Plaza Hotel's condos fail to turn a profit 15 years after bigwigs including Tommy Hilfiger splurged up to $25M on them as buyers spurn its cramped layouts, cheap finishes and small windows

Condos in New York's iconic Plaza Hotel are now listing below their original purchase prices, making them a rare money-losing Manhattan real estate investment, according to a new report.

Real estate pros say the building's awkward design quirks, including cramped layouts, cheap finishes, and rooms punctuated by columns, are depressing resale values, Curbed reported this week.

'Everything's a little off; it's not like you think it would be,' author Julie Satow, who wrote a book about the Plaza, told the outlet. 

After the units first hit the market in 2008, designer Tommy Hilfiger payed $25.5 million for the penthouse and reportedly spent another $20 million on renovations — but took 11 years to sell the unit for $31.5 million, down sharply from his $80 million asking price.

'When the original sales were going on, it was a crazy market and people paid ridiculous amounts of money without seeing their units, so there were a lot of lawsuits,' said Satow.

Satow said the original buyers complained about cheap finishes, including oak veneer over plywood instead of solid oak, Chinese marble instead of Italian, and hallway carpeting cheaply cut and pieced together in patchwork fashion.

Although many of those original finishes have since been replaced, the Plaza's landmark status prevents more radical renovations to the units, including the oddly placed columns found in some rooms.

Now, buyers who rushed to snap up the units 15 years ago are desperate just to break even.

In one example cited by Curbed, a couple from Florida who dropped $14 million on a three-bedroom Plaza condo sight-unseen in 2008 are now listing it for $13.9 million. 

Another three-bedroom, originally purchased for $14.375 million in 2008 is now listed for $14.15 million.

In comparison, some condos in 15 Central Park West, another classic building that also offers sweeping Central Park views, have flipped for double their original price, according to Curbed. 

The historic Plaza Hotel, designed in French Renaissance chateau-style and built at the beginning of the 20th century, has been featured countless times in pop culture - in movies, television shows and books, such as Eloise at the Plaza.

In the books and the film, Eloise is said to live on the 'tippy-top floor' of the building.

The Plaza was once owned by Donald Trump after he bought it in 1988 for $407.5million. 'This isn't just a building, it's the ultimate work of art. I was in love with it,' he famously said at the time. 

It is one of the main settings for Home Alone 2: Lost in New York - Trump makes a cameo appearance in the Plaza's lobby. 

Most recently in 2018 it was sold to the state of Qatar for around $600million via its government-owned fund Katara Hospitality.

The hotel's main entrance is on Fifth Avenue, on the building's west face, and the residential entrance is at One Central Park South, also known as 59th Street, on its north face.

However, condo owners have direct access to the hotel's Palm Court, Champagne Bar, Rose Club, Warren Tricomi Salon, Terrace Room, Grand Ballroom, Guerlain Spa, fitness center, shops and the private gardens and fountains.

One the the most famous units is the penthouse once owned by Hilfiger, who combined two units on the 18th and 19th floors after buying them in 2008 for a total of $25.5 million. 

Hilfiger spent heavily customizing the unit, but struggled to sell it for more than a decade after putting it on the market. 

Hilfiger once told CNN that he wanted the space to reflect an earlier era of the Plaza in the 1960s, when author Truman Capote held his famous Black and White Ball for the upper crust of Manhattan. 

The first floor makes heavy use of elegant black lacquered walls, coordinated with deep rich reds and even cheetah print. 

Hilfiger had reclaimed wood floors and vintage fireplaces from England installed in the unit, which is also decorated with antiqued mirrors. 

While some of the rooms are done in the crisp and elegant cream and gold colors one would expect to see inside a five-star hotel, others have much more personality. 

One of the bedrooms is done in a bright lavender, while the children's bedroom is decorated in a red and blue nautical theme that seems to be directly inspired by Hilfiger's own fashion lines.

Perhaps most distinctive is the dome which features a mural painted by Hillary Knight, the original illustrator of the Eloise books.

Just like Hilfiger's family, Eloise lives in the room on the 'tippy-top floor' of the Plaza Hotel, as the classic goes. 

Knight incorporated both Eloise and members of the Hilfiger family into the mural. 

Hilfiger said in the past he wanted to build 'a home' at the Plaza, put it on the market after he and wife Dee Ocleppo ended up spending most of their time at the family's Greenwich, Connecticut estate. 

After slashing his $80 million asking price multiple times over the course of 11 years, Hilfiger finally sold the unit in 2019, to car dealership tycoon Terry Taylor, who paid $31.5 million.

'He missed the market,' a broker told Curbed, speculating that Hilfiger could have gotten $55 million if his sky-high asking price hadn't scared off buyers