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The Port Tobacco Hamiltons descended from Alexander Hamilton, the planter, who arrived in the Port Tobacco River valley about 1714. By about 1730 Alexander and wife Elizabeth Hamilton had come into possession of a rather modest-size piece of property that lay close to the uppermost (northerly) reach of Port Tobacco Run, a short distance southwest of the present day community of White Plains, located on U.S. Route 301. Alexander was not destined to live long on his new plantation. His last will and testament, dated January 4, 1730/1, was admitted to probate in Charles County on February 20th that year by his widow, Elizabeth. Alexander left his dwelling plantation to his wife, Elizabeth, with certain items to be bequeathed later to his daughter, Mary, upon her marriage. His five sons, John, William, James, Patrick and Samuel received more or less equal shares of Alexander’s landed estate and personal property.

In 1741 Alexander’s sons, William, John and James, petitioned the Maryland Land Office for a re-survey of their father’s plantation. There had been questions for some time about the precise limits of the Alexander Hamilton property, which he had purchased from Edward Digges about 1714. Lawsuits brought by the heirs of Edward Digges had clouded the issue of property ownership for many years. Finally, things were straightened out when the Colony’s land agent approved the re-survey of the approximately 200 acres purchased from Digges. It turned out upon re-survey that the Alexander Hamilton estate totaled 248 acres, which included a surprise “surplus” of 48 acres. The sons of Alexander Hamilton called their new, tightly defined package “Spye Park.” It lay on the north side of Port Tobacco Branch just north of the much larger plantation known as Green’s Inheritance.

John Hamilton of Prospect Hill, La Plata, Maryland, was descended from James, fourth child of Alexander and Elizabeth Hamilton. James, 1715-1785, was born in Prince George’s County. He married Mary Ann Coombs. One of their sons, Francis, married Susana Blandford. Their children were Francis Patrick, Jane, Maria, John, Matilda, Susanna, Louisa, and Eliza. It was their son, John, who married Anne Catherine Hamilton, daughter of Lt. Edward Hamilton, and thereby came into possession of Prospect Hill.