Oprah sells her Orcas Island estate for $14 million

Oprah Winfrey has sold her Orcas Island estate for $14 million after purchasing it for $8.275 million three years ago.

The media mogul and philanthropist is associated with Madrona Tree LLC, which originally bought the $7.15 million property. Her business associate Bob Greene, of Seed Money LLC, purchased an adjoining property for $1.125 million. Both sales closed in the late spring of 2018.

The 43-acre Olga property is called Madroneagle and features a 10,251-square-foot home. It sold to Delaware-based Lophodytes LLC according to a story in the Puget Sound Business Journal.

Windermere broker Wally Gudgell represented Winfrey in the sale. Gudgell, who has been a broker on Orcas for 47 years, had the original listing of the property when Winfrey bought it, dealing directly through Greene. He says Winfrey visited Orcas and saw the house, but did not do any major improvements while owning it.

“They are all so busy and they already have several vacation homes so they just didn’t think it was worth investing a ton more money in it,” Gudgell said. “We now have a new person in our community who will hopefully donate and help others.”

Gudgell says Greene still owns a home on Orcas, and he and Winfrey will retain the other commercial properties they own together, including the building on Main Street that houses Brown Bear Baking; the Darvill Building that is home to Crow Valley Pottery and Darvill’s Bookstore; the Porter Station building, which rents to Island Thyme and The Madrona Bar and Grill; and Eastsound Square, home to a variety of retail stores and restaurants.

“They love Orcas and have been great landlords through COVID,” Gudgell said. “They have been improving all the buildings (they own) in Eastsound.”

Photo courtesy Windermere Real Estate/Orcas Island/Wally Gudgell
An image of the property from 2018.