Inside the Hitchcock estate after one year on the market

MILLBROOK — After decades of infamy and just over a year on the market, Millbrook’s Hitchcock Estate continues to exist in relative mystery.

After a notorious few years in the 1960s, little has been heard about the estate recently — a stealthy departure from its past. The appearance of last year’s listing provided the first glimpse inside the property in nearly a decade.

However, correct details about what had become of the house in recent years remained difficult to find. It remained clear, though, that the Hitchcock Estate was no ordinary house for sale.

Billy Hitchcock and his brother Tommy purchased the 2,087-acre property, which is roughly one-seventh the size of Manhattan, in 1963. Psychedelic pioneer Timothy Leary famously came to live in the house after being introduced to Billy through his sister Peggy Hitchcock.

There are so many rooms in the main house that some of the smaller ones lack a clearly-defined purpose.Photo by Charlie Greenberg

Following Leary’s time in the estate’s main house, it fell into disrepair and was boarded up. After undergoing some restoration by historian John Foreman, Tommy finished repairing the house to a liveable but not modernized state.

“My brother did a wonderful job fixing the big house and putting it back together,” Billy Hitchcock said. Tommy handled the maintenance of the estate and lived on it part time. However, upon his death in 2023, there was nobody to coordinate the property’s extensive maintenance needs, prompting the Hitchcock family to list the estate for sale, Billy said.

While the Hitchcock Estate is best known for its role in the psychedelic awakening, that period reflects only a small part of the broader segments of American society between which the estate serves as a nexus.

The estate has attracted numerous illustrious occupants throughout its history. The estate’s builder, Charles F. Dieterich, was a German-born industrialist who made his fortune in the acetylene gas business, building the estate to remind him of his native Bavaria; Charles Mingus wrote the song “Peggy’s Blue Skylight” about Peggy Hitchcock after visiting.

Old and new money, creators of and rebels against the establishment each have passed through the estate, leaving psychedelic artwork and Gulf Oil memorabilia testament to past times behind the open landscapes and ornate architecture.

Some of the smaller bedrooms in the main house are quite liveable and ordinary. TommyHitchcock III’s restoration efforts are visible in the newly-painted walls and trim.Photo by Charlie Greenberg

Often overshadowed by his involvement with Leary is Billy Hitchcock’s prominent lineage. Billy’s mother, Margaret Mellon Hitchcock, was the daughter of Gulf Oil founder William Larimer Mellon and the great-granddaughter of Mellon fortune founder Thomas Mellon.

Billy’s father, Tommy Hitchcock Jr. was referred to in 1956 by the New York Times as the greatest polo player in the history of the sport. Tommy Jr. was also F. Scott Fitzgerald’s inspiration for the character of Tom Buchanan in The Great Gatsby.

“My father was a pilot in the First World War. He was shot down by the Germans and escaped all by the time he was 19,” Billy said.

In World War II, too old to be a combat pilot, Billy said, Tommy Jr. was a test pilot for fighter planes when he was killed in an aircraft test.

The Hitchcock Estate has its own parallel history with that of the Village of Millbrook, with the scope of events and personalities it attracted seemingly beyond those that unfold on the other side of Route 44. But the estate today has a much quieter appeal about it.

Entering the estate from its far less conspicuous and more frequently used entrance on Valley Farm Road, it is not difficult to see what appealed to prominent people throughout the years looking for a getaway that existed apart from the rest of the world and their substantial places in it.

The main estate house on the Hitchcock estate in Millbrook was constructed in the late 19th century by German acetylene gas magnate Charles Dieterich.

At 14,000 square feet, the main house at the Hitchcock Estate was comparatively modest when architect James E. Ware added onto an existing farmhouse on several occasions to create the Bavarian-inspired building in the late 19th century. At 34 rooms, however, the scale of the house, and indeed the entire property, is not something that is commonly seen in Millbrook today.

Large estates built around distinctive mansions were a more typical sight in Millbrook at the time the Hitchcock Estate was built, but years of structure fires and property subdivision have made them increasingly rare. Regardless, the estate was unmatched in scale even at the time of its building.

The Bavarian influences on the main house and property’s smaller buildings, stone walls and patios give the property a surreal feeling of being in an abandoned fairy tale. Few people see the property today beyond the farmers and caretakers who keep it up — Billy Hitchcock, now in his eighties, lives in Texas and other members do not visit often, he said.

Tommy Hitchcock III’s restoration work is evident. Freshly painted, the main house looks quite tidy with the exception of some overgrown trees around the veranda. Windows broken during the Leary years have been replaced, though the house’s more ornate leaded glass windows remained intact.

It is a one-mile drive, without leaving the Hitchcock property, from the main house to The Bungalow, a second mansion on the property constructed by architect Addison Mizner in 1912. At 10,000 square feet, The Bungalow is not as intimate as the name suggests. It was designed by Addison Mizner of Palm Beach, Florida fame and was the home of Tommy and Billy Hitchcock when they were in residence.

“We all love the property,” Billy Hitchcock said. “We’re sorry to be letting it go after 60 years.” Given the estate’s large size — 900 acres larger than the Village of Millbrook — Hitchcock understands the interest the community has in its sale. “It’s hard to say where this is going to come out,” Hitchcock said, though he is committed to selling the property to someone who understands its value to the community.

Granted, there few more knowledgeable than Mr. Hitchcock about the ways something personal to a small number of influential people can in turn become important to countless others beyond the inner circle.