Cornelius Vanderbilt (called “The Commodore”) was the kingpin of the railroads in 19th century New York City. In the early days when dozens of train lines competed for street space and riders, he moved quickly to get the upper hand.
As a part of his master plan he built the Grand Central Depot, the first railroad station to consolidate the mess spread out across the city. To do this he had to buy a huge amount of property, and his efforts did not go unchallenged. Daytonian in Manhattan has a good summary of the battle he waged — and eventually won — to buy t the blocks between 42nd and 48th Streets and Lexington and Madison Avenues and then to build on almost all that space. The image below is just the tip of that particular iceberg.
H.N. Tiemann & Co., 42nd Street looking west from Park Avenue, showing Grand Central Station, New York City; copy negative of a circa 1880 photograph by an unknown photographer. H.N. Tiemann & Co. photograph collection, 1880-1916, New-York Historical Society