Bennington Homes for Sale

Welcome to Bennington, Vermont, a picturesque town nestled in the heart of the Green Mountain State. Known for its rich history, vibrant arts scene, and stunning natural beauty, Bennington offers a unique blend of small-town charm and modern conveniences. With a population of just over 15,000 residents, this friendly community is the perfect place to call home.

Bennington is steeped in history, boasting landmarks such as the Bennington Battle Monument, which commemorates a pivotal battle in the American Revolution. The town is also home to the Bennington Museum, where you can explore the region's artistic heritage and the works of renowned local artists. Outdoor enthusiasts will find plenty to love, from the scenic hiking trails of the Green Mountains to the tranquil waters of Lake Paran, perfect for kayaking and fishing.

When it comes to finding your dream home, Bennington offers a diverse array of properties for sale. Whether you’re seeking a charming historic home with character, a modern family residence, or a cozy cottage surrounded by nature, there’s something for everyone in this delightful town. With a mix of affordable options and stunning luxury homes, you’ll find the perfect fit for your lifestyle and budget.

Living in Bennington means enjoying a close-knit community, excellent schools, and a variety of local shops and restaurants that showcase the best of Vermont’s culinary scene. Experience the warmth and charm of Bennington—where your dream home awaits! Explore our listings today and take the first step toward making this enchanting town your new home.

Newest Bennington Homes for Sale

$365,000

3 Beds ⋅ 2 Baths ⋅ 5101687 MLS

Located in the heart of the charming North Bennington Village, this beautifully renovated home offers the perfect blend of classic character and modern convenience. Completely renovated interior in 2022, including a new roof, this move-in-ready home features three bedrooms and two beautifully updated bathrooms, with the added convenience of a first-floor bedroom and main-level laundry. The spacious kitchen is designed for both everyday living and entertaining, featuring a gas range, pantry, and ample cabinetry. The flexible living and dining area is highlighted by a cozy fireplace, while gleaming hardwood floors run throughout the home. An enclosed front porch serves as the perfect mudroom or welcoming entry, and the bright living room is filled with natural light. Upstairs, you'll find two additional bedrooms and a beautifully tiled bathroom with a walk-in shower. The home's extensive 2022 renovation included a new roof, furnace, electrical, plumbing, and insulation, along with updated finishes throughout, providing the comfort and peace of mind of a nearly new home. Outside, enjoy a partially fenced yard, ideal for gardening, pets, or outdoor gatherings, along with a detached one-car garage. Located within walking distance of North Bennington Village's shops, restaurants, parks, and local amenities, this thoughtfully renovated home is truly move-in ready.

12 Hall St, Bennington

$142,900

2 Beds ⋅ 1 Baths ⋅ 5101539 MLS

Very well kept single-wide mobile home on it's own land. Cozy 2 bedroom, 1 bathroom home with single level living. Living room, kitchen with dining area, main level laundry and more. Has 2 enclosed porches. The smaller one is used as a pantry and the larger one is heated. Outside 2 sheds and the sounds of the nearby babbling brook. Also has RV electric hook up.

60 Tori Ln, Bennington

$232,500

3 Beds ⋅ 2 Baths ⋅ 5101468 MLS

You can make this home your own! With a little TLC, this charming 3 bedroom, 2 bath, Cape has the potential to become the perfect home. Featuring a large, level yard, a two-car, detached garage, with attached outdoor room, mudroom to the kitchen, wood floors, fireplace (condition unknown) and with this central location, it offers endless possibilities. Whether you are looking to renovate, personalize, or invest, this is a fantastic opportunity to create your vision. Close to downtown, schools, skiing, shopping and a short ride to Albany NY and Williamstown, MA. Next to most everything you will need.

903 Gage St, Bennington

$260,000

4 Beds ⋅ 2 Baths ⋅ 5101031 MLS

Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to downtown restaurants, theater, and parks, the location is exceptionally convenient while still feeling like a true residential neighborhood. Inside, generous rooms, abundant natural light, hardwood floors, wide moldings, and original architectural details give the home warmth and personality. The spacious living room offers flexibility for gathering, relaxing, or creating multiple seating areas, while the adjoining dining room provides an inviting setting for everyday meals and entertaining. The bright kitchen features abundant wood cabinetry, generous counter space, a farmhouse-style sink, gas range, and direct access to the rear deck. Upstairs are four bedrooms and a full bath, offering ample flexibility for household needs, guests, a home office, or creative space. The primary bedroom includes two closets, and each bedroom has a ceiling fan and overhead light. The full basement houses the laundry and utilities, provides useful storage, and includes an additional toilet. There's a hot air furnace, Rinnai water heater, 100-amp panel, and town water/sewer. Outside, the rear deck overlooks the lawn, established garden beds, and a partially fenced area. A detached one-car garage adds convenient parking, storage, or workshop potential. The home is comfortable and offers a strong foundation. Exterior painting and porch restoration will be up to the next owner, creating an opportunity to refresh the property, make it their own, and build equity over time. With its gracious proportions, original charm, outdoor space, and exceptional location, 301 Elm St is ready for its next chapter.

301 Elm St, Bennington

$335,000

3 Beds ⋅ 2 Baths ⋅ 5101006 MLS

Welcome home to this meticulously maintained 3 bedroom, 1.5 bath ranch, perfectly nestled in a highly desirable neighborhood. Offering over 1,400 square feet of single level living space, this home combines classic charm, everyday comfort, and an unbeatable location. Rich hardwood floors flow throughout most of the home creating a warm and inviting atmosphere from the moment you step inside. The spacious layout offers comfortable living areas filled with natural light, generous-sized bedrooms, and a floor plan designed for effortless everyday living and easy entertaining. A charming breezeway connects the home to the attached one-car garage, providing a practical transition space that's perfect in every season while adding timeless New England character. Outside, the yard offers room to garden, play, or simply relax and enjoy the peaceful surroundings. Location is everything, and this home delivers. Tucked into an established neighborhood known for its welcoming feel, you'll be just minutes from downtown, where you can enjoy local shops, restaurants, community events, and everyday conveniences. Nearby walking trails offer the perfect setting for morning jogs, leisurely evening strolls, or weekends spent enjoying the outdoors. Whether you're buying your first home, looking to simplify with one-level living, or searching for a property in a neighborhood you'll love for years to come, this home offers the perfect blend of comfort, convenience, and lasting appeal. Don't miss your opportunity to make this exceptional ranch your own!

308 Crescent Blvd, Bennington

$275,000

3 Beds ⋅ 2 Baths ⋅ 5100537 MLS

Tucked into a private wooded setting on the outskirts of town, this distinctive 3-bedroom, 1.5-bath Adirondack-inspired chalet blends rustic character, flexible living space, and an exceptional connection to the outdoors. Its steep roofline, front balcony, exposed beams, and metal roof give the home memorable architectural presence, while the peaceful surroundings create a true retreat from the everyday. Inside, hardwood floors and dark ceiling beams add warmth and character to the main living and dining area, where a propane stove set against a brick hearth creates a cozy focal point. Brand-new windows throughout bring in abundant natural light, complemented by new French doors that open directly to the deck. The efficient kitchen offers generous cabinetry and slate-finish appliances, all included. An adjacent unfinished mudroom provides an opportunity to create a convenient entry and additional storage. A main-level bedroom and full bath offer the flexibility of one-floor living, comfortable guest accommodations, or work-from-home space. Upstairs, two bedrooms feature dramatic cathedral ceilings and exposed beams. One opens to a private covered balcony overlooking the yard and woods... an inviting place to enjoy morning coffee, read, or simply take in the quiet surroundings. A half bath completes the upper level. The basement adds valuable versatility with a laundry room, finished bonus room, workshop, and utility room. The detached 1-car garage provides even more space for a vehicle, tools, equipment, or recreational gear. Outside, there is plenty of room to enjoy every season, including a spacious deck, fire pit, private backyard, multiple woodland trails, and a charming screened outbuilding for bug-free relaxation, dining, or summer gatherings. Full of personality and surrounded by nature, this wonderfully distinctive Vermont home offers space to live, work, gather, and unwind.

2867 Chapel Rd, Bennington

$595,000

3 Beds ⋅ 2 Baths ⋅ 5099405 MLS

Nestled on 16.96 picturesque acres, this spacious 3-4 bedroom, 2 full bath home offers the perfect blend of privacy, comfort, and breathtaking Vermont scenery. Built in 1993, the home features a bright, open-concept great room with expansive windows that capture stunning views of the surrounding landscape. The inviting living area is anchored by a beautiful fireplace, creating a warm and welcoming space for relaxing or entertaining. The flexible floor plan provides three bedrooms plus an additional room that can easily serve as a fourth bedroom, home office, or hobby space. The walkout unfinished basement offers endless possibilities for future expansion, storage, or a workshop. Outside, you'll find an attached two-car garage along with a separate bonus garage, providing ample space for vehicles, recreational equipment, or additional storage. Set well back from the road, the property's 16.96 acres offer room to explore, garden, or simply enjoy the peace and beauty of Vermont. The home is serviced by a private well and efficient oil heat source, making it a wonderful opportunity for those seeking country living without sacrificing comfort.

1278 Harrington Rd, Bennington

$265,000

3 Beds ⋅ 2 Baths ⋅ 5099392 MLS

Welcome to this 3 bedroom, 1.5-bath Cape style home located in a planned commercial zone. Offering 1,688 square feet of well-designed living space on a manageable 0.26-acre lot, this inviting residence is perfect for comfortable family living. Offers beautiful hardwood floors gracing the upstairs bedrooms, as well as the spacious living and dining rooms—ideal for gathering with loved ones. The sunroom provides a bright and tranquil spot to relax or enjoy morning coffee, while the two-car garage ensures plenty of space for vehicles and storage.

128 Northside Dr, Bennington

$259,000

4 Beds ⋅ 2 Baths ⋅ 5098985 MLS

Well maintained and thoughtfully updated, this 4-bedroom, 2-bath home offers the ease of single-level living on a beautiful level one-acre lot in Bennington's desirable west end. Enjoy stunning mountain views from the spacious back deck or sip your morning coffee on the covered front porch. Inside, you'll find an updated kitchen, refreshed bathrooms, a cozy fireplace, central air conditioning, a 2023 roof, an updated heating system, and a spacious primary suite featuring a jetted step-in tub and separate shower. Offering the perfect blend of comfort, convenience, and low-maintenance living, there's also room to add your own personal touches over time. Enjoy a peaceful setting just minutes from downtown Bennington for dining, shopping, cultural attractions, and everyday conveniences, with easy access to multiple ski destinations. Conveniently located approximately one hour from Albany International Airport and about three hours from both New York City and Boston.

549 Houran Rd, Bennington

$210,000

5 Beds ⋅ 2 Baths ⋅ 5098066 MLS

Set on over 5.5 acres of private, natural surroundings, this unique split-level ranch with an auxiliary dwelling unit offers an exceptional opportunity for multi-generational living, rental income, or a private guest retreat. Surrounded by peaceful woodlands, the property provides a tranquil rural setting while remaining just a short drive from town amenities. The main residence features three bedrooms and one bathroom, with a comfortable, inviting layout that flows seamlessly from the kitchen to the dining area and into the living room, creating an ideal space for everyday living and entertaining. A rear deck overlooks the serene landscape, offering the perfect place to relax and enjoy the beauty of the outdoors. The detached guest house includes two bedrooms, one bathroom, and a kitchen space, presenting endless possibilities for extended family, visitors, or supplemental income. While the guest house would benefit from updates, it offers tremendous potential to create a charming secondary living space. With expansive acreage, privacy, and versatility, this property is a rare opportunity to bring your vision to life and enjoy the best of country living with convenient access to town.

118 Foster Dr, Bennington

$205,000

3 Beds ⋅ 2 Baths ⋅ 5098061 MLS

Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create a sophisticated culinary space. An updated powder room and engineered hardwood flooring throughout further enhance the home's timeless appeal. The second level offers three well-appointed bedrooms and a tastefully renovated full bath designed with both style and comfort in mind. A walk-up attic provides abundant storage, while the partially finished lower level expands the living space with a dedicated laundry area, a versatile bonus room ideal for a home office, fitness studio, or media room, and a utility room featuring a newer heating system (2020), oil tank (2022), and upgraded 200-amp electrical service. Relax and unwind on the covered front and rear porches, and enjoy the convenience of a detached shared garage. Blending classic architectural charm with carefully curated updates, this distinguished home offers an exceptional opportunity to enjoy low-maintenance living in one of the area's most desirable and convenient locations.

305 Weeks St, Bennington

$439,000

3 Beds ⋅ 3 Baths ⋅ 5097821 MLS

At the end of a quiet road in North Bennington, this beloved 1979 home is being offered for the first time by its original owner. Set on over an acre with a large private backyard, garden beds, wild blackberries, and a peaceful wooded backdrop, the property feels beautifully tucked away while remaining just a short walk to the Henry Bridge and the Walloomsac River. Inside, the home is timeless, warm, and wonderfully livable, with approximately 2,389 finished square feet, hardwood floors throughout, fresh interior paint, and abundant natural light. The main level offers a large living room with built-in shelving, an inviting kitchen and dining area, a mudroom entry, first-floor bedroom, full bath, and a den that provides versatile space for guests, hobbies, or everyday living. Upstairs, the flexible layout features two bedrooms and two bathrooms, a spacious office, generous closet space, a built-in dresser, and a Mitsubishi mini split for added comfort. The lower level expands the living space with a finished family/recreation room, laundry, storage, utilities, and updated mechanicals including a Buderus boiler and five heat zones. A separate exterior entrance leads to a large workshop, ideal for tools, projects, outdoor equipment, or creative use. Additional conveniences include public water and sewer, high-speed internet, cable, and school choice for kindergarten through sixth grade. With its wrap-around deck, natural wood trim, built-ins, generous windows and skylights, end-of-road privacy, and unmistakable sense of care, this is a rare North Bennington opportunity with space, flexibility, and enduring Vermont charm. Homes with this setting, history, and location do not come along often.

15 Polygraphic Ln, Bennington

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