Oprah Winfrey cashed in on an Orcas Island investment this week, selling a 40-acre waterfront estate for $14 million. 

Winfrey and a business associate bought the property in 2018, when her broker described the property as a “passive” investment. Benefiting from the region’s hot real estate market, Winfrey’s LLC sold the property for more than one-and-a-half times the roughly $8.3 million they paid in 2018.

The estate known as Madroneagle, overlooks the East Sound and includes a four-bedroom, five-bath home, gated entry, wine cellar and two fireplaces, plus a half-mile of West-facing shoreline, according to online listings.

The Puget Sound Business Journal first reported the sale.

The buyer is staying private for now. 

Jen Cameron, the Bellevue-based Coldwell Banker Bain agent who represented the buyer, declined to say who purchased the property or whether they plan to live at the estate. County records list an LLC registered in Delaware.

The sale was off-market, meaning the property was not listed for sale.


“The pandemic has fueled buyers like never before to properties on islands and waterfront. It’s given a much deeper appreciation for them,” Cameron said. “I also think they’re extremely difficult to find right now.”

As in the rest of Western Washington, home prices are up across San Juan County. 

The median San Juan County home sold last month cost $875,000, up nearly 41% from the same time in 2020, according to the Northwest Multiple Listing Service. (The sample size is small: 44 home sales closed this June, and 28 last June.)

Wally Gudgell, the Orcas Island Windermere agent who represented Winfrey and Bob Greene in the sale, said, “They were in the process of remodeling and they just realized in that process they were never going to be able to use it properly and it doesn’t make any sense.” 

The pair plans to hold on to several commercial properties on the island, Gudgell said.