Courtesy  of Williams New York

It’s hard to imagine today that people had to be lured to settle on the Upper West Side of Manhattan, but such was the case at the turn of the 20th century when the first New York City subway line opened. The Interborough Rapid Transit Line (IRT) started at City Hall, with the most epic of subway stations (now closed off to the public except on official Transit Museum tours). The Astors and other enterprising investors owned the land uptown, purchased in a speculative property boom. Now, the question was how to brand the area. No longer just for bachelors, apartment living was made luxurious and drew wealthy New York families out of their single family homes downtown and into apartments uptown. This change in not only location but also in lifestyle was often a hard sell, so the apartments had to be decked out in the latest modern amenities and features that single family homes couldn’t offer. The speculative investments paid off and many luxurious apartments of the Pre-War era are still some of the most coveted New York City addresses. Check out some of the oldest and most luxurious apartments and hotels of the Upper West Side:

1. The Dakota, 1884

Popular legend has it that The Dakota was so named because when it was built it was so far north it might as well have been like living in the Dakotas. Another theory is that Edward Clark, the building developer and former president of the Singer Sewing Machine company, chose the name because of his penchant for the Western states.

The Dakota was designed by architect Henry Janeway Hardenbergh, who also designed the Plaza Hotel. After four years of construction and going doubly over budget with a cost of more than $24 million dollars in today’s money, the Dakota welcomed tenants into its 54 suites in 1884. The units were designed for families and all told there were 500 rooms within the building. The Dakota was the first apartment building to make the Upper West Side, and apartment living, desirable. The Dakota still functions as a luxury apartment building and remains one of the most sought addresses in the city, with former residents famously including John Lennon and Yoko Ono as well as Lauren Bacall, Judy Garland and many prominent New York City figures.