This is the Clendening Mansion. This print from Valentine's Manual lists the location as 90th Street and 8th Avenue. This is incorect. John "Lord" Clendening was a wealthy New Yorker who made his fortune importing Irish textiles after the Revolution, at the end of the 18th century. He built this lovely mansion, complete with widow's walk and waving American flag, around 1811. It stood at what is now the southwest corner of Amsterdam Avenue and 103rd Street, in the northern fringes of the area known as Bloomingdale. As the grew, so did the demand for a clean reliable water source. Early New Yorkers were incredibly dumb when it came to clean drinking water. They were very adept at polluting their water sources. Finally someone put it together and figured that all the garbage strewn ponds and wells (some wells too close to cemeteries that contained the bodies of those who had died in cholera epidemics) were killing them. Long story short, and it is a long story, after building the Erie Canal system nothing seemed impossible. So supervised by Chief Engineer John B Jervis (like in Port Jervis, who had served as one of the engineers of the Canal system) an aqueduct system was designed to bring water from reservoirs in Westchester County all the way down to City Hall Park. Bringing water by the force of gravity alone, New York City's first aqueduct system sent water 41 miles through stone aqueducts which for the most part were underground. Except in Clendening Valley. Because of the dip in the landscape a plan had to be hatched.
There are the arches on the map from 1868. The streets and sidewalks of 98th, 99th, and 100th streets passed beneath those arches. The Clendening estate stretched from the north side of 99th Street to the south side of 105th Street and from Central Park West to the Bloomingdale Road. The estate was lost in 1845 and the farm disappeared within 20 years. By the 1870s, development demanded more water; the above ground aqueduct section was buried underground into a pipe siphon and the solid wall blocking 96th, 97th, and 101st Streets–along with the arched 98th, 99th and 100th streets - was torn down.
This is looking northeast from just south of 101rst street between Amsterdam and Columbus Avenues. The 104th Street 9th Avenue El station is in the distance and the remains of the aqueduct through Clendening Valley are in the left foreground. This is quite possibly the remains of the arch-way at 101rst street. The original Croton Aqueduct, one of the most important pieces of what made New York City, opened June 22, 1842, taking 22 hours for gravity to move the water the 41 miles to Manhattan. Almost immediately it was woefully inadequate. Construction on a new aqueduct began in 1885. The new aqueduct, buried much deeper than the old one, went into service in 1890, with three times the capacity of the Old Croton Aqueduct.
Clendening lived on his rural estate for many years, but in 1836 he lost most of his money when President Andrew Jackson refused to renew the charter of the United States Bank, in which Clendening was a major stockholder. The estate was sold in 1845 as forty lots for a total of $4500. Although the mansion was torn down the area was known as Clendening Valley well into the post civil war 19th century New York. On the site where Lord Clendening's house one stood, the Clendening Hotel rose in its place on the west side of Amsterdam Avenue at 103rd street. The Hotel survived until 1965 when it was torn down for furthest west building of the Douglas Houses complex.