5 Elegant Residences in Vermont and Maine and Connecticut Offering Privacy and Historic Charm

Tucked away in the serene University area, this Peytonwood retreat offers a rare blend of rural charm and waterfront allure on just under an acre of private land. Spanning over 4,000 square feet, the home welcomes you with a grand two-story foyer that flows into an expansive family area, complete with a fireplace for cozy evenings. The custom-designed kitchen, adorned with quartz counters and Z-line appliances, connects seamlessly to a dining space warmed by its own fireplace. A first-floor bedroom suite ensures comfort for guests, while upstairs, the luxurious primary suite features a designer bath and walk-in closet. Additional bedrooms, including a Jack-and-Jill en-suite and a separate au pair or in-law suite, provide flexibility. A third-level great room offers endless possibilities for recreation or work. Outside, a fenced yard beckons for outdoor living, with proximity to beaches, dining, and convenient transit options.

Situated in the vibrant core of historic downtown Boothbay Harbor, this impressive urban property spans over 9,750 square feet across three thoughtfully designed levels. In excellent condition, it currently houses three seasonal tenants, including two retail spaces and a charming restaurant, fostering a lively atmosphere. A unique highlight is the private dock and float system, seamlessly blending coastal access with city convenience. The third floor presents untapped potential for redevelopment, offering a blank canvas for creative visionaries to craft something extraordinary. This property not only provides a front-row seat to the bustling harbor life but also embodies the rich heritage of the area. Ideal for those seeking a dynamic lifestyle, it combines the energy of downtown living with the serene allure of waterfront proximity, creating a rare balance of work and leisure in an iconic setting.

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Rising above the rolling landscapes of Vermont, The Vermont Inn offers a rare blend of history and opportunity in the heart of the Killington Mountain area. This historic 1840s farmhouse, transformed into a charming inn since 1940, welcomes guests with 16 uniquely decorated suites and a 50-seat restaurant featuring a commercial kitchen. Outdoor patio seating, an adjoining pub, and an array of amenities—including a seasonal pool, hot tub, fitness center, steam sauna, and cozy lobby with a sun porch—create an inviting retreat. The spacious 3-bedroom, 2-bath innkeeper’s apartment ensures comfortable on-site living. Set on 5.1 acres with an additional 2.5-acre wooded lot, the property holds endless potential for expansion, whether for event spaces or private trails. Just minutes from Killington’s evolving ski hub, this inn promises a lifestyle steeped in tradition and growth.

Set amidst the tranquility of a rural landscape, this 1936 Colonial estate exudes timeless charm across its 3,700-plus square feet of thoughtfully maintained space. Positioned on a private, level 0.93-acre lot, the brick and cedar-sided home is surrounded by manicured grounds, featuring an inground heated Gunite pool and a bluestone patio ideal for relaxation or play. Inside, the entrance foyer with elegant archways opens to a south-facing living room, warmed by a fireplace and accented with moldings and recessed lighting. A quiet paneled family room, complete with built-in bookshelves and hardwood floors, offers a cozy retreat, while a glass-enclosed sunroom overlooks the serene patios. The expansive, remodeled kitchen boasts high-end appliances and flows into a bright breakfast area and open sitting space. Upstairs, four spacious bedrooms and three updated bathrooms await, with a partially finished basement adding extra versatility.

Set against the tranquil shores of Northwest Pond, The Shackteau emerges as a captivating French Country lakefront estate, offering 230 feet of private waterfront. This remarkable compound marries rustic European charm with modern sophistication, creating a serene family retreat once cherished as a boutique event venue. The main residence welcomes with an open floor plan, where a graceful gas fireplace anchors the seamless flow between living, dining, and a gourmet kitchen. Thoughtful details, including custom finishes, a spacious pantry, and a convenient first-floor laundry, elevate daily life. Two full baths, one ADA compliant with exterior access, cater to lakeside or garden pursuits. Embraced by the calm, non-motorized waters of Northwest Pond, this estate invites swimming, paddling, and quiet reflection, with kayak access to Lake Sherburne. The Shackteau stands as a timeless haven of peace and elegance.