The Stony Brook area (today's Nissequogue and Head of the Harbor) was settled in the seventeenth century (c 1640s) by Richard Smith, formerly of Southampton, who acquired a tract of some fifty-four square miles on Long Island's north shore and ultimately secured a royal charter that granted manorial status to his holdings. Present-day Smithtown evolved from Smith's manor, and his descendants remained prominent in the affairs of the region through succeeding generations. With his death in 1692, one-hundred-acre farms were devised to his numerous grandsons and substantial homesteads were conveyed to his surviving sons. Both Richard Smith (known as the Patentee) and his progeny first settled on extensive parcels in the northern section of the manor overlooking Stony Brook Harbor, and several of their Colonial-era dwellings were later incorporated into the nineteenth-century estates that are the subject of the Stony Brook Harbor Estates MPS theme. - NRHP, 13 October 1992