Montgomery, VT | 590 North Main Street

Welcome to this charming and cozy 4-bedroom, 3-bath chalet in Alpine Haven, ideally located just 3 miles from Jay Peak. Set across three levels, this spacious getaway comfortably sleeps up to 16 guests, making it an exceptional opportunity for a vacation home, family retreat, or investment property. The chalet offers the perfect combination of mountain charm, comfort, and convenience. With four bedrooms, three bathrooms, and plenty of room for guests to spread out, it is designed for memorable weekends, holidays, and year-round enjoyment.

Tucked away on 49.30 private acres, this charming 3-bedroom, 1-bath home at 942 Deer Run Lane in Enosburg offers the perfect blend of seclusion, natural beauty, and comfort. With 1,476 square feet of living space, the home provides a warm and inviting atmosphere ideal for 3 Season living or a peaceful retreat. Step outside onto the expansive deck, perfectly positioned to take in the truly spectacular mountain views an ideal spot for morning coffee, evening sunsets, or simply soaking in the tranquility of your surroundings. The property’s generous acreage offers endless possibilities, from recreation and gardening to exploring your own slice of Vermont wilderness. As a bonus, the property has maple trees ready to be tapped. If you’re looking for privacy, scenic beauty, and a place to unwind, this hidden gem delivers a rare opportunity to enjoy country living at its finest.

Charming Farmhouse with Mountain Views & Income Potential This charming two-story farmhouse, originally built in 1880, sits on open land with beautiful mountain views from the rear deck. Conveniently located on a state maintained road, the property offers easy access while providing a peaceful country setting. The owners in 2009 made numerous improvements, including a corrugated metal roof, vinyl siding, new Hardie board decking on the porch, and vinyl thermo windows. The updated kitchen in 2008 features Hickory cabinetry, a center island, marble countertops, and a spacious dining area perfect for everyday living and entertaining. A seasonal porch was converted into a year-round space and is currently being used as a private office. Upstairs, you’ll find three bedrooms and a full bathroom. A wonderful additional feature is a two level apartment with open floor plan with kitchen, dining area, livingroom and full bath. The upstairs offers a large one bedroom. Access to apartment located at the rear of the home, with its own private entrance, and a large deck overlooking gorgeous mountain views. It's currently rented full-time, providing rental income, but could potentially be used as an Airbnb or guest suite in the future. The property also includes a spacious three bay garage, offering plenty of room for vehicles, recreational equipment, storage, or a workshop. Ideally situated approximately 12 miles from Jay Peak Ski and Golf Resort and just 15 minutes from the Canadian border, this property is an excellent opportunity for a primary residence, vacation home, or investment property with rental potential.

Set well off the road on over 14 acres, this 1992 contemporary home offers a peaceful setting, room to explore, and plenty of possibilities. Surrounded by nature, the property provides a sense of privacy while keeping outdoor recreation and local amenities within easy reach. Inside, soaring ceilings and abundant natural light create an open, airy feel, while the spacious layout offers flexibility to make the home your own. With two bedrooms and a bonus room, two bathrooms, and a finished walkout basement, there's room for a variety of uses. The lower level offers additional living space with potential for guest accommodations or rental use. Multiple heating options, including wood, propane, and electric, offer flexibility throughout the seasons. A wood stove in the living room provides additional source of warmth and atmosphere, while a newer metal roof adds to the home's practical features. Outside, the expansive acreage offers trails to explore and a stream winding through the natural surroundings. A large garage equipped with electricity and its own wood stove provides valuable space for vehicles, storage, hobbies, or projects. The home would benefit from updates and improvements, presenting an opportunity to add your own style and value over time. Enjoy convenient access to Montgomery Center, known for its strong sense of community, local shops, and small-town Vermont character. Jay Peak Resort and nearby biking trails offer year-round recreational opportunities, while Burlington is approximately an hour away and Montreal is about 90 minutes away. With over 14 acres to enjoy and a location that feels tucked away without being isolated, this property offers an appealing combination of space, natural beauty, and potential.

Set in the heart of Montgomery Center with Jay Peak within easy reach, this home offers a comfortable blend of classic Vermont character, practical updates, and an inviting village setting. Step onto the covered front porch and inside, where warm wood floors, natural light, and original details give the home plenty of personality. The first floor flows through a welcoming dining area and into the kitchen, featuring white cabinetry, stainless steel appliances, a gas range, subway tile backsplash, and a distinctive pressed-tin-style ceiling. Continue toward the back of the home to a bright living room overlooking the greenery outside. Large windows fill the space with natural light, while the exposed brick chimney adds warmth and character. Two full baths add everyday convenience. Upstairs, three bedrooms feature wood flooring and natural light. Outside, enjoy both a covered front porch and a back porch overlooking the backyard, with green space and mature trees creating a pleasant outdoor setting. One of the highlights is the walkable Montgomery Center location, with village amenities including a restaurant, grocery store, school, and nearby bike trails within easy reach. Jay Peak and the area's extensive four-season recreation are just a short drive away. With fiber-optic internet, municipal water, village convenience, and access to some of northern Vermont's best-known outdoor destinations, this home offers an appealing combination of character, location, and Vermont living.

Excellent investment opportunity in the heart of Montgomery Center, just minutes from Jay Peak Resort. This well maintained two unit property has been successfully operated as a vacation rental and offers outstanding income potential, a flexible investment opportunity, or the option to live in one unit while renting the other. Located on a quiet, paved street just behind Main Street, the property enjoys a peaceful setting with very little traffic while remaining within easy walking distance of restaurants, cafés, the local market, shops, Spa Vermont, the Vermont Salt Cave, and other village amenities. The upper unit is accessed through the right-side entrance and features an open concept living, dining, and kitchen area, one bedroom, plus a bonus sleeping area with bunk beds, creating additional space for guests. The lower unit offers a comfortable one bedroom layout with a cozy living room, making both units ideal for vacation rentals or long-term occupancy. Guests are drawn to the property's location, just minutes from year round recreation at Jay Peak including skiing, golf, mountain biking, hiking, and the indoor waterpark. The Trout River sits just across the street, where a small sitting area provides the perfect place to enjoy morning coffee or relax by the water after a day of exploring. Offering proven short-term rental appeal, walkable village amenities, year round recreation, and no HOA or condo association fees, this is a rare opportunity to own an income-producing property in one of Northern Vermont's most desirable four season destinations.

Historic Charm Meets Modern Vermont Living! This beautifully refreshed home offers the perfect blend of historic character, modern updates, and country charm. Originally dating to the 1880s, the home is believed to have been part of a historic train station in Sheldon before being moved to Berkshire more than 100 years ago. The home's exceptional original construction includes remarkably thick wood floors and a solid wood structure that has stood the test of time. Inside, you'll find new wood flooring throughout, freshly painted walls, and cozy bedrooms featuring warm walnut/light-wood accents. The updated kitchen and bathroom offer modern convenience while retaining the home's rustic personality, including original wood slabs in the kitchen that have been preserved and painted for a charming country feel. The property also offers excellent potential for additional space. The substantial concrete cellar could possibly be finished, while the enclosed front and rear porches provide opportunities for mudrooms, entry spaces, or additional seasonal living areas. A drilled well provides a reliable water supply, and the expanded driveway offers ample front and side parking. Outside, enjoy beautifully maintained perennial gardens, shrubs, and lawn, along with peaceful mountain views from the rear of the home. The property is bordered by farmland protected by the Vermont Land Trust, offering a beautiful rural backdrop and added privacy. Wildlife including deer, moose, bear, and other native species can often be seen in the area. Located just 15 minutes from Jay Peak Resort, this is an ideal four-season property for skiing, hiking, golfing, and year-round recreation. Conveniently situated along the route from Burlington and Montreal, this home is an excellent opportunity for a first-time buyer, those seeking a Vermont getaway, or an investor interested in a potential short-term rental. Historic character, solid construction, beautiful surroundings, and an unbeatable locat