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The 10 oddest buildings in New York

By Diane Pham
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New York’s buildings are as diverse as its population, and across the city you’ll find a collection of structures that draw inspiration from numerous architectural styles that span globe—just look at the Beaux-Arts Grand Central Terminal, the Neo-Georgian brick townhouses of Greenwich Village, or the Modernist swoops that make up the Guggenheim Museum. And as wide-ranging as they may be, they somehow meld to create a perfect storm of creative expression and beauty. However, that’s not to say that straight up strange stuff hasn’t been built around town.

Ahead we’ve picked out ten of New York City’s oddest buildings, each constructed in places you’d never expect. From a bright orange pagoda-meets-Victorian-styled home in leafy Brooklyn to a wood cottage above a West Village apartment building, this is as fearless as architecture gets.

1. Palazzo Chupi, 360 West 11th Street

Photo: Courtesy Wikipedia Commons

Atop an unassuming former carriage house sits a bright pink palace that looks like it’s been yanked from from the banks of a Venetian canal. The Palazzo Chupi—named after the colorful lollipop you enjoyed as a kid—is actually the home of artist Julian Schnabel. Schnabel decided one day he needed more space and rather than adding a few more floors of brick to his existing historic structure, he dreamt up the audacious topper instead. While some locals applauded Schnabel’s temerity, others were repulsed, with one critic even describing the Palazzo as "an exploded MalibuBarbie house." Back in 2002, when the Times asked the artist why he built it, he responded with “I built it because I could. 

2. Japanese-Victorian house in Ditmas Park, 131 Buckingham, Brooklyn

Photo: Courtesy Wikipedia Commons

It’s hard to imagine that brownstone-filled Brooklyn was considered a “hotbed for architecture” in the early 1900s, but in a section of the borough located just south of Prospect Park you’ll find a wide selection of wood mansions, including this Japanese Victorian-inspired home. As one might guess, there are plenty of crazy stories surrounding this home, like that it was built for a Japanese ambassador, or that it was built in Japan and flown to the site. The reality, however, is far less titillating, as the home was actually constructed by developer Dean Alvord in 1902 as a marketing ploy to get people to check out his new 50-acre residential development of mansions. Today a retired school teacher owns the home and periodically offers tours to small groups.

3. Cabin on roof, 719 Greenwich Street 

Photograph: Courtesy George Steinmetz

Laura Ingalls Wilder meets Manhattan walk-up at this tiny cabin set atop a six-floor co-op in the heart of the West Village. This bucolic abode comes complete with a shingled roof, stone garden walkway, and its very own green meadow. But the cottage isn’t quite as rustic as it first appears at first glance. It’s actually a decorative bulkhead that rises over a hole punched into the roof of a loft below. The porch, however, is totally legit. 

4. Grecian temple, Henry Hudson Parkway near West 190th Street

Photograph: Courtesy Wikipedia Commons

Looking around the Financial District you’ll find that there is no shortage of buildings that take inspiration from the Greeks. But the northern tip of Manhattan isn’t quite where you’d expect to find a Grecian temple. Just off Henry Hudson Parkway near West 190th street and perched over 100 feet above the river is Inspiration Point. The two-story Doric-columned structure was erected in the 1920s as a resting point for leisure drivers and promenaders. Today, while only the street level section is open to the public (accessible only by bike or foot) the views are just as stunning and tranquil as they were almost 100 years ago. 

5. Townhouse with secret entrance, 58 Joralemon Street, Brooklyn

Photograph: Courtesy 6sqft

There’s no question that this brick townhouse is attractive, but if you take an extra minute or two to examine some of its finer details, you’ll eventually be left scratching your head over the blacked out windows and padlocked steel door. While most of the Brooklyn Heights’ homes are owned by the rich and famous, this three-story property actually belongs to the MTA and hasn’t been used as a home since 1846. Rather, this property hides both a massive air vent for the 4/5 train and a secret entrance to the underground. If you peek through the crack between the steel doors you can see the electrical room and a stairway leading to a below-ground tunnel. Sometimes MTA workers can even be seen hanging out on building’s the stoop. 

6. Pumpkin house, 16 Chittenden Avenue

Photograph: Courtesy Simone Song Properties

Lo and behold the famed “Pumpkin House,” named, as you may have guessed, after its Jack-o'-lantern-like fenestration. The unique stone house was built in 1925 to jut out over a cliff near the highest point in Manhattan just north of the George Washington Bridge. Since its construction nearly 100 years ago, only five people have owned the home, the most recent being interior decorator William Spink who purchased it in 2000. Just this last August Spink listed it for $5.25M, offering a new owner a chance to snag the rare property—and the rest of us a rare look into its interiors.

7. Gingerbread house, 8220 Narrows Avenue

Photograph: Courtesy Douglas Elliman

While not edible, this charming Arts and Crafts-styled home features irregular cuts of cacao-colored stone and a fairy-tale-inspired thatched roof that make it worthy of its moniker “The Gingerbread House.” The interior is just as incredible and comes covered in handcrafted details, including stained glass, intricate woodwork, coffered and painted ceilings, and plaster wall detailing. There are also several archways and four fireplaces to complete the storybook feel. The home is currently selling for $11M.

8. Recycled shipping container house, Williamsburg, Brooklyn

Photograph: Courtesy Airbnb

Though from the outside this house looks like the wild creation of an ambitious hobo, inside those six stacked shipping containers is a cozy modern space that’s been outfitted for comfort and convenience. The structure is actually New York City’s first ever shipping container home, pieced together by a local architect and her builder husband in 2013. The entire home clocks in at about 1600 square feet and includes a roof deck, a community garden, and a rental on the ground floor that can accommodate up to four people. That’s right, if you want to know what it’s like to sleep in a shipping container, you can book a stay through Airbnb for a mere $96/night. 

9. Mosaic house, 108 Wyckoff Street, Brooklyn

Photograph: Courtesy 6sqft

 

This house is almost impossible to miss, a collage of colorful beads and odd-and-ends sparkling amongst innocuous brick and brownstone buildings. As the story goes, the home’s owner, artist Susan Gardner, began the mural in earnest after the 9/11 attacks. She found the process so therapeutic that she invited her neighbors to join hoping that they would find a similar respite. Fast-forward 15 years and the mural is still growing, with Gardner, now 75, expanding on the work every summer. Reflecting on the artwork earlier this year, Gardner told the Journal, “I decided I wanted to be outside and be with people [after 9/11, so] I just started gluing things to my house.” 

10. Thomassons

Photograph: Courtesy Matthew Fargo

In New York City it’s not that uncommon to come across stairs that lead to nowhere or doors that appear to be awkwardly placed. As it turns out, these odd tectonic missteps actually have a name: “Thomassons.” A term coined by Japanese artist Genpei Akasegawa, Thomassons is used to describe any architectural feature that serves no purpose but is still maintained. But more amusingly, the word itself can be traced back to Gary Thomasson, an American baseball player who traded to Tokyo’s Yomiuri Giants in 1980. Despite all the fanfare surrounding Thomasson’s move, he went down as one of the Giants’ worst players, coming close to setting the league strikeout record. Thomasson spent most of his two-year contract on the bench but still raked in a hefty salary during his stay. In the eyes of Akasegawa, Thomasson was both “useless” and “maintained.”

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