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Many new buildings talk a big game about the jaw-dropping views and luxurious amenities to be enjoyed on their roof decks, but the roofs themselves tend to be aesthetically uninspired and a mish-mash of mechanical units and a cacophony of thoughtless enclosures. There is something to be said for the rooflines of many of New York's prewar architecture, however, which strived to make a statement in the skyline and inspire passersby at street level.

In the spirit of Valentine's Day, we take a look at the ten most beautiful rooflines in Manhattan. It is not surprising to note that the majority of them are New York City landmarks built during the first half of the 20th century. It would be heartbreaking to see these works of art lost, so here's an appreciation piece to our majestic pre-war icons that counteract NYC from looking like any other city. Happy Valentine's Day.

In this article:

The Oliver Cromwell, 12 West 72nd Street
The Oliver Cromwell, 12 West 72nd Street Central Park West
1040 Fifth Avenue
1040 Fifth Avenue Carnegie Hill
55 Central Park West
55 Central Park West Central Park West
15 Central Park West
15 Central Park West Central Park West
The St. Urban, 285 Central Park West
The St. Urban, 285 Central Park West Central Park West
The most phallic tower on our list (it is Valentine's Day), One Hanson Place is the most iconic pre-war skyscraper in Brooklyn and one of the best Art Deco towers in New York City. Erected in 1927 as the Williamsburgh Savings Bank Tower, the 512-foot structure was converted to 175 residential condominiums in 2006.

Designed by Halsey, McCormack, and Helmer in a Byzantine Romanesque style with Art Deco thrust, it was for many years the tallest building in Brooklyn until the fugly Brooklyner snatched the title in 2009. A series of taller buildings have risen since then, and yet none has been able to match the eminence of Brooklyn's clock tower. It is conveniently next to the Brooklyn Academy of Music, near a spaghetti of subway lines, and the Barclays Center/Atlantic Yards project.
It's incredible banking hall now used for events

One Hanson Place, #17A (Douglas Elliman Real Estate)

1 Fifth Avenue-nyc
An isolated skyscraper, a rarity in Manhattan, One Fifth Avenue was one of the first Art Deco towers in the city and it dominates Lower Fifth Avenue, Washington Square Park and Greenwich Village.

Designed in 1927 by Helmle & Corbett with Sugarman & Berger, this is one of the city's premier residential skyscrapers. Its dark brown masonry and strong verticality make this tall setback tower quite monolithic.

The building, Christopher Gray noted in a 1992 article in The New York Times, "is one of the city's most illusionistic statements, where flat brickwork is made to appear three-dimensional through false shadow effects."

1 Fifth Avenue, #18GK (Sothebys International Realty)

When 952-foot-tall 70 Pine Street rose in 1932, the tower yielded only to the Empire State and the Chrysler Buildings in terms of both height and Art Deco elegance. The 2016 apartment conversion instantly propelled the slender, setback landmark into the top ranks of New York City’s Art Deco-styled apartment buildings.

70 Pine Street, #5404 (Rose Associates)

The Pierre-04 (Brown Harris Stevens)
The Pierre is a New York City icon. The Parisian mansard roof adds romance to classic Central Park views. Gold-trimmed entry marquees complement the Renaissance elegance of the facade, designed by esteemed architecture firm Schulze & Weaver. The hotel has ranked among New York’s premier since its 1930 opening, and the 1959 conversion of the upper floors to co-ops only added to the building’s cachet. White-glove service is synonymous with the building’s amenities.

The Pierre, #512 (Douglas Elliman Real Estate)

While the building has undergone some questionable alterations, it remains one of the most recognizable on the Upper East Side skyline.
The 1930 building combines a luxury hotel with co-ops on the upper floors and offers Art Deco design, palatial layouts, high ceilings, and Central Park views elevated to a height that few other pre-war high-rises can match. Many upper-floor units span the whole floor, offering sweeping vistas in every direction.

The Carlyle, #200915 (Sothebys International Realty)

San Remo-02
This is the city's dreamiest apartment building, and its elegant design by Emery Roth for dividing the top of their 27-story building into two 10-story towers was the first such scheme in the city. Scarce availabilities within underscore the contentment of its residents.

The San Remo, #4C (Corcoran Group)

Crown Building-003 The Crown Building looking south down Fifth Avenue
The Crown Building, an ornate tower topped with an iconic copper-clad pyramid, has graced the corner of Fifth Avenue and 57th Street since 1921. Almost exactly 100 years later, a renovation transforms the former office building into The Aman, a bespoke addition to Billionaires’ Row. Residents of the 20 upper-floor condos have access to the services of the in-house hotel, which include a pool-equipped spa, a subterranean jazz club, a piano bar, a cigar bar, and a wine library. The penthouse offers a terrace with an outdoor pool and views of Central Park. See full details here.

Aman New York Residences, #16B (OKO REAL ESTATE LLC)

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No building has added more value to Fifth Avenue apartments than The Eldorado. Its twin spires grace the romantic Central Park West skyline and appear perfectly centered behind the Jackie O' Reservoir. The ornate yet austere skyscraper designed by Emery Roth exemplifies the gradual transition from classical opulence to avant-garde modernism.

The Eldorado, #22D (Brown Harris Stevens Residential Sales LLC)

The Pierre and the Sherry Netherland from the roof of The Plaza (Sotheby's)
There is probably a maiden with very long hair in the minaret in need of rescue, but what knight would dare mess with this building's impressive dragons holding large lamps above the second floor. Ah, romance!

The building has graced the Central Park skyline since 1927, channels elegance from the barrel-vaulted lobby to the tip of the copper spire. The Grand Army Plaza-adjacent building has hosted residents such as pilot and entrepreneur Howard Hughes, musician Diana Ross, director Francis Ford Coppola, Jim Henson of The Muppets, and TV host and judge Judy Sheindlin, better known as Judge Judy.
The Sherry Netherland Hotel The Sherry Netherland Hotel lobby. Authentic luxury.

The Sherry Netherland Hotel (background) from the roof of The Plaza
The Sherry Netherland, #1911 (Serhant LLC)

THe Woolworth Building-94 The Woolwrth Building (Alchemy Properties)
The Neo-Gothic Woolworth Building was the world’s tallest when it opened in 1913 and is among the world’s most beautiful to this day. While the broad, 30-story base remains used for offices, in 2016 the building’s slender upper portion transformed into 33 exclusive condominiums, which benefit not only from some of the city’s finest views but also top-notch services and a prime Downtown location overlooking City Hall Park.

The Woolworth Tower Residences, #46A (Douglas Elliman Real Estate)

Honorable Mentions

10 Gracie Square
778 Park Avenue

90 West Street
Barbizon 63




Would you like to tour any of these properties?
Just complete the info below.
  1. Select which properties are of interest to you:

Or call us at (212) 755-5544
Would you like to tour any of these properties?