Montgomery Real Estate

Welcome to Montgomery, Vermont – a hidden gem nestled in the heart of Franklin County. This charming town, surrounded by the breathtaking Green Mountains, offers a perfect blend of natural beauty and small-town charm. With its rich history, vibrant community, and stunning landscapes, Montgomery is an ideal destination for those seeking a peaceful retreat or a place to call home.

Montgomery boasts a quaint downtown area, where you can find local shops, cozy cafés, and friendly faces. The town's historic architecture reflects its storied past, adding character to the picturesque streets. Outdoor enthusiasts will revel in the abundance of recreational opportunities available, from hiking and biking in the summer to skiing and snowboarding in the winter at nearby Jay Peak Resort. The scenic beauty of the area is simply unmatched, with lush forests, sparkling rivers, and stunning mountain vistas providing a perfect backdrop for your outdoor adventures.

Community spirit thrives here, with numerous events and festivals throughout the year that bring residents together. From farmers' markets to seasonal celebrations, there’s always something happening in Montgomery. Families will appreciate the tight-knit community and the excellent local schools, making it a wonderful place to raise children.

Whether you're looking for a weekend getaway or a permanent residence, Montgomery offers a unique blend of tranquility and adventure. Discover the warmth and beauty of this enchanting Vermont town, where every day feels like a vacation in the great outdoors. Come explore Montgomery, and let it capture your heart!

Newest Listings in Montgomery

$275,000

2 Beds ⋅ 2 Baths ⋅ 5115052 MLS

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.

590 N Main St, Montgomery

$69,000

5110146 MLS

Fully wastewater permitted and ready for the next steps toward building, this 3.78-acre offering in Montgomery Heights combines two surveyed lots, 9 and 9A, in a wooded Vermont setting. With wastewater permitting, septic design work, survey, and related property documents already completed, much of the preliminary planning has been addressed. The approach is part of the setting: cross the river, wind gently uphill, and enter the peaceful loop of Montgomery Heights. Continue toward the top of Montgomery Heights, and just before the entrance to Ring Road, you’ll arrive at the property along a quiet private gravel road. From the road, the land rises gradually before beginning to level, creating possibilities for a future homesite among a mixed northern hardwood forest of birch, maple, and beech. Exposed quartz and areas of ledge add natural character, while seasonal mountain views provide another dimension to the landscape, with potential to thoughtfully enhance the views while retaining the property’s wooded setting. Montgomery Heights is an established private-road neighborhood, with nearby undeveloped land contributing to its tucked-away Vermont feel. With two surveyed lots, wastewater permitting already in place, varied terrain, mature hardwoods, and advance site planning completed, this property offers a strong starting point for bringing your plans to life.

Montgomery Heights Rd, Montgomery

$375,000

4 Beds ⋅ 3 Baths ⋅ 5109409 MLS

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.

919 Highland Dr, Montgomery

$300,000

4 Beds ⋅ 3 Baths ⋅ 5108545 MLS

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.

4166 N Main St, Montgomery

$425,000

3 Beds ⋅ 3 Baths ⋅ 5107420 MLS

Set on seven beautiful acres in Montgomery, this historic Vermont farmhouse offers an increasingly rare combination of character, natural beauty, privacy, and a life connected to the landscape and seasons. Inside, high ceilings, warm wood floors, two working fireplaces, and abundant natural light create inviting spaces with a wonderful sense of scale. Large, low-set windows bring the outdoors into nearly every room, framing views of the brook, ferns, mature maples, rhododendrons, gardens, and changing Vermont scenery. The garage opens directly into a spacious mudroom, with a full bath that also connects to the family room. Multiple living spaces offer flexibility, while upstairs are three bedrooms and a large, easily accessed attic providing exceptional storage. Step onto the screened back porch and listen to the brook and birds in the morning. The grounds feature mature apple trees, blackberry and raspberry bushes, lilacs, peonies, rhododendrons, and towering maples. Open lawn transitions to woods, with trails winding through the back acreage into the glades and along the rocky brook. Out the front door, morning sunshine invites walks along the beautiful gravel road with sweeping mountain views. Across the road, a deep, clear swimming hole offers a refreshing summer escape. The land opposite the property is not buildable, helping preserve the privacy and open setting. Jay Peak is a short drive away for skiing and year-round recreation, with forests and public lands offering endless opportunities to explore. Though wonderfully rural, Montgomery has a vibrant community with an art center, café, local events, and active village life.

3234 W Hill Rd, Montgomery

$265,000

3 Beds ⋅ 2 Baths ⋅ 5106676 MLS

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.

333 Main St, Montgomery

$700,000

4 Beds ⋅ 5 Baths ⋅ 5106645 MLS

Mountain views, complete privacy, and 20+ acres set the stage for this spacious Montgomery contemporary, offered furnished and just 20 minutes from Jay Peak Resort. Tucked among the trees with no neighboring homes in sight, the property offers a true Vermont retreat with room to explore the land on foot, skis, or snowshoes. Inside, the dramatic living room immediately captures your attention with three stories of windows, abundant natural light, and a floor-to-ceiling brick fireplace. The open main level flows into the dining area, where walls of glass bring the outdoors in and sliders open to the deck. The kitchen offers a gas cooktop, double wall ovens, butcher-block-topped island, and walk-in pantry, while a cozy study incorporates exposed brick for additional character. The main-level primary suite includes a large walk-in closet and private bath with dual sinks, glass-enclosed shower, and jetted tub. A half bath, laundry/mudroom, foyer, and attached garage complete this level. Upstairs are three additional bedrooms, a full bath, and a three-quarter bath, providing plenty of space for family and guests. The finished walkout lower level expands the living space with a game room, hobby room, and private sauna. Outside, lawns, woods, rock outcroppings, and expansive acreage create a wonderfully private setting against the backdrop of the surrounding mountains. Located just 4 miles from Montgomery Center and approximately 20 minutes from Jay Peak Resort, this is a four-season Vermont property equally suited for a primary residence or mountain getaway.

2145 Gibou Rd, Montgomery

$575,000

3 Beds ⋅ 2 Baths ⋅ 5098621 MLS

Tucked away on a quiet, private road just 25 minutes from Jay Peak Resort, this one-of-a-kind home may look like a classic Vermont Colonial, but don’t let its historic appearance fool you. **BUILT IN 2007**, it was thoughtfully designed to capture the character and craftsmanship of an older home while offering the benefits and comfort of newer construction. Set on 14± private acres, the property features open fields, mature woods, classic stone walls, and a beautiful brook winding through the land, creating a peaceful Vermont setting with abundant wildlife. Offering approximately 2,900 square feet of finished living space, the home includes 3 bedrooms, 2 bathrooms, and two spacious living rooms with plenty of room for family and guests. Throughout the home, gorgeous period-inspired details, antique architectural elements, warm woodwork, and unique finishes give it a character rarely found in newer construction. The gourmet kitchen features a professional 6-burner range, commercial dishwasher, and generous workspace, while the formal dining room showcases a stunning antique mahogany Empire table. Cozy gas stoves add warmth and ambiance throughout the home. Recent improvements include a new drilled well and an efficient HVAC system providing both heating and cooling for year-round comfort. High-speed internet makes working remotely or staying connected easy. Sold fully furnished, this property offers a truly turnkey opportunity for a full-time residence, Vermont getaway, or investment property. Enjoy campfires by the brook, explore your own trails, or spend the day skiing and golfing at nearby Jay Peak. A distinctive Vermont property combining privacy, acreage, historic character, and the advantages of a home built in 2007.

3818 W Hill Rd, Montgomery

$130,000

1 Beds ⋅ 5096566 MLS

Your Vermont getaway awaits! Tucked away on 10.5 private wooded acres in the sought-after Deep Gibou area of Montgomery, this unique retreat offers the perfect blend of seclusion, recreation, and rustic charm. Surrounded by nature and perched in one of Vermont's premier outdoor destinations, this property is ideal for those looking to escape the hustle and embrace a simpler way of life. Built in 1981, the cozy cabin features an open-concept kitchen and living area designed for gathering and relaxing after a day of adventure. Upstairs, the spacious sleeping loft provides room for family and friends, making it the perfect basecamp for weekend getaways or year-round enjoyment. Outside, you'll find everything needed to enjoy the great outdoors, including a storage shed for all your recreational gear, a fireplace for evening campfires under the stars The surrounding acreage offers complete privacy and endless opportunities to explore your own piece of Vermont wilderness. A short drive to from Jay Peak Resort and surrounded by an extensive network of hiking, ATV, snowmobile, hunting, and outdoor recreation trails, this property is a outdoor paradise. Whether you're seeking a hunting camp, recreational retreat, or simply a place to unplug and reconnect with nature.

801 Deep Gibou Rd, Montgomery

$389,900

5096173 MLS

The possibilities are endless with this historic 1885 property located in the heart of Montgomery Center! The main home features a charming 2-BR living space full of classic Vermont character and charm, making it perfect for an owner-occupied residence or vacation getaway. In addition to the main house the property also includes two, one bedroom 600 square feet accessory apartments and a 600 square foot Grandfathered commercial retail space right in the front, offering incredible income and investment potential. Located just minutes from Jay Peak Resort and surrounded by restaurants, shops, and year-round attractions, this property is perfectly situated for residential, rental, or mixed-use opportunities. Whether you are looking for a primary residence with income potential, employee housing, vacation rentals, or a unique investment property, this one deserves a serious look.

168 Main St, Montgomery

$389,900

4 Beds ⋅ 4 Baths ⋅ 5093902 MLS

168 Main St, Montgomery

$2,375,000

13 Beds ⋅ 15 Baths ⋅ 5093135 MLS

Escape the noise, traffic, and stress of metropolitan living and embrace the timeless Vermont innkeeper lifestyle with this exceptional hospitality property near Jay Peak Resort in the heart of the Northeast Kingdom. Surrounded by rolling mountains, fresh air, and four-season recreation, this unique property offers the rare opportunity to live and work in one of New England’s most scenic and sought-after destinations. Perfectly located near Jay Peak—renowned for some of the highest snowfall totals in the nation—this established inn attracts visitors year-round for skiing, snowboarding, hiking, mountain biking, golf, fall foliage, and destination travel. Whether you envision operating a boutique inn, farm-to-table restaurant, wedding venue, ski lodge, wellness retreat, or multi-use hospitality business, the possibilities here are truly endless. At the heart of the property is a welcoming restaurant and tavern space with seating for approximately 70 guests, creating an ideal setting for both travelers and locals alike. The fully equipped commercial kitchen and bar provide the infrastructure needed for a successful dining operation, special events business, or expanded hospitality concept. Cozy dining spaces, warm wood interiors, and classic Vermont character create an inviting atmosphere that guests remember and return to year after year. The inn offers comfortable guest accommodations, relaxing common areas, and the authentic charm today’s travelers seek when searching for a Vermont getaway experience. Guests can unwind after a day on the slopes beside a crackling fire, enjoy the peaceful mountain setting, and immerse themselves in the beauty of the Northeast Kingdom. This highly versatile property presents incredible opportunities for entrepreneurs seeking a lifestyle change, remote investors pursuing a hospitality venture, or anyone dreaming of trading city life for mountain living.

241 Main St, Montgomery

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Montgomery Real Estate

Newest Listings in Montgomery

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