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All in the Family: Why Multigenerational Compound Estates Are Thriving During the Pandemic

Andrew Sessa
·11 min read

Four years ago, when interior designer Ellie Cullman created a house for her three adult children and their families on the grounds of her considerable country estate in Connecticut’s Fairfield County, she never imagined how they’d take advantage of it these past few months. With the help of architect John Murray, she converted and expanded the late-19th-century seven-bedroom red-clapboard farmhouse—which her late mother-in-law had used for decades—thinking her kids would come up from New York “for the odd weekend, maybe a bit more in the summer,” she recalls. “I was basically bribing them to spend time with me.”

But this past spring, they were in residence full-time, sheltering in place during the pandemic. They cooked together in the large open kitchen, gathering on the screened porch and hanging out in the family room, with its 15-foot U-shaped sofa. Every Saturday, the four grandchildren stayed over with Cullman and her husband in the property’s seven-bedroom main house, which is dotted with American antiques and folk art and nestled in the woods on the other side of their land. “I’m thrilled because our lives would have been so different during this time if we hadn’t had this compound,” Cullman says, though she acknowledges that the constant togetherness has inevitably led to occasional bickering, as it probably would for any of us in the same boat. “Maybe,” she jokingly suggests, “I should have built them three separate houses.”

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Like the Kennedys on Cape Cod and the Bushes in Maine before them, those fortunate enough to do so today are creating properties designed not just for their immediate families but for multiple generations, and sometimes various branches, of their family trees. More vital now than ever, these homes have many of the hallmarks of the rambling shared estates of past eras, but they take the concept of the family compound in new directions, too. The designers helping 21st-century clients realize them report that these properties are as varied as the families who commission them.

Although there’s no single template, inside or out—compare Cullman’s rambling Connecticut estate to the modern Martha’s Vineyard beach house or the riverside farm in rural Georgia—their raisons d’être remain fairly consistent. “It’s about creating the bait to get all your children and their spouses and their kids to assemble at home,” says architect Bobby McAlpine. His eponymous firm has worked on a dozen or so multigenerational estates, ranging from a pair of parents-and-son white-clapboard farmhouses in suburban Salt Lake City to a rustic-chic Alabama hunting and fishing camp on 500 acres of ancestral property, a parcel that his client reassembled over the course of 10 years so some 30 to 40 members of his extended family could gather there for reunions every Thanksgiving and July 4.

Whatever the specifics of their style and size, the most successful family compounds today are resort-like, McAlpine finds, as enticing as a favorite vacation destination. “What kind of property will have the entertainment factor to hold everyone’s attention for a nice long visit?” he asks. “It ends up being a deconstructed boutique hotel of sorts.” People want a party barn, a big barbecue porch or outdoor kitchen, trails for hiking, gear for water sports. Not least of all, McAlpine says, they crave the freedom to put certain family members in the main house—and to create a little distance for others.

These ideas certainly informed the waterfront Hamptons property that Cullman’s firm, Cullman & Kravis, worked on for longtime clients. A Boston-area financier and his wife, they built their dream beach house, with contemporary shingle-style architecture by Ike Kligerman Barkley, when their three children were in their mid-teens and early 20s. As that generation grew older—acquiring significant others, ever-larger groups of friends and one big, messy dog—it became clear that everyone needed more, and more of their own, space.

“We recognized that my daughter might love me and my son-in-law might love me,” the matriarch explains, “but they may not want to spend all their time with me when they’re here.” And so, five years after buying the first plot of land, the couple acquired the plot next door to build their offspring a place of their own, one whose architecture, again by IKB, would echo that of the five-bedroom main house, while the furnishings and art would have a younger, more vibrant feeling.

The second house gave the family four more bedrooms and a second-floor, vaulted great room with living, dining, kitchen and bar areas, all with sweeping ocean views—plus art by the likes of Carol Bove, Spencer Finch, Rebecca Morris and Serge Alain Nitegeka. A key draw outside, complementing the main house’s infinity-edge pool, is the waterfront fire pit, something they’d long wanted. “It’s a magnet for us,” the homeowner says. Regardless of the separate pursuits the family members have earlier in the day, as the sun sets “we all grab a glass of wine and sit around that fire together.”

All three of the children and their partners moved to the 2.7-acre property in mid-March, temporarily leaving their homes in locked-down New York City. Their parents joined them later in the spring. Even as the second house “gives the kids the privacy to be away from us, which they want and need,” the owner concludes, “the beauty of this is that we are all here.”

That sort of together-apart dichotomy also defines the expansive compound that architect Patrick Ahearn designed on Martha’s Vineyard for a trio of siblings who wanted a place for their children and grandkids to congregate. After vacationing around the world together over the years, Paula Williams Madison says she and her brothers, Elrick and Howard Williams, “wanted a location where the entire family could gather not only to bond and have the next generation be very close, but where we could instill and perpetuate our family values”—ideals that their parents, Jamaican immigrants, had instilled in them when they were growing up in Harlem. “We wanted to make sure that, although we live all over the country, we didn’t lose that.”

Designing for the score of relatives who would be in residence for several weeks every summer—but keeping in mind that the house would sometimes be occupied by only a handful of people—Ahearn created a largely single-level building whose five one-bedroom suites occupy two long parallel wings. “We wanted each suite to be like a cottage, with its own living area and bedroom and a spa-like bathroom opening to a private courtyard—really like a nearly thousand-square-foot house in and of itself,” says Ahearn, who has designed more than 300 residences on the Vineyard in his 47 years of practice, many of them for extended families. All five suites are essentially identical in size. “I tell people only half-jokingly,” says Elrick Williams, “that the suites are equally spacious and luxurious because we didn’t want any arguments over which one of us Ma loved best.”

Connected by a central, communal section, the bedroom wings embrace a motor court at the front of the house and, at the rear, a vast outdoor entertaining area centered on an eight-foot-diameter circular hot tub and a huge pool surrounded by bluestone patios and grassy lawns. At the head of the motor court, an attached carriage house hosts a second-floor game room flanked by two dorm rooms for the youngest generation—one for girls, one for boys. Although the contemporary interiors, by designer David Lentz, are decidedly luxe, the exterior architecture takes as its inspiration the spare, gray-shingled cottages for which coastal New England is known, allowing the home to slip relatively seamlessly into its surroundings, despite its impressive size.

“We can have 20 family members in the house, and it can feel like there’s hardly anyone here, it’s so spread out,” says Elrick, though he notes the focus is firmly on togetherness during their annual reunions. The siblings themselves usually wake around 5 a.m. and gather in the kitchen, away from still-sleeping relatives, to talk over coffee about the day before and the day ahead. The kitchen adjoins a large open-plan living and dining room with glass doors leading to a pergola-covered terrace, the lawns and the pool.

By 8 a.m., the next two generations are up, and everyone’s fixing and eating breakfast together. From there, people start to go slightly separate ways. “Throughout the day,” Madison explains, “we have music playing on the outdoor speakers, reggae or jazz. Some of the kids are watching TV or movies or playing video games in the playroom. Others are at the pool or heading to the beach in a golf cart. A lot of the day is just spent swimming, laughing, running around the grass. We have huge areas for kicking a ball around or playing a game of soccer.” There’s a large room just for fishing equipment, too. “My brother is a licensed boat captain,” Madison says. “We all learned to fish as kids in Harlem.” So some people may be out catching dinner: “Elrick once got a 36-inch striper right from our beach. I cooked it up for everyone in the outdoor kitchen.”

When clients come to Ahearn looking for an extensive scope of spaces for multiple generations, as the Williams-Madison family did, he often tells them “you’ll have a richer experience if you break your program into pieces—a main house, a guest cabana, a carriage house, a barn.” This separation creates a campus-like feeling with a variety of settings indoors and out for people to gather or find some solitude. The possibilities of the place then start to seem so endless that people feel like they never have to leave.

That’s certainly the case for the Williams-Madisons. “For me, the most amazing thing about the property, and what we are blessed to have developed,” Madison says, “is that I get to be on Martha’s Vineyard but in my own little world, surrounded by my family.”

A desire to create a private world for his extended family wasn’t the initial driving force behind Atlanta architect Keith Summerour’s creation of his 800-acre Towerhouse Farm, but that’s how it has ended up. “It started out, in 2005, as a hunting retreat,” he says of the river-front homestead, 90 minutes south of Atlanta, where he has built anew or entirely renovated 10 rustic-chic buildings. “But then, over time, as more and more family started using it, it became much more than that.” His adult sons and their friends stayed over occasionally at first and then often; one of them started a business there, turning a barn into a brewery and co-opting a three-bedroom, board-and-batten guesthouse as his full-time home. Summerour’s mother-in-law, a frequent visitor, has been talking about moving into another cabin. “One of the things we found is that we literally cannot have enough housing,” says Summerour. “It’s like a bad piece of meat—the more you chew it, the bigger it gets.”

The four sons, one of their girlfriends and some additional friends all joined Summerour and his wife at the farm during the heat of the coronavirus outbreak, and in May his parents made a long-planned move there, from Alabama, to live out their golden years in a three-bedroom, country-vernacular home he had added just for them. The farm, which today sleeps up to 22, was a silver lining to the shelter-in-place period, he says.

“One of best aspects was the fact that with all the buildings, everyone has a separate place to go, but we also have a common gathering space: the porch of the main barn, which we call the Granary,” he says. The whole family would dine there nightly, cooking in the barn’s commercial-grade kitchen or ordering from local barbecue places. “The porch has a big fireplace,” Summerour says. “We’d have a fire from 7:30 in morning till 10 at night.” Then they’d watch movies projected on an interior barn wall.

“It has truly turned into a multigenerational place just organically, because everyone loves to be here,” says Summerour. And he’s grateful for that—especially these days. During quarantine, he remembers, “a week would go by, and we’d have no idea there was a rest of the world out there.”

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