Waterfront cottage, gingerbread house, other wintry retreat homes on the market

Blake Kerr remembers when his children, now aged 31 and 26, would sled down the slope of their home in Water Mill in the winter. Bundling up, marching around their wooded property, building snowmen: That's what Kerr remembers most this time of year.

Then the family would retreat back inside their cozy, shingle-style home.

"The house is very warm; it's like a big bear hug," Kerr said. "It's like you're inside an old, wooden ship. I fell in love with that."

Now, the house is on the market for $1.89 million, one among many wintertime retreats for sale on Long Island. Whether the houses feature snug gathering spaces, grand fireplaces, a gingerbread aesthetic or picturesque wintertime views, there's something seasonal about each of these six properties.

Cozy Sag Harbor cottage

A two-bedroom, one-bathroom cottage in Sag Harbor is on the market for $975,000. The annual property taxes are about $3,300, said listing agent Lori Barbaria, of Sotheby's International Realty.

Located on Wickatuck Drive, the house is close to Foster Memorial Beach, which residents can enjoy even during the colder months, Barbaria said.

"Everyone goes there year-round to sit in their cars and watch the sunset," she said. "It's magnificent."

The 800-square-foot cottage was built in 1959. It was first listed in September and has since dropped in price, Barbaria said.

"To get into Sag Harbor for under a million at this point is not easy," Barbaria said. "So this is a great starter house. They can live in it as is, they can double the size of it, they can add a pool. There's a lot they could do there."

The main living area features a wood-burning stove and pine floors, and is accentuated by wood beams across the ceilings and an old whaling spear, displayed overhead.

The cottage sits on a 0.17-acre lot. It is in the Sag Harbor Union Free School District.

"It's a nice winter escape," Barbaria said.

Wintertime gathering in Montauk

Standing tall on Farrington Road in Montauk is a five-bedroom, five-bathroom house, on the market for $2.55 million. The annual property taxes are $12,715.

The home sits on almost three-quarters of an acre, and is in the Montauk Union Free School District. It was first listed in November.

Coming to a total of 4,200 square feet, the house boasts three stories and two wraparound decks. From these vantage points, the homeowner can take in views of Fort Pond Bay, said listing agent Karen Hogan, of Town & Country Real Estate.

"When the house was first built years and years ago, the trees and whatnot had not grown, so you could see straight over," Hogan said. "Now that there's so much foliage, there's really not a straight view. But [during the winter] when there's nothing in your way, you have a seasonal view of Fort Pond Bay. And you always have a sunset."

The generously sized rooms could be ideal for holiday gathering, with multiple seating areas and a wood-burning fireplace to complete the picture.

"You can have 12 people at a dining room table, you can have a roaring fire going at the same time or you can have people sitting around the island," Hogan said. "It's definitely a family-inspired space."

A Sag Harbor winter chalet

A house that looks like it belongs on a mountaintop is for sale in Sag Harbor, listed at $3.15 million. The annual property taxes are $3,724.

The house was first listed for $3.485 million in October, before dropping in price. Located on Mount Misery Drive, the property is in the Sag Harbor Union Free School District.

With five bedrooms and six bathrooms, the exterior of this home is reminiscent of a winter chalet, said listing agent Traci Robinson, of The Corcoran Group.

"It's been painted a dark brown, and there are these cedar highlights of the railings," she said. "And there's an arched roof, so it sort of invites you in."

Each bedroom is en suite, allowing for plenty of privacy for potential guests, said Robinson.

"None of the bedrooms really back up into each other, since there are bathrooms in between each one," she added. "Everyone has their own private suite."

Highlights in the backyard include a patio, plunge pool, outdoor shower and fire pit. Part of the backyard greenery is made of AstroTurf, Robinson added.

"[The seller] brought in a lot of big boulders and stones, and that kind of creates an amphitheater, almost an arena, that keeps the backyard private," she said.

Inside, there is a gas fireplace and wood burning stove. The house totals about 4,200 square feet, on a 0.56-acre lot.

"Visually, it's very interesting," Robinson said. "That's why I call it mountain house, too. You're 10 minutes from the beach, but the outside of the house almost looks Adirondack-like, so it kind of melds the two."

Snowy views in Setauket

Complete with three fireplaces, this Colonial in Setauket is on the market for $3.84 million. Annual property taxes total $57,924.

Built in 2012, the house first hit the market in December 2023. It stands at 4,887 square feet on Van Brunt Manor Road. There are two gas fireplaces inside, and a wood-burning fireplace on the outdoor patio.

A showstopper of the property is the surrounding view of Port Jefferson Harbor and Long Island Sound, said listing agent Miriam Ainbinder, of Daniel Gale Sotheby's International Realty.

"The No. 1 thing is the vastness of the water," she said. "The view is almost 180 [degrees]. From every room, you see water."

There is a jetty and a staircase leading down to the beach, Ainbinder added. Inside, the house features an open-concept layout.

"There are transoms above all of the windows, so it's always bright, even when the sun's not shining," Ainbinder said. "It's very warm and cozy."

The house is in the Three Village Central School District.

Gingerbread house in Sea Cliff

Dubbed Hill View Cottage by the seller, this historic home in Sea Cliff is on the market for $1.1 million. The annual property taxes are $16,083.

The Victorian home was built in 1890, and is on the National Register of Historic Places, said listing agent Susan Castelli, of Daniel Gale Sotheby's International Realty. Visitors have remarked that the exterior resembles a dollhouse, Castelli said — but its frost-white trimming is also reminiscent of a cheery gingerbread house.

"It was originally built as a summer cottage," said Castelli. "And it sits up on the hill."

The house was listed in August and contains four bedrooms and three bathrooms, coming to a total of 2,054 square feet.

Located on Prospect Avenue, the Victorian contains several original features, including stained glass that can be found throughout the interior, Castelli said. Although the slate roof has been redone, its look adheres to the original period of the house, she added.

"The front fence is all handmade," said Castelli. "And it just has a beautiful, welcoming front porch."

Notable features include three levels of living space, radiant floor heating in the kitchen, a wood-burning fireplace, two-car detached garage and covered back porch. The property is served by the North Shore School District.

"The whole house has such a warm, welcoming, cozy vibe," Castelli said. "It's been a very happy house."

Water Mill cottage, enveloped in wildlife

Kerr's cottage on Scuttle Hole Road in Water Mill is on the market for $1.89 million, with annual property taxes of $3,933. Part of the lot is on wetlands, said listing agent Jane Gill, of Saunders & Associates.

Because of that, there are numerous birds on the premises throughout the year. Kerr has spotted great blue herons, turkeys and hummingbirds on the property.

"It reminds me of 'Where the Wild Things Are,' " said Kerr. "The house speaks for itself, and the location is great. It's nice to come home to birds chirping."

The property was listed in August. It features four bedrooms and three bathrooms, encompassing 1,512 square feet.

"This property is different because it's a wonderful, authentic cottage," said Gill. "It's an unusual house because today you really don't see that very often."

The house was built in 1987 and underwent several renovations in recent years, including the upper-level bathrooms (retiled two years ago), and the roof was upgraded in 2018.

The interior is reminiscent of a classic log cabin. "The kitchen cabinets are all cherrywood; the floor is wide plank pine; there are cedar beams on the ceiling; the walls are spruce," said Kerr. "It's a totally wood house."

The house is in the Southampton Union Free School District.

"It's got a coziness to it you don't see with a lot of properties on the market today," Gill said.

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.