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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.

The finest landmark skyscraper in Brooklyn and one of the best Art Deco towers in New York City, One Hanson Place was erected in 1927 as the Williamsburgh Savings Bank Tower and was converted to 175 residential condominiums in 2006.

Designed by Halsey, McCormack, and Helmer in a Byzantine Romanesque style, it was for many years the tallest building in Brooklyn at 37 stories and 512 feet. It is next to the Brooklyn Academy of Music and across from the Atlantic Yards project.

1-Hanson-Place-2 Interiors via Compass
From the Listing: One Hanson Place, one of New York’s most iconic landmark residential buildings, rises at the nexus of most of the most popular neighborhoods in Brooklyn: Fort Greene; Boerum Hill; Park Slope; Prospect Heights and Downtown Brooklyn. Miles of sky and unobstructed views south to the Verrazano and west to the Harbor and Statue of Liberty. An entrance gallery greets you at the front door and passes toward the home’s common area past a custom closet, bonus room, washer/dryer closet, and guest bath At the end of the corridor is the open living area whose corner exposures frame miles of open sky through five oversized windows. The marble-topped island kitchen and breakfast bar are the centerpieces of the large, open dining and living areas. The king-size primary bedroom includes a walk-in closet and grand bath with a new dual sink vanity, soaking tub and shower stall. See full description, images and floor plan here.

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-2 Interiors via Corcoran
From the Listing: Perched on the 19th floor of the prestigious tower at One Fifth Avenue, lies residence 19E, a spectacular one-bedroom, one-bathroom jewel box with unmatched light and views that will take your breath away. An entertainer’s living room with over 9-foot beamed ceilings, honey wood plank floors, and three oversized picture windows spanning south-facing views of One World Trade, Washington Square Park and West-facing views overlooking the West Village, Hudson Yards and beyond. An expansive dining area can easily fit a table of eight and is situated perfectly adjacent to the kitchen with quartz adorned countertops and an abundance of cabinet space. The primary bedroom is an enviable retreat with ample space that can host a king-size bed and cozy sitting nook. See full description, images and floor plan here.

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-2 Interiors via Rose Associates
From the Listing: Historic, iconic and stylish, 70 Pine Street offers an exceptional living experience. Offering oversized studio, alcove studio, one, two and three bedroom apartments with condo level finishes, giant walk in closets, and in-apartment washer/dryers. The building also features 2 floors of amenities including La Palestra Fitness and Wellness center, game room, children's playroom, screening room, bowling alley, golf simulator, Black Fox Coffee Shop, and City Acres Market & Food Hall. See full description, images and floor plan here.

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.

795-Fifth-Avenue-2 Interiors via Douglas Elliman
From the Listing: Dreaming of 5-star hotel services and waking up to Central Park views from your luxurious oversized one bedroom on Fifth Avenue? Live at The Pierre, where prime is an understatement and French iconic architecture meets New York chic with updates by Maeve Carr Design, this stunning residence is move-in ready, and perfect for full-time or pied-a-terre living. Welcome guests in through elegant double-wide doors, into your gracious marble entry foyer which leads to the expansive living salon with high ceilings, oversized windows, and multiple seating areas, with formal dining, as well as access to the sleek butler’s pantry and charming hidden kitchen, which features a custom wine fridge for up to 100 bottles and separate service entrance for the staff. See full description, images and floor plan here.

35 East 76th Street The Carlyle Hotel via LPC
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.

35-East-76th-Street-2 Interiors via Douglas Elliman
From the Listing: Embrace luxury hotel living at the legendary Carlyle, with 5-Star hotel services and amenities on the Upper East Side of Manhattan. Day and night, Residence 1803 enjoys both Western and Southern exposures, dramatic views of Central Park, city skylines and dramatic sunsets. Residence 1803 is a beautiful corner apartment that enjoys a lovely foyer entrance that leads you in to a spacious and well-proportioned living room with two split primary bedrooms with en-suite bathrooms. See full description, images and floor plan here.

San Remo-02
This is the city's most beautiful 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.

145-Central-Park-West-02 Interiors via Warburg Realty
From the Listing: First offering of an Impeccably renovated 5,000+/- square foot 10 (was 13) room home in the iconic San Remo. Enormous rooms, brilliant light, French doors opening onto the Park. Now configured as three bedrooms, four bathrooms and a powder room, plus a room-sized, fully built-out dressing room, this is the most glamorous and livable apartment available today on Central Park West. See full description, images and floor plan here.

Crown Building-003 The Crown Building looking 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.

The Eldorado from Central Park (via Brown Harris Stevens)
The Eldorado’s twin spires grace the romantic skyline of Central Park West near the Reservoir. The ornate yet austere skyscraper designed by Emery Roth exemplifies the gradual transition from classical opulence to avant-garde modernism.

From the Listing: Welcome to this sprawling 7 room home at the famed El Dorado (one of the finest white glove coops on Central Park West). This apartment is a blank canvas awaiting your special touch. Sunny exposures and city views from your open southern exposure, this home has a wonderful layout with large scaled rooms and great entertaining space. Three large bedrooms each with their own bath and a large staff room/forth bedroom. This apartment has beautiful architectural details including high beamed ceilings, beautiful moldings and herringbone floors. See full description, images and floor plan here.

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 (background) from the roof of The Plaza

781-Fifth-Avenue-2 Interiors via Fox Residential Group
From the Listing: Enjoy all of the comforts of home with all the services and conveniences of a five star hotel in the prestigious Sherry-Netherland, one of New York’s premiere landmarks, The Sherry-Netherland is at the southern end of Central Park. This triple mint and very unusual one bedroom, one and a half bath apartment has 10 large arched windows with sunny southern and eastern exposures that look over the city’s sweeping skyline. This fine property is for those who enjoy the very best and take note of small details. The pristine renovations done in the apartment incorporate the building’s historic elements such as coffered ceilings, intricate parquet floors and distinctive barrel vaulted entrance foyer.

The apartment is ready to move into and is being offered furnished. Monthly maintenance fee includes twice daily housekeeping with evening turn-down service, 24 hour doorman, concierge, elevator attendant, and monthly window cleaning.
See full description, images and floor plan here.

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.

2-Park-Place-2 Interiors via Sotheby's International Realty
From the Listing: Spanning over 6,711 SF of interior space on the 29th floor, this 5-bedroom, 4-bathroom plus two powder rooms is the perfect blend of Tribeca loft meets historic penthouse. With six skylights, up to 22-foot ceilings, and duplex terrace totaling 2,770 square feet, there is no shortage of natural light throughout this residence. Unmatched cinematic views of the surrounding cityscape in addition to unique sightlines of the building itself, The Pavilion residences offer a once in a lifetime opportunity to live in the iconic Woolworth Tower. The expansive professional kitchen has been outfitted with custom Dada cabinetry crafted by the Molteni Group, Calacatta Caldia marble countertops, and integrated Dornbracht fixtures. See full listing, images and floor plan here.

Honorable Mentions

10 Gracie Square
778 Park Avenue

90 West Street
Barbizon 63




Worldwide Plaza Apartments
Beekman Tower-03

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