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

$350,000

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

$459,000

3 Beds ⋅ 3 Baths ⋅ 5107420 MLS

Set on 7 acres in Montgomery, this classic Vermont farmhouse offers a special combination of character, space, privacy, and functionality. High ceilings, warm wood floors, abundant natural light, and two working fireplaces create inviting living spaces with a wonderful sense of scale while preserving the character that makes Vermont farmhouses so appealing. The garage provides direct entry into a spacious mudroom, an especially welcome feature through Vermont’s changing seasons. A full bath just off the mudroom also connects directly to the family room, creating an easy and practical flow. Multiple living and gathering spaces provide flexibility for everyday living and entertaining. The windows are a standout feature throughout the home. Set low to capture the surrounding landscape, they bring the outdoors into nearly every room, framing beautiful views of the brook, ferns, rhododendrons, mature maples, and changing Vermont scenery. Each season brings a different view right outside the windows. Upstairs, three bedrooms continue the comfortable layout. A large attic is easily accessed right off the foyer, providing an impressive amount of convenient storage. Outside, the screened in back porch offers a peaceful place to enjoy the sights and sounds of the property. Open lawn transitions to wooded acreage, mature maples frame the home, and a picturesque rocky brook winds through the landscape. Adding to the sense of privacy, the land across the road is not buildable, helping preserve the open setting. Close to Jay Peak and year round recreation, this Montgomery property brings together acreage, privacy, natural beauty, thoughtful updates, and the timeless character of a classic Vermont farmhouse.

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

$725,000

4 Beds ⋅ 5 Baths ⋅ 5106645 MLS

Tucked among the trees on 20+ private acres, this charming contemporary home offers a peaceful sanctuary surrounded by nature. Sold furnished, this home is ready to enjoy from day one. Designed with an open-concept layout, the main living space provides an inviting atmosphere for both family gatherings & entertaining. At the heart of the home, the kitchen comes equipped with a gas cooktop, double wall ovens, a center island featuring a butcher block countertop, and a walk-in pantry for even more storage. In the dining area, a wall of windows frames picturesque outdoor views, while sliding doors lead out to the deck, an ideal spot for enjoying your morning coffee or unwinding with an evening drink. The impressive living room features three stories of windows that flood the room with natural light. A cozy wood-burning fireplace with a floor-to-ceiling brick surround adds both warmth & elegant style. Just around the corner, a cozy study utilizes the exposed brickwork to create distinctive architectural character. Conveniently situated on the main level, the spacious primary suite serves as a quiet retreat, complete with a large walk-in closet & an en suite bath equipped with dual sinks, a glass-enclosed shower, and a jetted tub. The main floor also includes a half bath, a dedicated laundry/mudroom located off the attached garage, and a welcoming foyer with a large coat closet. On the top floor, you will find three comfortable bedrooms alongside a full bath & an additional three-quarter bath. The finished walk-out lower level adds versatile living space, featuring a game room, a dedicated hobby room, and a private sauna for ultimate relaxation. With complete privacy & no neighboring homes in sight, you can quietly unwind or explore your expansive acreage on foot, skis, or snowshoes. Located just 4 miles from Montgomery Center & a 20-minute drive from Jay Peak Resort. Come discover how this home welcomes every season with beauty & opportunities for adventure year round.

2145 Gibou Rd, Montgomery

$500,000

4 Beds ⋅ 2 Baths ⋅ 5106553 MLS

Privacy, character, and stunning mountain surroundings come together in this inviting log home on 50 acres with brook frontage, less than 20 minutes from Jay Peak. Built in 1991 and substantially updated in recent years, the 4-bedroom, 2-bath home offers more than 2,500 square feet of living space and the warmth and character you hope to find in a Vermont mountain retreat. Custom touches include old hand-hewn beams, wide softwood floors, a live-edge kitchen island, and an old barn-board pantry door. The kitchen and baths have been updated, along with new doors and windows, fresh paint, and numerous other improvements throughout. Tucked away on a private shared drive and completely out of sight from the road, the property offers exceptional privacy. Approximately 6 acres are open and beautifully maintained, while the balance is wooded with walking trails and frontage along a peaceful Vermont brook. The main level features an open kitchen with granite counters, dining and living areas filled with natural light, two bedrooms, a full bath, and laundry/mudroom. Upstairs, the spacious primary bedroom has a private balcony overlooking the field with views toward Jay Peak, plus a guest bedroom, sitting area, and 3/4 bath. Multiple Rinnai heaters and a woodstove keep things cozy, while Starlink provides high-speed internet. A large back deck overlooks the fields and long-range mountain views. From the natural wood and handcrafted details to the peaceful setting and brook, this is a property that truly feels like Vermont, a wonderful escape or an amazing place to call home. Enjoy nearby covered bridges, swimming holes, hiking, and year-round recreation at Jay Peak. Located in Montgomery, known for its scenic covered bridges, swimming holes, hiking, and easy access to year-round recreation, this is a wonderful Vermont retreat offering privacy and room to roam while remaining convenient to Jay Peak and village amenities.

3800 S Main St, Montgomery

$294,900

3 Beds ⋅ 2 Baths ⋅ 5106509 MLS

Overlooking Black Falls Brook with direct river access, this lovingly maintained Vermont farmhouse offers the perfect setting for a peaceful mountain retreat just outside the village of Montgomery. Located just a short drive to Jay Peak Resort with nearby access to VAST/VASA trail networks, this property puts year-round recreation right at your fingertips while providing a tranquil escape from the everyday. The inviting home offers 3 spacious bedrooms plus additional rooms ideal for a home office, guest space, or flex use. Two generously sized bedrooms and a full bath are conveniently located on the first floor, offering comfortable single-level living options. The spacious mudroom provides a practical entry point for coats, boots, and outdoor gear, while the well-appointed kitchen offers ample cabinetry and plenty of storage for everyday living and entertaining. Step outside onto the spacious deck to relax or entertain while enjoying the soothing sounds of the river below. The level yard provides plenty of room to spread out, garden, play, or simply unwind beside the brook. An attached garage offers convenient space for a vehicle or seasonal toys, with additional storage above for added versatility. A spacious detached garage provides ample room for vehicles, equipment, hobbies, or a dedicated workshop. A newer on-demand boiler, generator hookup, durable standing-seam metal roof, and weatherization updates ensure efficiency and added peace of mind for years to come. Tucked at the end of a paved, town-maintained road, this property offers privacy and serenity while remaining just minutes from local amenities and endless recreational opportunities. Whether you're seeking a year-round home, weekend getaway, or riverside basecamp for your Vermont adventures, this special property is ready to welcome you home. Come secure your own peaceful mountain retreat today!

218 Brook Rd, Montgomery

$229,000

1 Beds ⋅ 1 Baths ⋅ 5105878 MLS

Tucked into the woods on 1.2 acres just off Route 242, 111 Lower Ring Road offers exceptional privacy while being only about 10 minutes from Jay Peak Resort. Surrounded by mature forest and set well away from the road, this Vermont retreat has been lived in year-round and offers an inviting setting for enjoying northern Vermont in every season. Enter through the practical mudroom with space for boots, coats, and outdoor gear before stepping into the open-concept kitchen and living area. Warm wood details complement the kitchen's wood cabinetry, generous counter space, and movable island. A main-level bedroom and full bath create a comfortable, functional layout, while the loft above provides flexible additional space for an office, sleeping area, reading nook, or storage. Outside, the front deck is a natural spot to enjoy the wooded surroundings. Raised-bed gardens, open lawn, and a detached storage shed add to the property's versatility, while the surrounding trees create a wonderfully private setting. Equipped for year-round use with propane heat supplemented by electric baseboards, a drilled well, and on-site septic, this property combines a thoughtful layout, wooded privacy, and convenient access to Jay Peak and the four-season recreation of northern Vermont.

111 Lower Ring Rd, Montgomery

$259,000

2 Beds ⋅ 2 Baths ⋅ 5099614 MLS

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.

92 River St, Montgomery

$625,000

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 2007 built vintage styled Colonial offers the perfect blend of historic charm and modern comfort. Set on 14± private acres, the property features open fields, mature woods, classic stone walls, and a beautiful brook that winds 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, providing plenty of room for family and guests. The gourmet kitchen is equipped with a professional 6-burner range, commercial dishwasher, and generous workspace, while the formal dining room showcases a stunning antique mahogany Empire table and period details. Cozy gas stoves and antique architectural features throughout the home preserve its character, while thoughtful updates provide year-round comfort. Recent improvements include a new drilled well and an efficient HVAC system with heating and cooling, ensuring comfort in every season. High-speed internet makes it easy to work remotely or stay connected. Whether you're looking for a full-time residence, Vermont getaway, or investment opportunity, this property is being sold fully furnished, offering a truly turnkey experience. Enjoy campfires by the brook, exploring your own trails, or spending the day skiing and golfing at nearby Jay Peak. This is a rare opportunity to own a distinctive Vermont property where history, privacy, and nature come together.

3818 W Hill Rd, Montgomery

$395,000

1 Beds ⋅ 1 Baths ⋅ 5097443 MLS

Mountain Log Home on 36.9 Pristine Acres Nestled along a quiet country road, this stunning custom-built mountain log home offers complete privacy and tranquility. Situated on 36.9 pristine acres, including 1,700 feet of frontage on West Hill Brook, the property features a long private drive that ensures seclusion. Crafted from white cedar logs, this home boasts a warm and inviting atmosphere with a stone fireplace and vaulted ceilings. The open floor plan is complemented by beautiful pine floors and large windows that bring in natural light. The property offers a red spruce plantation, a popular deer yard, providing both beauty and wildlife viewing opportunities. Additional features include a standing seam steel roof, drilled well with a 30 GPM flow rate, underground electric service, a full concrete basement, and outdoor living spaces with a covered porch, rear deck with sliding doors and balcony off of bedroom, perfect for enjoying the peaceful surroundings. This exceptional property combines rustic charm with modern conveniences, offering a private retreat in a truly breathtaking setting. This is truly a turn key property, fully furnished from furniture to kitchen pots,pans and silverware. Just pack you bag and enjoy

3433 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

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