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

Situated in the vibrant heart of historic downtown Boothbay Harbor, this impressive urban property spans over 9,750 square feet across three dynamic levels. In excellent condition, it currently houses three seasonal tenants, including two retail spaces and a bustling restaurant, each contributing to the lively local scene. A standout feature is the private dock and float system, providing direct waterfront access and a unique connection to the harbor’s maritime charm. The third floor, ripe for redevelopment, offers endless potential to create additional value or tailor the space to new visions. This property seamlessly blends commercial opportunity with the rich character of Boothbay Harbor, making it an ideal setting for those seeking to immerse themselves in a thriving coastal community. Here, the rhythm of city life meets the serene beauty of the waterfront, offering a truly distinctive lifestyle.

Situated along the scenic mid-coast of Maine, this remarkable estate in the charming seacoast town of Belfast offers a rare blend of rustic allure and versatile functionality. Spanning 3.49 acres on bustling Route 1, the property boasts breathtaking views of Penobscot Bay, framed by a sprawling lawn perfect for hosting special events. The centerpiece is a welcoming Inn with six thoughtfully designed guest suites and a cozy two-bedroom apartment, complemented by a spacious commercial kitchen and a large porch ideal for potential dining ventures. Nearby, the updated Lodge features 13 rooms, a shared kitchen for extended stays, and a second-level veranda overlooking the water. Ample parking ensures convenience for guests, while the serene surroundings invite a lifestyle of tranquility and connection to nature, making this estate a true gem in Belfast’s coastal landscape.

Perched on an elevated expanse in the heart of Vermont’s breathtaking mountain landscape, The Vermont Inn offers a rare blend of historic charm and modern opportunity. Dating back to the 1840s, this farmhouse-turned-inn has welcomed guests since its conversion in 1940. Spanning 5.1 acres with an additional 2.5-acre wooded lot, the property boasts 16 uniquely decorated guest suites, a 50-seat restaurant with a commercial kitchen, and an adjoining pub. On-site living is effortless in the spacious 3-bedroom, 2-bath innkeeper’s apartment. Shared spaces invite relaxation, from the cozy lobby and sun porch to the seasonal pool, hot tub, fitness center, and sauna. Outdoor enthusiasts will appreciate the grill, fire pit, and potential for expansion—think event barns or private trails. Just ten minutes from Killington’s vibrant core, this iconic retreat is perfectly positioned to thrive amidst the area’s ongoing transformation.

Rising above the vibrant heart of downtown Wardsboro, the Wardsboro Country Store stands as a cherished local landmark along Scenic Route 100, one of Vermont’s most captivating and traveled byways. With breathtaking mountain views as its backdrop, this elevated gem serves as a vital hub for locals and travelers journeying to Stratton Mountain and Mount Snow Ski Resorts. Inside, it offers a delightful array of conveniences—gas, groceries, a deli, beer, wine, lottery, a full meat counter, and some of Southern Vermont’s finest sandwiches. Recent enhancements, including updated storefront, gas pumps, coolers, water tank, pump, and foundation, ensure modern reliability. Above the store, a spacious 3-bedroom, 3-bathroom living quarters awaits, perfect for owner occupancy or as a rental opportunity. An additional outbuilding provides versatile space for storage, expansion, or innovative business ventures, blending functionality with endless potential.

Set within the serene confines of a gated community in East Haddam, this fully renovated early-1900s Colonial estate marries historic elegance with modern convenience. A true equestrian haven, the property unfolds across a professionally landscaped corner lot, framed by lush fields, a tranquil pond, and classic stone walls. Inside, the home exudes warmth with hardwood and red slate flooring, a chef’s kitchen boasting high-end appliances, granite countertops, and custom cabinetry, alongside multiple living spaces adorned with plantation shutters. Four ensuite bedrooms offer comfort, including a first-floor primary suite with a handicap-accessible bath and a second-floor veranda retreat. For horse enthusiasts, a multi-section barn with six stalls, a tack room, turnouts, and frost-free hydrants awaits, complemented by three paddocks, a round pen, and a forthcoming outdoor riding arena. Privacy and pastoral beauty define this exceptional retreat.