Rosie O'Donnell buys $5 million home on Casey Key

Rosie O'Donnell's new house on Casey Key. Courtesy photo.

Rosie O'Donnell's new house on Casey Key. Courtesy photo.

NOTE: This story has been corrected to note the proper location of the house, which is not on North Casey Key Road.


Rosie O’Donnell, a versatile actress, comedienne and television personality known equally for being a philanthropist and gay rights advocate, has purchased a $5 million house on Casey Key Road.

O’Donnell’s deal, completed late Thursday, represents the highest-priced home sale on Casey Key this year, according to brokerage firm Premier Sotheby’s International Realty.

Built in 1998, the house has nearly 4,700-square-feet

The 51-year-old’s new place has four bedrooms and seven baths, and sits on a 0.78-acre beachfront lot.

The entertainer is expected to share the house with her wife, Michelle, and five adopted children.

The star of such films as “A League of Their Own” and “Sleepless in Seattle” and a moderator on TV’s “The View” from 2006 to 2007, O’Donnell sold a mansion on Miami’s Star Island last year for $16.5 million.



O’Donnell stumbled onto Sarasota. Some months ago, she tweeted that she was looking to buy “a certain kind of Jeep,” said Jill Friedman, who is one of O’Donnell’s nearly 700,000 followers on Twitter. Friedman, a Realtor, messaged O’Donnell that her brother could help.

When O’Donnell mentioned she was also looking for a new second home, Friedman urged her to visit Sarasota. She did, and Friedman and her business partner, Kevin Vale, of Coldwell Banker, showed O’Donnell around.

Listing agents in the transaction were Tom Hedge Jr. and Monica Barth, of Premier Sotheby’s.

O’Donnell is known for political run-ins with her “View” co-hosts — which led to her firing in 2007 — and for an infamous spat with developer Donald Trump.

Agents involved in the Casey Key sale said O’Donnell was delightful to work with.

“She was the same as you would think she is” from seeing her on television, Friedman said. “She is funny, smart, personable. Showing her property was pleasurable, a great experience.”

Rosie O'Donell has purchased this house on North Casey Key Road for $ 5 million. Courtesy photo / Premier Sotheby's International Realty.

Rosie O'Donell has purchased this house on North Casey Key Road for $ 5 million. Courtesy photo / Premier Sotheby's International Realty.

The sellers, William and Donna Brian, bought the house in 2005 for $4.6 million and remodeled it in 2009.

“They took a bit of a hit,” said Hedge, who listed the house at $5.85 million in March. Previously, it had been on the market beginning in 2011 at $6.7 million. “But they wanted to move on.”

The Brians are downsizing to a house two doors away they also own.

Hedge and Barth informed O’Donnell that her offer was accepted late one afternoon on the house’s patio overlooking the Gulf, while the group sipped champagne.

“It was like we had known each other for years,” Hedge said. “Rosie is phenomenal — easy, nonconfrontational, relaxed.”

Harold Bubil

Recipient of the 2015 Bob Graham Architectural Awareness Award from the American Institute of Architects/Florida-Caribbean, Harold Bubil is real estate editor of the Herald-Tribune Media Group. Born in Newport, R.I., his family moved to Sarasota in 1958. Harold graduated from Sarasota High School in 1970 and the University of Florida in 1974 with a degree in journalism. For the Herald-Tribune, he writes and edits stories about residential real estate, architecture, green building and local development history. He also is a photographer and public speaker. Contact him via email, or at (941) 361-4805.
Last modified: November 12, 2013
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