103 Circle Rd
ca. 1846

This two-story house was originally built in Enfield, Massachusetts, for Daniel B. Gillett. He was in the manufacturing and lumber business, and was part of one of the town’s oldest families. The building was moved to Staten Island in 1931 by builder Charles A. Wade for businessman Walter A. Tyler. Wade had capitalized on the interest in colonial and early-19th-century American history at the time, as well as the availability of authentic New England houses from the Swift River Valley, which was being razed for the construction of the Quabbin Reservoir.

The Greek Revival frame structure has a slate-shingled, low-pitched, hipped roof, with a subordinate, one-and-a-half story wing, both featuring six-over-six, double-hung windows. The classically-inspired ornamentation includes a cornice line with wide divided bands of trim, two-story vernacular Doric pilasters, and fluted Ionic columns and sidelights flanking the door at the recessed entry porch.

It was sold in the 1950s to Horace P. Moulton, vice president and general counsel of AT&T, and remains in use as a private residence. It was designated as a NYC Landmark in 2007.


167-177 Benedict Road

Constantino Paul Castellano was born to an Italian immigrant family in Brooklyn in 1915. He had a poultry distribution business, and would later venture into construction concrete. The success of these businesses was attributed to his ties to the mob, as he had become a member of the Mangano family in the 1940s, quickly rising through the ranks. In 1957, the organization came under the leadership of his brother-in- law, Carlo Gambino.

At the height of his power and wealth, Castellano built this lavish 17-room mansion. It was designed to resemble the White House and featured an Olympic-size swimming pool and an English garden. The mansion became his operations center, with high-ranking members of the Mangano family often visiting for business and social events. This prompted the FBI to put the property under surveillance, installing secret listening devices. Castellano was ultimately indicted for federal racketeering in 1984, among other charges. He was killed in an unsanctioned hit in 1985, and buried in the Moravian Cemetery. His death is believed to be the last time the head of a crime family was killed in New York City.


41 East Loop Rd
ca. 1925

Born in Wilmington, Delaware, Thomas Garrett Jr. moved with his family to New York in 1889. He was the great-grandson of Thomas Garrett, an abolitionist and leader in the movement, before the American Civil War.

Garrett graduated from Harvard Law School in 1899 and served as Assistant Corporation Counsel of NY for four years before joining the law firm of Davis, Polk, Wardwell, Gardiner & Reed, where he specialized in banking cases. He retired in 1938, and two years later was the Republican candidate for the House of Representatives. He purchased this plot from George Cromwell and built this house around 1925, at a total cost of $50,000 (almost $1M today), which became the most expensive residence on East Loop Road at the time. After the passing of his first wife, Dorothea Kobi, he married Lucille Stirn in 1934. The family continued living at the property until 1982.

26 East Loop Road

Ca. 1910

This block bounded by East Loop Road and East Entry Road is among the earliest to be developed for residential use in the area. It originally was the location of three great mansions, of which only one remains today.

The only remaining house of this group was the family home of merchant James
G. Clark Jr., who’s father and grandfather had been prominent physicians on Staten
Island. The striking two-story frame structure is located at 26 East Loop Road (2c), and
maintains many of its original Neo-Classical features, most notably a two-story porch
with a pointed pediment. After Clark’s death in 1930, the family sold the mansion to John
D. Leggett, a manufacturer from New Brighton. Leggett lived there with his family until
his passing in 1946. The lot was subdivided in 1986, and two new houses were constructed.

Photo: Courtesy of the NYC Municipal Archive

46 East Loop Road

Ca. 1910

This block bounded by East Loop Road and East Entry Road is among the earliest to be developed for residential use in the area. It originally was the location of three great mansions, of which only one remains today.

A remarkable two-and-a-half-story frame house with a grand porch framing its first floor once stood at 46 East Loop Road. It was the residence of May Richmond Walker and her husband Prof. Arthur L. Walker until 1951. Mrs. Walker, who came from a politically prominent family nationally, originally settled in Todt Hill in 1898 with her first husband, with whom she had two children. After becoming a widow, she married Mr. Walker in 1929, who was a professor of metallurgy at Columbia University School of Engineering. The lot was subdivided in 2012, and the house was demolished in 2016.

Photo: Courtesy of the NYC Municipal Archive

50 East Entry Road

Ca. 1910

This block bounded by East Loop Road and East Entry Road is among the earliest to be developed for residential use in the area. It originally was the location of three great mansions, of which only one remains today.

50 East Entry Road was once the site of a two-story frame structure with Colonial Revival and classical features. It was the family home of Johannes D. Hage, a successful Danish merchant who had emigrated to the United States in 1855. Hage paid the equivalent of $600k today for the mansion, where he and his wife Clara Merrick raised two children and remained for over 30 years. In 1975, the lot was subdivided and two new houses were built. The mansion was demolished in 2004.

Photo: Courtesy of the NYC Municipal Archive


1476 Richmond Road
1679; additions 1700, 1750, 1790, 1830

This picturesque one-and-one-half-story farmhouse is an interesting example of a late-17th-century rough-cut fieldstone structure, combined with later stone and frame additions built around 1750, 1790, and 1830, respectively.

The oldest wing has a steep medieval-style roof, with a massive Dutch fireplace and a chimney head supported on two wooden posts. It is located to the rear portion of the farmhouse, while later additions were built closer to the road. The two stone structures are built of undressed fieldstone, known as “Dutch construction”. The original house had eight rooms on the first floor and seven on the second floor, with a panelled fireplace.

It was built by Captain Thomas Stillwell, a prominent Staten Island citizen, who was granted the property in 1677. He passed it on to his son-in-law Nicholas Britton, who kept it in his family until 1915, when it was sold to the Antiquarian Society, now the Staten Island Historical Society. The organization furnished the house and opened it to the public.

Todt Hill-Dongan Hills, Staten Island

Todt Hill-Dongan Hills is an area filled with stately historic properties such as the Ernest Flagg Estate. This site consists of impressive fieldstone walls and archways, a gatehouse, and mansion that once belonged to one of New York City’s most prolific architects. Though already designated an Individual Landmark, the Iron Hills Civic Association is working to ensure that the currently for-sale estate falls in good hands and is safe from inappropriate development. This group is also concerned with the rapidly vanishing historic homes that sit atop the hills and is aiming to document and survey the historic grandeur of the neighborhood before it is too late.