Book 36, pages 508–509.]