Historic Cape Cod Estate That Sits Next to Famed Kennedy Compound Returns to the Market—With $6 Million Price Increase

An imposing waterfront estate in Hyannis Port that sits just a stone’s throw from the Kennedy family’s iconic compound has been put back on the market for the second time in a year—but this time, it’s had a $6 million price increase.

The enormous dwelling, which was originally built in 1914 and now boasts seven bedrooms and 7.5 bathrooms, is located on a rare 3-acre waterfront lot in the tony Massachusetts community. It comes with 500 feet of private beachfront.

It initially came on the market in October 2024 with an asking price of $19.8 million. The listing was removed in February of this year.

Now, it has returned—just in time for summer—with an even higher asking price of $25.8 million, as well as a newly added six-bedroom guesthouse, which was not included in the original listing, real estate agent Brian Dougherty, who is co-listing the property with his colleague, Maggie Gold Seelig, of MGS Group Real Estate, explains.

“The property was previously marketed briefly as just the main house, and has now been reintroduced to the market with the addition of a neighboring guesthouse that has six bedrooms,” he says. “So the total estate is 14 bedrooms and 3.2 acres of waterfront property.”

“For the first time ever, an additional six-bedroom guest house is included in this rare offering, creating a one-of-one multi-generational compound,” the listing states.

Known as “Port View,” the property is hailed in its description as “one of the most iconic oceanfront estates along the entire Northeastern seaboard,” with its impressive history rivaled by only a handful of properties—including the Kennedy family’s own Hyannis Port home, which became known as the “Summer White House” during John F. Kennedy‘s presidency.

It was at the Cape Cod retreat that JFK planned his presidential campaign in summer 1960, and it was there that his wife, Jacqueline Kennedy, retreated to after he was assassinated in 1963 at the age of 46.

Hyannis Port would be where Jacqueline crafted the image of Kennedy’s presidency as “Camelot” in the wake of his death, taking inspiration from his favorite Broadway musical and telling the media in her first official interview after his passing: “Don’t let it be forgot, that for one brief, shining moment there was Camelot.”

The home had been the site of many happy vacations for John and Jacqueline—and it went on to serve as a much-needed retreat for other family members over the years, becoming the site of an annual Fourth of July reunion.

Each year, dozens of extended Kennedy family members—from Robert F. Kennedy‘s daughter Kerry and her children with ex-husband Andrew Cuomo to Maria Shriver‘s daughter Katherine Schwarzenegger and her actor husband, Chris Pratt—gather at the property to celebrate the holiday.

Traditionally, images from Kennedy family gatherings were shared with the media, offering a glimpse of the dynasty’s lavish lifestyle. Today, those same glimpses are posted on social media—particularly, images from the famed July Fourth celebrations.

Now, another deep-pocketed homebuyer will have the chance to experience a similar slice of that idyllic experience from the comfort of their own historic abode—which appears to have been tailor-made for a traditional Fourth of July gathering.

“We have been in the good fortune of seeing the region’s most stunning properties, but when you get here, you really see a part of Americana,” Seelig previously told Realtor.com of the home.

“It’s sort of like, ‘if these walls could talk.’ There’s just so much history that it’s hard to articulate. There’s an incredible duality of looking back and looking forward.”

Dougherty agrees that it was almost impossible to put into words how special this property truly is—while also pointing out that it boasts another A-list connection in addition to the Kennedys.

“There’s almost a moment of silence when you arrive,” he says. “It’s one of the most photographed properties in New England. It has been seen in everything from all of the Kennedy brothers playing touch football to Jackie waterskiing. In recent years, there is an image of Taylor Swift walking in front of the beach.”

That image of Swift, 35, was taken during her short-lived romance with Kennedy scion Conor Kennedy in summer 2012, a relationship that proved so impactful, it prompted the singer to invest in her own Cape Cod dwelling—which was also recently put on the market for $14.5 million.

Adding to this home’s allure is the fact that dwellings in Hyannis Port are so rarely put on the market—particularly those that boast such impressive water frontage, or such spectacular views out over the Nantucket Sound.

In fact, there are just six homes in the town currently listed on Realtor.com—three of which are already pending sale.

Port View last traded hands in 1999, when the current sellers purchased it for $6 million. They have since poured more than $5 million into upgrading the property, adding a seawall and installing new oversized windows to ensure that the spectacular views can be enjoyed from almost every room.

“A gracious floor plan features walls of windows from which to enjoy spectacular 300 degree views, while tall ceilings and beautiful architectural details are found throughout, including the fireplaced living and dining rooms, tavern, wood paneled library, sun porches, third floor game room with mahogany inlay floors, and roof deck, all substantially renovated by current owners,” the listing notes.

Designed by “the legendary Olmstead brothers,” the beautifully landscaped lot also features an in-ground pool, hot tub, and fire pit.

In addition, the home features a sprawling stretch of land that is known as the “wedding lawn,” thanks to its suitability for hosting outdoor events, particularly during the summer months.

Speaking to Realtor.com when the home was originally listed in October 2024, Dougherty noted that the home’s many impressive amenities makes it ideal for every kind of buyer—whether that person is seeking a full-time Cape Cod residence or looking to snap up a summer getaway.

“If ever there was a property that is deserving of being called multigenerational, this is it,” he said. “You could park your car and be there all summer, but it could also be the New England home base and headquarters. It’s also 8.5 miles away from Hyannis Airport for private travel.”

Meanwhile, Seelig called attention to the property’s uncanny ability to feel expansive, yet cozy all at once.

“It doesn’t feel overwhelmingly large when you are there and can be cozy yet able to expand to accommodate a large-scale group,” Seelig said.

“We believe the next owner will be a person who appreciates how special this property is and will appreciate having a piece of history. It’s an opportunity to own a property in a location that’s truly one of one. There is no spot quite like this on all of Cape Cod.”