Montgomery Homes under $500,000

Welcome to Montgomery, Vermont—an enchanting small town nestled in the heart of Franklin County. Known for its stunning natural beauty and vibrant community spirit, Montgomery offers a unique blend of rural charm and modern amenities. With picturesque landscapes, rolling hills, and access to the pristine waters of the Missisquoi River, this town is a haven for outdoor enthusiasts and those seeking a tranquil lifestyle.

Montgomery is steeped in rich history, with its quaint downtown area showcasing beautiful historic buildings and inviting local shops. The community is known for its friendly atmosphere, making it an ideal place for families, retirees, and anyone looking to escape the hustle and bustle of city life. Whether you’re interested in hiking, skiing, or simply enjoying the breathtaking views, Montgomery has something for everyone.

For those considering a move to this idyllic town, you’ll be delighted to discover a variety of homes available for under $500,000. From charming single-family homes with character to modern constructions that cater to contemporary tastes, there’s a perfect fit for every lifestyle. These affordable options allow you to embrace the Vermont lifestyle without breaking the bank, making it easier to invest in your dream home.

Imagine waking up to the serene sounds of nature, with access to hiking trails and recreational activities right at your doorstep. Montgomery is not just a place to live; it’s a community where you can thrive. Come explore the possibilities and find your perfect home in this beautiful corner of Vermont!

Newest Montgomery Homes under $500,000

$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

$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

$425,000

3 Beds ⋅ 3 Baths ⋅ 5107420 MLS

*Open House - 9/20 from 12:00-2:00. All are welcome!* 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

$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

$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

$450,000

4 Beds ⋅ 3 Baths ⋅ 5088699 MLS

Tucked just off Route 242 on the way to Jay Peak Resort, this fully rebuilt Vermont farmhouse blends modern updates, flexible living space, and a peaceful riverside setting with over 244 feet of frontage along Hanna Clark Brook. Cross the steel bridge over the river and arrive at a home set above the brook with forest views, privacy, and easy access to year-round recreation at Jay Peak. Inside, the home has undergone a total interior rebuild with thoughtful updates throughout, including new siding, all new windows, new insulation, heat pumps providing both heating and air conditioning, and a garage expansion with cement flooring and a new garage door. High-speed internet availability also makes the property well suited for remote work or hybrid living. The kitchen is bright, functional, and designed for gathering, with generous workspace, counter seating, and an easy flow into the main living areas. Just off the living space, the front porch overlooks the brook and woods beyond. The first floor offers a spacious primary bedroom with walk-in closet and ensuite bathroom. Near the entryway, an additional room currently used as a bedroom could also work well as a guest room, office, or den. Upstairs, both bedrooms feature large closets with natural light windows, plus a full bathroom, oversized laundry room with storage and wash sink, and a spacious bonus living area ideal for a second living room, office, or reading space. Above, you’ll also find over 650 square feet of attic space with potential for future finished living space or studio space. Outside, mature landscaping, peaceful water views, and the sound of the brook create a classic Vermont setting. The large outdoor space offers excellent soil for gardening, recreation, or simply enjoying the outdoors. A move-in ready Vermont property with farmhouse character, extensive renovations, river frontage, and close proximity to Jay Peak is increasingly hard to find.

88 Cote Rd, Montgomery

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