ORLAND, Maine — Doug and Jeanne McLeod left their home in Winn early one recent morning and drove to Orland to open the family camp on Alamoosook Lake. The place had been shut up tight all winter. Doug hauled the short wooden dock out from under the porch and secured it at the water’s edge, waving away the black flies. Jeanne pulled some chairs out on the porch, checked the mousetraps in the kitchen and propped open the windows so the fresh spring breeze could blow through.

Later, they would hook up the plastic pipe that gravity-feeds water from a nearby pond to the kitchen sink, and move the kayak out onto the greening grass near the dock. Summer’s just around the corner.

The McLeods and their family have gone through the familiar rituals of opening up this little camp for decades. But this summer could be their last season at Alamoosook Lake. The beloved property is for sale.

“This camp located by the dam was built by our family in 1958 and we have maintained ownership until now,” reads the post on Craigslist. “Dad died leaving it to us 4 kids. Our kids have grown and some of us have moved far away, with the camp being underused.”

Jeanne McLeod, 70, said the decision to sell has been wrenching. But with her aging siblings scattered as far away as Florida and the next generation either not interested or unable to handle the financial obligations of owning the camp, she said, there really was no choice.

“The taxes, maintenance and insurance are high,” she said. “We’re the only ones who use it; the other three [siblings] pay and almost never get to use it. My son would love to keep it for his kids, but he can’t afford it.”

And so, reluctantly, the four siblings have agreed to find a buyer, hoping for a young family that will love the place as they have.

A cherished tradition challenged

All across Maine, from the wooded mountains on the western border to the open ledges of the islands off the coast, families love their seasonal homes. Large or small, elegant showplaces or rustic hideaways, these places are steeped in history and shared memories.

But, like the McLeods, many families find themselves facing difficult decisions about the future of these cherished vacation properties, many of which have been in the family for generations.

“It is in part a reflection of our changing society,” said Jerry Bley, a land use and environmental consultant in Readfield. “For one thing, the idea of going out to the island for the whole summer, the way families did back in the 1950s, is mostly a thing of the past. There are fewer families with that kind of seasonal lifestyle.”

These days, he said, it’s more common for busy family groups to rotate through the shared cottage for a week or two, depending on how much time the parents have off from work, children’s summer sports obligations, the vacation needs of family members and other factors.

In addition, families are more widespread geographically. Some members may want to subdivide the land and build a second cottage. Some have more money and more free time than others. Divorce, more common now than in generations past, further complicates things. The cost of maintaining the property is often a problem. And as the tribe expands, so does the possibility of friction between individuals and family groups, making the casual sharing of a summer home an exercise in frustration.

Despite these challenges, Bley said, the option of selling may be completely off the table. Instead, some landowners find ways to hand the vacation home over to the next generation in detailed legal arrangements aimed at keeping the property intact, ensuring its upkeep and minimizing family discord.

“Just because people have different objectives doesn’t mean they can’t come up with a solution,” he said.

Preserving family memories

“The draw of the summer camp experience is very strong,” said Mark Standen, a lawyer in Yarmouth who specializes in estate planning, property succession and family trusts. “People want to keep these properties in the family for as far as the eye can see.”

In estate planning, Standen said, “the cottage is not always the most financially valuable part of their legacy, but it is almost always the most emotionally valuable.”

There are many ways to plan for the management and inheritance of even a modest seasonal home, Standen said, including trusts and family business entities.

Larry and Marcia Sharp, in their early 70s, own a small cottage on a couple of acres on Cliff Island in Casco Bay. It’s part of an original parcel of about 4 acres purchased by Marcia’s parents after they honeymooned there in the 1930s.

“Our three kids grew up spending every summer on the island,” Larry Sharp said. The children, with a tribe of other youngsters, spent idyllic days fishing, swimming, building tree forts and exploring their island retreat.

“Who knows what kind of mischief they got into?” Sharp laughed. “It all made them very self-reliant.”

The family’s deep connection to the island led the elder Sharps to retire recently to Yarmouth from out of state, and so far two of their now-adult children have settled in Portland.

The Sharps are working with Standen to develop a limited liability company that eventually will allow their children to manage the family cottage as shareholders in a business. It’s a low-cost legal solution that can work well for smaller properties as well as larger ones, Standen said, ensuring shared decision-making and providing a mechanism for shareholders to adjust their degree of ownership without jeopardizing the stability of the business.

Standen said there are many ways to structure a succession plan for a seasonal property, and each family’s situation and solution is different.

“The devil is in the details,” he said, but a careful plan is key to a successful transition.

Forever protected — conservation easements

For Bley’s clients, the plan often includes placing a conservation easement on the property, a legal agreement that can permanently restrict subdivision, new construction, new roads, timber harvesting and other uses. Landowners donate or sell these development rights, typically working with a land trust, in exchange for tax benefits and the assurance that their beloved property will be forever managed in accordance with their vision. Even if the property eventually is sold, the provisions of the agreement remain in place.

Bley said many families find it difficult to reach agreement on the specific terms of a conservation easement. His job is to help them find common ground.

“People often come to me saying, ‘we can’t agree on anything,’ he said. “But that’s usually not true, it’s just old family dynamics getting stirred up.”

Land trusts focus on protecting properties with ecological, scenic or historic importance, according to Betsy Ham, director of land protection at the Maine Coast Heritage Trust. Families find many ways of working with land trusts, she said, and often realize significant financial benefits and peace of mind by selling or donating all or part of their property for conservation management.

“There are lots of land-rich and cash-poor individuals in Maine, including along the Maine coast,” Ham said. “Combined with other estate planning tools, receiving some income from conservation of the land can be a way to pass property down to the next generation while creating a source of income to maintain it and keep it in the family.”

The cycle of ownership

Ultimately, seasonal properties, large and small, go through a “cycle of ownership,” observed lawyer Mark Standen, and eventually pass into new hands.

“Families typically find ways to hold on to these places for three or four generations,” he said. “It gets more complicated with each generation, until some event triggers a sale and another family starts over in the same cycle.”

That thought is some comfort to Jeanne McLeod, contemplating what may well be her last summer at Alamoosook Lake. She was in eighth grade the year her father built the camp, and she recalls proudly helping him shingle the roof. She remembers water skiing behind her uncle’s boat, playing badminton with her cousins in the field up the road and wiffle ball with some kids from out-of-state whose family cottage was a little farther up the shore.

“In the evenings, we’d all get in the back of someone’s pickup truck and go up to Crosby’s” — a nearby takeout joint — “for a frosted root beer,” she reminisced. “Or we’d go to my uncle’s house; his sister played the accordion, and we’d all sing.”

She glanced around at the cottage.

“Now it needs a new roof,” she sighed. “It needs a lot of work; I understand that. But it’s brought us so much pleasure. We hate to sell it, but we’re all hoping someone will see what it is and enjoy it as much as we have.”

Meg Haskell

Meg Haskell is a curious second-career journalist with two grown sons, a background in health care and a penchant for new experiences. She lives in Stockton Springs. Email her at mhaskell@bangordailynews.com.