Inspired by the many artists who have called the Dakota home, and spurred by their own substantial arts philanthropy, these millennial billion-heirs have taken to hosting séances that are attended by their fashionable set of well-connected peers.
“I do believe in ghosts,” said Ms. Milstein, who, with her Instagram-ready look and tremendous means, exemplifies a new generation of philanthropist: the social justice warrior princess. “I may have watched far too many ghost TV programs, but I think there’s nothing wrong with believing in ghosts.”
Mr. Milstein, a finely curated man, added, “This is an apartment within a building that is so steeped in history that it’s impossible not to acknowledge the past.”
At the stroke of 5 p.m., a doorbell announced the arrival of Princess Noor Pahlavi, 24, a daughter of Iran’s exiled crown prince, Reza Pahlavi, and granddaughter of the late shah. She brought cheese.
“Mama Noor! Literally!” Ms. Milstein said, expressing delight at the gift.
“I had to get really Persian,” said the princess, who was wearing a short black leather Mugler dress and Saint Laurent heels. “It’s just, like, so controlling to bring food.”
“I think Jews can appreciate that as well,” Ms. Milstein replied.
The other guests included two of Ms. Milstein’s former classmates at Barnard College, Sarah Pierce and Julia Pissarro, a great-granddaughter of the Impressionist painter, both 24; Eli Rivkin, 23, Mr. Milstein’s boyfriend and a Yale classmate, who is the son of a former ambassador to France; Maddy Bohrer, 24, an artist; and Ben Piper, 32, and Paul Peglar, 33, who are musicians.
The attractive clique was very dressed up, and in the mahogany-paneled drawing room with its brooding Victorian décor the scene resembled a crossover episode of “Gossip Girl” and “The Addams Family.”
In hushed tones, the conversation turned to contacting the dead.
“Have you guys seen ‘Hollywood Medium’?” asked Princess Noor, referring to the E! network show featuring Tyler Henry, a purportedly psychic 20-year-old. “I believe in this stuff.”
“Not to be, like, really a downer, but there’s a lot of tragic death in my family, after the revolution,” she said, referring to Iran’s revolution of 1979, which dethroned her grandfather. “So I have creepy stories like that, too.”
The group nodded thoughtfully. And with the mood established, they took their places around a Steinway piano and prepared to summon the spirit of Mr. Bernstein.
The Milstein siblings have been cutting a dash on the city’s junior philanthropy circuit recently, making sizable donations to institutions like the NewYork-Presbyterian/Morgan Stanley Children’s Hospital, and serving as Young Fellows of the Frick Collection.
Articulate, with shining brown eyes and a shared interest in fashion, they are not unambitious, professionally or socially. They recently engaged a press agent, R. Couri Hay, to publicize their good will.
Ms. Milstein works in business development for Joy, a tech start-up that makes interactive photo albums. For the séance, she wore a pink-and-gray striped halter dress and embroidered lace-up sandal bootees, both by Fendi.
Mr. Milstein, who graduated from Yale in May, paired a green Fendi blazer with a Club Monaco top, Rag & Bone trousers and Gucci fur-lined leather slippers, personalized with tiger appliqués. A light coating of tinted foundation smoothed out his cheeks and forehead.
The family fortune can be traced to Morris Milstein, a canny Russian émigré who founded the Circle Floor Company in 1919. Family lore has it that he ran multiple businesses with different names using a single set of stationery, printed “Office of the Undersigned.”
His sons, Paul and Seymour, grew the flooring company into a real estate and construction empire, but open warfare broke out in the early 2000s among the next generation. One faction was led by Paul’s son Howard Milstein; the other by Seymour’s son, Philip L. Milstein, who is Larry and Toby’s father.
“It was one of the more legendary family squabbles in the history of New York City real estate,” said Amir Korangy, the publisher of The Real Deal, a real estate trade magazine that covered the legal battle between the cousins. “There was a $5 billion family fortune at stake, and it tore the family in two.”
After the schism, the companies Milstein Properties and the Emigrant Bank went to Howard, while Philip and his sister, Constance Milstein, founded Ogden CAP Properties, which owns One Lincoln Plaza and other prime real estate.
Such wealth allows Larry and Toby to control personal foundations that disburse up to $1 million each, every year. Beneficiaries include such uncontroversial groups as Charity: Water, New Museum and the Lincoln Center for the Performing Arts, as well as more socially minded causes like the Coalition for the Homeless and anti-gun-violence campaigns.
For some groups, the Milsteins open their home, and it was a gathering for an arts charity, A BroaderWay, that inspired them to try a musical method for connecting with the house spirits.
“As young adults celebrating the arts, what better way to pay respect to the presence of the history here than singing a few notes from their favorite songs?” Mr. Milstein said. “It’s a modern séance that’s rooted in the music of the individuals that inhabited this place. You can feel the vibrations of them, and that means they’re there.”
The Milsteins’ three-bedroom apartment, which occupies the northeast corner of the second floor and was purchased for $20.5 million in 2008, is a great place to conjure the dead.
It is decorated in a style pegged to the Dakota’s 1884 German Renaissance-style architecture, with heavy wooden furniture, brocade drapes with tassels and Victorian allegorical paintings of the type whose eyes move in vintage horror films.
Vibrations from the subway line, buried below, periodically pass through the rooms like commuting poltergeists.
To set the séance mood, a grapefruit-and-cucumber Tocca candle scented the air, as a candelabrum flickered dramatically on the piano. Crystal ice buckets chilled mini-Champagne splits alongside a bottle of Jack Daniel’s and an arrangement of pastel macarons.
The mood was simultaneously somber and expectantly gay, like that of a family dressed for the reading of a will in which they were expecting good news.
Ms. Pierce, who shed an Adrienne Landau fur to reveal a black tuxedo dress by the Kooples, exuded a midcentury movie-star charisma. She said that friends describe her look as “Lindsay Lohan, but predrugs.”
Ms. Pissarro wore an Isabel Marant black shirred cocktail dress; Mr. Rivkin was in Ralph Lauren.
They assembled around the piano as if it were a coffin, and Mr. Milstein distributed pages printed with the lyrics of songs associated with the Dakota’s departed talents.
Standing by the keys, Ms. Milstein proposed a toast in which she drew a link between Mr. Bernstein’s progressive causes and her own generation’s social activism.
“He was also an activist; he brought a lot of activist figures in here,” she said. “Right here, the pink — oh my God, the pink panthers, LOL — the Black Panthers,” she corrected herself. “Like, he’s organized a lot of major activist groups here.”
(The composer’s son, Alexander Bernstein, later clarified that no Black Panthers ever visited the Dakota apartment, although an infamous fund-raiser had been held at his family’s previous apartment on Park Avenue.)
“To Lenny!” she said, raising a tumbler of whiskey.
The group touched glasses, and, accompanied by Mr. Peglar on piano, began a medley that included Mr. Bernstein’s “Maria” from “West Side Story, “Imagine” by John Lennon, and, playing along with the evening’s theme, Taylor Swift’s “I Don’t Wanna Live Forever,” recently popularized by Zayn Malik.
In execution, it was more Beyoncé than séance-y.
For 20 minutes, the only spirits present appeared to be the Jack Daniel’s. But as the Steinway tinkled and voices filled the room, vibrations rose from deep beneath the earth, like a musical giant shifting in its grave.
Or perhaps it was the A train.