In June 1651, with his brother, Constant, and partners, Thomas Middleton and Thomas Rouse, he purchased the whole of Shelter Island first from a non-resident Englishman and then again the next year, from the Manhanset Indians, whose sachem, or chief, was called "Yoki." Nathaniel was the only one of the partners who lived on a Shelter Island, and he eventually bought out his partners’ shares. The Shelter Island enterprise involved barrel-making, using the stands of local white oak for shipping the West Indies tobacco, sugar, molasses and rum back to England. The family kept African slaves, along with employing Native Americans and others, to help run the plantation, the largest such operation in the north.
Personal life
Between 6 July and 8 August 1653, he married Grisell Brinley, daughter of Thomas Brinley, one of the Auditors General of the Revenues for Charles I, and later for Charles II. Grisell was a younger sister of Anne Brinley, who in England had married Governor William Coddington of Rhode Island in January 1650. When the Coddingtons returned to Rhode Island in mid-1651, Grizzell came along as a ward of Coddington. Grisell and Anne’s brother, Francis, would also join his sisters in the New World, fleeing Cromwell’s England, and establishing the American Brinleys in Newport, RI and Boston, Mass. Another Brinley sister, Mary, would marry Nathaniel's brother, Peter Sylvester. The Sylvesters were friends with Quaker founder George Fox, whom he entertained on at least one occasion on Shelter Island. They offered a place of refuge for several of the persecuted early Quakers in New England at a time when it was dangerous to do so.
Death
He died in 1680.
Legacy
His grandson, Brinley Sylvester, replaced the existing home and built Sylvester Manor on Shelter Island in 1737, which remains standing and in the family to this day. An 11th generation descendant, Bennet Konesni, turned it into a non-profit farm. Shelter Island families descended from Sylvester include Dering, Sprague, L'Hommedieu, Havens and Hudson. Franklin Delano Roosevelt was Nathaniel and Grisell Sylvester’s sixth great-grandson, through their eldest child Grisell Sylvester Lloyd. A contemporary archaeological dig, from 1999-2005, called the Sylvester Manor Project, a project overseen by the University of Massachusetts Boston, seeks to shed light on the Sylvester estate as it existed in the 17th and 18th centuries.
