Homes for Sale near Mt. Anthony Union Middle School

• 

  

  

  /42

  $499,000

  $150K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,740 Sq Ft

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262

  Welcome to Rod and Gun Club Road, where privacy, comfort and country living come together on Offering 2,740 sq ft, with a full useable basement, sitting on 4.43 beautiful acres. This fully renovated ranch-style home offers approximately 2,740 feet of living space, plus a full useable basement, providing plenty of room for everyday living and entertaining. The thoughtfully designed interior

  

  Wendy Larson

  Hooscik Realty

  211 Rod and Gun Club Rd, Shaftsbury, VT 05262
• 

  

  

  /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
• 

  

  

  /13

  $229,000

  • Land
  • 0 Sq Ft

  468 Skyboro Rd, Pownal, VT 05261

  Beautiful property featuring an impressive 835.9 feet of road frontage and over 10 partially cleared acres of private land in Pownal, Vermont. This land is situated on a private road with rolling woods, making it an ideal location to build a dream home or a vacation getaway. It offers easy access to Route 7, providing a quick drive north to the Bennington, Vermont area and local ski resorts.

  

  Sheryl Morehouse

  BISHOP WEST REAL ESTATE

  468 Skyboro Rd, Pownal, VT 05261
• 

  

  

  /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
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  /38

  $299,000

  $26K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  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

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201
• 

  

  /33

  $279,000

  $20K 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

  $799,000

  $76K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,462 Sq Ft

  636 Dexter Rd, Shaftsbury, VT 05262

  The Dexter Road Farmhouse, Circa 1800 In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic nearby backroads to write “Stopping by the Woods on a Snowy Evening." Dating back more than 225 years, this charming farmhouse offers a rare opportunity to own a piece of Vermont history while embracing the slower pace and natural beauty that define the region. Tucked away

  

  Kristin Comeau

  TPW Real Estate

  636 Dexter Rd, Shaftsbury, VT 05262
• 

  

  /41

  $550,000

  • 5 Beds
  • 2 Baths
  • 1,974 Sq Ft

  971 S Stream Rd, Bennington, VT 05201

  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,

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  971 S Stream Rd, Bennington, VT 05201
• 

  

  /17

  $198,900

  • 2 Beds
  • 1 Bath
  • 1,332 Sq Ft

  348 Center St, Pownal, VT 05261

  Tucked into the rolling countryside of Pownal, this one-of-a-kind property offers something increasingly hard to find: space, story, and the freedom to make it your own. Set on 4.15 private acres, Once home to a beloved local dairy bar a second cabin and additional outbuildings, all awaiting the right buyer's vision and craftsmanship. Whether you're dreaming of a restored country residence, a

  

  Sheryl Morehouse

  Bishop West Real Estate, Inc.

  348 Center St, Pownal, VT 05261
• 

  

  /60

  $200,000

  • Land
  • 58.1 Acres
  • $3,442 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
• 

  

  /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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  /39

  $539,000

  • 3 Beds
  • 2 Baths
  • 2,065 Sq Ft

  262 Dwyers Camp Rd, Shaftsbury, VT 05262

  Well designed and newer home on 10.085 acres in Shaftsbury, VT. Offering 3 bedrooms, including main level primary bedroom and 2 full bathrooms. Cathedral ceiling formal dining room and modern kitchen with dining area and breakfast bar. Large living room with vaulted ceiling and lots of light. Main level laundry and rear mudroom finish the first floor. Upstairs there is a wonderful loft area, 2

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  262 Dwyers Camp Rd, Shaftsbury, VT 05262
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  /10

  $109,000

  • Land
  • 30.8 Acres
  • $3,539 per Acre

  0 Old Gale Hill Rd Unit 5099471, Shaftsbury, VT 05262

  30 acres of Heaven located on a private road just 20 minutes from the center of Shaftsbury . There is a mix of hardwoods, evergreens and wet lands around the pond. this is suitable for a dry camp. A slice paradise to get away to in the Green Mountains.

  Dan Mason Perrott Realty

  0 Old Gale Hill Rd Unit 5099471, Shaftsbury, VT 05262
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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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  /14

  $224,000

  $14K PRICE DROP

  • 1,222 Sq Ft

  117 Putnam St, Bennington, VT 05201

  This beautifully renovated 2-unit home by JDN Properties offers 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 residence with a luxurious upstairs primary suite and kitchenette, use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize

  Dan Mason Perrott Realty

  117 Putnam St, Bennington, VT 05201
• 

  

  /43

  $619,000

  • 4 Beds
  • 2.5 Baths
  • 2,692 Sq Ft

  34 Monument Ave, Bennington, VT 05201

  Set along tree-lined Monument Avenue in prestigious and historic Old Bennington, the Spargo House offers a rare opportunity to own a distinctive piece of Vermont history. Dating to circa 1800, this remarkable home was once the longtime residence of noted author, historian and collector John Spargo, founder and longtime director of the Bennington Museum. Just below the Bennington Battle Monument,

  Jeffrey Dorman

  34 Monument Ave, Bennington, VT 05201
• 

  

  /28

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,608 Sq Ft

  107 Jefferson Ave, Bennington, VT 05201

  Terrific in town location for this 3 bedroom, 2 bathroom home in Bennington. Offering living room, large kitchen, formal dining room and office/study. Covered porch and patio. Privacy bushes and yard. Property is being sold "as-is".

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  107 Jefferson Ave, Bennington, VT 05201
• 

  

  /50

  $150,000

  $10K 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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  /31

  $90,000

  $35K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  109 Evergreen Dr, Bennington, VT 05201

  House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front porch,

  Zachary Zupan EXP Realty

  109 Evergreen Dr, Bennington, VT 05201
• 

  

  /6

  $199,900

  • 3 Beds
  • 2 Baths
  • 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
• 

  

  /22

  $499,000

  • 3,648 Sq Ft

  938 Vt Route 7a, Shaftsbury, VT 05262

  Strong income potential and a versatile unit mix make this 4-unit property an outstanding investment opportunity. Offered at an attractive 10% cap rate, the building features two 2-bedroom, 1-bath units, a spacious 3-bedroom, 1-bath unit, and a 1-bedroom, 1-bath apartment, appealing to a wide range of tenants. This well-positioned property offers dependable rental income and the flexibility that

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  938 Vt Route 7a, Shaftsbury, VT 05262
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  /36

  $259,000

  • 4 Beds
  • 2 Baths
  • 1,768 Sq Ft

  549 Houran Rd, Bennington, VT 05201

  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

  Abi Gregorio

  549 Houran Rd, Bennington, VT 05201
• 

  

  /11

  $179,900

  • 2 Beds
  • 1 Bath
  • 848 Sq Ft

  302 U S 7 S, Woodford, VT 05201

  Over 3 acres, a brook and lots of woods for walking. Room for a terraced garden, tons of parking and minutes to Bennington! This 2 bedroom ranch style home has a huge eat in kitchen and a lovely big living room with lots of windows. There is a bonus sun room with laundry. Owners are using an attached shed as a chicken coop! Sweet find at this affordable price!

  Christine Lewis Brattleboro Area Realty

  302 U S 7 S, Woodford, VT 05201
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  /52

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  113 Main St, Bennington, VT 05201

  Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

  Lindsey Martin Maple Leaf Real Estate

  113 Main St, Bennington, VT 05201
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  /48

  $429,000

  • 2 Beds
  • 2 Baths
  • 7,000 Sq Ft

  3310 Vermont 346, Pownal, VT 05260

  Former Church Offers So Many Opportunities. What might be your dream or requirements? This 1889 Church located in the quiet country village of North Pownal, Vermont, could fill them, however big or small. A single family home for all seasons and celebrations? A wedding venue? A place to live and work, rolled into one with plenty of space no matter what you do, from sculpting to computer imaging?

  Paul Harsch HARSCH ASSOCIATES

  3310 Vermont 346, Pownal, VT 05260
• 

  

  /45

  $357,500

  $8K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,735 Sq Ft

  19 Royal St, North Bennington, VT 05257

  Welcome to this beautifully updated four-bedroom home, ideally located in a sought-after North Bennington neighborhood. Situated on over half an acre, this property offers the perfect balance of privacy and convenience—just steps from scenic hiking trails and close to Bennington College. Step inside to discover a freshly renovated kitchen and bathroom, complemented by new flooring throughout the

  Lindsey Martin Maple Leaf Real Estate

  19 Royal St, North Bennington, VT 05257
• 

  

  /43

  $319,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  683 Water St, North Bennington, VT 05257

  Much larger than it looks and completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much "like new". All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  683 Water St, North Bennington, VT 05257
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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
• 

  

  /51

  $1,795,000

  • 3 Beds
  • 3 Baths
  • 5,228 Sq Ft

  2167 Myers Rd, Shaftsbury, VT 05262

  Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the

  Kelley Mccarthy Mahar McCarthy Real Estate

  2167 Myers Rd, Shaftsbury, VT 05262
• 

  

  /27

  $189,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,485 Sq Ft

  432 South St Unit D2, Bennington, VT 05201

  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

  Abi Gregorio

  432 South St Unit D2, Bennington, VT 05201
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  /7

  $997,000

  • Land
  • 23,086 Sq Ft
  • $1,881,132 per Acre

  153 Northside Dr, Bennington, VT 05201

  Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

  Lori Hurley Four Corner Properties LLC

  153 Northside Dr, Bennington, VT 05201
• 

  

  /9

  $279,000

  $16K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,206 Sq Ft

  116 S Branch St Unit 118, Bennington, VT 05201

  Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

  Julie Glover Mahar McCarthy Real Estate

  116 S Branch St Unit 118, Bennington, VT 05201
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  /8

  $250,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  924 Vt Route 7a, Shaftsbury, VT 05262

  Full of character and opportunity, this charming 2-bedroom, 2-bath home in Shaftsbury offers an affordable entry into homeownership or a fantastic addition to an investment portfolio. Once serving as the local post office, the property has a unique history and a cozy footprint that makes it ideal as a starter home, downsizing option, or rental property. Recent improvements include a beautifully

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  924 Vt Route 7a, Shaftsbury, VT 05262
• 

  

  /3

  $1,295,000

  • Land
  • 52.61 Acres
  • $24,615 per Acre

  00 Montgomery Rd, Pownal, VT 05261

  A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

  Ann Greenwood Alton + Westall Real Estate Agency, LLC

  00 Montgomery Rd, Pownal, VT 05261
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  /60

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 3,295 Sq Ft

  142 Schenkar Rd, Pownal, VT 05261

  Welcome to your own private oasis! Set on 30 private wooded acres, this well-maintained three-bedroom, 2.5-bath Colonial presents a rare opportunity to enjoy expansive acreage, exceptional mountain views (including the Bennington Battle Monument!), and peaceful surroundings in a highly versatile tri-state location near the Vermont, Massachusetts, and New York borders. The 2,083 square-foot home

  Erin McCormick KW Vermont

  142 Schenkar Rd, Pownal, VT 05261
• 

  

  /43

  $2,100,000

  • 4 Beds
  • 3 Baths
  • 3,780 Sq Ft

  1228 Skiparee Rd, Pownal, VT 05260

  Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena

  Christiane Carroccio TPW Real Estate

  1228 Skiparee Rd, Pownal, VT 05260
• 

  

  /60

  $574,900

  $5K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 2,529 Sq Ft

  126 Simeon Dean Rd, Shaftsbury, VT 05262

  Horse enthusiasts take notice! Barn Recently renovated w New Electric, 3@12x12 stalls, new Loft & Heated Tack Rm added, or use as desired, Hobby Shop, Antiques, Storage. Wonderful Newly Fenced Pasture & Paddocks & Fencing around house for children or pets. Charming audible Paran Creek from the porch w/nearby adjoining access to serene 6acre Spring Fed Pond. Total of 17.47 acres for your complete

  Denise Byers Green Mountain Premiere Properties

  126 Simeon Dean Rd, Shaftsbury, VT 05262
• 

  

  /15

  $389,000

  New Construction

  • 4 Beds
  • 2 Baths
  • 2,516 Sq Ft

  319 Chester Knoll Dr, Bennington, VT 05201

  Build Your Dream Home—Without Starting From Scratch Now is your chance to own a brand-new home and still make it your own.This beautifully designed new construction home is currently underway and offers buyers the exciting opportunity to select their own finishing touches and create a space that reflects their style and vision.Featuring 4 bedrooms and 2 full bathrooms, this thoughtfully

  Lilli West Maple Leaf Real Estate

  319 Chester Knoll Dr, Bennington, VT 05201
• 

  

  /52

  $285,000

  $4K PRICE DROP

  • 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
• 

  

  /48

  $230,000

  • 3 Beds
  • 1.5 Baths
  • 1,128 Sq Ft

  104 Short St, Bennington, VT 05201

  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

  Lindsey Martin Maple Leaf Real Estate

  104 Short St, Bennington, VT 05201

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