I’ve always been saddened to hear about generational homes that finally reach the end of the line for one reason or another. I know homes at Chautauqua Institution have suffered that fate as times change and the difficult realities of keeping a summer place prove to be daunting. Sometimes it comes down to money, but there’s other reasons, too.

We’ve got stories like this that ended well in our county: the family that now owns Sheldon Hall has been a great caretaker of its history and aesthetic. The house is lucky that a new story is being told within its walls. Not all homes share the same fate.

The Lenhart Hotel is another property where the family came to the end of the line of interest in ownership. Things change. Kids move away and create new lives elsewhere. And selling a place, as we’ve seen, isn’t always a simple process. Won’t it be nice to see the front porch full of people at the hotel one day again?

I’ve been working on an article about a woman in New Hampshire who is facing the sale of her generational farmhouse, a beautiful legacy from an inspiring era of New England architecture. It has been beautifully maintained and continues to be a showstopper, despite the fact that her husband is now living in a care home. Her daughter is an ambitious woman working in technology, and the grandson is kind of clueless about the past. So, the older woman has been going it alone and has managed to keep the place afloat by selling off some of the acres. If you’ve watched Yellowstone, you know this is a story as old as the hills. The past and the future aren’t always friends. So, I’ve been interested in this topic–a topic about change, and the difference in values and culture from one generation to another and how it affects inheritance and life planning.

For generations, the Smith family called a sprawling farmhouse in upstate New York their home. Built in the late 1800s, the house was passed down through four generations, each adding their own touches while preserving the charm of the original structure. It was the site of countless Sunday dinners, weddings, and even funerals. But when the upkeep became too much and property taxes skyrocketed, the family had no choice but to sell. For Sarah Smith, a fourth-generation owner, the decision felt like losing a family member. “This house is where I learned to ride a bike, where my grandparents told stories by the fireplace,” she said. “Selling it felt like erasing a piece of who we are.”

The Smiths are far from alone. Across the country, generational homes are being sold at unprecedented rates. Rising costs of maintenance, the allure of urban living, and shifting family dynamics are just a few of the factors driving this trend. According to a 2023 study by the National Association of Realtors, 65% of Americans who sold a generational home cited financial pressures as their primary reason. Yet behind these statistics lie deeply personal stories of loss.

Sometimes, the decision to leave a generational home isn’t purely financial. Family dynamics often play a role. When the Johnson siblings inherited their parents’ mid-century home in Syracuse, they couldn’t agree on what to do with it. One sibling wanted to renovate and keep it, another wanted to sell, and a third wanted to rent it out as an income property. The disagreements led to years of tension and, ultimately, the decision to sell the home. “It was heartbreaking,” said Claire Johnson, the eldest sibling. “We lost the house, but we also lost a sense of unity as a family.”

The emotional weight of leaving a generational home can be especially heavy for those who feel a deep connection to their family’s history. In Charleston, South Carolina, the Robinson family owned a stunner of a home that had been in their family for over a century. The house, with its hand-carved woodwork and expansive front porch, was a tangible link to their ancestors. But as development encroached and property taxes became unmanageable, the Robinsons made the agonizing choice to sell. “We’re heartbroken,” said Mary Robinson. “This house was more than just a place to live; it was a testament to our resilience and heritage.”

So, what’s lost when a generational home is sold? Beyond the tangible, it’s the intangible–the sense of belonging, the shared memories, the continuity of tradition. In many ways, these homes are anchors, grounding us in a world that often feels untethered. When they’re gone, there’s a sense of drifting, a feeling that something irreplaceable has been lost.

In the end, old historic homes remind us of where we come from and who we are. I hope places like the Lenhart and the beautiful homes at Chautauqua Institution endure the test of time. These special places serve to anchor our communities. I know I’m sentimental: I’m still hoping we can go roller skating at Midway again one day.