Adorable little happy girls sledding in winter snowy day. Family vacation on Christmas eve outdoors

Residential Roundup: Winter “Wow” Homes

By Megan Montemarano

Although the weather can’t seem to recently make up its mind, it’s important to embrace the winter season, no matter what surprises it may bring. With a fresh snowfall comes fresh opportunities to head outside into the frigid yet invigorating air. This is especially true when a home caters to wintery weather, because let’s face it—a snow day is a stay-at-home day.

Sledding, ice fishing, skating, hockey, snowmobiling—you name it, these five outstanding residences have it.

Two friends explore the land of frozen trees, Lake Bled, Slovenia.

907 Norfolk Road—New Marlborough, Mass.

This restored, move-in-ready 52-acre estate in New Marlborough, Mass., encompasses an original farmhouse, guest house, additional building lot with mountain views, horse barn, orchards, hiking and riding trails, as well as a picturesque pond. That being said, in the colder months, this property is a winter wonderland, offering thrilling opportunities to skate on the beautiful pond, and perhaps go on a snowshoe or cross-country ski adventure across the estate’s sweeping grounds and hiking trails. “My kids and their friends had an ice skating party, bonfire and all, on the beautiful pond that is part of the property,” comments listing agent Marc Bachman. To top it off, the home is located within close proximity to Ski Butternut, a popular resort on Warner Mountain in the Berkshires.


Bachman’s kids playing ice hockey on the property, bonfire and all!

 For more information: Marc Bachman, 646.637.6304,

364 East Wakefield Blvd.—Winchester, Conn.

Lakefront living in Winchester, Conn., during the winter months means stunning views, and when it’s cold enough, a frozen playground. Yes, you heard it right. This expansive body of water right outside the back door of this award-winning, custom-designed home will most likely freeze over, and when it does, the possibilities for brave outdoor enthusiasts are endless. The current owners describe the Highland Lake scene as full of activity, from skating and hockey to snowmobiling, ice fishing and more.

Close-up of skates on player feet during ice hockey. Hockey player practising on a frozen pond outdoor. People playing amateur hockey. Winter playing, fun, snow.

For more information: Jennifer Roller, 860.459.0805,

36 Swifts Lane—Darien, Conn.

This exceptional Darien, Conn. home rests on nearly two acres of prime land with over 160 feet of direct frontage on Gorham’s Pond, a sacred waterfront retreat in town. Accessed by a private road, this secluded nature lover’s residence is ideal for pulling sleds, and of course, ice skating and playing hockey once the pond has frozen over. Although recently less common with New England’s unseasonably warm winter weather, skating outside surrounded by nature’s plentiful offerings is simply unbeatable.


Connecticut Post features article on Gorham’s Pond

For more information: Pam Roberts, 203.249.7646,; Mitch Roberts, 203.536.2202,

92 North Road—Chesterfield, Mass.

With 103 acres of land in Chesterfield, Mass., this stunning horse farm naturally has a wide variety of ways to enjoy outdoor winter activities. “In addition to incredible equestrian facilities, the property also has a pond that was ‘reconstructed’ for swimming in the summer and skating in the winter,” says George Cain, who represents this unique New England listing. “There are also some nice slopes on the farm’s 103 acres for sledding.”


For more information: George Cain, 917.861.3855,

85 Sugar Hill Road—Salisbury, Conn.

Known as Sugar Hill Farm, this over 110-acre property certainly lives up to its name. Surrounded by protected land with gently rolling hills, open pastures, light woodlands and 50-mile views to the east, south and west, this Litchfield County estate is made for a good old-fashioned sled ride. The 9,100 square-foot French manor house sits at one of the highest residential elevations in Connecticut. Its ideal sledding hill follows a private, winding drive down the property, overlooking beautiful scenery—just picture it with the snow! There is also a three-acre, spring-fed swimming pond on the grounds, which in the colder weather provides a chance for the ultimate private skating session.

boy sledding down a snowy hill on a blue inflatable sled

For more information: Ira Goldspiel, 917.626.3481,; Rick Distel, 646.417.2720,; Fred Bond, 917.209.2253,

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