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Billionaires' Row skyline, including 432 Park Avenue and 111 West 57th Street (Flickr - Diane Wildowsky) Billionaires' Row skyline, including 432 Park Avenue and 111 West 57th Street (Flickr - Diane Wildowsky)
As far as the world's most famous skyline is concerned, everyone has opinions. Architecture critics muse about what new buildings say about current design trends and what they mean for the future of the city. Locals are concerned about how supertalls and/or unconventional architecture will affect their light and views, not to mention their property values. Additionally, real estate agents must wonder if open houses in these buildings are being attended by serious buyers or curiosity seekers.

Sometimes, buyers find that it's what's inside that counts – i.e., the apartments and amenities are more compelling selling points than the building's architecture. Other times, locals come to accept the unusual new buildings as the latest sign of character in their neighborhood. This article takes a look at New York City residential buildings that have drawn the most surprising comparisons, examines their performance, and highlights notable listings inside.

Jenga Tower
56-Leonard-Street-01 56 Leonard Street (The Corcoran Group)
The Lower Manhattan skyline has seen an incredible transformation in the years following the 9/11 attacks with new, distinctly shaped high-rises taking shape. Among them was 56 Leonard Street, which was designed with each floor rotated from the floors above and below, not to mention private balconies in every unit. This has resulted in comparisons to a popular game; but fortunately for residents, the uniquely created floors are fixed too firmly in place for one misstep to send the whole building toppling. It has ranked among the city's best-selling buildings in past years and continues to rack up some of the highest-priced contracts.

Living room with balcony access 56 Leonard Street, #17AEAST (Compass)
From the Listing: Soaring eleven-foot ceilings, floor-to-ceiling windows, solid white oak flooring, efficient central air and heating, private terrace, custom designed storage, one and a half bath and well designed kitchen are just some of the custom designed features of this apartment. The kitchen has Sub-Zero fridge, Miele oven, cooktop, fully vented hood and dishwasher, along with Corian countertops and well designed storage. The half bath off the living area has an exquisite sculpted stone vanity; there is media storage and separate side storage with your own washer/dryer. The bedroom has a walk-in closet and ensuite bath with radiant heat floors, separate free-standing soaking tub, separate walk in shower and double vanity. See floor plan and full details here.

Trash Can
432-Park-Avenue-01 432 Park Avenue (Douglas Elliman)
The airy design of 432 Park Avenue has been likened to a trash can, and it turns out that's on purpose: In 2015, when it took the skyline and real estate market by storm, co-developer Harry Macklowe said he and designer Rafael Vinoly were inspired by the pattern and "push-pull between negative and positive" of a trash can designed by Austrian-Moravian architect Josef Hoffmann. Early buyers did not seem to object to the design, which resulted in stratospheric sales and attracted the likes of former power couple Jennifer Lopez and Alex Rodriguez. However, a February 2021 report about construction woes like water damage, elevator malfunctions, and swaying in the wind may have turned some luxury buyers away.

Penthouse living room with fireplace and corner windows 432 Park Avenue, #PH96 (Official)
From the Listing: The full-floor apartment encompasses 8,255 square feet of the grandest living, with soaring twelve-and-a-half-foot ceilings throughout and twenty-four windows stretching ten feet by ten feet each, offering spectacular full-circle panoramic views in all directions. The penthouse’s private elevator entry opens into a ninety-three-foot-long great room of monumental proportions fit for grand entertaining, with sunset exposures to the north, east, and south, and a wood-burning fireplace. The formal dining room is well suited for stately dinner receptions. To the left, the chef’s kitchen, with park views and an intimate family dining space, is equipped with white lacquer cabinetry, Miele stainless steel appliances, swaths of contrasting marbles on the floors and countertops, and Dornbracht fixtures. See floor plan and full details here.

Toilet seat
151-East-58th-Street-01 One Beason Court (Compass)
One Beacon Court is the residential component of the full-block Midtown complex that includes the Bloomberg offices. Glass walls curve around the courtyard to create a graceful statement at street level, but result in a somewhat unfortunate shape when viewed aerially. That does not seem to have bothered powerhouses like Jack Welch, Steve Cohen, Beyonce, and Brian Williams, all of whom have owned apartments in the building in the past.

Corner Great Room One Beacon Court, #46AB (Compass)
From the Listing: This exquisitely crafted apartment was masterfully renovated into a five-bedroom home by internationally celebrated designer Tony Ingrao and then further updated by the current owner to bring the apartment to a new standard of excellence. The entry gallery creates the perfect canvas for an art collection. The impeccable finishes, like the use of exotic woods, onyx and marble, exemplify the fine details that can be found throughout the apartment. The corner living and dining rooms boast 11 ft ceilings, floor-to-ceiling windows, and unobstructed city views. A wet bar with wine storage is conveniently located off the dining room. Across from the gallery is the primary bedroom wing with an expansive walk-in closet, northern exposures, and an ensuite bathroom. See floor plan and full details here.

Love child of a Dustbuster and Mach3 razor
111-West-57th-Street-01 111 West 57th Street (The Corcoran Group)
A few blocks up from 432 Park Avenue (see above), 111 West 57th Street is located amidst Billionaires' Row mainstays like 220 Central Park South, Central Park Tower, and One57. It has been compared to "the love child of a Dustbuster and Mach3 razor," but is in fact the combination of the landmarked Steinway Hall and a staggering, skinny new tower. The Steinway Hall component has proven popular in recent months, with lofts in that section regularly ranking among the top contracts, but a penthouse near the top of the new tower closed for $47.2 million in March 2023.

Penthouse with wall of windows facing the city skyline 111 West 57th Street, #PH76 (The Corcoran Group)
From the Listing: Available for immediate occupancy, Penthouse 76 at 111 West 57th Street is a spectacular, one-of-a-kind residence that offers the grandeur of expansive indoor-outdoor living across two full floors, all with breathtaking, unobstructed 360-degree vistas that are perfectly centered over Central Park to the north, and river-to-river over Manhattan’s iconic city skyline to the south. The residence is designed around a dramatic, central entrance gallery with white macauba stone floors and a gracefully proportioned oval staircase connecting the upper and lower levels. The Great Hall is an entertainer’s dream with views of Central Park to the north highlighted by floor-to-ceiling windows and 14’ ceilings. See floor plan and full details here.

Big ugly cantilever
251-West-91st-Street-01 The Westly (MOSO Studio)
Located in the heart of a condo building boom on the Upper West Side, The Westly is distinguished by its cantilever over the three-story building next door. Locals complained, but the Department of Buildings found it to be in compliance with building codes and regulations. Upon completion, the cantilever allows for unique, spacious floor plans and a roof deck with enough room for a pool and lounge area. Earlier this spring, a penthouse in the building set a new price record for a condo above 86th Street.

Corner Great Room with open kitchen The Westly, #12B (Serhant LLC)
From the Listing: Airy and bright, this chic corner condo is a study in modern sophistication. A foyer adorned with a herringbone pattern oak flooring and custom moldings leads into an open-concept living room, dining room, and kitchen with dual exposure and easy access to a pristine powder room with a Calacatta gold marble walls and floors and a custom oak vanity with Waterworks faucets and a stunning Michelangelo marble slab countertop. The kitchen is equipped with gleaming cremo delicato marble slab countertops, striking singette papyrus mosaic marble backsplashes, sleek Waterworks fixtures, marble-clad oven vents, custom walnut finish Italian cabinetry by Aster Cucine, a Wasteking garbage disposal, and fully-integrated appliances from Gaggenau. See floor plan and full details here.

To be determined
Bland box o'condos
15-West-86th-Street-01 15 West 96th Street (The Agency)
Right outside the Upper West Side/Central Park West Historic District, two modest townhouses were demolished to make way for a 22-story tower with apartments starting on the sixth floor. Locals and critics derided the new building's design, but the developers are optimistic that buyers will appreciate the apartments' incredible privacy, private outdoor space, and close proximity to Central Park.

Living room
From the Listing: Occupying the entire floor, residence 17 boasts 360-degree exposures, floor-to-ceiling windows, and two incredible private outdoor spaces. The foyer opens up to the grand living room, showcasing the corner of floor-to-ceiling windows and exceptional southern and eastern views from the private 90-square-foot balcony. Sunlight fills the space, highlighting the 5-inch white oak herringbone pattern flooring throughout the kitchen, hallways, living and dining rooms. Suitable for any level chef, the wrap around kitchen features custom Bilotta white matte cabinetry, Taj Mahal Quartzite countertops, backsplash and peninsula, a Bertazzoni master series appliance package, and a paneled refrigerator and dishwasher. See floor plan and full details here.

Evil Sauron vibes
9-Dekalb-Avenue-01 The Brooklyn Tower (Douglas Elliman)
Between its 1,066-foot height and neo-Deco crown, The Brooklyn Tower is an immediate standout in the Downtown Brooklyn skyline. The landmarked Dime Savings Bank is part of the new development, and the new tower was inspired by its hexagonal composition. Earlier this spring, the New York Post reported that locals were less than impressed, comparing it to an evil corporation's headquarters and the Eye of Sauron as depicted in the Lord of the Rings trilogy. But as construction winds down, more recent headlines have centered on the building's amenities, which include an outdoor pool around the bank's Gustavino dome and a 66th-story basketball court.

Corner living room with oversized windows
From the Listing: Located at an elevation of 569’ in the sky, this exceptionally proportioned corner residence offers sprawling vistas over the Brooklyn skyline, the New York Harbor, Verrazano Bridge, and the Statue of Liberty. A gracious entry foyer unfolds into the spectacular corner great room with western exposures, ceiling heights up to 11 feet, and floor-to-ceiling windows that frame spectacular views over Brooklyn, the New York Harbor, and the Statue of Liberty. Richly layered materials such as mahogany, antique rubbed bronze, and white oak flooring in a custom honey stain create a warm and intimate interior. The centerpiece of the great room is the exceptionally crafted, open kitchen with island designed by Gachot Studios. See floor plan and full details here.
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