While geographically diverse, these properties share common elements. They aren’t by any means on the wrong side of town, but they also aren’t typically in a hot spot. For example, rather than Seattle’s elite, pricey community of Medina, where Bill Gates and Jeff Bezos have homes along what is called the Gold Coast, he chose the more suburban Mercer Island, where he bought on the less-desirable south end of the island. In Los Angeles, his compound is in what’s called “Beverly Hills Post Office,” where homes can sell for about half of those in Beverly Hills proper. His ranch in Idaho is over the Teton Pass from the ritzy ski area of Jackson Hole, Wyo., near where the workers who can’t afford Jackson live and commute. His property on the peninsula he bought on Lopez in the San Juan Islands, Wash., is on the island’s less prestigious side, far from the village. Yet the homes he built were impressive estates.
Paul Allen, the late co-founder of Microsoft, spent a considerable part of his wealth—estimated at about $20 billion—on real estate, leaving behind an impressive collection of properties.
“In my experience, prestige properties like this are usually kept,” says Bernie Vogel, the chief executive officer of Silicon Valley Law Group. Seattle Seahawks General Manager John Schneider said recently that the NFL team, owned under the Paul G. Allen Trust, won’t be sold and that Jody Allen is now officially the Seahawks chair.
In 1993, real-estate agents say Mr. Allen bought two pieces of property near the small town of Tetonia, on the Idaho side of the Tetons, about an 80-mile drive (that is treacherous in winter) from Jackson, Wyo. One was 2,400 acres of land abutting the Targhee National Forest, which in turn abuts Grand Teton National Park; the property was owned by businessman William Louis-Dreyfus. According to Paul Lawrence, the real-estate broker representing the late Mr. Louis-Dreyfus, the deal happened after a Vulcan employee walked into a local real-estate office and announced Mr. Allen was looking for land in the area. Mr. Allen paid the non-negotiable, $7.25 million asking price 10 days after he took a helicopter ride over the property. Mr. Lawrence says Mr. Allen was very quiet and told him he was looking at it as a place to visit and not just as an investment.
Former staff, which included about a dozen employees when the hotel was running, say Mr. Allen was rarely there. One former cook says she saw him only once in the six years she worked there. When he or his guests did visit, arriving on a private plane to the Driggs airport, they stayed in a separate, two-bedroom owner’s house on the property. Until last year, the ranch would open to the public on one day a year for an annual Nordic ski race, but now it is closed to the public. The caretaker lives there in a separate house. By comparison, the 935-acre Teepee Creek Ranch a few miles away is for sale for $6.95 million.
Frank Schenk, of Mauna Kea Realty, says he would estimate the property to be worth $50 million just for the land alone. The property came with a small harbor, dredged in the 1950s, along with structures that were on a small slice of state property. Big Surf Trust was allowed to buy the public land. Real-estate agents say Mr. Allen owns another large undeveloped property up north on the island and sold a couple of golf villas at the Mauna Kea resort several years ago.
In April 1997, a trust connected to Mr. Allen bought film director John Landis’s 8,086-square-foot home and swimming pool for what brokers told The Wall Street Journal at the time was close to $10 million. The two-story, 1950s-era Spanish-style house, built in three sections around an inner courtyard, is part of a three-lot compound that now includes two homes and a total 3.25 acres. Before Mr. Landis, actor Rock Hudson lived there for 20 years. The neighborhood, called the Crest Streets, is in an area known as Beverly Hills Post Office. It shares the prestigious 90210 ZIP Code with Beverly Hills but not the same schools and police force, and has lower values, says Tomer Fridman, a broker with Compass. Mr. Fridman says the area is having a renaissance, with a spec house recently selling for $42 million, but that a similar home in Beverly Hills would go for about twice the price.
A few months after the purchase, Mr. Allen also closed on a nearby 120-acre piece of land atop Benedict Canyon for $19.5 million—a significant discount from its original listing price of $40 million. Called Enchanted Hill, the property had a 10,000-square-foot, 20-room mansion designed by architect Wallace Neff and a 70,000-gallon pool that was originally built in the 1920s by screenwriter Frances Marion and her husband, movie-star cowboy Fred Thomson. Historic renderings and photographs show it as a stucco Spanish hacienda with arched doorways and windows, stone floors, a red tile roof, a cobbled court, a guesthouse and tiled fountains. Mr. Allen tore all that down.
Enchanted Hill was listed months before Mr. Allen’s death and remains on the market with a price of $150 million. “Paul Allen’s vision for the property was always to combine the matchless views and topography with incomparable design to produce something of enduring value,” said Ada M. Healey, vice president of Real Estate for Vulcan, in the ad sales material. “Our hope is the next owners will bring this same careful approach to this extraordinary property.”
Lopez Island, Wash. – Estimated Value: $120 million to $150 million
After Wally Gudgell, managing broker with the Gudgell Group on Orcas Island, brokered the deal for Mr. Allen to buy the 387-acre Sperry Peninsula in 1996 for $9 million, both he and Mr. Allen received death threats, he says. The land had housed Camp Nor’Wester, a summer camp for children, since 1945, and there were protests when Mr. Allen’s lawyers informed the camp it couldn’t stay and moved some of the buildings.
Mr. Allen, who bought the property under a trust, built a series of cedar and stone buildings, including his 13,000-square-foot, five-bedroom residence; a 5,440-square-foot, nine-bedroom bunkhouse; a 3,150-square-foot beach house; another two-bedroom, 3,160-square-foot house; a two-bedroom, 1,924-square-foot caretaker’s cottage; and a swimming pool. Richard Carter, a drama and literacy teacher on Lopez Island and former head of the group that tried to convince Mr. Allen to let the camp stay, says the homes are tasteful, low-lying, modern, Northwest-style structures on highly manicured grounds, with what he describes as a big rusty sculpture you can see from the water. Local residents say Mr. Allen was never seen on the island and they suspect he was only there a few weeks a summer.
Real-estate agents say the building is sought after because it is small and most apartments have a full floor. In 2016, hedge-funder Daniel Nir and Jill E. Braufman sold their fifth-floor unit at the building for $52 million, making it the biggest sale of the year. It was advertised as 7,500 square feet, with 12-foot ceilings and wood-burning fireplaces. While Mr. Allen’s apartments are unique because they include the penthouse and are above the tree line in Central Park, the market has softened at the high end. Real-estate agents estimate the combined unit would go for about $50 million and take more than a year to sell.
As the owner of the Portland Trailblazers, Mr. Allen was a fixture at games in Portland, about a 3½-hour drive from Seattle. Mr. Allen’s trust owns a two-bedroom, two-bathroom, 907-square-foot pad in the Fountain Plaza Condominiums at the Koin Center, a mixed-use building in the heart of downtown. The trust bought the condo for $795,000 in 2017. Andrew Berlinberg, an agent with Keller Williams, says the city’s condo market has since softened due to a glut of high-end apartments built over the past five years. In the past year, four similarly sized condos have sold for between $700,000 and $837,526, based mainly on the level of updating, taking an average of 260 days to sell and typically after several price reductions, says Mr. Berlinberg.
The main house, on a steeply sloped site, was built by Horace McCurdy, a Northwest construction magnate and shipbuilder. Architects Charles Moore, William Turnbull and Arthur Andersson of firms Moore Andersson and William Turnbull Architects, won a nationwide competition to design more buildings on the property.
Mr. Andersson estimates the cost of the project at the time was about $20 million, and describes it as a “series of delicate wood buildings” with courtyards in-between, an apple orchard and a salmon ladder.
The total value of the property is estimated around $130 million.
Property records show the trust that bought the former 20-acre estate of artist Georgia O’Keefe, Sol y Sombra, 3 miles outside of Santa Fe, is registered at Vulcan’s headquarters in Seattle. Locals say it is common knowledge that Mr. Allen was behind the 2000 purchase. But, as with most of his properties, no one tied to the transaction will speak on the record, and it is hard to find anyone who saw him. “I live four doors away and drive by the gate every time I go to town and I never saw him,” says Neil Lyon, of Sotheby’s International Realty. At the time of the sale, Sol y Sombra had a five-bedroom, 9,685-square-foot, 1930s main house, a 5,000-square-foot lodge, a guest cottage, a carriage house and gardens. The list price was $12.2 million; the sale price wasn’t revealed.
In 2013, just after Vulcan announced it was opening a Palo Alto, Calif., office, a trust tied to Mr. Allen and his sister spent $27 million on a 22,005-square-foot, six bedroom, six bathroom house on a 1.97-acre lot in Atherton, a town in Silicon Valley known for its large properties and billionaire residents. The spec house, built by Pacific Peninsula Group, has a spa, a theater, seven fireplaces, a five-car garage and a two-bedroom guesthouse. The property also has a swimming pool and caretaker’s house. Listing photos at the time showed it as very contemporary, with white walls, high ceilings and large, wood-framed windows and doors. Outside, there are stone patios, a fire pit and manicured lawns.
According to real-estate agents, Mr. Allen owns an 18-bedroom mansion called Villa Maryland in Cap Ferrat in the south of France. However, none of those agents have ever seen Mr. Allen. According to the Los Angeles Times, Mr. Allen held a pirate-theme party in 1996 during the Cannes Film Festival, inviting some 200 people and sticking a huge model pirate ship in the swimming pool. Tabloids reported Brad Pitt and Angelina Jolie stayed at Mr. Allen’s estate in 2008.
The Octopus Yacht is a 400-foot mansion on the sea that Mr. Allen built in 2003. It has eight decks and includes 12 guest cabins, a huge owner’s suite, a music studio, a movie theater, a gym with a basketball court, a hair salon, a library, a dining room that seats 24, and an outdoor pool and cabana bar. It was designed for adventure, able to handle the ice of the Antarctic, with a crew of 60, a helicopter and two submarines. The yacht’s interior designer Jonathan Barnett says Mr. Allen asked for sophisticated materials and details. The foyer has a double-story staircase, a multideck skylight and art everywhere, including a sculpture of giant guitars that play songs every half-hour. “He was a very stylish guy,” says Mr. Barnett.