5 Luxe New England Retreats from Coastal Maine to Connecticut

From its elevated setting in Biddeford Pool, this 4-bedroom, 4.5-bath residence captures the ease of coastal living with views and privacy. Classic craftsmanship meets refined seaside elegance, with a layout designed for effortless entertaining. Every bedroom includes an en-suite bath, and a first-floor suite adds everyday flexibility. Upstairs, the primary retreat reads like a true sanctuary, featuring dual walk-in closets, a sitting area, and a private deck where sunset moments become part of the routine. A hand-carved staircase sets a gracious tone, while the gourmet kitchen connects seamlessly to elegant living and dining spaces. The great room centers on a wood-burning hearth, and a three-season porch extends the home into the night air. Outside, an Italian-imported pizza oven invites lingering alfresco gatherings, supported year-round by a state-of-the-art geothermal system.

Along the shores of Lake Winnipesaukee in desirable Alton, 240 Black Point Road captures a rare, wide-angle perspective across the water toward Moose Island, Ship Island, Little Barndoor Island, and Barndoor Island, with peekaboo views of Wolfeboro. From its elevated setting, the day unfolds with both sunrise and sunset, and summer fireworks can be enjoyed right from the expansive deck. A contemporary five-bedroom main home is complemented by a separate cottage, offering a thoughtful setup for guests or extended family. Along the water-facing side, a wall of windows brings in natural light while keeping the lake present year-round. Comprising two lots, the property balances function and flexibility: 154 feet of frontage with three dock slips and a storage shed at the water’s edge, plus a level back lot of approximately half an acre with a substantial garage for boats and recreational storage.

From its elevated setting in Killington, this brand-new home sits on 0.88 acres in one of the area’s most sought-after locations, with arguably one of the best views in town. Inside, volume takes center stage: soaring ceilings reach 28 feet in the den, with 12-foot heights in the upstairs common areas and primary suite, and 10 feet in the basement. Anderson windows pull in abundant natural light, while a real masonry fireplace wrapped in native granite stone anchors the open living area. The chef’s kitchen is outfitted with GE Profile appliances, three ovens, a Blanco barn sink, and a septic-safe disposal. Moen matte finishes, custom woodwork, and ¾” knotty pine tongue-and-groove accents pair with Danaher-finished yellow pine floors and Chicago brick tile in each bath. Multi-zone HVAC, whole-house spray foam, a heated garage, ski room cubbies, generator readiness, and 3,000+ unfinished square feet complete the offering—minutes from the lifts and Killington’s access road.

Along the road from Highland Lake in Andover, this well-established wedding and event venue pairs seamlessly with a successful bed-and-breakfast on over six scenic acres. Rich with New England charm and character, the property is currently operated as a thriving inn and destination for celebrations, retreats, and special events. Ten guest suites each include a private en-suite bath, while a separate attached two-bedroom apartment offers flexible space for owner occupancy, staff housing, or additional accommodations. A detached two-story barn anchors the venue program, complemented by expansive grounds suited to outdoor ceremonies, tented receptions, and gatherings. Warm architectural details and spacious common areas create an inviting atmosphere, with the added appeal of future potential for condominium or additional residential development on the first lot, subject to local and state approvals. Life here can unfold as hospitality, home, or both.

Set on 80 rolling acres in historic Woodstock, Connecticut, this private aviation estate pairs contemporary architecture with rare, purpose-built infrastructure. At its center, a striking home is defined by soaring ceilings and a dramatic two-story fireplace, while a completely finished walk-out lower level opens to views of a pristine private pond. The property’s FAA-approved, commercial-grade airstrip—Toutant Airport (0CT8)—brings true fly-in capability, designed for pilots and collectors who value both access and seclusion. A massive, state-of-the-art aircraft hangar adds a dedicated, self-sufficient setup with its own private well, septic system, heat, and a fully finished luxury pilot lounge. With seven vehicle bays and an emphasis on privacy, the compound reads as a turnkey retreat where everyday life can move seamlessly between sky, land, and water.