Oprah's Orcas Island House: Madroneagle, 2018 to 2021

Oprah Winfrey's name arrived on Orcas Island in the spring of 2018 and left it in the summer of 2021. In between, a company tied to her held Madroneagle, a gated estate of about 41 acres near the village of Olga. It sits on the eastern shore of East Sound, the long inlet that nearly cuts Orcas in two, in the San Juan Islands between Seattle and Vancouver.

We reported the purchase on May 31, 2018, the day the sale closed, and we called the compound hers. We were not first, and we were not entirely right. Seattle magazine credited Variety, TMZ, and the San Juan Islander with the early reports, and within a week the island's own weekly, the Islands' Sounder, had interviewed the broker on the deal and complicated the picture. This page is the longer version: what the county's deed records show, what the island paper corrected, and what we got wrong ourselves.

The parcel record, the map pin, and the precise address sit behind the ropes on Oprah Winfrey's Orcas Island home profile. For the rest of her map, from Montecito to Maui, start with our guide to Oprah Winfrey's houses.

Two parcels, two companies

Madroneagle changed hands as two separate properties from the same sellers, Kathleen Dickinson and Ron McDowell. San Juan County's deed history dates both deeds to May 20, 2018. The Sounder, quoting the broker, put the closing at May 31, which is the date we ran with. The larger parcel, about 31 acres with the house on it, went to Madrona Tree LLC for $7.15M. The smaller one, about 10 acres, went to Seed Money LLC for $1.125M.

Buying through a company keeps a person's own name off the public deed. That is why the sale first surfaced as two unfamiliar company names, one based in West Hollywood and one in Telluride, Colorado, according to the San Juan Islander's transactions column. Our 2018 piece tied the two together by noticing that both companies shared an administrator. The island paper put it more plainly. Wally Gudgell, the Windermere broker who handled the sale, told the Sounder that Winfrey was associated with Madrona Tree, and that “a business associate of Winfrey's, Bob Greene, is the principal of the other purchasing entity.” Greene is her longtime trainer, and Seattle Agent Magazine later described him as her property manager too.

The county record carries the next step, which the 2018 coverage could not. On September 17, 2018, four months after the purchase, Seed Money deeded its parcel to Madrona Tree for $1,145,768, a little more than it had paid. From then on, one company held the whole estate. That smaller parcel has no buildings on the county's roll. It is about 10 acres, roughly half of it assessed as waterfront, and the county's parcel map describes it as undeveloped. What Greene's company bought was shoreline and trees, not a second house.

The guest house that was never hers

The first round of coverage said the deal took in a guest house, and our original story went further. It described a second home on the bluff above the beach, which the previous owners called the Gallery House, and counted it as part of her purchase.

A reader on the island told us otherwise, and we added a correction: the Gallery House had belonged to the same owners, but it went to a different buyer. The Sounder's interview settled it on the record. Gudgell said the guest house had sold separately, to other clients, more than a year before, and that the properties had once been marketed together but had not been for several years.

Our correction also passed along island talk about who that buyer was and what he did with the house. We could not source either claim, so neither appears here.

What the county says is there

The Sounder, and most of the national coverage after it, called Madroneagle a 43-acre estate. The San Juan County Assessor's records add up to a little less: about 30.9 acres on the house parcel and 10.1 on the other, a shade under 41 in all. Close to 13 of those acres are assessed as waterfront, the strip the county values for its shoreline. The rest it calls backland, meaning the ground behind it. Both parcels are filed in what the assessor calls the Rosario waterfront neighborhood.

The buildings are younger than the island's reputation might suggest. The county dates the main house, its decks, its basement, and most of the garages and sheds around it to 2007. A smaller cluster on the same parcel, with its own garage and basement, dates to 1999. A greenhouse on the roll dates to 2023, two years after Oprah's company sold, so it belongs to the current owner's time.

Our 2018 article said a well-known island designer built the homes. We have found no record and no reputable report naming a designer or builder for Madroneagle, so that claim is off this page.

Both parcels' legal descriptions, the county's short written definition of each lot, include a conservation easement. A conservation easement is a recorded limit on what an owner may build or clear. The ones the San Juan Preservation Trust has written since 1979 are permanent and bind every later owner, according to HistoryLink's history of the trust. The county records we read do not say who holds Madroneagle's, so we cannot tell you its terms. They do tell you it is there.

Olga, Rosario, and older money

Olga is one of the island's early settlements. William Moore settled there in 1860, according to HistoryLink's history of Orcas, and the village's old strawberry processing plant now houses an artists' cooperative gallery organized in 1981.

Orcas was a farming island first. By 1895 it had a productive agricultural economy, which competition from irrigated orchards in eastern Washington and California wore down over the following decades. Tourism took its place.

Wealthy newcomers are an old story here. The shipbuilder Robert Moran was diagnosed with heart disease around 1904, bought his first land on Orcas the next year, and eventually held more than 5,000 acres, about 15 percent of the island. His 54-room mansion, Rosario, was finished in 1909 on the same side of East Sound, and it is the name the assessor still uses for Madroneagle's neighborhood. Rosario became a resort in 1960 and joined the National Register of Historic Places in 1977. Moran gave the state 2,731 acres in 1921, and that land is Moran State Park. Protecting the scenery on purpose came later. The San Juan County Land Bank formed in 1990 to buy scenic land for the public.

Three years, and no move-in

The broker's word for the purchase in 2018 was “passive.” There was, he told the Sounder, no sign Winfrey meant to live there, and the next three years bore him out. The Seattle Times reported in 2021 that a remodel began and then stalled. Gudgell, by then representing her on the way out, told the Journal of the San Juan Islands that Winfrey had visited and seen the house but made no major improvements, and that with several vacation homes already, she and Greene “didn't think it was worth investing a ton more money in it.”

On July 19, 2021, Madrona Tree deeded both parcels to Lophodytes LLC, a Delaware company, for $14M, according to the county's deed history. That was about $5.7M more than the two 2018 purchases together. Seattle Agent Magazine, citing the Puget Sound Business Journal, called it the highest price ever paid for an Orcas Island property and placed the buyer in the greater Seattle area. No one has publicly named a person behind the company.

The part of Orcas she kept

Our 2018 article closed on a rumor. Locals told us that Winfrey or Greene had bought commercial buildings in Eastsound, the island's main village, among them the building that houses Brown Bear Baking and a shopping plaza. We had not confirmed it then.

By 2021 the island paper had. The Journal reported that the two still owned the Main Street building housing Brown Bear Baking; the Darvill Building, 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, a cluster of shops and restaurants. Gudgell told the Sounder they had been improving every building they owned in the village, and that Greene still owned a home on the island.

That list dates from July 2021, the last time the island paper printed it. If you go to Orcas, the bakery on Main Street is the part of this story you can walk into.