5 Distinctive New England Retreats from Penthouse to Waterfront Cottages

In the heart of Burlington, atop the historic Liberty House, this two-story penthouse pairs architectural heritage with modern comfort—and includes private interior access to the building’s iconic cupola. Reached from the second level by ladder, the cupola delivers 360-degree panoramic views across Burlington, Lake Champlain, the Green Mountains, and the Adirondack Mountains. A thoughtful renovation complements an open, inviting floor plan with soaring ceilings, abundant natural light, and timeless character throughout. The spacious one-bedroom loft design places the primary bedroom suite and full bath on the upper level, creating a quiet retreat above the living spaces. Outside, a private rooftop terrace frames westerly views and sunsets over Lake Champlain and the Adirondacks. Liberty House adds an all-inclusive feel with on-site laundry, a fitness center, private workspaces, pet wash stations, a dog park, secure access, elevator service, and well-lit off-street parking.

Originally the site of the area’s first Little Stone Church, “The Little Stone Church on Meetinghouse Hill” brings Belfast’s local history into daily life with uncommon grace. After a fire, the building was thoughtfully rebuilt to preserve much of its historic character and architectural influence, resulting in a residence that still carries the spirit of its past. Inside, the former sanctuary becomes a dramatic great room, where original wood floors stretch beneath soaring church windows and abundant natural light. Detailed trimwork—recreated by A.E. Sampson & Son of Warren and inspired by original Dutch Reform craftsmanship—adds a quiet sense of artistry and continuity. It’s a setting that feels both contemplative and lived-in, inviting slow mornings, luminous afternoons, and evenings framed by the building’s enduring presence.

Along the water’s edge on Big Diamond Pond in Stewartstown, New Hampshire, 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 easy days on the pond and direct access to the North Country’s outdoor recreation—linking straight into the Swift Diamond Riders snowmobile trail system and hundreds of miles of ATV trails from your doorstep. Inside, an open-concept layout is designed for both entertaining and everyday living, anchored by a large kitchen with a gas flame broiler. A loft overlooks the living area, while expansive windows frame the pond and mountains beyond. The primary suite features a private full bathroom, and an upstairs bedroom sits beside the loft and a 3/4 bath for guests.

Set on the highly desirable Route 302 corridor in the heart of Raymond’s Lakes Region, 1254 Roosevelt Trail offers a rare mix of residential comfort and practical flexibility. Across approximately 0.60 acres, four well-established structures create a versatile footprint: a residence, two separate commercial spaces, and a Quonset hut. With excellent visibility and accessibility, the setting suits everything from a primary home or seasonal retreat to mixed-use and commercial possibilities, including the option of a turnkey business package available separately with inventory, systems, branding, and social media. Daily life here is shaped by the surrounding landscape and easy access to outdoor recreation—just minutes from Sebago Lake, Panther Pond, and Long Lake, with boating, hiking, and year-round activities close at hand. Windham, Naples, and the greater Portland area remain within easy reach for shopping, dining, and essential services.

Size: – sf

Along the water’s edge in Boothbay Harbor, these charming coastal cottages are tucked within a protected cove, where sunset views become part of the evening rhythm. Spacious waterside decks extend living outdoors, while private docks make it easy to slip into days on the water without leaving home. Lush seaside landscaping frames the setting with a soft, natural presence, enhancing the sense of retreat. Thoughtfully renovated and offered fully furnished, the cottages are presented as true turnkey escapes—ready for summers built around salt air, shared meals on the deck, and lingering light over the harbor. The Portside Cottage adds a private beach, offering a quiet stretch of shoreline for unhurried mornings and spontaneous dips. Offered separately or together, the experience feels effortless, seasonal, and deeply coastal.