Rosie O’Donnell sells Midtown East penthouse for $4.75M

Photos represent a previous listing. Courtesy of Brown Harris Stevens
Rosie O’Donnell has found a buyer for her Manhattan penthouse, two years after first listing it and a few months after moving to Ireland. The comedian first put her home at 255 East 49th Street on the market for $8,300,000 in 2023; it entered contract for $4,750,000 earlier this spring.


As 6sqft previously reported, O’Donnell decided to sell her Midtown home after relocating to Los Angeles in 2021 with her daughter. After long-time adversary Donald Trump’s inauguration in January, she moved to Dublin, Ireland, where she plans to get Irish citizenship.
According to the New York Post, the triplex sold on April 23 to a shell company, Sky Space LLC. The sale marks a $3.25 million loss for O’Donnell, who paid $8 million for the apartment in 2017.
After listing for $8.3 million in May 2023, the penthouse’s price dropped to $7.95 million a few months later before being taken off the market. It returned in April 2024 for $7.5 million and saw a few more price cuts before a contract was signed for $4.75 million this past March.
The home is just one of two penthouses at Sterling Plaza, a full-service condominium off Second Avenue in the Turtle Bay neighborhood. Measuring nearly 3,400 square feet, the apartment takes up three levels and includes a huge private rooftop.
The living room has over 760 square feet of entertaining space, with a honed black granite wood-burning fireplace at the center. A glass-enclosed dining room overlooks the East River and beyond, and the kitchen is decked out with all Gaggenau and Miele appliances.


The primary suite takes up its own corner on the first level, with a spa-like bathroom that has a walk-in steam shower, a free-standing tub, and heated floors.

Described in the listing as “Guggenheim-inspired,” the staircase leads to the 32nd floor, which has two more bedrooms. This level, which has its own entrance, also has a private Swedish sauna, full bath, and a balcony.


The 1,620-square-foot private roof deck has direct views of the Chrysler Building and the Empire State Building and an enclosed bar that is party-ready.
[Listing details: Sterling Plaza, 255 East 49th Street, #PHA at CityRealty]
[At The Corcoran Group by Caroline Bass]
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