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Hill and neighborhood in Staten Island, New York, USA

Grymes Hill is a 374 feet (114 m) tall hill formed of serpentine rock on Staten Island, New York. It is the second highest natural point on the island and in the five boroughs of New York City. The neighborhood of the same name encompasses an area of 0.894 square miles (2 km2) and has a population of 8,263 people. The hill also includes parts of the Silver Lake neighborhood. The area includes part of ZIP Codes 10301 and 10304.

The hill is named after Cayetana Susana "Suzette" (née Bosque) Claiborne Grymes, daughter of Felicidad Fangui and Bartolomé Bosque, and wife of prominent New Orleans lawyer and member of the First Families of Virginia, John Randolph Grymes. Her first husband was the first governor of Louisiana, William Charles Cole Claiborne. She settled on Staten Island in 1836. Her daughter Athenais Grymes married New York banker, Louis A. von Hoffman, one of the founders of the Knickerbocker Club.

Neighborhoods around Grymes Hill include Ward Hill to the north, Silver Lake to the west, Sunnyside and Emerson Hill to the south, to the southeast is Concord, and Stapleton and Stapleton Heights to the east. The east side of the hill is defined by Van Duzer Street and Richmond Road to the intersection with the Staten Island Expressway, which, with Clove Road, defines the southern side. On the west is Victory Boulevard. Some claim Cebra Avenue for the northern border, while others believe that the border is Louis Street.

Grymes Hill, which has views of Lower New York Bay and the Narrows, Ownership of of the hillside was assumed by the Trust for Public Land. They encouraged concerned neighbors to form SANC to maintain and improve the land as a nature preserve open to the community. Starting in the mid 19th century, breweries dug caves into the hill to use in the production of beer. Some of these caves off of Van Duzer Street were later incorporated into a popular restaurant, which provided catering for the movie The Godfather during shooting on Staten Island. The restaurant has since closed, and the entire site was redeveloped with a townhouse complex.

Grymes Hill was carved by a receding glacier. The Staten Island Serpentinite, which is the serpentine or soapstone area that extends from New Brighton to Richmond, includes the hill country of the island. In places where glacial erosion was limited the stone weathered into a soft, yellowish, fractured condition to which the name "soapstone" is applied, but where the weathered stone was eroded the rock is hard and dense in texture and dark green in color. Deeds of 1836 and thereabout show that the hill was known as Castleton Heights. Grymes Hill was part of a land grant in 1687 to Thomas Dongan, who served as Governor of the Province of New York.

Grymes Hill is ranked the 4th safest neighborhood in New York City out of 229 according to Niche. The median household income is in the top 15% in the United States. Howard Avenue on Grymes Hill is considered one of the most exclusive and most expensive areas of Staten Island.

Most homes in the neighborhood are private residences, many of which were constructed for Manhattan businessmen. The neighborhood has many fine homes dating from the 1920s that overlook New York Harbor. Real estate developer Fred Trump constructed several hundred two and three bedroom residences in the late 1940s. These are 423 garden apartments along Howard Avenue and Arlo Road. Fred Trump's son, the developer and later U. S. president Donald Trump, sold these apartments to an unrelated corporation in 2007. Grymes Hill Manor Estates was built in 1953 as rental garden apartments, and switched to co op status in 1983. It has 152 apartments centering on Seth Court, with many on both sides of Arlo Road, and a few on Howard Avenue and Stratford Avenue. Two high rise apartment buildings at the foot of Howard Avenue converted to condominiums following a major fire in one. There are several apartment buildings on Victory Boulevard. Two new apartment buildings have been constructed facing the Staten Island Expressway. One was turned into condominiums in 2004. The other is being offered as senior citizen housing.

The only public park on Grymes Hill is Hero Park, a 2 acre park donated in 1920 by Dr. and Mrs. Louis A. Dreyfus. Adjacent to (and owned by) Wagner College is the site of a former Roman Catholic high school, named Augustinian Academy after the order of friars who ran it; the school closed in 1969. Near the foot of the hill, on Foote Avenue, is P. S. 35, the Clove Valley School, a K 5 school which is ranked 10 out of 10 by GreatSchools. org, 85th of 2,395 New York elementary schools according to SchoolDigger and received an overall A Grade by Niche. Also located on Grymes Hill is Casa Belvedere, a center for Italian culture and studies in Italian language and culture which is located in the Louis A. and Laura Stirn House which was listed on the National Register of Historic Places in 2010, and designated a NYC Landmark in 2001.

Grymes Hill is served by the local and limited buses. The express buses provide rush hour service to and from Manhattan.

Governor Thomas Dongan (1634–1715) in 1687 was granted a 5,100 acre manor, of which Grymes Hill was a portion. Daniel D. Tompkins (1774–1825), an American politician and the sixth vice president of the United States. In 1815, he established a settlement along the eastern shore of the island with the purchase of the Van Buskirk Farm in New Brighton, and property on Grymes Hill. His main residence was located on Fort Hill, near Fort Place which burned down in 1874. Oroondates Mauran (1791–1846), a merchant of New York, who in subsequent years became the owner of the first Italian Opera House, purchased his Grymes Hill home in 1831. In winter he lived in Manhattan and in the summer on Staten Island. Furthermore, together with Cornelius Vanderbilt he owned the Staten Island Ferry. He was also one of the oldest members of the Union Club of the City of New York. Suzette Grymes, wife of the noted New Orleans lawyer John Randolph Grymes (1786–1854), bought land in 1836 around Howard Avenue and what is now Grymes Hill Road. John J. Cisco (1806–1884), a merchant in the dry goods business in New York, who retired at the age of thirty six with a fortune. Some eleven years later, in 1853, he was appointed by President Pierce, Assistant Treasurer of the United States, and placed in charge of the Sub Treasury in New York. He purchase the house erected in 1855 by Ernest Cazet, under the superintendence of Frederick Law Olmsted, the noted landscape architect. Capt. Jacob Vanderbilt (1807–1893), brother of Cornelius "Commodore" Vanderbilt, built a mansion on Grymes Hill in the midst of wood and open land, covering a large area. General Thomas Jordan (1819–1895), owned the Unker dwelling, a 30 acre property with beautiful views. Edward King (1833–1908), President of the Union Trust Co. of New York, owned a house here. Charles Wallace Hunt (1841–1911), an inventor, business executive, and President of the American Society of Mechanical Engineers. He invented new methods in the storing and handling of coal. He purchased his residence on Grymes Hill in 1900. W. Butler Duncan I (1830–1912), a New York banker and railroad executive, in 1858 purchased a mansion on 20 acres of land from Madame Grymes. Louis A. Dreyfus (1867–1920), a local maker of chewing gum, built his former estate on what it is today part of the 13 acre Notre Dame Academy, an all girls Catholic elementary and high school. built Horrmann Castle at 189 Howard Avenue in 1910. The building was torn down in 1968. William Butler Duncan II (1862–1933), a leader in American yacht racing and naval service, adopted son of W. Butler Duncan I.
Louis A. Stirn (c.1864–1962), a silk importer, built his home in 1908 at 77 Howard Avenue. In 2006, the Stirn mansion became a New York City Landmark and is now called Casa Belvedere. James J. Murphy (1898–1962), a United States Representative from New York.

Eileen Farrell (1920–2002), Metropolitan opera star, moved to Staten Island from Connecticut in 1944. She lived with her family on Grymes Hill. Matthew J. Titone (1961– ) is an American politician and lawyer. Colin Jost (1982– ), comedic actor, writer and Weekend Update host for Saturday Night Live.