Bennington Homes under $350,000

Welcome to Bennington, Vermont, a charming town nestled in the picturesque Green Mountains, where history, nature, and community come together to create a truly unique living experience. Known for its rich heritage and vibrant arts scene, Bennington offers residents a blend of small-town warmth and cultural richness. With its stunning landscapes, including the iconic Bennington Battle Monument and the lush surroundings of the Green Mountain National Forest, outdoor enthusiasts will find endless opportunities for hiking, biking, and exploring the great outdoors.

For those looking to plant roots in this idyllic setting, Bennington boasts a variety of homes available for under $350,000. Whether you’re a first-time homebuyer, a growing family, or someone seeking a cozy retreat, you’ll find a diverse selection of properties that cater to all lifestyles. From charming historic homes with character to modern, energy-efficient builds, the real estate options are as varied as the stunning scenery that surrounds the town.

Living in Bennington means enjoying a strong sense of community, with local farmers' markets, art galleries, and seasonal festivals that celebrate the town’s heritage and creativity. With excellent schools, friendly neighbors, and a welcoming atmosphere, it’s no wonder that so many people are drawn to call Bennington home.

Explore the possibilities of homeownership in this enchanting town and discover why Bennington is not just a place to live, but a place to thrive. Your dream home awaits in this beautiful corner of Vermont!

Newest Bennington Homes under $350,000

$285,000

3 Beds ⋅ 2 Baths ⋅ 5113739 MLS

Welcome to this spacious three bedroom, two bathroom ranch in a highly desirable neighborhood, offering approximately 3,000 square feet of finished living space and plenty of room to grow. Conveniently located near local shopping and amenities, this home offers the space, location, and flexibility you’ve been looking for. Since purchasing the home, the owners have completed numerous improvements, including installing laminate flooring throughout the upstairs living areas, addressing foundation work, and making necessary plumbing improvements in the bathrooms. These updates, along with a newer boiler and a roof less than six years old, provide a solid foundation for the next owner. The home offers comfortable one-level living with a walkout lower level that provides tremendous flexibility for additional living space, a recreation area, home office, or potential in-law accommodations. With three bedrooms and two full baths, there is plenty of room for a growing family or extended family. Heating options are another great feature, with oil heat, a pellet stove, and a wood-burning fireplace offering three ways to keep the home comfortable. Outside, you’ll find an above-ground pool, a paved driveway, and a spacious two-car garage. If you’ve been looking for a large ranch in a desirable neighborhood with room for family, entertaining, hobbies, or even extended family living, this could be the one you’ve been waiting for. Schedule your showing today!

38 Center St, Bennington

$145,000

2 Beds ⋅ 2 Baths ⋅ 5112929 MLS

Enjoy the convenience and value of this two bedroom, 1.5 bathroom end-unit condo. Offering easy first-floor living, this home is a great option for first-time buyers, downsizers, or anyone looking for a comfortable, manageable place to call home. The practical layout includes two bedrooms, providing flexibility for guests, a home office, or additional living space. Discover the simplicity of condo living and the ease of having everything on one level. Ideally located just minutes from downtown shops and restaurants, while still within walking distance of peaceful hiking and nature trails. Whether you're looking to simplify your lifestyle or find an affordable path to homeownership, this is an opportunity worth exploring.

432 South St Unit B3, Bennington

$325,000

3 Beds ⋅ 2 Baths ⋅ 5112061 MLS

Have you bought your seasons pass to Crotched Mountain yet?! If you haven't you better! This sweet little property just around the corner from the ski area is going to make someone very happy. Live here or buy as an investment and enjoy steady income renting it out. This property has new flooring, and is freshly painted. It's a clean slate awaiting your finishing touches. Crotched Mountain Golf resort is a few miles down the road. Whole house generator will keep you up and running even in the worst storms! Cozy up next to the pellet stove and watch the snow fall after hitting the trails. Buyers and Buyers agents to do their own diligence. Property is approximately 250 ft onto a class 6 town road that is not town maintained. Be prepared to have a vehicle with decent ground clearance and 4 wheel drive in the winter months. Buyer will be responsible for road maintenance and winter plowing access. Sold as-is. Seller has not lived at the property so first hand information is limited.

208 Onset Rd, Bennington

$329,000

3 Beds ⋅ 2 Baths ⋅ 5111698 MLS

Charming Bennington home with classic character, hardwood floors, and a bright enclosed sun porch! This inviting property offers a comfortable blend of traditional charm and everyday functionality, with spacious living areas. The generous living room provides plenty of room for comfortable seating and entertaining, while the sun porch offers a wonderful additional space to enjoy the changing seasons, morning coffee, reading, or simply relaxing surrounded by natural light. The home offers a warm, practical layout with attractive wood flooring and ample windows throughout. Outside, the property sits above the street with stone retaining walls, creating a private and inviting setting. The attached garage provides convenient parking and storage, with additional driveway space. Located in Bennington, this home provides easy access to the area's shops, restaurants, services, schools, and outdoor recreation. Whether you're looking for a home with classic Vermont character, 110 Coulter St offers a great opportunity to make a property your own.

110 Coulter St, Bennington

$219,000

2 Beds ⋅ 1 Baths ⋅ 5111442 MLS

As the old saying goes... LOCATION, LOCATION, LOCATION! Situated on a large corner lot in the desirable village of North Bennington, this one level home is brimming with potential. There is plenty of space inside and several rooms that can be configured to fit your needs. The great room has a vaulted ceiling and a slider to an enclosed porch that overlooks a private backyard. The kitchen with island has brand new flooring. The spacious primary bedroom has a big closet and connects to a room that could be an office or study with a walk-in closet. A metal roof and vinyl siding are both a plus. The property itself extends right to the banks of Paran Creek with direct access to the water. It's the perfect spot for a picnic table as you listen to the soothing sounds of nature. Set just 0.6 miles from Lake Paran, this location puts swimming, kayaking, fishing, walking trails, and events right at your fingertips. The village itself is part of the appeal. Stroll to local shops, eateries, and community gathering places. Whether you're looking for an incredible investment or a wonderful place to call home, this property is truly a catch.

2 North St, Bennington

$249,500

3 Beds ⋅ 2 Baths ⋅ 5111369 MLS

Conveniently located in the heart of Bennington, this charming 3-bedroom, 2-bath Cape offers a wonderful combination of comfort, privacy, and walkability. Set along a newly paved road with sidewalks, you can leave the car at home and head downtown for a meal or enjoy some of Bennington’s favorite local events. Easy highway access is nearby, yet the home feels surprisingly tucked away with its spacious yard and privacy fencing. Inside, 1,271 square feet of finished living space offers a comfortable, open feel, with the living room flowing naturally into the dining and kitchen areas, perfect for everyday living and gathering with friends and family. The well-appointed kitchen features abundant wood cabinetry, a double sink, newer black appliances. Newly refinished hardwood floors add character throughout the main living areas. The generously sized main-floor primary bedroom features an ensuite full bath with wainscoting. while two additional bedrooms are upstairs. A second full bath off the living room includes full-size laundry, adding to the ease of main-floor living. Both baths have been updated with tile floors, pedestal sinks, and fiberglass tub/shower surrounds. Two additional bedrooms upstairs, one features a walk-in closet. Recent improvements include a hybrid heat-pump water heater and 200 AMP electrical panel, meaningful updates to the home’s major systems. Outside, the fully fenced side yard is a true highlight, with plenty of room for gardens, play, pets, entertaining, or simply enjoying your own private outdoor space, complete with apple tree. The large .41 acre lot includes more land between garage and stone wall to meet your expanding needs. The garage/barn accommodates one vehicle with additional storage or hobby space. Ample driveway parking allows for multiple cars. An inviting and affordable opportunity to put down roots, with room to enjoy both home and yard while keeping downtown Bennington close at hand.

230 Beech St, Bennington

$165,000

2 Beds ⋅ 1 Baths ⋅ 5111064 MLS

Affordable homeownership awaits at 128 Burgess Road in Bennington! This compact 2-bedroom, 1-bath home offers approximately 840 square feet of living space with a practical layout and low utility costs. Several recent exterior improvements include brand-new siding, new rear entry stairs and a new electrical meter board in Spring 2026. The home also features vinyl replacement windows, including one newly installed side window. The main level includes the kitchen, dining area, living room and first-floor laundry. Upstairs are two bedrooms with hardwood flooring and a full bathroom with tile flooring that includes a shower/tub combo with a tile surround. Outside, the manageable 0.08-acre lot includes a fully fenced yard that slopes gently and is easy to mow. Exterior basement access provides additional utility and storage space. The property is accessed via deeded right-of-way driveway and parking, tucked off the street for added privacy. Conveniently located near downtown Bennington, you can walk to parades, festivals, and restaurants. An attainable opportunity for an investor or owner-occupant who wants to add their own finishing touches.

128 Burgess Rd, Bennington

$315,000

3 Beds ⋅ 2 Baths ⋅ 5110700 MLS

There is something special about a home that has been truly loved, and you can feel it the moment you step inside. Exceptionally clean, beautifully cared for, and thoughtfully maintained, this inviting three-bedroom home is tucked into a peaceful little neighborhood with nearby walking trails and a stream that adds to the sense of calm and community. Inside, the home feels bright, comfortable, and easy to settle into. The spacious kitchen and dining area is meticulously kept and offers plenty of room for everyday meals, conversation, and gathering. The large front-to-back living room gives you even more space to stretch out, relax, or entertain, with sliding doors leading directly to the deck and bringing the outdoors in. A convenient half bath is located on the main level, while upstairs you’ll find three bedrooms and a full bath. Soft neutral paint throughout creates a fresh, welcoming feel and makes it easy to picture your own style here. A chair lift between floors is already in place, offering an added accessibility feature for those who may benefit from easier movement throughout the home. Outside, the same pride of ownership continues. The exterior is in great condition, a carport provides convenient covered parking, and the surrounding neighborhood offers a lovely setting for evening walks, quiet mornings, and time spent outdoors. This is not just a clean, well-kept house, it is a home that has been cared for with pride and ready for its next chapter. Some photos have been virtually staged to show you just how easy it would be to transform this into a fresh, modern home.

314 Chester Knoll Dr, Bennington

$165,000

2 Beds ⋅ 1 Baths ⋅ 5109415 MLS

Tired of renting? Discover the charm, convenience, and value of this adorable two-bedroom bungalow - an ideal opportunity for first-time buyers, downsizers, investors, or anyone looking for a cozy second home in town. Tucked away from the hustle and bustle, this historic home is just a short walk from downtown shopping, restaurants, transportation, and everyday conveniences. Inside, you'll find a move-in-ready space with a welcoming dining area just off the kitchen, a spacious primary bedroom, and warm natural light. Step outside and enjoy the covered wraparound porch - always a Vermont favorite. Off-street parking adds an extra layer of convenience. If you're looking to simplify, this charming little jewel is ready to welcome you home!

220 Gage St, Bennington

$240,000

3 Beds ⋅ 2 Baths ⋅ 5109090 MLS

Well maintained and updated 2011 double wide with 3 bedrooms and 2 full bathrooms situated on 1.33 acres in Bennington. Offering new flooring through most of the house and new appliances. Large living room, kitchen and laundry room. Primary bedroom has a private full bath. Nice property and great location.

2200 Chapel Rd, Bennington

$349,900

5106581 MLS

Side-by-side duplex in a sought-after area in the heart of Bennington, offering the charm of yesteryear with modern conveniences. This well-maintained property presents an excellent investment opportunity, whether you're looking for a rental property generating substantial income or the option to owner-occupy one unit while renting the other to help offset your mortgage. Boasting many tasteful renovations and updates in recent years, both units feature gorgeous refinished hardwood floors and a spacious, functional layout. Each unit offers a living room, dining room, kitchen, and half bath on the first floor. Upstairs, you'll find three bedrooms, an office space, and a full bath. Each unit has its own large, inviting front porch with peeks of mountain views, perfect for relaxing or enjoying time with family and friends. Private back decks overlook the spacious backyard, while a three-car garage provides additional parking and storage. A full basement is divided between the two units, providing separate storage and laundry areas, while a walk-up attic offers even more storage space. Each unit has its own electrical and heating systems, with utilities paid by the tenants. Additional features include forced hot air heating systems with new ductwork, town water and sewer, and a classic slate roof. Ideally located near Southwestern Vermont Medical Center, public transportation, scenic hiking trails, and Bennington's vibrant Main Street, with its shops, restaurants, and year-round community events. A wonderful opportunity to own an income-producing property in a convenient Bennington location while enjoying the character and charm of a classic Vermont home.

219-221 Washington Ave, Bennington

$165,000

2 Beds ⋅ 1 Baths ⋅ 5106352 MLS

Cute, cozy, and move-in ready! This freshly renovated 2-bedroom, 1-bath home has been updated from the ground up and offers comfortable, low-maintenance living in a convenient Bennington location. Recent improvements include a brand-new kitchen and bathroom, new flooring, fresh paint, new baseboards, new roof, front porch and expanded driveway. The home features electric baseboard heat along with a pellet stove for added warmth and comfort, plus washer and dryer hookups. Public water and sewer add to the convenience. Small and easy to maintain, this charming home is ideal for a first-time buyer, someone looking to downsize, or anyone searching for a turnkey property. Conveniently located close to shopping, dining, recreation, and all the amenities Bennington has to offer. Move right in and enjoy!

301 Beech St, Bennington

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