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$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
$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
$190,000
5 Beds ⋅ 2 Baths ⋅ 5098066 MLS
Invest in the potential with this unique split-level ranch and guest house. This property presents an exceptional opportunity for anyone looking to roll up their sleeves and bring a property back to life. Set on expansive acreage surrounded by peaceful woodlands, the property offers a tranquil rural setting while remaining just a short drive from town amenities. The main residence features three bedrooms and one bathroom, with a practical layout flowing from the kitchen into the dining area and living room. A rear deck overlooks the wooded landscape, providing a peaceful spot to enjoy the surrounding natural setting. The detached guest house offers two bedrooms, one bathroom, and a kitchen area, creating potential for a separate living space, guest quarters, multi-generational living, or rental income. The property offers flexibility and plenty of possibilities for those willing to put in the work. With its acreage, privacy, two separate living structures, and versatile layout, this property offers tremendous potential for the right buyer. Bring your vision, tools, and imagination and transform this property into something truly special.

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
$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
$140,000
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
$135,000
2 Beds ⋅ 2 Baths ⋅ 5096615 MLS
Townhouse style condo on the north side of Nathaniel court. Living room, kitchen, and half bath downstairs. Upstairs is the full bath with laundry and 2 bedrooms. All units have new roof within the last 5 years. No pets allowed. No smoking. Dues are $760 a quarter.

432 South St Unit C10, Bennington
$264,900
4 Beds ⋅ 2 Baths ⋅ 5096457 MLS
The renovations are done, just move in! Nearly everything is NEW at 109 County Street, including the price! In addition, the seller is offering a $5K credit towards the buyer’s closing costs. This extensively renovated 4BR/2BA home with a fully fenced yard gives you the opportunity to enjoy the benefits of a much newer home without the time, expense, and stress of renovating one yourself. Featuring 3 generous bedrooms and a bathroom w/tiled shower on the second level, and a first floor bedroom, bathroom, and laundry on the main level. New roof. New windows. New siding. New insulation. New Deck. New electrical. New plumbing. New walls. New flooring. New Appliances. New lighting. New doors and trim. Fresh paint. And that's just the beginning. The beautifully renovated kitchen features brand-new cabinetry, countertops, and stainless-steel appliances, while the updated bathrooms offer modern fixtures and finishes. This renovation goes far beyond a fresh coat of paint- the seller has invested in the major systems and countless details that make home ownership truly low maintenance. This is the kind of house where you can unpack your boxes, and start living. No renovation projects. No wondering what needs to be replaced next. No spending your weekends working on the house. And now there's even more value: the seller is offering $5K toward the buyer's closing costs with an acceptable offer. That's money you can keep in your pocket for moving expenses, furnishings, or simply enjoy the benefit of a lower cash requirement at closing. Whether you're a first-time buyer, downsizing, looking for an investment, or simply want a beautiful home without a renovation project, this property deserves a look. Located just minutes from downtown Bennington, shopping, restaurants, schools, and everyday conveniences, 109 County Street combines extensive updates with practical location and exceptional value. Why buy a home that needs work when you can buy one where the work is already DONE?

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
$80,000
4 Beds ⋅ 2 Baths ⋅ 5096159 MLS
Situated on a peaceful dead-end street, this home offers tremendous potential for investors, contractors, or buyers looking to create their dream home. The property features 3 bedrooms, with the possibility of a fourth, along with 2 bathrooms, providing a highly desirable layout and ample living space. With some vision, care, and updates, this home can be transformed into a beautiful residence in a convenient location. Just minutes from the high school and only a short distance from downtown Bennington's shops, restaurants, and local amenities. The price is firm, and the sale will require an all-cash transaction.

107 Lyons St, Bennington
$460,000
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
$249,900
5095558 MLS
Bring this historic gem back to life and unlock its incredible potential! Rich with the timeless character and charm of a late-1800s home, this unique property features spacious rooms and many original architectural details waiting to shine again. The building includes three two-bedroom units, including a generously sized two-story unit with a kitchenette and full bathroom on the upper level. Enjoy a large covered front porch, private off-street parking in the rear, and a storage shed for added convenience. Ideally located near downtown shopping, restaurants, recreation facilities, and public transportation, this property offers both charm and accessibility. Whether you're an investor, renovator, or someone with a vision, this is a rare opportunity to build equity and restore a piece of history. With strong income potential and endless possibilities, this property is ready for its next chapter. Don't miss out!

406-408 Gage St, 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
$299,000
3 Beds ⋅ 2 Baths ⋅ 5095149 MLS
Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out. The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even a pantry! The kitchen flows seamlessly into the dining room and the the living room, creating an open and inviting atmosphere where family and guests can easily gather. Laminate flooring throughout the first floor provides durability and a clean, cohesive look. Convenience is key with a practical mudroom entry and first-floor laundry. The full bathroom on the main level features a relaxing soaking tub with jets, perfect for unwinding after a long day. Upstairs, you'll find three comfortable bedrooms with attractive wood flooring, along with a half bath. The primary bedroom includes a walk-in closet, offering excellent storage and organization. Additional living space awaits in the partially finished basement, which is already prepared for radiant heat, providing exciting possibilities for future expansion. Recent energy-efficient improvements include heat pumps for year-round heating and cooling, as well as added attic insulation to enhance comfort and reduce utility costs. Appliances have all been updated rescently – Microwave, dishwasher, heat pump system, stove, washer, dryer, and refrigerator, and a basement refrigerator and chest freezer. The boiler was also replaced in 2022. Outside, the property offers even more versatility with two outbuildings for storage, along with a charming gazebo that creates the perfect setting for outdoor relaxation, or entertaining. Combining functional updates, flexible living space, and attractive outdoor amenities, this property is ready to welcome its next owners home.

262 Union St, Bennington
$499,900
2 Beds ⋅ 3 Baths ⋅ 5094280 MLS
Set on 3.11 peaceful acres with mountain views and a wonderful sense of privacy, 193 Finley Drive offers the rare combination of one-floor living, generous finished space, and excellent garage capacity in a convenient Bennington location. This 2-bed/3-bath home features a thoughtful main-level layout, with each bedroom offering direct access to a 3/4 bathroom. The primary bath also includes laundry, creating true one-floor convenience. Main living spaces are warm, bright, and inviting, with hardwood floors, bay windows, abundant natural light, and a distinctive two-sided brick fireplace with gas insert anchoring both the living and dining rooms. Built-in shelving adds character and function, while the easy flow between rooms makes the home comfortable for everyday living and welcoming for guests. The galley kitchen sits at the center of the home, with space for a breakfast table and direct access to the large deck. Big picture windows frame the surrounding greenery and mountain view, bringing the setting beautifully indoors. The finished lower level adds substantial flexibility, featuring a spacious rec room with wet bar, pool table, and gas stove. It's an ideal space to enjoy game nights, hobbies, movie watching, or relaxed entertaining. This level also includes a half bath, updated utilities, and a large storage room. With both an attached 2-car garage and a detached 2-car garage, there is outstanding room for vehicles, storage, equipment, workshop space, or recreational gear. Outside, the property feels private and established, with open lawn, mature landscaping, garden space, and room to enjoy the quiet surroundings. Built in 1987 and offered by its original owner, this property presents a special opportunity for buyers seeking space, privacy, mountain views, main-level living, and exceptional utility in one complete package.

193 Finley Dr, Bennington
$595,000
5 Beds ⋅ 3 Baths ⋅ 5093651 MLS
Step into this beautifully built post-and-beam house by well-known local builders Blue Heron Construction. Built in 1989 in classic Blue Heron style with an earthy exterior and a warm, glowing, golden interior, the house retains its original features, just waiting to be embraced by its next occupant. The location of the home couldn’t be better, nestled on 9+ secluded acres in North Bennington. Create your own walking trails or explore the lovely rural roads in the neighborhood. Practical and cultural amenities are just minutes away by foot, car, bike or snowshoes. Entering the home through the brick-floored mudroom, you arrive in a large, open living/kitchen area with high ceilings, exposed beams and a cozy wood stove. Surrounding this inviting space, you will find a master bedroom with bathroom annex, a dining room, an office/library, and a second ground floor bedroom. Up the bespoke wooden staircase are 3 more rooms with bathroom and separate entrance, perfect for extended family or multi-generational living. Back downstairs, you will be stunned by the size of the huge, heated workshop, with plenty of room for a woodworker, potter, jeweler, painter or sculptor to work their magic. Above this workspace is a large second-floor studio apartment with private entrance and a spacious screened porch. A substantial barn/garage with a loft area provides even more space for vehicles, equipment, storage, or future expansion. If you’re looking for multi-generational living, short or long term rental opportunities, or room for home-based business, this house could be perfect for you. The property is accessible from College Road but also has approximately 100 feet of road frontage on Matteson Road which could present future building opportunities, subject to local approvals. This house is a spacious North Bennington jewel. Move in right away, or take your time with a retrofit, as this house offers the versatility and flexibility to be whatever you want it to be.

81 Honeysuckle Ln, Bennington
$74,900
5092066 MLS
Expansive 2.25-acre level lot situated on a quiet, private dead-end street. This is an amazing opportunity to build a dream home, a weekend retreat, or a spec house for investment. The property features 306 feet of road frontage, has been perc tested, and includes septic plans for a three-bedroom system. Located on the outskirt of town, but still close proximity to historic downtown Bennington and its vibrant Main Street, which offers shops, restaurants, and year-round community events. It is also conveniently located just 30 minutes from Manchester, VT, and Williamstown, MA. Additionally, it is within approximately 45 minutes of several ski resorts, including Mount Snow, Stratton Mountain, Bromley Mountain, and Jiminy Peak.

Brambley Ln, Bennington
$350,000
2 Beds ⋅ 2 Baths ⋅ 5090266 MLS
Brand new 2026 construction offering the ease of single-level living with thoughtful, ADA-compliant design throughout. This energy-efficient home features 2 bedrooms and 2 full bathrooms, including a well-designed primary suite, plus convenient in-unit laundry. The open-concept layout is highlighted by a spacious kitchen and a cathedral ceiling that brings in abundant natural light and an airy feel. Enjoy year-round comfort with radiant heat throughout and efficient mini-split heat pumps. Step outside to a private back deck—perfect for relaxing or entertaining. A one-car attached garage adds convenience and additional storage. Located in a well-maintained and welcoming HOA, this property offers excellent walkability to nearby amenities, making it ideal for a variety of lifestyles. Listing agent is owner.

524 Jennings Brook Dr, 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
$695,000
4 Beds ⋅ 2 Baths ⋅ 5089246 MLS
Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the serenity and natural beauty for years to come. The thoughtfully designed open-concept main level features a bright and inviting living area, ideal for entertaining or relaxing while taking in the surrounding landscape. The primary bedroom and an additional guest bedroom are conveniently located on the main floor, along with a three quarter bath. A versatile loft area provides the perfect space for a home office, study area, or cozy kids’ hangout. The finished lower level expands the living space with two additional guest bedrooms, full bath, mechanical room with laundry hookups and ample storage. A one-car garage adds convenience and functionality. Step outside to the expansive deck designed for exceptional three-season living, where you can unwind, entertain, and enjoy amazing views in complete privacy. Fully renovated and move-in ready, including a new roof installed in 2024 as well as new furnace, new skylights, new flooring on the lower level and more, this special property combines modern comfort with the peace and beauty of a protected natural setting.

515 Quarry Rd, Bennington
$250,000
3 Beds ⋅ 2 Baths ⋅ 5088382 MLS
Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as a home office, adding flexible living space to fit today’s lifestyle. The main level includes a first-floor bedroom and ¾ bath, along with a sunroom perfect for relaxing and enjoying the surroundings. Upstairs are two additional bedrooms, including the primary suite, plus a large storage area. This home does need a little TLC, including some carpet and paint updates, but offers tremendous potential and great bones. Additional features include an attached one-car garage and a large back deck for outdoor enjoyment. Conveniently located within walking distance to downtown, the hospital, and the monument, this condo is a fantastic opportunity to make it your own.

103 Jennings Brook Dr Unit 103, Bennington
$550,000
5 Beds ⋅ 2 Baths ⋅ 5088350 MLS
Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home. Situated on over 17 acres, this property offers not one but two barns, established fenced pastures, and the kind of setting that feels like a Vermont dream. Listen to the breeze move through the grass, watch the leaves change color in the fall, and enjoy the privacy and beauty that surround you. Inside, you’ll find five bedrooms and two full bathrooms, with space that invites family dinners, holiday gatherings, and everyday moments that make a house feel special. The usable basement offers excellent storage, workshop potential, tool space, or room for tack and farm equipment. Whether you have horses, farm animals, or simply want the charm and comfort of country living, this property offers the Vermont lifestyle so many people dream about. This is more than a house it’s the feeling of finally coming home.

971 S Stream Rd, Bennington
$475,000
5087850 MLS
Positioned in the heart of Bennington’s commercial corridor on 12.82 open acres, 22 Morse Road present a prime development opportunity. Offering excellent visibility and accessibility along one of the area’s primary commercial arteries, the property is ideally situated for a variety of commercial, retail, service, mixed-use, or redevelopment possibilities. The location provides convenient access to both Vermont Route 7 and Vermont Route 279, creating direct connections to Albany and New York’s Capital Region, as well as Southern Vermont and Western Massachusetts. Surrounded by established businesses, national retailers, restaurants, lodging, and employment centers, the site benefits from strong daily traffic counts and regional connectivity. With existing commercial infrastructure and a highly accessible location near the New York and Massachusetts borders, this property offers exceptional potential for investors, developers, or end users seeking a strategic foothold in the greater Bennington market.

22 Morse Rd, Bennington
$265,000
3 Beds ⋅ 2 Baths ⋅ 5087836 MLS
Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout. Enjoy the convenience of first floor laundry, a beautiful front porch perfect for morning coffee or evening cocktails, and a private backyard ideal for entertaining, gardening, or simply relaxing while still enjoying the benefits of in town living. Owned and cherished by the same family for many years, this property has been exceptionally cared for and offers too many updates to count. From the inviting turquoise staircase to the unique character and charm found throughout the home, every corner tells a story. Take a stroll to local coffee shops, dinner spots, and community events, or enjoy hearing music drifting from the nearby Park-McCullough concert series on summer evenings. This home offers the perfect balance of neighborhood living, privacy, and small town charm. A true North Bennington gem full of warmth, character, and uniqueness this is a must see property. Call today for your private showing. This one will not last long!

8 West St, Bennington
$265,000
2 Beds ⋅ 3 Baths ⋅ 5087755 MLS
BACK ON MARKET! Enjoy low-maintenance living at The Birches of Bennington, ideally located just minutes from Crotched Mountain for skiing, snowboarding, hiking, and year-round outdoor recreation. This spacious 2-bedroom, 2.5-bath condo features a bright and inviting living room with a cozy wood-burning fireplace, perfect for relaxing after a day on the slopes. The open-concept kitchen and dining area offers abundant cabinet and counter space, appliances, a breakfast bar, and sliding doors leading to the back deck for easy indoor-outdoor living. Upstairs, you’ll find two generously sized bedrooms, each with its own ensuite bath. The primary suite includes two oversized double closets and a private balcony with views of the mountain slopes. The unfinished lower level provides excellent potential for a recreation room, home office, gym, or additional living space. Conveniently located just 90 minutes from Boston and about an hour from Manchester and the Seacoast region, this is the perfect opportunity to enjoy four-season living in a sought-after mountain community. Don’t miss your chance to live where you play! SELLER FINANCING AVAILABLE

69 Birch Glen Dr Unit 12, Bennington
$180,000
5087361 MLS
Unlock the potential of this spectacular 58.1 +/- acre woodland property in historic Bennington. The groundwork for your future home or getaway is already laid with a State-approved wastewater permit in place for a three-bedroom single-family residence, allowing you the flexibility to design your build. Further simplifying your plans, the property offers the rare advantage of connecting to the municipal water supply at the road. Essential utilities are right at your fingertips, with power readily available along the town-maintained, plowed Chapel Road near utility pole #25, and Xfinity providing high-speed cable internet, TV, and phone services. An existing roughed-in driveway provides a solid starting point for accessing the expansive acreage. Backing directly up to the 926-acre state-owned Bald Mountain recreational area, this woodland is an outdoor enthusiast's dream. The diverse landscape features approximately 30 acres of manageable hardwood timber and 28 acres of softwoods on the higher ground. Beech and red oak provide excellent wildlife habitat, while existing woods roads offer private trails for cross-country skiing, hiking, and ATVing with distant views of the Green Mountain National Forest. The land benefits from reduced taxes by being enrolled in Vermont's Current Use program, with six acres thoughtfully excluded to accommodate your development. Conveniently located just minutes from downtown Bennington, you have quick access to local dining, the Bennington Museum, and the historic Bennington Battle Monument. Seize the rare opportunity to craft your perfect Vermont lifestyle on this expansive woodland canvas!

1073 Chapel Rd, Bennington

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