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Billionaire Robert Toll’s NYC Penthouse Hits Market for $22 Million

Although, about seven years ago though, the 5,180 square foot home became a little excessive for the empty nesters.

Billionaire Robert Toll’s NYC Penthouse Hits Market for $22 Million
The penthouse has a 40-foot-long great room. (Courtesy of SERHANT./by Krisztina Crane of Evan Joseph Studios)

Jane Toll remembers the exact time and date she and her husband, billionaire real estate developer Robert Toll, officially moved into their triplex apartment on the 29th, 30th, and 31st floors in a building less than a block from Central Park on New York’s Upper East Side.

“We had gutted the 30th floor, and it was New Year’s Eve, 1999,” she recalls. “We had a very, very big party.”

It would be the first of many in the airy space, which the couple has now listed for $22 million. The Tolls, who are prolific philanthropists, used the main 30th floor space for political events and cultural fundraisers. “We’ve held events for all of them,” she says. “From a fundraiser for the Met Opera, to one year when we had one early on for Tammy Duckworth, and she had a guest booster—it was Obama when he was just a senator, and it was so exciting.”

About seven years ago though, the 5,180 square foot home became a little excessive for the empty nesters. And so the couple moved downtown and rented the house out.

“It was getting to be more space than we needed, but we rented it because my husband refused to sell,” says Toll. “He said, ‘it’s a work of art. We have paintings, why can’t we have this too?’” (Most recently, StreetEasy shows the apartment renting for $50,000 a month.)

Billionaire Robert Toll’s NYC Penthouse Hits Market for $22 Million
Billionaire Robert Toll’s NYC Penthouse Hits Market for $22 Million

Eventually, Toll continues, “I said, ‘Enough with the work of art, we have to sell it.’”

And so, finally, they will. They’ve put it on the market with Tamir Shemesh, leader of the Shemesh Team at the brokerage Serhant. “I think I just bullied him long enough that he said OK,” Toll says, of her husband. “We realized we’re not going to go back uptown.”

Best View in the City

When the Tolls bought the apartment, located on the corner of East 85th street and Madison Avenue, they’d already been living nearby—10 floors down, to be exact. “When the building was first built, it was just after my husband’s company went public,” Toll explains, in reference to luxury homebuilder Toll Brothers’ initial public offering,  which took place in 1986. “There was this building, and we had this check.”

Billionaire Robert Toll’s NYC Penthouse Hits Market for $22 Million
Billionaire Robert Toll’s NYC Penthouse Hits Market for $22 Million

It was only when the top floor became available that Toll and her husband decided to move. “My husband is a view man,” she says. “And the view from the 30th floor is probably the best view in the city—you see 360 degrees. It’s pretty incredible.”

The apartment they bought, though, was not designed in an aesthetic Toll found compelling. She and the previous owner “had different styles, shall we say.” Whereas the former owners had a warren of small rooms, “we opened it all up, so that you could see 180 degrees of the city wherever you were,” she says.

In an era where it takes 18 months to get a dishwasher delivered, the single year Toll says it took to fully gut renovate the apartment might sound fantastical. And yet she recalls that the entire process was seamless, from start to finish. 

Billionaire Robert Toll’s NYC Penthouse Hits Market for $22 Million
Billionaire Robert Toll’s NYC Penthouse Hits Market for $22 Million

She placed particular emphasis on the primary suite, which occupies about a third of the 30th floor and includes a humongous bathroom with northern views, so that you can sit in the bath “and look at the George Washington Bridge,” Toll says. “You can be in there at night and watch all the lights come on.”

The couple also paid singular attention to the apartment's striking wood paneling, which covers walls and ceilings in the kitchen, bathroom, bedrooms, and entertaining areas. The design, Toll says, “was kind of deco, but light and modern.”

They subsequently filled the house with their world-class art collection. “The collecting is mostly my husband,” Toll explains. “Because I don’t have the guts to spend that kind of money, but he collected a lot of Impressionists, and then we moved on to German Expressionists.”

Comfortable Privacy

The 29th floor had been designed as a gym; the Tolls converted it into a mother-in-law suite, “which in our case actually was for my mother,” Toll says. It has its own kitchen, living room, walk-in closet, full bath, and balcony. 

Billionaire Robert Toll’s NYC Penthouse Hits Market for $22 Million
Billionaire Robert Toll’s NYC Penthouse Hits Market for $22 Million

The 30th floor has another two balconies and a large, west-facing terrace, and contains the primary bedroom suite with its own dressing room, study, and full bathroom. The rest of the floor has a large kitchen, another en-suite bedroom, and a massive 40 foot-long living room with three exposures.

Upstairs, on the 31st floor, there’s another two en-suite bedrooms connected by a light-filled gallery; each of those bedrooms opens onto its own terrace.

The apartment proved adequate—great, even—in accommodating the couple’s five children, most of whom were college-age or older at the time they moved in. “One or two lived there when they were in university, so the top floor was their work/ study/ play area,” Toll says. “We all had our own spaces, which is one of the beauties of this apartment: Over the years different people lived there with us, and it always still felt private.” 

Elevators stop at a private vestibule on the 30th floor; the upper and lower floors are reached via internal staircases.

The penthouse, then, is uniquely suited to a hybrid remote-work era, where a large family can coexist peacefully as they live, work, and play.

“It’s a good apartment for people who have guests, and it’s a good apartment for people who might want to help, because the mother in law apartment can be a staff apartment,” Toll says.

But, she adds, “even though it has a lot of space, it never felt cavernous—it’s not overwhelming,” she concludes. “It’s comfortable.”

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