2286 Richmond Road 
ca. 1683

This Dutch Colonial style farmhouse is divided into two distinctive wings, believed to have been built at different periods. The oldest section is a two-story wing with a gambrel roof, attached to a newer one-story wing with a gable roof. Both are constructed with irregular fieldstone and wood above the first story, and feature the characteristic footprint, height, rooflines, and small window openings of the style.
The house was originally built by Abraham Lakeman in the late-17th century, on property he inherited from his father. It remained as his family home until 1714, when it was sold. In 1751, the house and farm were purchased by Aaron Cortilieu (Cortelyou), one of the original members of the Moravian Church at New Dorp and a descendant of the Huguenots who emigrated in 1652. He left the property to his daughter Elizabeth, who was married to Richard Seamons. They sold the house in 1794 to Joseph Taylor, remaining in their family for many years. It was sold a few more times during the 19th and 20th century, maintaining its use as a private residence. It underwent extensive restoration work in 2001, which also removed modern additions. In 2015, the house was part of LPC’s Backlog initiative, a plan to address the properties that had been calendared prior to 2010 but had not been acted upon. After series of hearings and reviews, 30 properties were prioritized. The Lakeman-Courtelyou- Taylor House was included on this list and became a NYC Landmark in 2016. The following year, however, this designation was overturned by the City Council.

2205 Richmond Road 
1844 Church 
1878 Parsonage 
1914 Parish House 

Established in 1748, the New Dorp Moravian Church is the second oldest church in Staten Island. Moravians are among the earliest Protestant denominations, arriving in New York during the 1730s and 1740s. In 1763, they purchased a plot of land for the construction of a small church, which was consecrated at the end of the year. A parsonage was built sometime later, with records showing that it was expanded around 1820, with a Sunday School established in 1829. The congregation’s sustained
growth prompted the construction of a new church in 1844, funded by members from different parts of the world, including a $1,000 contribution from Cornelius Vanderbilt (equivalent to $40K today). The Greek Revival structure features a porch with columns typical of the style, and a bell tower. It underwent extensive repairs in 1892, and again in 1955. At this time, the tower was replaced by a steeple, the auditorium was enlarged, the basement was modernized, and new offices and a chapel were also constructed. A new parsonage was built in 1878 by William H. Vanderbilt, son of Cornelius. A new parish house was built in 1914, again with a substantial donation from the Vanderbilt family. Adjacent to the church is the 113-acre cemetery, which holds the remains of early settlers and noted community members. Among them is the Vanderbilt family, whose Mausoleum was designed by Richard Morris Hunt. The land was originally used as a free public burial ground until 1819, after which the Church began charging fees to non- members. It would later undergo several expansions and improvements, becoming an architectural and landscape staple.

1929 Richmond Road 
1924, Ernest Flagg 
New York City Individual Landmark 

In 1923, McCall’s Magazine announced the development of a series where a group of noted architects would design small houses based on functionality, affordability as well as beauty. The plans for each would be made available to readers for a fee. Eight proposals were published between 1924-25. House sizes ranged from four to seven rooms, and construction costs from $4,000 to $13,500. Flagg’s design was at the low end of the scale in both categories. The house was built on a main road, as he wanted it to be easy to find if people wanted to observe the building process, or when it was completed. His goal was to prove his theory that good design could be achieved in smaller buildings at a fraction of the cost. Flagg chronicled the entire process in succeeding articles, including adjustments to the original plans and new construction methods. Although isolated from other buildings from the Estate, the design maintained many of his signature elements, like a retaining wall which forms part of several structures. The McCall Demonstration House brought national attention to Flagg’s work, which had already found an audience through his 1922 book Small Houses. It was designated as a NYC Landmark in 1987. Photo by Frank J. Johns, 1967.

285 Flagg Place 
1918-21, Ernest Flagg 
New York City Individual Landmarks 

Known also as House-on-the-Wall, this roadside stone cottage is complementary to Flagg’s Bowcott, located on a similar location at the northeastern edge of the estate. Its main façade is comprised of a retaining wall built along the embankment, which incorporates setbacks from the building line on the lower sections to create a wider view of it from the road. Unlike Bowcott, Wallcot’s walls don’t replicate the road’s curvature, maintaining a straight line. The structure does follow the terrain’s slope upward, with a garage built on higher ground, which was later connected to the main section of the house. This gives the cottage the same appearance of being nestled into the terrain and its landscape. The lower section houses the living room, dining room, two large bedrooms and, originally, two smaller bedrooms for servants. The chauffeur’s apartment was located at its northwestern end, with a projecting gabled portico highlighting the garage portion of the building. The main entrance is marked by a gabled hood-roof, supported by large ornamental brackets. Underneath, a flight of steps leads up through an open stone-walled round-arched vestibule. It was designated as a NYC Landmark in 1987.

16 Flagg Court 
ca. 1900, Ernest Flagg 
New York City Individual Landmark 

Located at the northwest edge of the estate, this large fieldstone water tower remains as one of its most distinctive outbuildings. It was originally taller, and had a conical roof with a windmill on top and a water wheel. Some brackets are still visible on the highest section. The roof was originally supported by posts located on the interior of the structure, which also held a narrow walkway. The top section has a series of round-arched windows, and is crowned by an indented brick parapet. This last modification was done during the 1950s. A secondary tower was built also around 1900 and used as a pump house. It was located on the center axis, approximately 160 feet northwest of the entry court gate. It was included in the 1983 boundaries expansion of the 1967 NYC Landmark designation.

79 Flagg Court 
ca. 1900, Ernest Flagg 
New York City Individual Landmarks 

Originally a two-story structure, the stable is the largest outbuilding on the Flagg Estate. Located on the northern edge of the property, it faces the swimming pool and aligns with the central axis that shapes the group. It had entrances at both ends, which were framed by one-story buildings that marked driveways for secondary roads that led to north gateways. They have since been removed, as well as the continuation of Coventry Road, which paralleled the rear of Flagg’s property and connected Todt Hill and West Entry Roads. In 1947, an attic story was added by St. Charles Seminary and the three original dormers were removed from the steeply-pitched gable roof. The roof lantern was maintained, and is flanked by two chimneys. It was included in the 1983 boundaries expansion of the 1967 NYC Landmark designation.

63 Flagg Court
ca. 1908, Ernest Flagg
New York City Individual Landmark

Located 100-feet northwest of the Gardener’s Cottage, the Palm House was part of an area occupied by greenhouses which ran along the perimeter wall. Some of them were connected to it through a pipe system, which distributed the heat generated from large chimneys located at each end of the structure. It was originally a low one-story structure of fieldstone covered by a gable roof. The center section of the southwest slope was filled by a large skylight. The property was severely altered in 1987, when a two-story structure was added on the southwest side, thus changing the façade expression. It was included in the 1983 boundaries expansion of the 1967 NYC Landmark designation.

45 Flagg Court
ca. 1908, Ernest Flagg
New York City Individual Landmark

Built around the same time as the addition to the Gatehouse, this double-cottage was originally a long rectangular building of whitewashed fieldstone. Its northeast façade was incorporated into the perimeter wall, which continues south and sets the boundaries of a backyard. It was Flagg’s first exploration of a typology he described as “cloister house”, designed around a central square or courtyard. He would later add another structure to the rear, also attached to the perimeter wall, which created an L-shaped house plan. Over
the years, further alterations to the house have obscured the initial layout. The northwest section has two-stories and gabled windows which break the eaves. The southwest section has one-story and a basement, and also features a pair of gabled windows on the attic. Entrances are marked by pent roofs carried on brackets. It was included in the 1983 boundaries expansion of the 1967 NYC Landmark designation. Photo by Jean Prahbu.

209 Flagg Pl

1898-1908 renovations, Ernest Flagg
New York City Individual Landmark
Located at the highest section of the property, Stone Court was Ernest Flagg’s country residence, which he purchased in 1898. The imposing 32-room mansion was built of fieldstone, like many of the surrounding outbuildings and cottages. It features several variations of the colonial tradition, such as an enlarged scale, massive chimneys, and a circular balustraded observation deck atop a traditional gambrel roof. The façade on Flagg Place is framed by an axially- arranged formal garden on an elevated terrace, and the main entrance is marked by a two-level veranda supported by Doric columns on the first story and by posts on the second. Flank wings to the main building were added later on, and a large swimming pool and fountain on the central court completed the complex, which was completed around 1917. After Flagg’s death in 1947, the estate became the St. Charles Seminary. Ten years later, the southwest pavilion and logia were demolished and replaced by the current two-story administration building. Further modifications have been done over the to accommodate its current use. It was designated as a NYC Landmark in 1967. Plans to develop a portion of the property have been pursued by the owners since 2006, with a proposal presented in 2018 which added 19 single-family homes, a new roadway and offered to restore parts of the mansion. Although those plans did not succeed, the estate continues to be up for sale.

181 Flagg Pl
1898-1908 renovations, Ernest Flagg
New York City Individual Landmark

This two-story single- family house was constructed of fieldstone at the same time as Stone Court. The oldest section is a one-story, L-shaped, gabled-roof structure, which was incorporated as part of the retaining wall. An extension was added around 1908, consisting of a one-and-one-half story structure with gambrel-roof on the northwest side. Through the years, additions and modifications have been made to the house, including glass panels to the attic, but it maintains its cohesiveness and signature elements, such as the chimneys topped by curved ventilator caps. It was designated as a NYC Landmark in 1967.

95 W Entry Rd
1916-17, Ernest Flagg
New York City Individual Landmark 

Flagg envisioned his estate populated by many small stone houses, evoking the ancient Anglo-French or Norman villages of England and France. Bowcott was the first of the experimental stone cottages he constructed, receiving its name for the way it bends with the road. Viewed from the principal façade, the house appears to nestle into the terrain, while the rear elevation creates a clear public-private boundary. This is representative of Flagg’s idea of buildings that belong to the site, with structure and topography aligned. Bowcott was the first domestic architecture project where Flagg used mosaic rubble. Instead of worked stone, he used quoins made of concrete-blocks with vertical reinforcing rods filled with concrete. The stone was sourced from a quarry he had established on the grounds. It has been observed that this technique pre-dates the general usage of concrete block by some twenty years. The main floor was used as the living and dining rooms, while the attic had several bedrooms and a sitting room. Additional bedroom space was provided by a large one- story room at the west corner. The basement was possibly used as a kitchen. Dormers, chimneys and gables were used to provide a picturesque effect, a detail Flagg used often. It was designated as a NYC Landmark in 1987.

5 W Entry Rd
ca. 1900

This two-story cottage was initially part of the Flagg Estate, and was transferred to the Richmond Country Country Club in the early 1900s. It displays many of Flagg’s signature design elements, such as gambrel roofs, gabled windows and curved top chimneys. It also maintains more direct a stylistic relationship with Stone Court, implying that it could be one of the earliest structures to have been built. During the 1920s and 30s, it was the residence of New York Curb Exchange broker Gilliat Schroeder. Born in New York, he graduated from Columbia University in 1902 and was a member of the Board of Governors of the Exchange. Schroeder moved to Todt Hill with his first wife Helen Stevens, a relative of business tycoon John Jacob Astor, their two children and his mother-in-law. After the passing of his wife in 1927, he married Louisa Rapallo Donald the following year, and relocated to Manhattan by the end of the 1930s. He retired in 1932, and passed away in 1942.

135 Flagg Pl
ca. 1840

The Richmond County Country Club was organized in 1888, as a social club which offered fox hunting and other sports. The original clubhouse occupied a two-story Victorian mansion, located on the grounds of the former Vanderbilt estate, near Ocean Terrace and Little Clove Road. In 1897, the Club moved to its present location in Dongan Hills (known at the time as Garretson) to accommodate the rising interest in golf. George Cromwell, Club member and Staten Island’s first borough president, assisted with the purchase of a 35-acre estate that included a large home. The house was presumably built by Agatha Mayer and purchased in 1878 by Junius Alexander, who had made his fortune on Wall Street and through the railroad business. He lived there with his family until his death in 1893. At the time, one side of the house had extensive grass lawns, which became a nine-hole golf course for the Club before it was sold in 1908 for residential development. A new course layout was designed by Robert White in 1916. He was the first President of the Professional Golfers’ Association of America, and a founding member of the American Society of Golf Course Architects.

103 Circle Road 
ca. 1846 
New York City Individual Landmark

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 lonic 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 Rd
1980

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 Road 
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 Underground Railroad 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), wich 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.

26-90 E 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. 50 East Entry Road (2a) was once the sight 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. A remarkable two-and-a-half- story frame house with a grand porch framing its first floor once stood at 46 East Loop Road (2b). 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. 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.

1476 Richmond Rd
1679; additions 1700, 1750, 1790, 1830
New York City Individual Landmark / National Register of Historic Places – Property 

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.