5 New England Retreats from Ski-In Luxury to Lakeside Acreage

From its elevated setting in Newry, this reimagined Maine retreat pairs cabin character with a quietly polished sense of comfort. Privately set on a serene, wooded lot just minutes from Sunday River, it’s designed to move easily between lively weekends and slower, off-duty days. Four bedrooms include two elegant en suites, while a light-filled great room brings natural warmth to everyday living and entertaining alike. A secondary living area and a main-level screened porch offer inviting places to read, gather, or simply exhale. Downstairs, the lower level becomes its own getaway, with a game room, bar, media lounge, and additional accommodations—ideal for hosting with ease. Outside, an expansive deck looks out to the tranquil setting, where a hot tub and fire pit set the tone for après-ski evenings, even after a stop at The Matterhorn Ski Bar.

Set on a very rare holding within the Carry Pond Association, this 60-acre stretch of prime woodland pairs seclusion with a true water-and-woods lifestyle. The land offers over 2,800 feet of frontage on pristine East Carry Pond—an inviting place to launch a canoe and cast a dry fly to rising native Maine brook trout. Beyond your own shoreline, the gated association expands the experience with access to West Carry Pond, Middle Carry Pond, and Little Otter Pond, each noted for fine brook trout fishing. Miles of ATV and snowmobile trails weave through a broader network of thousands of acres of pristine Maine woodland, along with private access to multiple blue ribbon trout ponds and miles of trout streams. Located in Maine Wildlife Management District 8, it’s also well known for big game, predator hunting, and upland birds—an outdoorsman’s setting in every season.

Originally built in 1936 and meticulously maintained, this brick-and-cedar-sided Colonial is set on a private, level, landscaped .93-acre lot in North Haven. Outdoor living centers on an inground heated Gunite pool framed by a bluestone patio, with plenty of room for play and quiet afternoons alike. Inside, an entrance foyer with graceful archways opens to a south-facing living room with fireplace, moldings, and recessed lighting. Tucked into a quieter wing, a paneled family room or library pairs random-width hardwood floors with a second fireplace, built-ins, and bookshelves. A new French door leads to a heated sunroom wrapped in walls of glass overlooking the patios and grounds. Entertaining flows easily from the generous dining room to the expanded, remodeled kitchen with Sub-Zero, Wolf cooktop, and double ovens, plus an east-facing breakfast area and open sitting/TV space. Four second-floor bedrooms, three remodeled full baths, and a partially finished basement round out daily life.

Originally built c.1825, this Greek Revival residence in Milford pairs timeless character with a thoughtfully restored presentation, all just steps from downtown’s shops and the iconic Suspension Bridge. Within its generous living space, an Accessory Dwelling Unit creates a flexible layer of privacy and possibility—well-suited to extended family living, a dedicated work-from-home setup, or potential rental income. The layout supports an easy rhythm of daily life, with room to spread out while still feeling connected to the energy of town. Set close to the center of Milford, weekends can begin with a walk into downtown and end back at home with the comfort of a restored historic setting. It’s a place designed for living today while keeping a clear line to its early-19th-century roots.

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Steps from Sugarloaf’s trail network in Carrabassett Valley, this fully furnished condo is designed for days that begin on the slopes and end around the table. Ski-home access via the Little Stubs Trail behind the condo pairs naturally with a light-filled, open floor plan and vaulted ceilings anchored by a wood-burning stone fireplace insert. The upgraded kitchen brings high-end appliances, refreshed cabinets, and new countertops into the heart of the main level, while two living areas create welcome flexibility—one for big, cozy dinners, another for a kids’ hangout zone. Downstairs, a generous extra living room is warmed by a gas stove, opening to a large lower deck with a hot tub. A winter shuttle stop sits at the end of the road, with the base lodge, restaurants, and bars under a 10-minute walk.