Photo credit: MW Studio / Udom Surangsophon courtesy of Compass.

Millionaire private investor and man-about-town Bradley Zipper purchased this Little Italy townhouse in 2004 to use as a massive bachelor pad where he could host celebrity soirees and lavish business events for up to 400 guests. After dropping $3.385 million on the property, he hired Cortney and Robert Novogratz, the famous husband-and-wife design team, to deck it out. The result definitely fit the bill, rocking a 900-bottle wine cellar that’s a replica of one in a Meatpacking District club, a 14-foot mahogany and pewter bar imported from Paris, and a vintage 1940s pool table surrounded by graphite walls. Zipper started trying to unload the house in 2013, first for $15 million, then $13 million, next as a $35,000/month rental, and again in 2015 for $15.5 million. Now the six-story 5,000-square-foot townhouse with six outdoor spaces is for rent once again asking an adjusted-for-inflation $40,000/month.

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Photos by Will Ellis of Donna Dotan Photography, courtesy of Compass

This beautifully renovated three-bedroom co-op at 421A Union Street sits atop a historic row house across the street from the Park Slope Food Co-op and a block from Prospect Park. Asking $2.25 million, the duplex-plus-roof-deck offers three outdoor spaces–including a gorgeous glass-walled sunroom–and stunning Manhattan views.

Fun in the sun, this way

Here’s a top-floor, one-bedroom duplex condop at 61 Lexington Avenue in Kips Bay that’s nicely updated, bright, and pretty sizable for the price–and if you like the simplistic stlye, it’s available fully furnished. But the best part is the 300-square-foot private terrace off the master bedroom on the second floor. It boasts sweeping city views, surround sound, an outdoor TV, grill, storage shed, and built-in seating for 10 with cushion storage .

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This 2,223-square-foot three-bedroom triplex condominium looks for all the world like a modern townhouse–or, as the listing says, a Tribeca loft or a Hamptons house–in the heart of Chelsea. Topped by a  rooftop terrace and lit by a 300-square-foot skylight, the three-bedroom home is definitely unique for a condo.

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Offered by the original owners, this truly one-of-a-kind penthouse atop Williamsburg’s Mill Building has been dubbed the “House on the Roof,” but it could easily be mistaken as a luxurious mountaintop chalet. The red-roofed two-bedroom penthouse is wrapped in glass that opens to a massive rooftop terrace complete with a full kitchen setup. And it’s now asking $2.85 million.

You’ve gotta see this one

The West Village co-op 92 Horatio Street is featuring a duplex apartment up for rent, and it’s got lots of personality. This unit is decked out with dark wood beamed ceilings, two brick fireplaces, and a spiral staircase taking you up to a private roof terrace. The one bedroom also boasts some extra space in the form of a home office. There have been no shortage of quirky co-ops up for sale in this building, but this one is up for rent asking $6,500 a month.

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This top-floor two-bedroom condominium at 4 Downing Street in Clinton Hill, we’re told, is “an iconic turn of the century building recently completely reimagined and overhauled as a boutique condominium.” Said overhaul was undertaken in 2015 by Barrett Design and Development on what was previously the indeed-iconic Broken Angel House, once among Brooklyn’s most unique landmarks. Artist Arthur Wood purchased the original tenement building in 1979 for $2,000 and subsequently transformed it into a whimsical, livable sculpture, complete with stained glass windows made from bottles and glass, a cathedral-like glass addition, and brick wings. It was also the backdrop for the documentary “Dave Chappelle’s Block Party.” The two-bedroom unit is on the market for $1.55 million; it was purchased as new construction two years ago for $1.42 million.

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In the middle of a lovely cobblestoned block in the coveted West Village, the five-story Federal-style townhouse at 334 West 12th Street was built in 1853, but its charms hold up against its neighbors in the Greenwich Village Historic District and beyond. Asking $6.95 million, the 20-foot-wide single-family townhouse has two entrances, five bedrooms, a rear garden that looks like something out of an Italian villa, a large south-facing terrace with views of the Freedom Tower, and its crowning jewel, a skylit solarium brimming with greenery.

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This one-bedroom condo at Soho‘s 118 Wooster Street is offering up plenty of unique features to its next buyer. For one, the 1,250-square-foot interior got a cozy sleeping nook to hold a second bedroom. Then, under 20-foot ceilings, a massive great room, plus a formal bedroom, await. The stairs take you up to a glass atrium, which opens to an 800-square-foot roof deck with a water and electric hookup. For all these indoor and outdoor perks, it’ll cost $2.649 million.

Go see the roof deck

Scale to the top of the historic brick townhouse at 111 East 10th Street in the East Village and you’ll find this charming one-bedroom co-op now on the market for $875,000. The walk-up may not be great, but there are lots of benefits of living on the top floor here. The ceiling has been heightened and expanded to include a row of skylights, and there’s direct access to a private rooftop garden. The unit is part of a unique, coveted cooperative comprised of six 19th century townhouses that sit within the landmarked St. Mark’s Historic District, holding 29 residences total.

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