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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 One Hanson Place, #19H (Compass)
From the Listing: Come home to this spacious and sun-filled 1,359-square-foot two-bedroom / two-bath condo with spectacular 20-foot living room ceilings and tall, arched windows framing placid views above Brownstone Brooklyn. You are greeted at the entry door by a burst of sun streaming through the wide and deep living and dining areas. Outside, your open views extend beyond the New York Harbor, Verrazano Bridge, and Statue of Liberty. 19H’s custom kitchen features Viking appliances, lava stone counters, and plenty of storage space. There are freshly refinished chestnut flooring and CitiQuiet windows. A suburban-sized primary suite large enough for a king-size bed, office furniture, and sitting area with room left over. 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 up high in the Tower of One Fifth Avenue, the landmark, art deco, doorman building, sits this special apartment which has incomparable and infinite northern views of the Empire State building and the Chrysler building, and it also has commanding western views to the Hudson River and beyond, as well as views of Washington Square Park. This is a wonderful New York apartment that has a large bedroom with three exposures, a designer, open kitchen with a dining room (originally a den/second bedroom) and a corner living room with striking views of all of Manhattan through all glass, picture windows. The apartment also has central air-conditioning, beautiful oak plank floors, walk-in closets, state-of-the-art kitchen appliances and lots of built-ins. 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 70 Pine Street, #2405 (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, spacious closets, and in apartment washer/dryers. The building also features 2 floors of amenities including La Palestra Fitness and Wellness center, a 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 The Pierre, #1401/1403 (Sotheby's International Realty)
From the Listing: Step through double doors into a beautiful foyer framing the large, bright and sunny living room. There is a faux fireplace which adds to the loveliness of this wonderful apartment. The primary bedroom has extremely high ceilings and a large picture window facing Central Park and the exciting skyline of Central Park South and West. The separate dressing room has a walk in closet and many closets surrounding its space. The bath has a separate shower, a large tub and wash basin all in mint condition. 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 The Carlyle, #1412/17 (The Corcoran Group)
From the Listing: Suite 1412/17 is a 3-bedroom, 3-bath residence with a private south facing terrace and oblique views of Central Park. Situated at the corner of Madison Avenue and 76th Street, the Carlyle has been a classic landmark of Manhattan’s elegant Upper East Side since 1930. A quintessential New York City institution, the landmarked hotel is a showcase of great art, purveyor of privacy, security and sanctuary of luxury and refined taste. 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 The San Remo, #4C (The Corcoran Group)
From the Listing: Perfectly situated in the premier prewar co-operative, The San Remo, this extraordinary thirteen into ten room corner residence has been expertly renovated by the renowned architectural firm Hottenroth + Joseph with C-Squared Contracting executing the construction. Drenched in sunlight, this stunning residence has three magnificent entertaining rooms overlooking Central Park. The residence features 10-foot ceilings, original restored Emery Roth historical details, custom millwork and moldings, raised doorways, twenty-three windows, solid Mahogany doors, Nanz hardware, and Waterworks fixtures. 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.

300-Central-Park-West-2 The Eldorado, #18J (Douglas Elliman Real Estate)
From the Listing: Located in one of Central Park West’s finest cooperatives, this beautiful 3-bedroom, 3-bath apartment in the famed Art Deco building was designed by the legendary architect Emery Roth and completed in 1931. After arriving on your private elevator landing, you are led into a grand gallery. The living room has direct views of the Central Park Reservoir and Hudson River with eastern, western, and northern exposures, and opens onto a terrace. A dining-room that seats eight flows into a cook’s dream eat-in kitchen. 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. 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 The Woolworth Tower Residences, #38B (Sotheby's International Realty)
From the Listing: This sprawling two-bedroom, two and a half-bath home offers 2,548 square feet of gracious living space and three breathtaking exposures of sweeping city and river views. This luxurious tower residence is complete with an oversized eat-in kitchen, ceilings up to 11’3” high, and solid oak herringbone floors throughout. The sun-flooded professional kitchen has been outfitted with custom Dada cabinetry crafted by the Molteni Group, Calacatta Caldia marble countertops, and integrated Dornbracht fixtures. A full suite of Miele appliances, inclusive of a wine fridge and dishwasher, truly makes this kitchen extraordinary. See full listing, images and floor plan here.

Honorable Mentions

10 Gracie Square
778 Park Avenue

90 West Street
Barbizon 63




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