Newest Homes for Sale in Bennington, VT

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  /25

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,688 Sq Ft

  171 Garbrooke Dr, Bennington, VT 05201

  Welcome to this inviting Cape-style home offering 3 bedrooms, 2 baths and a comfortable layout designed for both everyday living and entertaining. The main level features an open-concept kitchen and dining area that flows directly onto a huge back deck—an ideal spot for summer dinners, gatherings or simply relaxing while overlooking the secluded, wooded backyard. With both a living room and

  Lilli West Maple Leaf Real Estate

  171 Garbrooke Dr, Bennington, VT 05201
• Explore Bennington

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  /36

  $349,900

  • 2,584 Sq Ft

  219-221 Washington Ave, Bennington, VT 05201

  Side-by-side duplex in a sought-after area in the heart of Bennington, offering the charm of yesteryear with modern conveniences. This well-maintained property presents an excellent investment opportunity, whether you're looking for a rental property generating substantial income or the option to owner-occupy one unit while renting the other to help offset your mortgage. Boasting many tasteful

  Matt Waddington Hoffman Real Estate

  219-221 Washington Ave, Bennington, VT 05201
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  /39

  $189,900

  • 2 Beds
  • 1 Bath
  • 462 Sq Ft

  301 Beech St, Bennington, VT 05201

  Cute, cozy, and move-in ready! This freshly renovated 2-bedroom, 1-bath home has been updated from the ground up and offers comfortable, low-maintenance living in a convenient Bennington location. Recent improvements include a brand-new kitchen and bathroom, new flooring, fresh paint, new baseboards, new roof, front porch and expanded driveway. The home features electric baseboard heat along with

  Floyd Amidon Maple Leaf Real Estate

  301 Beech St, Bennington, VT 05201
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  /50

  $330,000

  $15K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,750 Sq Ft

  1141 Burgess Rd, Bennington, VT 05201

  Completely renovated, turnkey single-level home offering mountain views, modern finishes, and a beautiful country setting. All major systems and cosmetic updates were completed within the last year, including a brand-new roof and new windows.The light-filled interior layout features 2 bedrooms, 2 full bathrooms, brand-new wood flooring across all main living areas, plush new bedroom

  Kate Barry EXP Realty

  1141 Burgess Rd, Bennington, VT 05201
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  /53

  $1,695,000

  • 3 Beds
  • 2.5 Baths
  • 4,120 Sq Ft

  1944 Monument Ave, Bennington, VT 05201

  Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-square-foot one-bedroom

  Kelley Mccarthy Mahar McCarthy Real Estate

  1944 Monument Ave, Bennington, VT 05201
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  /2

  $58,000

  • Land
  • 20,908 Sq Ft
  • $120,833 per Acre

  33 Asa's Way, Bennington, VT 05257

  This lot in beautiful North Bennington is ready to go! Building plans have been drawn up and available to come with the property for an approx. 2200 sq ft 3 bed, 2 bath home with decks facing the mountains. This lot has the electric, water, and sewer available at the street. Beyond having school choice for the elementary it also boasts being the second highest elevation lot in the development,

  William Paquin Maple Leaf Real Estate

  33 Asa's Way, Bennington, VT 05257
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  /33

  $349,000

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,911 Sq Ft

  21 Russett Dr, Bennington, VT 05201

  Tucked into a beautifully maintained neighborhood, 21 Russett Drive is the kind of home that feels welcoming the moment you arrive. Beautiful landscaping, a charming Dutch door, and a thoughtfully cared for yard give this property an almost secret garden feel private, inviting, and full of character.Inside, the versatility of this home truly shines. The main level offers a comfortable living

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  21 Russett Dr, Bennington, VT 05201
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  /52

  $179,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  130 Morgan St, Bennington, VT 05201

  200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities. Showings start 8/18/2026

  Dan Mason Perrott Realty

  130 Morgan St, Bennington, VT 05201
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  /37

  $375,000

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  291 Springhill Rd, Bennington, VT 05201

  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.

  Faith Rhodes Maple Leaf Real Estate

  291 Springhill Rd, Bennington, VT 05201
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  /4

  $349,000

  • 3,637 Sq Ft

  710 Main St, Bennington, VT 05201

  Well-maintained four-unit property ideally located in downtown Bennington. This versatile multi-family offering features just the right amount of yard space for outdoor enjoyment, along with ample off-street parking. The property includes two one-bedroom units, one two-bedroom unit, and one spacious four-bedroom unit, providing a flexible mix of rental options. With a strong rental history and

  Dan Mason Perrott Realty

  710 Main St, Bennington, VT 05201
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  /2

  $75,000

  • Land
  • 11.2 Acres
  • $6,696 per Acre

  0 Mount Anthony Rd, Bennington, VT 05201

  A beautiful opportunity awaits on Mount Anthony Road in Bennington, Vermont-11.2 acres of wooded land nestled along a quiet, scenic dirt road. This property offers the perfect blend of seclusion and convenience, giving you the best of both worlds. Currently wooded, the land can be selectively cleared to reveal potential stunning views of the surrounding Vermont landscape. Imagine building a camp

  Kelley Mccarthy Mahar McCarthy Real Estate

  0 Mount Anthony Rd, Bennington, VT 05201
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  /15

  $162,500

  $7K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 819 Sq Ft

  432 South St Unit A11, Bennington, VT 05201

  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

  Colt Hazell Flex Realty

  432 South St Unit A11, Bennington, VT 05201
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  /12

  $49,000

  • Land
  • 9,147 Sq Ft
  • $233,333 per Acre

  2 Belvedere St, Bennington, VT 05201

  Here is the blank slate for your Vermont home, offering beautiful views of the Green Mountains and a location that is just steps from a 160-acre wildlife preserve with numerous hiking trails, wetland viewing platforms, and abundant wildlife. This cute corner lot is mostly level, cleared, and ready to build, with town water and sewer available at the street. Bring your imagination and come and

  Dan Mason Perrott Realty

  2 Belvedere St, Bennington, VT 05201
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  /32

  $350,000

  • 2,586 Sq Ft

  110 Short St, Bennington, VT 05201

  Secure a smart, low-maintenance income property featuring four well-kept units—two 2-bedroom and two 1-bedroom—on a dead-end road. This is turnkey living for tenants and hassle-free ownership for you. Three of the four units have dedicated washer/dryer hookups and each unit is fully separated utilities (electric, gas or oil, hot water), so tenants manage their own bills and turnover is smooth.

  William Paquin Maple Leaf Real Estate

  110 Short St, Bennington, VT 05201
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  /21

  $132,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft

  60 Tori Ln, Bennington, VT 05201

  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.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  60 Tori Ln, Bennington, VT 05201
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  /30

  $595,000

  • 3 Beds
  • 2 Baths
  • 2,379 Sq Ft

  1278 Harrington Rd, Bennington, VT 05201

  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

  Kelley Mccarthy Mahar McCarthy Real Estate

  1278 Harrington Rd, Bennington, VT 05201
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  /59

  $190,000

  $20K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,200 Sq Ft

  118 Foster Dr, Bennington, VT 05201

  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

  Lindsey Martin Maple Leaf Real Estate

  118 Foster Dr, Bennington, VT 05201
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  /53

  $205,000

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  305 Weeks St, Bennington, VT 05201

  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

  Lindsey Martin Maple Leaf Real Estate

  305 Weeks St, Bennington, VT 05201
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  /37

  $539,900

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  811 Middle Pownal Rd, Bennington, VT 05201

  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

  Jeffrey Dorman

  811 Middle Pownal Rd, Bennington, VT 05201
• 

  

  /50

  $140,000

  $20K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,575 Sq Ft

  127 Dewey St, Bennington, VT 05201

  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

  Lindsey Martin Maple Leaf Real Estate

  127 Dewey St, Bennington, VT 05201
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  /14

  $135,000

  $5K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 948 Sq Ft

  432 South St Unit C10, Bennington, VT 05201

  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.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  432 South St Unit C10, Bennington, VT 05201
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  /42

  $180,000

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  105 Hicks Ave, Bennington, VT 05201

  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

  Angela Bevin Maple Leaf Real Estate

  105 Hicks Ave, Bennington, VT 05201
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  /4

  $80,000

  • 4 Beds
  • 2 Baths
  • 1,465 Sq Ft

  107 Lyons St, Bennington, VT 05201

  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

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  107 Lyons St, Bennington, VT 05201
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  /54

  $460,000

  $35K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,312 Sq Ft

  498 Townline Rd, Bennington, VT 05201

  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

  Betty McEnaney Diamond Realty

  498 Townline Rd, Bennington, VT 05201
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  /52

  $299,000

  $10K PRICE INCREASE

  • 3 Beds
  • 1.5 Baths
  • 1,411 Sq Ft

  262 Union St, Bennington, VT 05201

  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

  William Paquin Maple Leaf Real Estate

  262 Union St, Bennington, VT 05201
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  /43

  $499,900

  $50K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 3,105 Sq Ft

  193 Finley Dr, Bennington, VT 05201

  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

  Jenifer Prouty Hoffman Hoffman Real Estate

  193 Finley Dr, Bennington, VT 05201
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  /3

  $69,900

  $5K PRICE DROP

  • Land
  • 2.25 Acres
  • $31,067 per Acre

  0 Brambley Ln, Bennington, VT 05201

  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

  Matt Waddington Hoffman Real Estate

  0 Brambley Ln, Bennington, VT 05201
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  /60

  $695,000

  • 4 Beds
  • 2 Baths
  • 1,614 Sq Ft

  515 Quarry Rd, Bennington, VT 05201

  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

  Vicki Wilson Maple Leaf Real Estate

  515 Quarry Rd, Bennington, VT 05201
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  /29

  $250,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft

  103 Jennings Brook Dr, Bennington, VT 05201

  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

  Kelley Mccarthy Mahar McCarthy Real Estate

  103 Jennings Brook Dr, Bennington, VT 05201
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  /3

  $475,000

  • Land
  • 12.82 Acres
  • $37,051 per Acre

  22 Morse Rd, Bennington, VT 05201

  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

  Paul Carroccio TPW Real Estate

  22 Morse Rd, Bennington, VT 05201
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  /33

  $265,000

  $34K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  8 West St, Bennington, VT 05201

  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

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  8 West St, Bennington, VT 05201
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  /60

  $180,000

  $20K PRICE DROP

  • Land
  • 58.1 Acres
  • $3,098 per Acre

  1073 Chapel Rd, Bennington, VT 05201

  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

  Curtis Trousdale Preferred Properties

  1073 Chapel Rd, Bennington, VT 05201
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  /20

  $475,000

  $24K PRICE DROP

  • 6 Beds
  • 6 Baths
  • 9,000 Sq Ft

  425 Main St, Bennington, VT 05201

  15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R

  Chris Long BHG Masiello Brattleboro

  425 Main St, Bennington, VT 05201
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  /23

  $219,000

  $16K PRICE DROP

  • 1,860 Sq Ft

  205 County St, Bennington, VT 05201

  This well maintained 2-unit home exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family. use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize rental income with separate 2-bedroom and 3-bedroom units, this property is designed to adapt to

  Dan Mason Perrott Realty

  205 County St, Bennington, VT 05201
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  /27

  $209,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,075 Sq Ft

  1083 Main St, Bennington, VT 05201

  Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  1083 Main St, Bennington, VT 05201
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  /7

  $55,000

  • Land
  • 22,215 Sq Ft
  • $107,843 per Acre

  24 Asa Way, Bennington, VT 05257

  Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience.Public water and sewer are available,

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  24 Asa Way, Bennington, VT 05257
• 

  

  /5

  $55,000

  • Land
  • 20,908 Sq Ft
  • $114,583 per Acre

  29 Asa Way, Bennington, VT 05257

  Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home.Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process.

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  29 Asa Way, Bennington, VT 05257
• 

  

  /24

  $215,000

  $20K PRICE DROP

  • 1,300 Sq Ft

  340 Pleasant St, Bennington, VT 05201

  Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with

  Melissa Nebelski Real Broker LLC

  340 Pleasant St, Bennington, VT 05201
• 

  

  /6

  $199,900

  • 1,176 Sq Ft

  2 Hamlin Ave, Bennington, VT 05201

  2-Unit Multi-Family with Professional-Grade Workshop!Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast,

  Lori Hurley Four Corner Properties LLC

  2 Hamlin Ave, Bennington, VT 05201

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