On a quiet stretch of South Main Street, tucked deep away inside the forest up a winding private road so steep you need a four-wheel-drive to access it, stands a 8,000-square-foot architectural marvel that most Cohasset residents barely know exists. 

Known affectionately as the “Castle on Main,” Hilltop Castle has captivated the imaginations of those lucky enough to glimpse its turrets and steep gables, yet for decades it remained a private—and sometimes troubled—secret.

Over the years, Hilltop Castle changed hands multiple times, experiencing long periods of neglect, vandalism, and even squatters. 

Yet its charm persisted through it all: the grand stonework, soaring fireplaces, sprawling back lawn, and winding staircases that thread through four or five floors of the sprawling estate. 

“You have to really have a vision for this place,” says proud new owner John Jenkins, a Lakeville resident and small business owner. “Every room is a story, every corner a challenge—and an opportunity.”

The core Jenkins family – which includes John and his wife Jill, his son, Cohasset residents Mike Jenkins and his wife Katie, her parents, Chris and Margaret of Cohasset, and John’s daughter Katie and her family in nearby Hanover, including five grandchildren – are all affectionately supportive of this patriarch’s grand vision. 

Built in 1928 in a Tudor Revival style with Normandy influences, the castle was originally commissioned by Cohasset resident James William Eustis as a wedding gift for his daughter Eleanor and her husband, Major Clifford Farrington, and designed by architects Derby and Robinson. 

Robinson even traveled to England and Normandy to study castle design firsthand, ensuring that Hilltop Castle would be both authentic and unique. Labor costs alone exceeded $125,000—roughly $2 million today—and some materials, including granite for the castle’s fireplace, were imported all the way from Egypt.

“She lived here for three years, got a divorce, and moved out,” John says. “I like to say that just proves money can’t buy you love.”

Over the decades, Hilltop Castle changed hands multiple times, including ownership by New York antiques dealers and Austrian immigrant Raimund Vanderweil, who added a cedar closet room, converted the maids’ quarters into guest rooms, and installed a well imported from Spain. 

Previous owner George Gialtouridis won the property at auction in 2017 during a bank foreclosure, and planned to fix it up, according to a 2021 article in the Cohasset Mariner. Those plans never materialized. 

The Jenkins family also first encountered the castle back a decade ago. “The real estate broker warned us the place was haunted,” John recalls, laughing. His son Mike’s wife, Katie, unsettled by the warning, declined to move in—but the seed had been planted. 

Last year, when a video of the castle was posted on Instagram by Boston real estate agent Brian Gagnon, John saw it as a second chance to take on the property himself. “I knew the castle needed someone who cared about it, not someone looking to flip it or develop the land,” he explains.

Since purchasing the property in March, the Jenkins family has undertaken the monumental task of restoring both the structure and its grounds.  Sadly, in recent years the property has been vandalized, with anything of value stripped away. The floors are riddled with litter and debris by unknown squatters. 

John recounts days spent hauling debris into a 30-yard dumpster and clearing truckloads of overgrown vegetation. “We just started with three rooms, and it was like Helter Skelter. But seeing the potential—that’s what keeps you going.”

Restoration isn’t just about cleaning up the past. For John, it’s about envisioning the castle’s future. “I’d love to see local organizations use it—maybe a music group or a horticultural club. Even small gatherings for under 50 people,” he says. The sprawling back lawn could someday be a perfect venue for a wedding or photo sessions.  

He’s also considering short-term rentals to allow others a chance to experience this hidden treasure while ensuring it remains a family legacy. 

Once the castle is ready to reemerge, the family hopes to host a festive soiree to mark the milestone—a glimpse of the revival to come.

John, who describes himself as a “dreamer,” is determined to ensure the castle remains a family treasure for generations. “It’s not just about restoring a building,” he says. “It’s about preserving a piece of history, a piece of Cohasset, for the people who come after us.”