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$439,900
5 Beds 2 Baths 5102441 MLS
Bennington is a great small town rich in history where you will find the Contoocook River. Students attend the wonderful schools in the Contoocook School District. Full of timeless charm and character, this unspoiled Village Colonial offers warm, inviting spaces and the opportunity to make it your own. Inside, you’ll find lovely, homey rooms accented by wood flooring and original details that reflect the home’s classic New England heritage. The kitchen is typical for an antique colonial with plenty of storage, a tin ceiling, and a view of the side yard. With five bedrooms, there is plenty of space for a growing family, guests, or flexible use such as a home office or hobby room. Currently, there is a first-floor bedroom that could be turned back to its original parlor. There is a "mud-room" where you will find the laundry, a walk-up attic, plenty of sitting areas, and space to spread out. Adding to its appeal is a spacious 18x28 barn, perfect for hobbyists, storage, or workshop space. The property is connected to town water and sewer, adding everyday convenience to its historic appeal. A rare chance to bring new life to a charming village home with great bones, character, and potential.

16 Francestown Rd, Bennington

$169,900
2 Beds 2 Baths 5102057 MLS
Enjoy easy first-floor, one-level living in this two-bedroom, one-and-a-half-bath condominium in Bennington’s Nathaniel Court community. The comfortable layout features an open living and dining area, a functional brand-new stainless steel kitchen appliances, laminate flooring, and plenty of natural light throughout. Both bedrooms offer inviting spaces, while the in-unit washer and dryer add everyday convenience. Association services include landscaping, snow removal, and trash removal, providing a low-maintenance lifestyle. Sidewalks and a location close to downtown Bennington make it easy to access local shops, restaurants, cultural attractions, and other area amenities. Whether you are purchasing your first home, downsizing, or looking for a convenient Vermont getaway, this well-located condo is ready to welcome its next owner.

432 South St Unit A11, Bennington

$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

$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

$249,000
5100263 MLS
Investment opportunities like this are few and far between! Located in a desirable mixed use district, this well maintained four unit one bedroom apartment building offers an excellent opportunity for both seasoned and first time investors. The property features four one bedroom apartments with full bathrooms, each with its own unique character and appeal. Two of the front/lower units have been thoughtfully renovated within the past five years and feature updated appliances, fresh paint throughout, and modern finishes. The two rear units are occupied by long term tenants who are happy to remain, providing immediate rental income and stability. Outside, you’ll find a spacious yard, ample off street parking, and a convenient walkable location close to local amenities. Tenants are responsible for their own electricity and hot water, with each unit having its own dedicated hot water heater. The owner currently pays for heat, water, sewer, trash removal, snow removal, master insurance, and property taxes. Whether you’re a seasoned investor or looking to expand your investment portfolio or purchase your first multifamily property in a location where multifamily opportunities are rarely available, this property is one you won’t want to miss. Schedule your showing today and discover the possibilities this exceptional investment has to offer.

250 North St, 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

$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

$230,000
3 Beds 2 Baths 5097604 MLS
Blending vintage charm with modern updates, this beautifully refreshed 3-bedroom, 2-bath home offers comfortable in-town living close to local amenities. Recent improvements include a newer roof installed just three years ago and new flooring throughout, creating a fresh and inviting atmosphere. Other additions include new kitchen appliances, furnace, and heat pump hybrid water heater, making the home incredibly efficient. The bright, open, kitchen is filled with natural light and features a sliding door leading directly to the private brick patio, perfect for outdoor dining, entertaining, or relaxing. A covered front entrance adds welcoming curb appeal, while the enclosed porch provides excellent potential as a practical mudroom entry. Upstairs, you'll find generous attic space offering abundant storage possibilities. Outside, the backyard is enhanced by a charming newly added shed complete with a screened-in section, creating an ideal retreat for hobbies, gardening, or enjoying warm summer evenings. This move-in-ready home combines character, functionality, and modern convenience.

104 Short St, Bennington

$539,900
4 Beds 3 Baths 5097526 MLS
Thoughtfully crafted with a distinctive European-inspired character and beautifully updated throughout, this custom-built 4-bedroom, 3-bath home offers the perfect blend of quality craftsmanship, privacy, and convenience on a picturesque, landscaped lot just minutes from downtown Bennington. The bright and inviting interior features a beautifully renovated kitchen, spacious living areas with hardwood floors, and a stunning primary suite featuring a custom walk-in closet and a spa-inspired bath with heated tile floors. Offering exceptional flexibility, two of the four bedrooms are currently configured as home offices, while the versatile floor plan easily adapts to a variety of lifestyles. The bonus room includes plumbing for a future kitchenette, creating excellent potential for an in-law suite or multi-generational living. Step outside to enjoy the expansive deck, impressive stone patio, terraced gardens, and peaceful outdoor spaces designed for relaxing or entertaining. The detached two-car garage offers additional storage along with a heated workshop complete with water and electricity, making it ideal for hobbies, projects, or extra workspace. Additional highlights include an updated heating system, updated septic system, pull-down attic access with generous storage, and a whole-house fan for added comfort. This exceptional property combines timeless character, thoughtful updates, and remarkable versatility in a peaceful country setting.

811 Middle Pownal Rd, Bennington

$150,000
5 Beds 2 Baths 5096965 MLS
Opportunity awaits with this spacious property offering incredible potential for investors, renovators, or buyers looking to create their dream home. Currently configured as a single family residence, this home features 5 bedrooms and 2 bathrooms. At one point it was a 2 unit home and could potentially be again. Inside, you'll find generous living space ready for your vision and updates. A fully enclosed front porch provides additional usable space, while the rear mudroom offers a practical everyday entry. Whether you're looking to restore the home's character, add value through renovations, or explore income-producing possibilities, this property presents a wealth of opportunity. Conveniently located close to downtown, shopping, dining, walking trails, and the hospital, the location adds to the property's appeal. Bring your ideas and imagination, this is a rare chance to transform a property with outstanding potential into something truly special.

127 Dewey St, Bennington

$269,900
4 Beds 2 Baths 5096457 MLS
Welcome to your like-new home in the heart of Bennington! Within easy walking distance of the vibrant downtown district, this beautifully renovated 4-bedroom, 2-bath New Englander has been completely transformed into a truly turnkey property. Nearly every aspect of the home has been updated, allowing you to enjoy the benefits of modern, low-maintenance living from day one. Extensive improvements include a brand new roof, all new windows, energy-efficient insulation, new flooring throughout, new appliances, and countless modern finishes designed for comfort, style, and peace of mind. The bright and inviting main level showcases an eat-in kitchen with stylish finishes and direct access to a spacious deck and fully fenced yard, perfect for summer dining, entertaining, or simply relaxing outdoors. A first floor bedroom, full bathroom, and laundry area offer the convenience and flexibility of single-level living. Upstairs, you'll find three additional bedrooms and a generously sized bathroom featuring a beautifully tiled shower, providing plenty of space for family, guests, or a home office. With all the major updates already completed and every detail thoughtfully refreshed, this is truly low-maintenance living. Just a short stroll to downtown shops, restaurants, cafes, and community events, this is a rare opportunity to enjoy a completely renovated home in one of Bennington's most convenient locations. Just unpack and enjoy!

109 County St, Bennington

$180,000
3 Beds 2 Baths 5096423 MLS
Opportunity awaits at this unique property with an exceptional setting along the Walloomsac River. A true Vermont farmhouse offering three bedrooms and two bathrooms, situated on a flat, park-like lot with mature landscaping, open green space, and beautiful river frontage. The serene setting creates a peaceful atmosphere rarely found in properties with such versatile potential. A large barn provides abundant storage, workshop space, or the opportunity for a variety of future uses. Inside, the home is ready for renovation and updates, making it an ideal project for investors, entrepreneurs, or buyers looking to bring their own vision to life. The main level features a well designed layout, highlighted by a spacious eat-in kitchen, a full bathroom, and a cozy living room with a pellet stove. The front door leads to a covered porch overlooking the scenic golf course at Mount Anthony Country Club. A separate dining room and a versatile room that can serve as a bedroom, den, or home office complete the first floor. Upstairs, a generous landing provides additional living space as a family room, along with two bedrooms and a shared three-quarter bathroom. With commercial zoning already in place, the property offers flexibility for a wide range of permitted uses beyond residential living (subject to local approvals). Whether you're seeking a live/work opportunity, business location, investment property, or a charming riverside renovation project, this property combines a peaceful natural setting with outstanding potential. Bring your ideas and unlock the possibilities of this rare offering. Conveniently located near the local country club and golf course, with easy access to nearby walking trails, the property offers an appealing blend of recreation, nature, and opportunity.

105 Hicks Ave, 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

$389,000
5096068 MLS
Recently updated two-family apartment building located in a historic downtown village district. This versatile property offers two spacious 3-bedroom units, with one unit providing the potential for up to 5 bedrooms, creating flexibility for larger households, multi-generational living, or additional rental income. Both units are currently vacant, making this an ideal opportunity for an owner-occupant to live in one unit while renting the other, or for family and friends to purchase and enjoy together. Relax on the screened-in porch and enjoy views and the soothing sounds of the Contoocook River flowing nearby. Conveniently located with easy access to Peterborough, approximately 40 minutes to Concord, and less than an hour to Manchester for commuting. Outdoor recreation is close at hand with skiing at Crotched Mountain Resort and golf at Crotched Mountain Golf Club. A unique opportunity to own a move-in-ready multi-family property in a charming New Hampshire village setting.

30-32 Main 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

$179,000
2 Beds 2 Baths 5095599 MLS
Looking for easy, low maintenance living in a location that puts everything within reach? This inviting first floor condo offers comfort, convenience, and affordability all in one package. Featuring two bedrooms, a bright and welcoming living room filled with natural light, a spacious kitchen with generous counter space, ample storage, and the convenience of having your kitchen, bathroom, laundry, bedrooms, and living areas all on one level. Step outside to the additional sitting area, perfect for a reading nook, or cozy retreat, and enjoy the peaceful sounds of the nearby brook just outside. The beautifully maintained grounds add to the appeal, and the condo association takes care of the work for you. Landscaping, snow removal, and trash service are all included, allowing you more time to enjoy life and less time worrying about maintenance. Whether you’re searching for your first home, looking to simplify your lifestyle, seeking a weekend getaway close to skiing and outdoor recreation, or wanting the ease of first-floor living, this condo offers endless possibilities. Enjoy being just minutes from downtown restaurants, coffee shops, the library, shopping, and local amenities while still having a peaceful place to call home. Affordable opportunities like this don’t come along often. Move in, make it your own, and start enjoying all the benefits of convenient condo living. Schedule your showing today!

106 Park St Unit 9, Bennington

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