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Penthouse at Chelsea Mercantile Penthouse at Chelsea Mercantile
Technically speaking, a building's penthouse is the apartment on the highest floor, which naturally provides the best views in the building and the greatest possibility of having a private roof deck. Given the prestige and higher price point these units command, developers and owners often outfit these homes with fabulous finishes further making them the most coveted units in a building.

Earlier this week, the New York Post broke the news that the palatial 7,000-square-foot penthouse at the Tower at Gramercy Square went into contract after just 30 days on the market. The reported buyer is Grindr founder Joel Simkhai who sold his app for nearly $250 million in 2018. The five-bedroom, 6.5-bath aerie comes with a 5,680-square-foot private terrace with space for a plunge pool, 18-foot-high ceilings, and sweeping views of the Manhattan skyline.
Gramercy Square Tower In-contract penthouse at the Tower at Gramercy Square (Douglas Elliman)
For those suffering from FOMO, there is still another smaller Gramercy Square penthouse on the market asking $9.345M. The four-building Gramercy Square complex debuted in 2019 and offers all residents access to the Gramercy Club, an 18,000-square-foot amenity package designed by La Palestra which includes 20,000-square-feet of private garden spaces, a 75' foot lap pool, fitness, and yoga studio, children's playroom, resident lounge, screening room, golf simulator, wine cellar, and a meditation studio designed by MNDFL.
34-Gramercy-Park-East-01 Image via Evan Joseph for Sotheby's International Realty (By Montclair Film Festival -, CC BY 2.0,
Shortly after this penthouse in a modern condominium entered contract, The Tonight Show host Jimmy Fallon and wife Nancy Juvonen (not pictured) put their Gramercy Park penthouse, located in "New York City's first cooperative," on the market for $15 million. The 4,950-square-foot home is a combination of four apartments spread over three floors, decorated with antiques finds from all over the world, and renovated to feature rare vintage wallpaper, a soundproof pantry, a show-stopping kitchen, ultra-private bedrooms, a custom staircase, a hidden playroom with monkey bars and secret hatch doors, and a "saloon room" with vintage barback, wet bar, and gas fireplace. It would seem that the only thing missing is a terrace, but the apartment comes with a key to Gramercy Park.

In any building and any era, penthouse apartments are synonymous with upper echelons of luxury. Below are superlative penthouse homes that represent the epitome of penthouse life.

The Highest and Priciest Publicly Marketed
432 Park Avenue interiors All images of 111 West 57th Street via Douglas Elliman
From the Listing: Triplex Penthouse 72 is a spectacular, one-of-a-kind penthouse residence that offers the grandeur of expansive indoor-outdoor living across three full floors, all with breathtaking, unobstructed 360-degree vistas that are perfectly centered over the entirety of Central Park to the north, and river-to-river over Manhattan's iconic city skyline to the south. The triplex boasts 7,130 of beautifully finished interior sq ft with four bedrooms and five and a half bathrooms. The extraordinary private loggia is 1,367 sq ft and provides for an elevated, sheltered open-air entertaining experience unrivalled on Central Park South. See full details here.

212 Fifth Avenue interiors All images of 53W53 via Corcoran
From the Listing: Enjoy dramatic 360-degree views of Central Park, Hudson River, East River, the downtown skyline, and beyond from this one-of-a-kind full-floor Duplex Penthouse Residence located in the new Jean Nouvel-designed tower soaring above The Museum of Modern Art.

Situated on the 76th and 77th floors, and at nearly 800' in the sky, this 7,973 SF (740.7 SM) four-bedroom Penthouse is accessed by direct elevator entry into a gracious foyer leading to a massively scaled living room with soaring double-height ceilings, grand proportions, and the rich attention to detail of a bespoke privately commissioned home. Nouvel’s innovative exposed structural system, known as the diagrid, is expressed like a graceful, abstract piece of sculpture creating a one-of-a-kind residence unlike any other in the world.
See floor plan and full details here."

Most Expensive Downtown
443 Greenwich Street interiors All images of 551W21 via Corcoran
443 Greenwich Street interiors
443 Greenwich Street interior and exterior
443 Greenwich Street exterior
443 Greenwich’s original grand and historic, landmarked facade has been meticulously restored and its interiors transformed by CetraRuddy Architects. This Tribeca condominium offers an unparalleled combination of space, luxury finish, location, and privacy. Read more.

All images of 56 Leonard, #PH6061 via Compass
From the Listing: TOP TWO FLOORS AT 56 LEONARD. Take your place among the New York City skyline in one of the most breath-taking Penthouses ever offered.

Set atop the iconic Herzog & de Meuron designed 56 Leonard, this trophy duplex encompasses 7,779 interior square feet and three exquisite terraces totaling 1,252 exterior square feet. From its unrivaled vantage point at the absolute top of the building, 360-degree vistas unfold at your feet and stretch across the harbor, Manhattan, Brooklyn and beyond. Towering 19-foot ceilings and soaring double-height windows accentuate the bright airiness of the home, while Appalachian white oak and premium stone pave the floors.
See floor plan and full details here.
56 Leonard Street #PH53-54 floor plan Floor plan via Compass

100 Barclay Street interiors All images of The Puck Penthouses via The Modlin Group (Photo credit: Michael Weinstein)
Photo credits: Michael Weinstein.
100 Barclay Street interiors Primary Bedroom
View to the east
From the Listing: This exceptional private home offers 7,241 sq.ft. interior and 5,158 sq.ft. exterior living space featuring 5 Bedrooms, 7.5 Baths, Library, Gym, Home Theater, Wine Cellar and stunning landscaped private terraces with a Yoga Lawn, Putting Green, Spa Tub, and Wet Bar. See floor plan and full details here.
100 Barclay Street #PENTHOUSE floor plan Floor plans via Modlin Group
100 Barclay Street #PENTHOUSE floor plan

Largest in Size
219 East 44th Street interiors (via Sotheby's International Realty)
219 East 44th Street interiors Kitchen
219 East 44th Street interiors Bedroom
219 East 44th Street views Penthouse views
From the Listing: A singular opportunity to secure exclusive occupancy of an extraordinary aerie, an elegant 14,000 square foot Penthouse duplex comprising two full floors located high atop the prestigious white-glove condominium which stands immediately above the Museum of Modern Art. See floor plan and full details here.
219 East 44th Street #PH floor plan Floor plan via Sotheby's International

100 Barclay Street entrance 35 Hudson Yards, PH via Corcoran
From the Listing: GRAND FULL-FLOOR FIVE-BEDROOM PENTHOUSE WITH 360 DEGREE RIVER AND CITY VIEWS WITH AN EAST FACING PRIVATE TERRACE. Enter this remarkable 10,171 square foot penthouse that encompasses the entire 90th floor by private elevator. The expertly planned residence boasts a gracious entry foyer, 14-foot ceilings and lavish satin finish 7.5 inch wide French oak floors. The expansive corner great room features southern views extending for miles towards downtown Manhattan, the Freedom Tower and beyond. See full details here.

Manhattan's Least Expensive
244 Madison Avenue, #PHJ All images of 244 Madison Avenue, #PHJ via Douglas Elliman
From the Listing: A modern gem at the elegant prewar Murray Hill Plaza, this Top Floor Penthouse studio apartment with a sleeping loft is spacious, airy and beautifully designed. A hallway with generous closets welcomes you into contemporary living space graced by12' high beamed ceilings, wood floors, a walk-in closet, stylish kitchen with dishwasher and south-facing living room. A spiral staircase leads up to the bonus 13'x13' loft area. See floor plan and full details here.
Murray Hill Plaza foor plan Floor plan via Douglas Elliman

25-19 43rd Avenue interiors All images of 50 East 8th Street via Douglas Elliman
25-19 43rd Avenue interiors Kitchen
A north/eastern-facing studio in this luxurious new building boasts generous space and ceiling heights reaching nearly 10' high, complete with wide plank oak hardwood flooring. A thoughtfully designed open kitchen finished with quartz stone counters and a tiled snow & ice backsplash is equipped with a full suite of stainless steel appliances. Read more.
25-19 43rd Avenue #PH7 floor plan Floor plan via Douglas Elliman's Rubin Team

Biggest Price Improvements
All images of W Downtown via Compass
211 West 14th Street interiors Kitchen
211 West 14th Street outdoor space View south
From the Listing: It is very rare to find an apartment that has everything from luxury amenities, fine finishes, detailed touches, and warm hospitality. New York City is famous for the architecture and culture, you would have the luxury to see everything this city has to offer from your masterpiece. From the iconic statue of liberty, world trade center, empire state building and the majestic Hudson river. See floor plan and full details here.

42 White Street interiors All images via Compass
From the Listing: This palatial penthouse is surrounded by iconic views and serviced by the world-class team at the Ritz-Carlton Battery Park. Floor-to-ceiling glass windows facing south and west provide picture-perfect views of the Statue of Liberty, the Hudson River, Governor's Island, and the Verrazano Bridge. Enjoy stunning sunsets from every room in this sky-high home - the views belong on a postcard. See full details here.

Notable Picks
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From the listing: A remarkable, no-stone-unturned renovation has combined four different apartments over three floors to create a home like no other in New York City. Celebrating the bones and architecture of the famed 34 Gramercy Park East, while transforming the space into a singularly enhancing home, this jewel box is perched atop the southwest corner of the historic landmark. Features of the approximately 4,950-square-foot home include original, restored window frames and casings throughout, original, restored hardwood floors throughout, and the highest quality fixtures and finishes combined with a curated collection of treasured vintage and antique finds from around the world. See full details here.

(DOuglas Elliman)
From the Listing: VIEWS, VIEWS, VIEWS!!! Upon entering the windowed foyer one is introduced to the brilliant light filling PHA. With airy 10’ ceilings, the living/dining area faces north and west and offers a comfortable space with spectacular views to entertain and relax. See full details here.

From the Listing: This penthouse stunner is an alluring retreat, offering over 3,900SF of extraordinary indoor and outdoor living. Masterfully redesigned and reimagined, every detail has been thoughtfully considered to meet the demands of a contemporary lifestyle. Captivating views and the seamless merging of art and architecture abound in this exceptional 3-bedroom, 3.5 bath terraced residence. See floor plan and full details here.

From the Listing: Full-Floor Penthouse with Wrap Terrace, Helicopter Views, and 2 Deeded Parking Spaces.

Perched at the pinnacle of the Belaire Condominium, PH4 is the crown penthouse of the Zeckendorf designed skyscraper. Occupying the entire 50th floor atop the building, this special home features stunning panoramic views from all 4 exposures - including skyline, river, bridge, and park views. PH4 is a full-floor, triple mint, luxury home that was gut-renovated to exacting standards by the award-winning Pier, Fine Associates Architects; the penthouse's scale, volume, and thoughtful layout make it perfect for both grand entertaining and luxurious family living spanning nearly 4,000 square feet of combined indoor and outdoor living.
See floor plan and full details here.

From the Listing: Peacefully located on Mercer Street between Broome and Grand, the penthouse at 47 Mercer Street has an astonishing volume of space and light, both indoor and out. The key locked elevator, exceptionally large, opens into a generous private vestibule which foretells the interior space with its glass and aluminum walls. See floor plan and full details here.

From the Listing: Perched at the pinnacle of 1 Sutton Place South, one of Manhattan'ss iconic residential buildings, this unparalleled penthouse is a contemporary tour de force exemplifying the best of the best in New York. See floor plan and full details here.

From the Listing: This four-bedroom triplex penthouse with rooftop terrace is graciously appointed with 10'4'' ceilings, generously proportioned living spaces, exquisite glass staircase, and four and a half bathrooms. See full details here.

From the Listing: This oversized floor through 3,820 sq. ft. (approximately) loft apartment offers five bedrooms, three full baths and a powder room. The apartment has double exposure and features a landscaped south-facing roof deck and a large north-facing balcony equaling approximately 1,860 sqft of private outdoor space. See floor plan and full details here.

From the Listing: Welcome home to the Penthouse at Altes House where you will enjoy 1,563 square feet of bright, open space spread over 2 floors with 3 bedrooms and 2.5 bathrooms. This boutique condominium provides residents with a luxurious oasis in the heart of Alphabet City and boasts a 64 square foot balcony of the living / dining room and a 336 square foot private roof terrace with stunning views of the city skyline!. See floor plan and full details here.

From the Listing: This exquisite, four or five-bedroom duplex penthouse spans approximately 4,400 square feet of interior space with an additional landscaped 548 square foot terrace located directly off of the apartment's main living area. This space was thoroughly and thoughtfully renovated at a level of quality rarely found. Almost every room in the apartment boasts panoramic city views of both the Central Park West skyline and Midtown'sGoliaths. See floor plan and full details here.

From the Listing: Every room of this bright, breathtaking penthouse leads out onto the four private, usable terraces with open views. This home is one of only two newly constructed penthouses discreetly perched atop the recently converted full-service Philip House, boasting a rare combination of complete privacy and tranquility. The large set-back terraces act as outdoor living rooms, delivering privacy and extraordinary peace and quiet. This mint, meticulously detailed contemporary classic Carnegie Hill duplex is infused with light all day long through an abundance of large windows that captivate wide-open views over the most convenient and desirable neighborhood on the Upper East Side. See floor plan and full details here.

From the Listing: ;This exquisite Penthouse melds a bespoke collection of striking finishes with soaring ceiling heights, floor to ceiling windows, grand room dimensions including four bedrooms, four bathrooms and one powder room and is the epitome of contemporary chic boutique living. See floor plan and full details here.

From the Listing: Imagine an indoor-outdoor lifestyle offering privacy, tranquility, extraordinary light, and skyline views, in the best Tribeca location. Imagine curling up by the wood-burning fireplace in winter, then retreating to one of two cozy media areas to watch a movie. Imagine stepping outside to barbecue a delicious meal and then dine on one of your three gorgeous and secluded terraces from Spring through Fall. See floor plan and full details here.

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