The next time you’re denied entry to an exclusive club, you may just be one snub away from changing the course of history. Or at minimum, finding a really nice summer home. At least, that was the case for Joseph P. Kennedy Sr.
For nearly a century, the Kennedy Compound in Hyannis Port, Massachusetts, is where one of America’s most influential families has come to celebrate, bond, play, and grieve. The sprawling six-acre waterfront estate, with its three white-clapboard houses and manicured lawns stretching down to the sea, has been the backdrop for some of the most pivotal moments in American history.
Outside the Kennedy Compound, Hyannis Port.
The Early History of the Kennedy Compound
The Kennedy saga in Hyannis Port began, rather unexpectedly, with a game of golf. In 1926, Joseph P. Kennedy Sr., already a millionaire with grand ambitions—his business ventures included banking, stock trading, movie production, and liquor sales—found himself rebuffed by the exclusive Cohasset Country Club, much closer to Boston. This rejection, likely stemming from anti-Irish Catholic sentiment prevalent at the time, led Kennedy to seek greener pastures—or rather, more welcoming fairways.
His search brought him to the Hyannisport Club on Cape Cod, where he and his wife, Rose, were warmly received. Drawn by the club’s welcome and the area’s natural beauty, the Kennedys initially rented a summer home there known as the Malcolm Cottage in 1926. This modest retreat, built in 1904 by local Cape Cod resident Frank Payne for the Malcolm family, would become the cornerstone of the Kennedy legacy in Hyannis Port.
Exterior view of the Kennedy Compound, pictured here in 1964.
Enchanted by the locale and sensing its potential, Joseph P. Kennedy Sr. purchased the Malcolm Cottage in 1928 for $25,000—a considerable sum at the time, but one that would prove to be a visionary investment. This acquisition marked the beginning of the Kennedy Compound. Joseph soon set about renovating the property, transforming the quaint cottage into a grand retreat.
The Kennedy Compound “Big House”
The centerpiece of the compound, affectionately known as the “Big House,” quickly became more than just a summer retreat. Joseph P. Kennedy Sr., with his characteristic flair for grandeur, expanded the original structure into a 21-room mansion, complete with 12 bedrooms, a steam room, and—in a nod to his Hollywood connections—a 50-person theater in the basement.
John F. Kennedy and wife Jacqueline Kennedy run toward the house at the Kennedy compound in June 1953.
Rose Kennedy, the family matriarch, left her indelible mark on the Big House’s interiors. With a keen eye for antiques and a refined taste, she decorated the home with a stunning collection of 17th- and 18th-century American furniture, art, and rugs. This curated assemblage of 135 pieces not only adorned the Big House but also eventually extended to the President’s House, another property in the compound that was later acquired.
The Big House witnessed the growth of Joseph and Rose Kennedy’s children, including future president John F. Kennedy, who spent many formative summers here from the age of nine. This grand residence served multiple purposes for the Kennedy family. It was a summer retreat where the family could escape the pressures of public life, a gathering place for holidays and celebrations, and eventually a de facto political headquarters.
The Expansion of the Kennedy Compound
As the Kennedy family’s influence grew, so did their presence in Hyannis Port. In the 1950s, two significant additions were made to what would become known as the Kennedy Compound.
Senator John F. Kennedy and wife Jacqueline Kennedy at the Kennedy compound in June 1953.
In 1956, John F. Kennedy, then a rising political star, purchased a smaller home at 111 Irving Avenue. This property, later dubbed the President’s House, would serve as JFK’s personal retreat and, during his presidency, a Summer White House.
In 1959, Robert F. Kennedy acquired a property on 28 Marchant Avenue, adjacent to the other Kennedy homes. This acquisition completed the trio of residences that would form the core of the Kennedy Compound, spanning six acres along the waterfront.
Life at the Kennedy Compound
The Kennedy Compound was more than just a collection of houses; it was the backdrop for the family’s quintessential New England lifestyle. Days were filled with sailing on Nantucket Sound, golfing at the Hyannisport Club, and the now-famous touch football games on the expansive lawns.
Jacqueline Bouvier, Eunice Kennedy, and Jean Kennedy perch on the porch of the Kennedy compound in June 1953.
Though private, the Kennedys were part of the local fabric, frequenting Cape Cod landmarks like Four Seas ice cream shop and enjoying meals at local restaurants. These outings endeared them to locals and offered glimpses of their relatability.
JFK at the Kennedy Compound
The Kennedy Compound wasn’t just a family home. JFK hosted press conferences and political meetings here during his presidency, turning the estate into a Summer White House. Journalists like Walter Cronkite and Barbara Walters went to Hyannis Port, and their interviews with the Kennedy brothers became part of the national narrative.
Senator Ted Kennedy and NBC News’s Barbara Walters during an interview at the Kennedy Compound on May 29, 1970.
In triumph and tragedy alike, the compound served as a backdrop. It was here a young Caroline Kennedy woke her father on the morning after his election victory with a cheerful, “Good morning, Mr. President.” And it was to this haven that Jackie Kennedy retreated in the aftermath of JFK’s assassination, crafting the enduring “Camelot” narrative that would define his legacy.
Triumph, Tragedy, and Waiting at the Kennedy Compound
The Kennedy Compound has been a stage for both celebration and sorrow. It was Jackie’s refuge after JFK’s assassination, where the family gathered to grieve and find comfort in each other.
Joe Kennedy and other family members stand outside of the family compound waiting for news about JFK Jr. and Carolyn Bessette Kennedy.
But perhaps no moments were more poignant than those following the loss of John F. Kennedy Jr. and his wife, Carolyn Bessette Kennedy, on July 16, 1999. That weekend, dozens of Kennedys had gathered at Hyannis Port for Rory Kennedy’s wedding. The celebration turned instantly somber as news broke that John Jr.’s plane had disappeared en route from New Jersey. With the tent still set up for the wedding festivities, the family waited together in agonizing uncertainty, holding a private outdoor mass on the lawn as the Coast Guard, Navy, and Air National Guard searched the waters off Martha’s Vineyard.
When the search ended after five days and the worst was confirmed, the Kennedy Compound again became a place for mourning and solace. The family found comfort in Catholic ritual, gathering under the white wedding tent for mass, later moving to the sea to fulfill John Jr.’s wish to be buried in the Atlantic waters. Their shared grief echoed the aftermath of earlier tragedies.
John F. Kennedy Jr. chats with Arnold Schwarzenegger (Maria Shriver’s ex-husband) at the Kennedy Compound in 1995.
Who Lives at the Kennedy Compound Now?
Today, the Kennedy Compound stands as a U.S. National Landmark. Ethel Kennedy, Robert’s widow, resided in her family home until her death on October 10, 2024.
The Kennedy Compound, Hyannis Port.
In growing numbers, the Kennedys still gather at the family compound for its traditional Fourth of July celebration. Each year, dozens of extended Kennedy family members—including RFK’s daughter Kerry and her children as well as Maria Shriver’s daughter Katherine Schwarzenegger and her husband, Chris Pratt—gather at the property to celebrate the holiday. In July of 2024, Kerry Kennedy shared an Instagram video of the family members assembled for their annual portrait.
Though the compound itself is closed to the public, visitors to Cape Cod can explore the John F. Kennedy Museum and Memorial in nearby Hyannis.
Julia Cancilla is the engagement editor (and resident witch) at ELLE Decor, where she oversees the brand’s social media platforms, covers design trends and culture, and writes the monthly ELLE Decoroscope column. Julia built her background at Inked magazine, where she grew their social media audiences by two million and penned feature articles focusing on pop culture, art, and lifestyle.
