A Look At The Most Gorgeous Kennedy Homes Through The Years

Few political families in American history have interested the public for quite as long as the Kennedys have. From the unique and powerful people they kept in their inner circle and the Kennedy family's most troubled marriages to the tragic story of Rosemary Kennedy and all the horrific and unexpected deaths that plagued the family, there's never been any lack of intrigue when it comes to this dynasty. 

What's been perhaps most captivating when it comes to the Kennedys is how much money they had. Joe Kennedy, John F. Kennedy's father, had an estimated net worth of $500 million at his death in 1969, which would be equivalent to around $4.2 billion today. Suffice it to say, there was plenty of money to go around. And with that money, the family purchased some of the most spectacular properties imaginable — and they were located across the globe. Take a look at the most gorgeous Kennedy homes through the years. 

In many ways, John F. Kennedy lived an idyllic East Coast life (aside from all the tragedy surrounding the Kennedy family), and it started at birth. JFK was born in 1917 at his family home in Brookline, Massachusetts, a suburb of Boston. The future president's parents, Rose Fitzgerald Kennedy and Joseph P. Kennedy, had purchased the house about three years prior, not long after getting married. The house was marked by its beautiful colonial exterior and its well-crafted interior, which was particularly spacious for the times. In 1920, the Kennedys sold their home to some family friends and moved to a different house in the same neighborhood, though they did eventually repurchase it. After JFK's shocking death, Rose donated the home to the National Parks Service, and it officially became a national historic site in 1969.

The home has gone through some turmoil of its own, too. In 1975, two men threw a firebomb into JFK's birthplace in protest of JFK's brother, Ted Kennedy, who was serving in the United States Senate at the time, and his support of school integration through busing. One of the men was later identified as James "Whitey" Bulger. "He was all rah-rah-rah about fighting busing," a source later told The Boston Globe of his attack. "He wanted to make a point. He liked to say he was doing something active to fight busing. He was and is a racist." The home underwent some renovation to restore it and reopened a year later to the public.

Jacqueline Lee "Jackie" Kennedy Onassis didn't have it too bad as a child, either. Her parents, Janet Norton Lee and John Vernou Bouvier III, were well-to-do socialites. When Jackie was 10 years old, her parents divorced. Two years later, the future first lady's mother tied the knot with Hugh D. Auchincloss, an heir to an oil fortune. Jackie's family moved into Auchincloss' huge home on a sprawling Virginia estate — we're talking 23,000 square feet on seven acres. The estate, which is located on the Potomac River, is called Merrywood House, and it is exceptionally beautiful. "I always love it so at Merrywood — so peaceful ... with the river and those great steep hills," Jackie wrote of her home as a teenager, per the book "Jacqueline Bouvier Kennedy Onassis: A Life," as reported by the Wall Street Journal.

Merrywood is still very much intact, and while it's been renovated multiple times since Jackie lived there, it's as grand as ever. In 2017, the property went up for sale for just under $50 million (a bargain!), boasting nine bedrooms, a gym, indoor and outdoor pools, a tennis court, and staff quarters, among other features. When Jackie wasn't at Merrywood, she spent time at her grandfather's estate in the Hamptons. Also situated on seven acres, the home is only (only!) 8,500 square feet, and it is believed to have been built in 1917, which is coincidentally the year that Jackie's first husband, John F. Kennedy, was born. The Hamptons home went on sale for $55 million in 2023.

It's one thing to be wealthy enough to own your own vacation home, but if that home also happens to have its own name? That's an entirely different level of rich. Look no further than Domaine de Beaumont, the Kennedy family's fabulous retreat in the French Riviera. In 2023, the property, where John F. Kennedy reportedly learned how to swim, hit the market at a staggering $35.5 million price point. "This truly is a unique property, just 10km from the vibrant city of Cannes, you step into a period property surrounded by exceptional grounds and views, where peace, privacy and space are king," the real estate agent said to the New York Post of the estate.

And the property is truly exceptional. The primary building spans nearly 12,500 square feet and houses nine bedrooms, many of which are ensuite, and it includes a movie and game room, a formal dining room, and a marble staircase. As if there weren't enough space, there are additional structures that serve as staff quarters and a pool house, the former of which holds a wine cellar and the latter of which has a pizza oven. There's also a gorgeous pool and well-manicured outdoor space. While the Kennedys likely didn't have all the modern amenities the vacation spot has now, it wasn't exactly a modest abode way back when. The Kennedys have known the good life for a long time.

The size of the Kennedy family's wealth cannot be overstated; calling just one of their properties home would be a dream for most. The family left their mark along the entire East Coast, stamping a particularly prominent print in Massachusetts. After first renting a cottage in Hyannis Port, Joseph and Rose Kennedy bought what they would later refer to as the "Big House" in 1929. Joseph and Rose continued buying abutting property until the family had a compound. The parents renovated the Big House to feature 11 bedrooms, a sauna, and a movie theater, and it featured a pool and a tennis court outside. Robert and Ethel Kennedy and John and Jackie Kennedy would eventually have their own homes on the property, too.

There, the Kennedy family created many memories together. In the book "White House by the Sea," author Kate Storey describes one of the Kennedy family's Thanksgiving celebrations at their compound. "She took center stage in the living room, demonstrating by swinging her hands to one side, her hips to the other, her feet staying planted on the plush rug," the book says of Jackie teaching her kids how to do "The Twist," as reported by WWD. "Jack sat back in his chair with a small cigar, smiling, watching his family together, laughing and teasing like they had in that living room when they were kids."

Lest anyone think one spectacular vacation house was enough, the Kennedy family continued to expand their vacation property portfolio. In 1933, just a few years after scooping up the first bit of land that would become their compound in Massachusetts, Joseph and Rose Kennedy bought a gorgeous beachfront home in Palm Beach, Florida. Palm Beach was close to Rose's heart as she had spent time there each year since she was a child, and it quickly became a special place to John F. Kennedy. JFK sought respite at his parents' Palm Beach home whenever he was sick, and he had happy memories there, too, eventually bringing his own family along to enjoy all the place had to offer. He even spent one final weekend in Palm Beach just before he was assassinated. "He was like anybody else, in penny loafers with no socks and khaki slacks, shopping and looking in the windows," one of Palm Beach's former chamber of commerce presidents said of JFK, as reported by Palm Beach Daily News.

It's easy to see why JFK liked spending time at the Palm Beach property. A Mediterranean style home, it spanned over 15,000 square feet and featured 11 bedrooms, a tennis court, and a pool. A property steeped in American history, the Kennedys' Palm Beach estate reportedly sold in 2020 for $70 million.

There are a lot of Kennedys to keep track of. Robert F. Kennedy, one of John F. Kennedy's brothers and the father of former presidential candidate Robert F. Kennedy Jr., and his wife, Ethel Kennedy, owned a home in Virginia called Hickory Hill. (This, of course, was in addition to their place on the Kennedy compound.) A countryside estate, the property was first owned by JFK, but RFK purchased it after Jackie Kennedy suffered a miscarriage. The home had enough space for their many, many children, and it was big enough to accommodate last-minute get-togethers with other political figures and government officials. "I don't know how Ethel tolerated it, frankly. Because Bobby would call up at the last minute, and say uh, 'Ethel, I'm bringing out uh, 10 of us, 12 of us, 20 of us, uh, can you fix some lunch?' And we'd spend the afternoon discussing some problems," former United States Attorney General Nicholas Katzenbach told American Experience of the time spent at Hickory Hill

The home originally had a stately red brick exterior, but it was eventually painted white. Over the course of its existence, it's had 13 bedrooms and a badminton court, as well as a pool, and there's always been plenty of space for children to play outside. Ethel put the property up for sale in the early 2000s, reportedly asking $25 million for the nearly 8,000 square foot home. It sold in 2009 for $8.25 million, and the new owners made some necessary renovations while maintaining its integrity.

The Kennedys had so much money that it didn't really matter whether they rented or bought homes. And sometimes it must've been easier to rent, because that's exactly what John F. Kennedy and Jackie Kennedy did as newlyweds. For six months in 1954, JFK and Jackie rented a Georgetown townhouse. At just over 3,000 square feet in size, the townhouse was a pipsqueak of a home compared to some of the other Kennedy properties, but it was still massive compared to the average American home. In 2023, the home hit the market at $2 million, boasting a wood fireplace, oak molding and floors, and a back garden.

Jackie worked hard to make the place home while she and JFK lived there. The future first lady caused damage that would cost over $4,300 in today's prices by painting furniture and having JFK hang artwork. While the owner of the house wasn't too happy about the damage, the housekeeper, Mattie Penn, took a liking to Jackie and taught her some of the basics of taking care of a home. "Many thanks, Mattie. If you have any spare time, hope you will come and cook me a dish of collards. They will kill me or cure me," Jackie once wrote to Penn, as reported by The Washington Post.

Just before John F. Kennedy was assassinated, he and Jackie Kennedy finished working on Wexford, their 166-acre ranch property in Virginia. There isn't a ton of information available on the property from the Kennedy era because the family, unfortunately, wasn't able to spend much time there, and Jackie wanted it to remain private. "I don't want it [Wexford] to be exploited and photographed all over the place just because it was ours. It's the only house Jack and I ever built together, and I designed it all myself," Jackie said in "The Kennedy White House: Family Life and Pictures, 1961-1963," as reported by Forbes.

Jackie reportedly sold the estate a year after JFK's assassination, and it's been sold again a number of times since, including in 2017 for $2.85 million. In 2017, the 5,000 square foot home boasted five bedrooms, a pool, and a tennis court, and the land included a horse barn. And to make it even more presidential, Ronald Reagan rented the home for some time just before he was sworn in. "This house may not be perfectly proportioned — but it has everything — all the places we need to get away from each other — so husband can have meetings ... wife paint ... all things so much bigger houses don't have. I think it's brilliant!" Jackie said of the home, as reported by Mansion Global.

Jackie Kennedy's life was never the same after John F. Kennedy died. And immediately following his death, she had lots of decisions to make, including where to live. Lyndon B. Johnson was sworn in as president the same day JFK was assassinated, meaning Jackie was no longer first lady, so she had to move out of the White House. Jackie and her children headed to the Riggs-Riley House, a historic property in Georgetown that has housed many politicians and military officers. W. Averell Harriman, a member of JFK's administration, had just moved in when the president was shot, and he let Jackie and the kids stay there until she found another place about a year later. In 1971, Jackie and her children would return to the White House to see the unveiling of JFK's official portrait.

The Riggs-Riley House is a large home — it sits at nearly 9,000 square feet and has eight bedrooms and six bathrooms — but it is far better known for its famous residents and guests than its looks. "The house was not beautiful architecturally and was rather awkward in many ways as those Georgetown houses are, but it had charm," decorator Billy Baldwin said of the place in his autobiography, as reported by The Washington Post. Two of the home's famous guests have included Bill and Hillary Clinton, and it was once ordered to be under federal surveillance by Richard Nixon.

Jackie Kennedy dated a handful of men before and after John F. Kennedy — Jackie even received an unexpected proposal from a longtime friend in the wake of JFK's death — and she eventually married the famously wealthy Aristotle Onassis. The widow reportedly inherited millions from Onassis after his death in 1975, and she spent at least some of it on a beautiful estate in Martha's Vineyard, which she purchased in 1979. The property, called Red Gate Farm, spanned 340 acres, and in 2019, it was put up for sale by Jackie's daughter, Carolyn Kennedy, and her husband, the duo asking for $65 million. At the time of the listing, the property included multiple structures, the main of which spanned nearly 6,500 square feet. The five-bedroom abode includes a pool, chef's kitchen, tennis court, barn, and boathouse.

"When she found Red Gate Farm, it was a perfect expression of her romantic and adventurous spirit," Carolyn said of the property when it went on the market, as told by Homes & Gardens. "The dunes and ponds and rolling hills of Aquinnah gave her the chance to create a world where she could be so close to nature, close to her family and friends, and, most importantly, close to her beloved books." The land was sold to Martha's Vineyard Land Bank and the Sheriff's Meadow Foundation, two local land preservation groups.