Henry Lee’s 1746 will mentions “pictures,” which were very likely portraits. His will states, “I give and bequeath to my Son Richard and to his Heirs all the pictures in my Home.” These were very likely portraits of Henry Lee and other family members. John Lee of Cabin Point was his eldest son, his next eldest son was Richard of Lee Hall, and then Henry Lee of Leesylvania. It is therefore highly probable that there were at least two portraits of this Henry Lee – one at Cabin Point with his son John, which was inherited by Henry in 1767, and another portrait at Lee Hall, which was inherited by Richard along with the house upon Henry’s death in 1747.
The reference to a second portrait of Henry Lee appears in son John Lee’s 1765 will: “I give to my brother Henry Lee my picture and those of my Father and mother.”
See: Edmund Jennings Lee, ed. Lee of Virginia, 1642-1892: Biographical and Genealogical Sketches of The Descendants of Colonel Richard Lee (Philadelphia, 1895), 131-136, 285-287.