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$375,000
3 Beds 2 Baths 5104363 MLS
Tucked into Bennington's established Spring Hill neighborhood, this inviting 3 bedroom, 2 bath home offers nearly 2,000 square feet of comfortable living space with a setting that makes it easy to enjoy the outdoors. From the backyard, follow the grass walking trail to the community owned pond, a wonderful extension of your outdoor space and a beautiful spot to enjoy the changing Vermont Seasons. Inside, the living room opens naturally to the kitchen and dining area, creating a connected space for everyday living and entertaining. A separate family room provides plenty of room to spread out and features a woodstove hookup, ready to add warmth and ambiance on chilly evenings. The four season sunroom is a standout, offering a cozy year round spot for morning coffee, reading, relaxing or simply enjoying the backyard views. The home is ready for some cosmetic updating, offering the perfect opportunity to bring your own style and vision while building on an already comfortable and functional layout. Three bedrooms, a deck overlooking the backyard, attached garage and paved driveway, there's plenty here to work with. Add your personal touches and make this Spring Hill home your own.

291 Spring Hill Rd, Bennington

$739,900
3 Beds 3 Baths 5102468 MLS
Owner-built and thoughtfully maintained, this spacious home offers room for everyone with three bedrooms, three bathrooms, a three-car direct-entry garage with a walk-up attic, and equestrian amenities including a three-stall stable, fenced pasture, and nearby area trails. Follow the slate walkway to the 16' x 25' storage barn, or enter from the covered porch and enjoy the quiet surroundings. Inside, a bright and welcoming foyer opens to a staircase and balcony hall, a private living room with a rock-faced wood-burning fireplace, and a formal dining room with wainscoting. The kitchen features stainless steel appliances, granite countertops, a pantry closet, desk area, breakfast bar, and a sunny breakfast nook that flows into the family room and out to the 11' 15" x 31' 2" rear deck overlooking an owner’s garden area. Hardwood and tile flooring run throughout the home, and all floors are heated with oil-fired radiant heat. The newly renovated primary bath includes a walk-in shower, double sinks, cabinetry with linen storage, tile flooring, and fresh paint throughout. The basement-level recreation room features new flooring, a built-in entertainment center, and a newly constructed bar area with a sink. The walk-out basement also provides an ideal shop or workspace. A place for everyone, this property is only moments from the center of Bennington, skiing at Crotched Mountain, Crotchet Mountain Golf Club and just 4 miles from NH Route 202.

97 Onset 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

$189,000
4 Beds 2 Baths 5096338 MLS
This well-maintained New Englander offers the perfect balance of classic character and comfortable living. Featuring four bedrooms and two updated bathrooms. The home provides spacious, comfortable living throughout. The recently renovated kitchen is both stylish and functional, while the updated bathrooms add contemporary appeal. Large rooms and a thoughtful layout create a welcoming atmosphere for everyday living and entertaining. Outside, you'll find a deep, fully fenced backyard with plenty of room for recreation, gardening, or pets. A beautiful deck provides the perfect setting for outdoor dining, relaxing, and entertaining. Enjoy the convenience of an in-town location within walking distance of downtown restaurants, shops, and local attractions. The property is also just minutes from services and all the amenities Bennington has to offer. Albany airport is 45 minutes driving, ski areas to the north and east, also approximately 45 minutes, NYC and Boston are both a 3 hour drive.

209 Depot St, Bennington

$480,000
4 Beds 3 Baths 5095717 MLS
If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the owners in the '80s. The 3300+ square feet of living area on the upper level and another 3300+ on the lower level ready to be finished. As you can see, the lower level has plenty of windows and will be very flexible space to use. The two-car garage is attached to the house. From there, into the mudroom. The kitchen is very generous...There's room for your breakfast table, a couple of easy chairs and a love seat, and the woodstove will make this a cozy country kitchen to be. This is a 'cooks dream'. The commercial range will make your friends jealous, as will the pantry and stained glass on the upper cabinets. Off the kitchen is a large sunroom which leads out to the deck. Large dining room perfect for entertaining and a very comfortable formal living room. There are two guest rooms that share a tile bath. The primary suite has its own tile bath and a room that could be a nursery or an office. The lower level is ready to finish into living space if you need it. A few spots will need a bit of TLC, but the end result will be fantastic. Several updates have been done. For the handyman or animal lover, there is a 23x46 foot barn with room for several vehicles or machinery. There are two garage doors, and it even has a pit for working under your vehicles. The open land is gorgeous. Stonewalls and woodland await. If you enjoy sunny locations, this is a perfect spot. There is enough land to enroll the property into Vermont's Current Use program. This may be the spot you have been waiting for! Available due to owner relocation.

498 Town Line Rd, Bennington

$299,000
3 Beds 2 Baths 5095251 MLS
Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you’ll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026. What truly sets this property apart is its incredible versatility. The bonus space presents endless possibilities for a home based business, professional office, hobby space, expanded living area, or potential in-law accommodations. Whether you’re looking for room to grow, work from home, or create a space tailored to your lifestyle, this home offers the flexibility to make it happen. The generous lot and rear garage access provide additional opportunities for future improvements. Buyers may appreciate the potential to enhance accessibility and functionality with a redesigned driveway configuration, such as a circular drive, while maximizing the usefulness of the garage space and expansive yard. Enjoy the convenience of being just minutes from downtown Bennington’s shops, restaurants, coffee houses, and local attractions, while still enjoying the privacy of a large lot. With easy access to area hiking trails, ski resorts, and major routes to Boston and New York, this property combines location, character, and opportunity in one exceptional package.

89 Merson St, Bennington

$179,000
3 Beds 3 Baths 5089968 MLS
Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to own a large condo unit with the space and versatility of a single-family home, paired with the ease of low-maintenance living. The main living level boasts an open-concept kitchen, dining, and living area ideal for entertaining, along with a half bath with laundry, a spacious bedroom with en-suite bath, and an additional bedroom. The third floor serves as a stunning private retreat featuring a second primary en-suite, skylights, and flexible bonus space perfect for a home office, library, exercise area, or cozy reading nook. Just minutes from downtown Bennington’s shops, restaurants, recreation, and cultural attractions, this move-in ready condo offers low-maintenance living without sacrificing space or style. A truly unique offering in a highly convenient location!

432 South St Unit D2, Bennington

$269,000
3 Beds 1 Baths 5083898 MLS
This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back deck. Featuring replacement windows for energy efficiency, a paved driveway, and ample yard space, this property is ideal for anyone seeking extra room to play and entertain. Sidewalks and streetlights make evening strolls safe and pleasant, and the proximity to downtown ensures you're close to shopping, dining, and public transportation. For outdoor enthusiasts, the location is unbeatable: just 10 minutes from Prospect Ski Area, 30 minutes to Mt. Snow, 45 minutes to Albany Airport, 3 hours to New York City or Boston, and 2 hours to Hartford. This home is ready for your finishing touches to make it truly your own.

951 Gage St, Bennington

$230,000
3 Beds 1 Baths 5068744 MLS
Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry. Step inside to find gleaming newly upgraded flooring, a warm and inviting layout, and stylish updates throughout, including new kitchen and bathroom cabinetry. The bright kitchen flows seamlessly into the dining and living areas, creating an ideal space for everyday living and entertaining. Relax on the covered front porch and enjoy your morning coffee while taking in the neighborhood atmosphere. Outside, the large detached garage offers excellent space for vehicles, hobbies, or additional storage, while solar panels help keep energy costs low. Combining the charm of downtown living with thoughtful modern improvements, this move-in ready home is one you won’t want to miss. Schedule your private showing today!

113 Main St, Bennington

$529,000
3 Beds 3 Baths 5067086 MLS
Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can be surmised that this property was for the intent of upper management housing for the farm. With sprawling views to the north, south and west, this location does not disappoint! A typical farmhouse style home that esthetically blends rustic and modern elements for easy living. A generously sized kitchen is perfection for entertaining and for spending time with family and friends. The living room invites a space for conversation, a cozy fire during the chilly Vermont evenings, or simply relaxing taking in the divine views at sunset. More casually, the family room offers exposed beams, vaulted ceilings and abundance of natural light. A formal dining room is strategic to the kitchen for holidays and family gatherings. The second floor boasts three bedrooms and two bathrooms, while the third bath is on the first level for convenience. And have I mentioned the renovated space above the garage? Wow! Breathe in the fresh air, take a walk up a country road and hunker down for the most genuine, spectacular sunsets. This is the type of special property that you will not want to miss.

58 Mount Anthony Rd, Bennington

$357,500
4 Beds 2 Baths 5048567 MLS
Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience, just steps from scenic hiking trails and close to Bennington College. Step inside to discover a freshly renovated kitchen and bathroom, complemented by new flooring throughout the home. Brand new first floor half bath and mudroom entrance recently added. The dining room features a sliding glass door that opens to a spacious back deck, perfect for outdoor dining and relaxing. A covered front porch adds classic New England charm and a welcoming touch. With a large attached garage offering plenty of storage and workspace, this home is as practical as it is inviting. Whether you're enjoying the peaceful surroundings or entertaining guests, this home provides comfort, style, and a true sense of place in a friendly, walkable neighborhood. Don’t miss this North Bennington gem, schedule your showing today!

19 Royal St, Bennington

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