A Diamond in the Rough A Trip Through Tottenville

Often given short-shrift in media coverage of the New York City real estate game, Staten Island is a historically rich borough which—contrary to what your Manhattan-centric friends may try to tell you—is not a four hour trek away. The fifth borough’s character-filled neighborhoods can be a welcome contrast to the constant activity—and expense—of Manhattan.

One such neighborhood is Tottenville. Surrounded by water on three sides and the town of Richmond Valley to the north, Tottenville is the southernmost point—not only of New York City, but of New York State as well.

Ye Olde Tottenville

Historically speaking, Tottenville is a treasure. Like most New York City neighborhoods, it has undergone several different manifestations of itself over the centuries. The first settlers of Staten Island were the native Algonquin Indians, who were forced to give up their land to the Dutch upon that group’s arrival around 1630.

One of Staten Island’s first prominent residents, Captain Christopher Billop, re-christened the land Bently Manor, named after the ship he sailed to America in 1667. It was not until 1869 that the area was renamed Tottenville after the revolutionary war hero Gilbert Totten. Tottenville’s colonial past is evident today in some of the town’s significant landmarks, like the Bethel United Methodist Church, which was built twice in the same spot due to structural damage caused by a fire—once in 1840 and again in 1886.

Tottenville has also seen its share of seafaring industry come and go over the years. Shipbuilding waxed and waned in the community and finally was put to rest when the demand for ships made out of materials other than wood made the community’s woodcraft obsolete.


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