Hotel St. Moritz, 1932. The Hotel St. Moritz (seen at center) was designed by Emery Roth and constructed in 1930. The 36-story hotel is highly ornamented at the base and the upper floors, while the middle of the building is largely plain. W. Parker Chase described the hotel in his book, "New York, The Wonder City, 1932", "a picturesque cliff, amidst towering trees to the north, and other soaring skyscrapers to the south." Named for a Swiss resort town, the hotel offered long-term and short-term residence. It quickly became a popular hotel among professional athletes and theatrical figures. In the 1930s the hotel add the Café de la Paix, a sidewalk cafe that claimed to the be city's first. In 1950 the hotel underwent a complete redesign and renovation, updating the interiors to a mid-century style. The hotel's Rumpelmayer’s Café offered guests and visitors pricey coffee and ice cream. The hotel was sold a number of times in the last decades of the 20th century with its owners including Harry Helmsey and Donald Trump. Trump had plans to encase the facade in glass, gut the interiors, and convert it to condos. That plan was thwarted by a new buyer in 1999. Changing hands a few times once again, the building was finally purchased and converted into a Ritz-Carlton hotel-condominium. During this conversion the deteriorated ornamentation at the topmost floors were stripped and replaced with copies of the originals. Though the windows replacement was non-historic, the conversion was generally historically sympathetic (for a non-landmark building).

New York Athletic Club, 1911. While this address is best know as the St. Moritz Hotel, prior to that classic Emery Roth building, this plot was occupied by the club house of the New York Athletic Club. Constructed in the late 1890s, the Athletic club moved into the building in October 1898. The eight-story building was lavishing decorated. The private club, founded in 1868, is considered the foundation for amateur athletics in the United States. In 1928 the club sold their 1898 building for $2.5 millions (in 1930 the Hotel St. Moritz would be completed on the lot) and moved into their new (and still occupied) City House, one block over on Seventh Avenue and Central Park South.

The Coronet, 1912. The Coronet is a 10-story brick and stone Beaux-Arts building completed in 1902. It aimed to be a high-class, modern apartment building. And high class it was with balconies, carved lions’ heads, heavy scrolled brackets, an impressive two-story arched opening, and stone parapet at the roof. By the 1970s the building was suffering from the loss of wealthy tenants. Some of its grand architectural features were lost including the parapet and some of the balconies. In 1976 the building was converted to an 85-apartment condominium. Today the building still stands, though it does not exude the grandeur it once presented.

When the Vanderbilts, Astors, and Rockefellers moved uptown, the hotels quickly followed. The gravitational shift of New York's social scene meant that prestigious hotels like the Waldorf-Astoria were no longer in the thick of it. However, developers are never too far behind a trend and soon some of the world's most luxurious hotels sprouted next to the mansions of Fifth Avenue.