Lines of boats sit quietly on Dering Harbor, barely a ripple on the water beneath them. A car rounds the bend of Cedar Avenue, unhurriedly. Meanwhile on North Ferry Road, stores are closed, and drivers slow down to wave at the few pedestrians nearby. 

This is Shelter Island during the offseason. Every year, a community known for its splashy summer fun and visitors who come and go by ferry slows to a calmer pace as the air starts to chill.

John Kaasik, 68, lives here year-round. He built his house in the '80s. It functioned as a bed-and-breakfast for a while, until the pandemic struck. Now, the eight-bedroom, five-bathroom structure houses himself, his wife and two of his four children, who moved back in after college.

"I'm just so attached to this place," said Kaasik, looking out toward the crunchy leaves on his lawn and the empty street below.

Full-time residents of Shelter Island, along with Montauk and Fire Island, relish the fall and winter for their peace and privacy. But real estate agents are tasked with marketing beach retreats when there's snow on the ground.

"During the summer months, we are selling something our clients can easily see and enjoy," said Mariah Ostler, a real estate agent with The Corcoran Group, based in Southampton. "During the winter or fall, we really have to paint that picture for them."

So when restaurants close, ferry schedules shift and snowbirds take flight, what's left for those who stick around?

Wintertime on Shelter Island

Kaasik grew up in Shelter Island, and now directs the musicals and plays for the school district there. He frequently takes the ferry to venture off the island. It runs every 10 to 20 minutes from 5 a.m. until midnight during the offseason.

"I like finding excuses to drive up to civilization," Kaasik said. "Riverhead would be the nearest civilization for us."

The few neighbors that he has are also here year-round, and some of the people he grew up with still live nearby.

"We just had a class reunion," Kaasik said. "We had 17 kids in our graduating class, and we had about 10 of us there."

In the wintertime, the school is the center of the action, he said — residents show up for basketball and volleyball games, along with the annual theatrical production.

There is a life adjustment when living in a beach town year-round. For instance, there aren't enough carpenters on Shelter Island, Kaasik said. There are volunteer ambulance and fire departments, but the closest hospital is in Greenport and requires ferry service,  he added.

There are no chain restaurants or fast-food establishmentsin on Shelter Island: "I would love a Dunkin' here, but the nearest one is in Southold," Kaasik said.

I like finding excuses to drive up to civilization. Riverhead would be the nearest civilization for us.

— John Kaasik, of Shelter Island

Originally from Costa Rica, Karen Springer moved to Shelter Island 13 years ago. She was drawn to the tight-knit nature of the community. As a real estate agent with The Corcoran Group, she often works with prospective buyers coming from Europe and Latin America.

"A lot of the agents here, they advertise that they grew up here, but I have a different perspective of the island," Springer said.

More people have discovered Shelter Island in recent years: "I think the island has changed, especially after COVID," said Springer. "More families have moved here from the city."

Brokers who work out east agree that their day-to-day tends to decelerate as soon as the weather gets cold. They face the question: How do you get a client excited to buy a beach house while they're donning heavy coats, maybe even with snow on the ground?

It gets dark very early and we don't have electricity in the roads; we don't have lights. A lot of people go away that time of the year, so it's very quiet.

— Karen Springer, The Corcoran Group agent

Selling houses is challenging from December through March, Springer said. She uses social media to promote the winter happenings of Shelter Island, like restaurants that offer events with hot cocoa for families during Christmastime.

"Right now, we are still trying to advertise winter rentals," Springer said. "We try to show the houses with a nice fire pit, all these cozy places."

Showing the houses in person is another story. "The weather of course gets very cold," she said. "And it gets dark very early and we don't have electricity in the roads; we don't have lights. A lot of people go away that time of the year, so it's very quiet."

A deserted East End

They call it "Tumbleweed Tuesday."

It's the day after Labor Day, where everything on the East End seems to change. This Tuesday annually marks the start of the offseason, locals say, when fair-weather friends leave town and beloved summer staples close for the foreseeable future.

"There are different year-round timelines, where things open and close," said Lewis Gross, owner of 668 The Gig Shack, a restaurant in Montauk. "We open The Gig Shack for the St. Patrick's Day parade, which is mid-March. A lot of things open then, but then there's sort of a lull for a while, until Memorial Day."

Gross, 71, recently retired from his dentistry practice in Manhattan and now mostly lives in Montauk (he also has a loft in Tribeca). He bought his four-bed, two-bath ranch three decades ago, for about $200,000. So far this year, homes in Montauk have closed for prices ranging from $1.45 million to $5.2 million.

"[Montauk] has a nice mix of both year-rounders and visitors, so there's always new energy coming in," he said. "I think we'd like to see it become more year-round, but it still hasn't quite attained the year-round business climate."

David Elze, 44, has lived in Montauk most of his life. He works at Hooked, a seafood restaurant in town. Due to affordability factors in Montauk, he recently listed his house. The three-bed, two-bath home is on the market for $950,000.

"It's kind of hard to keep up with the cost of living and rent and everything else," Elze said.

Living in Montauk during the offseason, "there are things you might not think about," he said: Public restrooms get locked, bus routes change and there are fewer trains to and from Manhattan. And mostly, Elze's neighbors are only around during the summer.

Communities like Sag Harbor, albeit nearby, differ from Montauk during the offseason, Gross said. "Sag Harbor has a bigger local infrastructure, and the businesses are more self-supportive," he said.

Lorraine Pharaoh Brandon is a Sag Harbor native and still resides there. As a Douglas Elliman broker, Brandon said there's an "ebb and flow" in her neighborhood during the offseason.

"The weekends tend to be more swelling in population," she said. "But then during the week, it quiets down again."

"During the winter, that's when you get your serious buyers, because they're not distracted with barbecues and the beach and whatever social commitments they have going on."

— Lorraine Pharaoh Brandon, Douglas Elliman broker

Credit: Douglas Elliman Real Estate

The bare trees of winter and fall can allow for better visibility of the property and nearby beaches, Brandon said, adding, "especially if the property sits high and you have a good proximity to the water, you'll be able to see it."

Cold weather brings in motivated clients — but there are still challenges.

"During the winter, that's when you get your serious buyers, because they're not distracted with barbecues and the beach and whatever social commitments they have going on," she said. "They're really focused on buying property."

Elze is looking at properties in upstate, hoping to buy some land and build a home there.

"It's unfortunate that people have to make that hard decision to move away, but there's definitely a very strong, local community," he said.

Frosty Fire Island

September and October are the best times to be out here because it's still warm, but all the crowds are gone.

— Lauren Chenault, of Ocean Beach

The change of season is particularly difficult for real estate agents working on Fire Island.

"There are no cars here, so when we're looking at houses, we're typically on foot, bike or golf cart," said Alyssa Caravella, of Fire Island Sales & Rentals. "So we always kid around that the people who come here in January when there's snow on the ground must really want a beach house."

The Fire Island ferry schedule also changes drastically this time of year. During the summer, anyone can catch a ride to Ocean Beach every hour, from 7 a.m. until 10:30 p.m. There are typically five round-trip ferries a day in the fall and winter months.

"There are no cars here, so when we're looking at houses, we're typically on foot, bike or golf cart."

— Alyssa Caravella, Fire Island Sales & Rentals agent

Credit: Fire Island Sales & Rentals/Julia Matuozzi

"If we have someone interested in seeing a property and we're setting up an appointment to see the house, everything is navigated around the ferry schedule," Caravella said.

As for selling properties, Caravella must make sure the homes are photographed before the owners leave for the season: "We have people who shrink wrap their furniture, bring their bikes inside, take all the comforters away," she said.

This time of year, many contractors are hard at work on Fire Island to prepare homes for the summer. "The minute they can pick their hammers back up the day after Labor Day, it's full speed until July Fourth of next year," Caravella added.

Lauren Chenault, 32, has been living with her husband and three children in Ocean Beach for nine years. Her three-bed, one-bath house has been in their family for generations, she said.

"This is what we call 'local summer,' " Chenault said. "September and October are the best times to be out here because it's still warm, but all the crowds are gone."

Chenault and her family have their usual spots: CJ's and Dockside, two eateries that stay open year-round. The family also has their own boat and a driving permit, for residents only, so they can come and go without relying on the ferry, she said.

"It's quiet," Chenault said. "And we are so far from the other side, and everything that's going on," she added with a laugh.

Fire Island fifth and sixth graders can take part in the Environmental Education program with Bay Shore students, Chenault added, where they go to the bay and learn about nature together. Her children are ages 9, 7 and 4.

There are 35 students total in the Fire Island School District this year, which includes pre-K to sixth grade, Chenault said.

"Our kids will go do stuff with Bay Shore kids because when they go to middle school and high school, they can choose either Bay Shore or Islip," she said. "So we try to get the fifth and sixth graders integrated with those kids just so they can see how middle school works, and make some new friends."

Selling summer — in the winter

Jennifer Wisner, a real estate agent for The Corcoran Group in Southampton, said there are specific words she includes in her listings around this time of year in hopes of shifting away from that chilly mindset.

" 'Retreat' is a big word," she said. "Or 'investment.' Investment is a great word because people like to put these homes up as summer rentals."

But once the client is in the door, it can be hard for them to envision what their summer retreat will look like without the lush greenery or open pool in the backyard. Wisner displays photos showing the property during the summer months around the home or on a bulletin board for prospective buyers.

"And you can walk around the property and let them know what will be blooming," she added.

"The winter is very slow, and is more about connecting with people."

— Mariana Nunes, Compass real estate agent

Credit: Kelli Hull

Mariana Nunes is a real estate agent with Compass, based in Westhampton Beach. She lives and sells properties in Remsenburg, along with Southampton. The area is "a little bubble," she said: Spring is busy, there's downtime midsummer and then the fall brings another rush of potential buyers.

"In the fall, people have left their summer homes and they now want to look for their full-time home to buy, because they don't want to rent anymore like they did last season, or they're getting ready to say goodbye to the Hamptons and putting it on the market for next year," Nunes said.

Because we live here, we're able to really show [potential buyers] the way and let them know, this is what you have to look forward to, even though it's not here right now.

— Mariah Ostler, The Corcoran Group agent

Remsenburg is a sleepy town in any season, Nunes said, and the population is split down the middle between year-rounders and visitors. Still, the area experiences an offseason slowdown. "The winter is very slow, and is more about connecting with people," Nunes said.

Ostler lives in the Eastport area with her family, and sells homes from Hampton Bays to Bridgehampton and beyond. While working with clients in the winter, she'll show them menus of restaurants that have closed for the season, or videos capturing the view from the beach. But she can no longer walk potential buyers down to the beach or to her favorite spots that have temporarily closed.

Ostler, 33, was born and raised in the area, and after going away to college, "I couldn't come back soon enough," she said. Now, she's raising her three children, ages 13, 10 and 8, there.

Despite the reserved winters out east, it's worth getting through it for the sunny days ahead, Ostler said.

"Because we live here, we're able to really show [potential buyers] the way," she said, "and let them know, this is what you have to look forward to, even though it's not here right now."

By Rachel Weiss

rachel.weiss@newsday.com@RachMWeiss

Rachel Weiss joined Newsday in 2016. As a real estate/living multimedia reporter, Rachel writes feature stories and contributes to and appears in on-camera video packages. She was the lead reporter on Newsday’s LI Acts of Kindness series.