May 20, 2025
Talk show titan Rosie O'Donnell has officially closed the chapter on her Manhattan real estate — and it's a costly goodbye.
According to the New York Post, the comedian just sold her glitzy Midtown East penthouse triplex for $4.75 million, swallowing a jaw-dropping $3.25 million loss from the $8 million she paid in 2017.
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The listing in the upscale Sterling Plaza lingered on the market before finally finding a buyer on April 23, according to city records. The new owner is a shell company named Sky Space LLC.
Despite the building's luxe features, including a 24-hour doorman, live-in super and a panoramic rooftop terrace, the property was a tough sell.
‘I was never someone who thought I would move …’
From the Big Apple penthouse to the Emerald Isle retreat, O'Donnell is closing one door and opening another, even if it came with a multimillion-dollar price tag.
With four bedrooms, three baths, a glass-wrapped dining room with East River views, a two-person sauna, six walk-in closets and a Guggenheim-esque spiral staircase leading to a 1,620-square-foot rooftop deck, the 3,381-square-foot space was nothing short of high-end.
But even with all the bells and whistles, the market didn’t bite at the original value.
Caroline Bass of Corcoran held the listing but declined to comment via a brokerage spokesperson.
The timing of the sale comes as O'Donnell, 63, leaves the U.S. behind and starts anew in Ireland with her 12-year-old child. The Emmy winner confirmed the move in a heartfelt TikTok video.
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“I was never someone who thought I would move to another country,” she told fans. “That’s what I decided would be the best for myself and my 12-year-old child. And here we are.”
She cited the political climate in the U.S. as a driving factor for the move, seeking a safer environment and equal rights. O'Donnell is in the process of obtaining Irish citizenship due to her grandparents' origins.
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Tips for making a big move
If you're planning on selling due to a life change, like divorce, health crisis or retirement, you’ll want to keep in mind some strategic planning and have a clear-eyed approach.
In the U.S., specialists now cater specifically to homeowners navigating these transitions. And if you’re facing a major lifestyle change, leaning on this support can make all the difference, not just for your peace of mind, but for your bottom line.
You could start with a Certified Relocation and Transition Specialist (CRTS). These pros guide homeowners through major life shifts, especially older adults downsizing or moving to senior living. Beyond the logistics of packing and coordinating moves, CRTS experts offer emotional support.
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Need help figuring out where to go next? A retirement housing navigator might be your best asset. These specialists help older adults evaluate future housing options, from retirement communities to aging-in-place strategies, and they streamline the selection process to make things easier.
Don’t forget about your real estate agent. Choose someone with relocation experience who understands how to price your home and can help you find a property that suits your new lifestyle. They should know how to position your listing for maximum appeal in today’s market and help you avoid common seller pitfalls.
Before listing, you should consider a pre-listing home inspection. Finding any issues early means you can make repairs before buyers enter the picture so you can potentially avoid price negotiations later and boost your home’s appeal from day one.
First impressions matter, and that’s where staging comes in. Decluttering and depersonalizing your home helps to create a vision for buyers to see themselves in your space. Staging can shorten its time on the market and even drive up offers.
Selling a home can unlock significant equity, but it's not all profit. You’ll face costs like agent commissions, taxes and new-home purchase expenses. That's why consulting a financial advisor is critical. They can help you map out the short-term impact and ensure your long-term goals remain intact.
Big life changes like O’Donnell’s can be stressful, but selling your home doesn’t have to be chaotic or costly. With the right professionals, a clear strategy and a firm grip on the numbers, you can turn a challenging transition into a smart financial move.
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Jessica is a freelance writer with a professional background in economic development and small business consulting. She has a Bachelor of Arts in Communications and Sociology and is completing her Publishing Certificate.
