5 Distinctive New England Waterfront Retreats and Coastal Penthouses

Commanding views from the top floor of Burlington’s historic Liberty House, this two-story penthouse pairs architectural heritage with modern comfort in a layout unlike any other in the building. Centered on the floor, the residence includes private interior access to the iconic cupola—reached by ladder from the second level—where 360-degree panoramas sweep across Burlington, Lake Champlain, the Green Mountains, and the Adirondacks. A thoughtful renovation keeps the spirit intact, with soaring ceilings, abundant natural light, and an open, inviting plan anchored by a spacious one-bedroom loft design. Upstairs, the primary bedroom suite includes a full bath. Outside, a private rooftop terrace frames westerly views and sunsets over the lake. Liberty House adds on-site laundry, a fitness center, private workspaces, pet wash stations, a dog park, secure access, elevator service, and well-lit off-street parking—just moments from downtown, the waterfront, and the Burlington Greenway.

Along the Route 302 corridor in the heart of Raymond’s Lakes Region, 1254 Roosevelt Trail offers a rare mix of everyday livability and business-forward flexibility. Set on approximately 0.60 acres, the property combines excellent visibility and accessibility with proximity to the area’s most celebrated outdoor destinations. Four established structures create a versatile footprint: a residence, two separate commercial spaces, and a Quonset hut—well-suited to mixed-use ambitions, a home-based business, or a seasonal retreat with room to grow. Minutes from Sebago Lake, Panther Pond, and Long Lake, the setting invites boating, hiking, and year-round recreation. A turnkey business package is available for separate purchase, including inventory, systems, branding, and social media, allowing operations to begin without the typical startup runway. Easy access to Windham, Naples, and greater Portland rounds out the day-to-day convenience.

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Along the water’s edge on Big Diamond Pond in Stewartstown, this year-round retreat pairs 200 feet of private waterfront with mountain views and crystal-clear water. Set on a private dead-end road near the New Hampshire Fish & Game boat launch, it’s positioned for a true four-season rhythm, with direct access to the Swift Diamond Riders snowmobile trail system and hundreds of miles of ATV trails right from your doorstep. Inside, an open-concept layout is tailored to both entertaining and everyday living, anchored by a large kitchen with a gas flame broiler. Expansive windows keep the pond and mountains in constant view, while a loft overlooks the living area for an airy sense of connection. The primary suite includes a private full bathroom, and an upstairs bedroom sits beside the loft and a 3/4 bathroom—ready for family and guests.

Rising above Belfast on Meetinghouse Hill, “The Little Stone Church on Meetinghouse Hill” offers a rare blend of local history and Old World charm. Once the site of the area’s first Little Stone Church, the building was thoughtfully rebuilt after a fire, preserving much of its historic character and architectural influence. Inside, the former sanctuary now lives as a dramatic great room, where original wood floors and soaring church windows bring a sense of volume and quiet grandeur. Abundant natural light moves through the space, highlighting detailed trimwork inspired by the original Dutch Reform craftsmanship and recreated by A.E. Sampson & Son of Warren. It’s a home shaped by its past, designed for everyday life, and best appreciated in the shifting light of the great room.

Along the water’s edge in a protected cove in Boothbay Harbor, these charming coastal cottages are designed for days that begin on the deck and end with sunset views over the harbor. Spacious waterside decks extend the living space outdoors, while private docks make it easy to slip into the rhythm of summer on the water. Lush seaside landscaping brings a sense of privacy and softness to the shoreline setting, framing the cottages as relaxed retreats rather than formal getaways. The Portside Cottage adds a rare touch: its own private beach. Thoughtfully renovated and offered fully furnished, each cottage is truly turnkey—arrive, unpack, and let the season unfold at an unhurried pace. Offered separately or together, they invite a waterfront life measured in tides, light, and long evenings outside.