Exclusive | Rosie O’Donnell has sold her NYC penthouse –

She traded the Big Apple for the Emerald Isle — and took a multimillion-dollar loss on the way out.

Talk show host and comedian Rosie O’Donnell has finally sold her long-lingering Midtown East penthouse at a loss.

O’Donnell sold the triplex unit at Sterling Plaza, located at 255 E. 49th St. in Midtown East, for $4.75 million on April 23, according to records filed last week with the city register.

The records show the unit, which appears to be a two-unit combination that she purchased in that condition, is now in the hands of a shell company — one aptly named Sky Space LLC. Further information on the new owner could not immediately be confirmed.

The penthouse had lingered on the market for two years with several price cuts from its original $8.3 million ask. Russ Ross Photography, Inc.

That sale figure represents a $3.25 million loss from the $8 million she paid for the apartment in 2017.

Initially listed in spring 2023 for $8.3 million, the property saw a series of reductions, eventually falling to $7.5 million before going into contract in early March, the deed also shows.

Despite the building’s amenities — including a 24-hour doorman, live-in superintendent, and a sprawling rooftop terrace — the apartment proved difficult to sell.

Caroline Bass, of Corcoran, had the listing. Bass, via a brokerage spokesperson, declined to comment on the deal.

The sale coincides with O’Donnell’s decision to leave the US and relocate to Ireland with her 12-year-old child. Russ Ross Photography, Inc.
The dining area. Russ Ross Photography, Inc.
A balcony. Russ Ross Photography, Inc.

The 3,381-square-foot aerie includes four bedrooms, three bathrooms and a range of upscale features. Those include a glass-enclosed dining room with East River views, a sauna for two, six walk-in closets and a Guggenheim-inspired staircase leading to a 1,620-square-foot roof deck.

O’Donnell, 63, confirmed in a TikTok video that she relocated to Ireland with her 12-year-old child, Dakota.

“I was never someone who thought I would move to another country,” she said. “That’s what I decided would be the best for myself and my 12-year-old child. And here we are.”

Rosie O’Donnell announced her move to Ireland following President Trump’s re-election. Rosie O’Donnell/Instagram
The home features a rooftop deck accessed by a Guggenheim-inspired staircase. Russ Ross Photography, Inc.
One of four bedrooms. Russ Ross Photography, Inc.
An ensuite bathroom. Russ Ross Photography, Inc.

In the same video, O’Donnell pointed to political frustrations as a primary reason for her departure. She has publicly voiced concerns over President Donald Trump’s re-election campaign, stating that American politics had taken a toll on her.

The Manhattan sale is not O’Donnell’s only real estate loss.

In 2021, she sold her longtime estate in Saddle River, NJ, to affordable housing developers for $1 million less than its purchase price after years on the market.

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