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Rosie O’Donnell Buys $5 Million Dollar House on Casey Key

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The strange story of how Rosie O'Donnell came to buy a $5 million dollar house on Casey Key.

October 28, 2013


Rosie O'Donnell Casey Key house

Florida real estate sure has its twists and turns. Take, for example the strange story behind Rosie O’Donnell’s new home on Casey Key. It all started when the comedian/TV personality decided to, in effect, downsize and sell her 11,000 square foot home (with 12 bedrooms and 11-and-a-half baths) on exclusive Star Island in Miami.

Rosie O'Donnell Casey Key house

Rosie O'Donnell Casey Key house

Rosie bought the place in 1999 for $6.79 million and put a lot of money into it. She even built two separate guest cottages on the property. But with a new girlfriend—and now wife, Michelle Rounds—well, you know how it is. The new wife doesn’t want to live in the old wife’s house.

Rosie O'Donnell Casey Key house

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So they found a place a little farther up the coast, in Jupiter, which just happened to belong to Olivia Newton John. The girls put in an offer ($5.5 million) and the contracts were being put together. Then, as some minor repairs were being done to the house, the way they are when you’re buying and selling a house, one of the contractors shot himself in out by the pool and unfortunately died.

Rosie O'Donnell Casey Key house

Rosie O'Donnell Casey Key house

Olivia immediately performed an exorcism to clear the house of bad energy and hopefully save the deal but Rosie just didn’t feel right about it. So she started looking around again and then, through a chance Twitter encounter with Sarasota Realtor Jill Friedman, she discovered the house on Casey Key.

Rosie O'Donnell Casey Key house

Rosie and Michelle’s new home, at the more exclusive north end of the key, was built in 1998 and remodeled in 2009. It’s not enormous, just 4,669 square feet, and has only four bedrooms, which may be a problem with five kids, one of whom is an infant. (Luckily, there are seven bathrooms.) The style is “Carribbean beach house” and it’s really very unpretentious.

The only catch? They’re neighbors with Stephen King. His horror classic Duma Key, about haunted beachfront mansions, takes place, well, pretty much right where Rosie’s new home is.

Hope she kept that exorcist’s phone number…

Rosie O'Donnell Casey Key house

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