Waldorf Astoria New York (designed by Schultze and Weaver), and the General Electric Building (by the architects Cross & Cross) stand within a block of one another. Both buildings were completed in 1931, and both bear enviable exterior elements typical to the period, like geometric detailing and distinctive crowns that dramatically shape the silhouettes of the buildings.

“The dance between those two great Art Deco buildings was something that people interested in the New York skyline noticed right away,” said Andrew Dolkart, an architectural historian and professor of historic preservation at the Columbia University Graduate School of Architecture, Planning and Preservation. “While the tops of the buildings look different, they have a similar aesthetic, so they work well together.”

However, it wasn’t until construction began on The Towers of the Waldorf Astoria, a luxury condominium tower that spans the upper 33 levels of the 52-story landmark building, including two new top-floor penthouses nestled inside its crowning cupolas, that eye-level views of the General Electric Building’s stylized Gothic crown were fully revealed. (The hotel on the lower floors remains closed for renovations.)

Along with stunning views of that crown, a majority of the north-facing residences in the block-wide building also provide protected overhead views of the recently restored terra-cotta-tiled dome of St. Barts Episcopal Church next door.

Skidmore, Owings, & Merrill, the firm overseeing the restoration of the Waldorf Astoria New York Hotel, as well as the construction of the new residences.

Condo sales began early last year, and available units range from a $1.825 million studio to a four-bedroom unit for $18.5 million.

VU New York stretches 36-floors high, far above many of its surrounding structures. Its height provides vistas of the uptown skyline, the East River, and many of the hidden architectural gems in between.

Residents on some of the lower level floors of VU New York will have direct sightlines of the two-story mansard roof crowning the historic 69th Regiment Armory Building on Lexington Avenue, which has hosted everything from the legendary 1913 Armory Show to early 1950s NBA Finals games. (Today, the structure serves as the headquarters of the New York Army National Guard’s 1st Battalion, 69th Infantry Regiment.)

Upper-floor units with western exposures will have overhead views of the architecturally distinct structure, the first armory in New York City (built after the Seventh Regiment Armory) that was not modeled after a medieval fortress.

Constructed in 1906 by Hunt & Hunt, the Armory’s slate-covered mansard roof was originally just one story with circular dormer windows. In 1926 the roof was raised by the architect George M. McCabe to create more storage for the Armory. Rectilinear and round-headed windows with classical copper surrounds were added. The end result is a French Beaux-Arts-inspired structure with architectural details that can be appreciated from afar, but that are most impactful at eye level.

Woolworth Building at 233 Broadway was the tallest in the world from 1913 to 1930. Commissioned by the “five-and-dime” store magnate Frank Winfield Woolworth, the great neo-Gothic skyscraper was designed by the architect Cass Gilbert to resemble a medieval European cathedral, and is often referred to as New York’s “Cathedral of Commerce.”

Along with elaborate ornamental stonework, all but the lower four floors of the Woolworth Building feature a terra-cotta facade that from a distance reads as limestone, but upon closer inspection is a polychromatic scheme of vibrant blue, green and golden yellow glazes.

“The intention was to use color in a nuanced way that blended in with the sky,” said Ms. Willis, of the Skyscraper Museum. “Woolworth and Gilbert were serious about the building’s stature as an artistic work, or ‘Architecture’ with a capital ‘A’.”

Over a century later, Alchemy Properties has transformed the top floors of the 58-story building into 32 condominiums known as The Woolworth Tower Residences, where some residents can have up-close-and-personal views of the building’s intricately detailed exterior, including its gargoyles, ogee arches, copper roof, and windows framed by colorfully glazed terra-cotta panels.

record-breaking $110 million, but is currently offering the penthouse as a “white box,” or raw space, for $79 million after giving it a price cut in 2019. Other available units include a five-bedroom apartment listed at $29.95 million and a two-bedroom condo for $5.45 million.

R.H. Robertson’s iconic Park Row Building. When it was completed in 1899, the 391-foot-tall, landmark building was the tallest in the world, and once housed the offices of The Associated Press news agency.

The exterior of 15 Park Row is marked by classical architectural elements, including columns and pilasters, projected ornamental balconies, and most noticeably, a pair of four-story cupola towers with copper domes that cap the building and help distinguish it in the skyline.

“One critic referred to them as rabbit ears,” Mr. Dolkart said of the cupolas. “They were designed to draw attention to the building.”

Today, certain residents at 25 Park Row, a newly constructed 50-story luxury condominium building with 110 units located right next to the Park Row Building, can enjoy front-row-with-popcorn views of the cupolas. Additionally, every single residence in the building offers northwest views of City Hall Park and Woolworth Building, a consideration which the architect Rick Cook of CookFox said played heavily into the architectural design of the building.

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