Jeremy Wolff, a photographer based in upstate New York, is part owner of a six-bedroom beach house near Hyannis on Cape Cod in Massachusetts that has been in his family since the 1940s. His co-owners? Nearly 30 relatives, including eight cousins and their families, who book their visits on a family website.
“There’s sometimes some tension—like, ‘You always get the upstairs front bedroom’—little squabbly things like that,” Mr. Wolff said.
The joy of having an heirloom vacation home in the family sometimes comes with a side order of angst: costly upkeep, perpetual repairs and ancient yet enduring sibling rivalries. A legacy lake house or mountain lodge may be shared by scads of siblings and cousins, who have to figure out how to divvy up prime vacation weeks and holidays, to say nothing of property taxes and maintenance responsibilities. Basic decisions—like reupholstering Grandma’s sofa—are anything but basic when a dozen or more relatives have to sign off.
“The process of the family deciding and agreeing on replacing the fabric literally took five years,” said Mr. Wolff.
Elisha Cooper, an author whose children’s book “River” was just published, owns one-sixth of a 2,000-square-foot, four-bedroom cottage with a wraparound porch on Black Point in East Lyme, Conn. that his great-grandfather built in 1913.
“It’s basically a porch with a cottage attached,” said Mr. Cooper, 48, who lives with his wife and two daughters in New York City. The house, which was placed in a family trust in the mid-1990s, is shared by three branches of his extended family, in New York, Massachusetts and London. “I split my branch’s share with my brother,” said Mr. Cooper, adding, “at some point, we’re each going to own a toilet.”
The uninsulated cottage occupies a prime 1.3-acre spot on a grassy hill overlooking the salt marsh and ocean. In 2016, the town assessor appraised its value as $945,000. Mr. Cooper’s share of taxes and insurance comes to several thousand dollars a year. This year, it is his turn as manager of the Black Point property, which involves overseeing its maintenance and the schedule: each branch gets 42 prime spring, summer and fall days, to be meted out among its individual members (the home is boarded up for the winter). Major holidays are divvied up, “so if somebody takes Labor Day, someone else is going to take July 4th,” Mr. Cooper said.
There are pitfalls to sharing an heirloom home that happens to be full of heirlooms. “My cat got obsessed with this old wooden model boat and knocked it off the piano—that was a family drama,” Mr. Cooper recalled. “I had to spend $3,000 to re-rig and fix the boat because it was an antique.” Some of his relatives prefer a more low-tech approach to home repairs: “There’s a broken chair and it’s just left with some tape on it—or twine, done in a nice bow.”
Family summits take place on Memorial and Labor Day weekends.
“We all gather—my aunt flies in from London—and we sit on the porch and we talk. These are big decisions, like ‘Do we cut the field?’ and ‘How is that going to affect the monarch butterfly migration?’” Mr. Cooper said. “We never argue, that’s because we are New Englanders. We silently and very politely disagree.”
Some farsighted matriarchs and patriarchs endow trusts so that legacy properties will stay in the family with minimal discord or generational financial strain. Gerry and Del Carrier, who own a 5,000-square-foot mountain ski home in New Hampshire’s White Mountains, created a trust in 2013 so that their five children, nine grandchildren and three great-grandchildren can enjoy the house “in perpetuity,” in Mr. Carrier’s words.
“We estimated taxes, we estimated the maintenance—we are leaving them with very adequate financing so that it will not be a burden,” said Mr. Carrier, 84, a retired dentist who owns a second home in Vero Beach, Fla.
Mr. and Mrs. Carrier, who is 83, acquired the half-acre lot with views of Mount Washington for $1,500 in 1968, building a modest three-bedroom home where they brought their children every weekend. In 2005, they embarked on a $750,000 remodel and expansion, adding a wraparound porch, a dining room spacious enough for 25, a large bunkroom for the grandchildren and a bedroom suite for each of their children—a critical element for maintaining family harmony. There are seven bedrooms in all. At the time they established the trust, the house was appraised at $1.2 million, Mr. Carrier said.
His children and grandchildren use the house throughout the year, coming for the fall foliage, skiing in the winter, hiking and kayaking in the summer. The entire clan gathers there every Christmas.
“For as long as I can remember, every Friday night my father piled his five children into a station wagon to go to a retreat where we could just bind together as a family,” said Michelle Carrier-Trial, 59, a lawyer based in southeastern Massachusetts. She and her younger brother are the home’s two trustees: ultimately, each of the siblings will own an equal share in the house. “After my parents are gone, we hope to keep it the same way for our children,” she said.
Sometimes, however, a beloved home can become an albatross for the current generation. As a child, Schuyler Grant spent every summer at her grandparents’ seaside vacation home—just down the beach from her great-aunt Katharine Hepburn—in the Connecticut borough of Fenwick, an enclave of grand Victorian-era cottages on Long Island Sound. Built in 1868, the six-bedroom shingled house has a deep porch, its own pebbly beach and four generations of Grant and Hepburn family history.
“Every time I would come through the door, I was bathed in this smell of the house—it was like a portal to this whole other world of tennis lessons and duck belts,” said Ms. Grant, who lives with her husband and three daughters in Los Angeles. “It was extremely buttoned up—I used to have to dress for drinks every night in Laura Ashley smocks.”
Ms. Grant, 49, founder of Kula Yoga Project, in New York, and her husband Jeff Krasno, 48, founder of Commune, an online learning platform, bought the 5,400-square-foot Fenwick home in 2009 from her aunt, the actress Katharine Houghton, for $1.8 million, public records show. Their family shares the house with Mr. Krasno’s father and stepmother, Richard and Carin Krasno, who contribute toward the costs of maintaining the property and who visit every August and September from their home in Coral Gables, Fla.
“Everybody has to be their highest self—it can get really difficult,” Ms. Grant said of the dynamics. Plus: “There’s always one leak in the house that they haven’t been able to fix in 160 years, so it comes with a certain amount of buckets.”
The family spends nearly $50,000 annually in property taxes, including a Fenwick borough tax. Standard maintenance and upkeep adds another $27,000 every year. That doesn’t include the cost of reshingling the house or replacing its rattling, circa-1970s windows; the latter cost about $100,000. Ms. Grant, who offsets these expenses by renting out the house for part of the summer, reluctantly put it on the market for $3.375 million last year.
“The expense is so great, the emotional and financial upkeep is so massive, that if you are not really there then it’s so hard to justify,” said Ms. Grant. “Our dream is that we find this awesome family that wants to buy the house, but they are a little cash-strapped and have to rent it back to us in August.”
Tips for Keeping Grandma’s House in the Family
1. Make sure your descendants actually want the house. “It’s common sense: the heirs don’t always have the same values,” said Jonathan Miller, president of Miller Samuel Real Estate Appraisers and Consultants. He advises clients “to really survey their family and have a talk about it—the children should be an active part of the planning.”
2. To head off family feuds, spats over remodeling, prime holidays, or a push to sell, transfer ownership of the house to a limited liability company, with a user agreement that sets out terms and conditions. Or create a trust for the property with its own bylaws. That way, Grandma can make sure that everyone plays by her rules for the cottage long after she’s gone.
3. That roof is going to spring a leak sooner or later. Create a dedicated fund for maintenance, taxes and other costs, supported by annual contributions from family members. Note: If you break a lamp or a doorknob comes off in your hand, fix it yourself or prepare for frost at the Labor Day clambake.
4. Have an exit strategy. Any long-term plan should factor in the possibility that descendants may need to sell. Outline provisions for doing so. “Personal situations are going to change,” said Mr. Miller. “Many of these owners are between a rock and a hard place, trapped between nostalgia and hard economic reality.”
5. Remember: It’s just a house. “It’s really more about the family itself than the real estate,” Mr. Miller said. “Those Thanksgiving meals and family get-togethers were special because of the occupants of the house—not the house itself.”