Photo credit: VHT Studios

Normally, our eyes widen at an apartment that measures 3,455 square feet inside, but this Upper East Side penthouse offers that much space outside. It comes in the form of one massive wrap-around terrace on the main level plus a smaller terrace off the upper-level bedroom suite. If that wasn’t enough, the interior measures a whopping 4,020 square feet, including five bedrooms, a dining room that can seat 30, a massive skylight, and floor-to-ceiling glass windows wrapping around, and more. Located at 45 East 66th Street, it’s asking $12.5 million.

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Photo credit: Allyson Lubow

After the current owners bought this Park Slope penthouse in 2011, they completed some beautiful renovations throughout, including a sleek kitchen, refinished wood floors, and even a “pet nook” underneath the stairs. The loft-style triplex is located in the Carriage House on the Slope, a 24-unit condo at 231 15th Street. It has three bedrooms, two large balconies, and incredible New York Harbor views.

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All renderings courtesy of Concierge Auctions and Nest Seekers International

A three-level penthouse apartment in a Billionaires’ Row building with pre-approved, construction-ready designs will hit the auction block next month. Currently listed for $40 million and appraised at $100 million after renovations, the apartment at 150 Central Park South will sell with no reserve to the highest bidder during an online auction hosted December 18 to December 22 through Concierge Auctions. Plans from SPAN Architecture call for a five-bedroom, five and a half bathroom penthouse with four terraces and unobstructed Central Park views.

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Photo Credit: Gamut Photos for Sotheby’s International Realty

The listing for this $3,250,000 three-bedroom co-op in Murray Hill touts the property as a “true penthouse,” explaining that it “sits on top of the building proper and is accessed through a private entrance at rooftop level.” That location (which sounds pretty darn good to us!) also affords the home at 244 Madison Avenue an incredible rooftop terrace, complete with cozy built-in seating and dining, as well as views of the Empire State Building and Midtown skylines.

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Photos by Evan Joseph

The Emerson is the latest boutique condo in Chelsea to abut the High Line. Located at 500 West 25th Street, the 10-story building has just eight full-floor units, including the duplex penthouse, which has just hit the market for $16 million. The incredible four-bedroom home has 5,100 square feet of interior space along with nearly 2,600 square feet of outdoor space spread over two terraces and a roof deck with views of the High Line, Hudson River, Empire State Building, and Hudson Yards.

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Listing photos courtesy of Brown Harris Stevens

How’s this for a work-from-home setup? The top floor of this triplex penthouse at 1158 Fifth Avenue is a “jewel box” solarium with a glass-enclosed arched atrium and five picture windows overlooking Central Park. Listed for $15 million, the four-bedroom home is classic Upper East Side with oversized living spaces, two landscaped terraces, and even a separate one-bedroom guest residence within the building.

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Listing photos courtesy of The Corcoran Group

The Metal Shutter Houses is a contemporary condo designed by Pritzker Prize-winning architect Shigeru Ban in 2008, at the beginning of West Chelsea‘s starchitect boom. Today, despite its many notable neighbors, the boutique building at 524 West 19th Street still offers some of the most covetable homes. The penthouse unit is now listed for a reduced $8.9 million. Not only does the home span two floors, but it has a 20-foot, upward-pivoting, glass wall that opens to a large terrace to create a massive indoor/outdoor living space. There’s also another private terrace off the master bedroom, two balconies, and a huge roof deck complete with a hot tub. Oh, and let’s not forget the direct views of Hudson Yards and the Empire State Building.

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Photo by Tim Fisher, Courtesy of Related Companies

The triplex penthouse at late architect Zaha Hadid’s High Line-hugging condo building has sold for just over $20.2 million, a significant price cut from its initial asking price of $50 million in 2016. Penthouse 37 at 520 West 28th Street measures 6,853 square feet and boasts a massive private rooftop terrace with a glass-walled lounge and enough space for 100 guests. As the Real Deal first reported, the buyer of the apartment is Wesley Edens, co-founder of private equity firm Fortress Investment Group and co-owner of the Milwaukee Bucks.

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Photo Credit: James Smolka/ Brown Harris Stevens

One of New York City’s most storied apartments has just hit the market. John Lennon’s former penthouse at 434 East 52nd Street, where he briefly lived with his mistress May Pang during the 1970s and famously spotted a UFO, is asking $5.5 million. The 4,000-square-foot triplex in the Southgate co-op, located where Sutton Place, Beekman, and Midtown East meet, was also where the iconic photos of Lennon wearing a tank top that said “New York City” were taken.

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Photos courtesy of Compass/Martin Eiden Team

For classic Upper West Side living, there’s nothing quite like the co-ops that line West End Avenue. But this penthouse at 465 West End Avenue takes things a step further, exuding all the pre-war elegance you’d hope for, along with a glass solarium and a massive, 2,900-square-foot terrace. It’s currently asking $2,775,000.

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