Homes for Sale near Bennington Regional Day Program

• 

  

  /2

  $225,000

  • 6 Beds
  • 2 Baths
  • 2,112 Sq Ft

  303-305 Gage St, Bennington, VT 05201

  Low maintenance duplex in Bennington. Offering good rental history and income. 2 -3 bedroom units, newer systems, vinyl siding and more. Walking distance to town. schools and recreation.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 471-3314

  303-305 Gage St, Bennington, VT 05201
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  /4

  $249,000

  • 5 Beds
  • 3 Baths
  • 2,184 Sq Ft

  137 Park St, Bennington, VT 05201

  Terrific income producing property. 2 - 1 bedroom units and a 3 bedroom unit with a garage. Close to town and modern systems. Good rental history. Is in a flood zone but owner has found a good flood insurance company.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 444-8271

  137 Park St, Bennington, VT 05201
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  /19

  $225,000

  • Land
  • 17 Acres
  • $13,489 per Acre

  1801 S Stream Rd, Bennington, VT 05201

  Welcome to 1801 South Stream Road a picturesque 16.68 acres of timeless Vermont charm property. This beautiful parcel features two classic Vermont red barns full of character and charm, that offer endless potential. With some repairs, they could be ideal for livestock, storage, or workshop space ready to support your vision for country living. A picturesque pond, in need of a little TLC, offers

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 317-7489

  1801 S Stream Rd, Bennington, VT 05201
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  /41

  $320,000

  • 5 Beds
  • 2 Baths
  • 2,418 Sq Ft

  226 North St, Bennington, VT 05201

  This beautifully detailed 1880 Victorian in Bennington's residential commercial district offers flexibility and income potential all in one. Currently operating as a successful, fully furnished Airbnb, this 5-bedroom, 2-bath property is ready for its next owner. Whether you're an investor looking for cash flow or a buyer seeking a spacious and charming single family home. The main level

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 327-7149

  226 North St, Bennington, VT 05201
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  /38

  $650,000

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  359 Hickory Hill Rd, Bennington, VT 05201

  Welcome to this beautifully updated Center Hall Colonial, privately set on 2.58 wooded acres at the end of a peaceful cul-de-sac just minutes from downtown and major highways. The three bedroom, two and half bath home is truly move in ready, offering the perfect balance of comfort, style, and privacy. Step inside to an open concept main level where the kitchen flows seamlessly into the

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 633-6530

  359 Hickory Hill Rd, Bennington, VT 05201
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  /11

  $185,000

  • 4 Beds
  • 2 Baths
  • 2,643 Sq Ft

  905 County St, Bennington, VT 05201

  Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 204-5943

  905 County St, Bennington, VT 05201
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  /4

  $199,900

  • 5 Beds
  • 2 Baths
  • 1,478 Sq Ft

  32-34 Sage St, Bennington, VT 05257

  Duplex in North Bennington offering 1 way street location. decent yard and 2 - 2 bedroom units. Good investment potential in a walkable and sought location. Town water and sewer.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 402-4994

  32-34 Sage St, Bennington, VT 05257
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  /20

  $750,000

  • 4 Beds
  • 5 Baths
  • 6,650 Sq Ft

  338 Main St, Bennington, VT 05201

  Don't miss your opportunity to own one of the area's most prestigious properties. The "Marble Bank" is located at the intersection of US Route 7 and Vermont Route 9 and is currently the landmark Fiddlehead Gallery. This property offers unique and grand architecture to go along with its high visibility location. Downtown's redevelopment and thriving new businesses make this location even more

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 347-6655

  338 Main St, Bennington, VT 05201
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  /4

  $279,000

  • 4 Beds
  • 4 Baths
  • 2,080 Sq Ft

  123 Bradford St, Bennington, VT 05201

  4 unit apartment building with great rental history and income. Front and back porches and balcony. Great location. Showings to begin 6/10/2024

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 210-1728

  123 Bradford St, Bennington, VT 05201
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  /16

  $145,000

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

  755 Main St, Bennington, VT 05201

  Many possibilities with this property located on Main Street in Bennington. Zoned village commercial but currently a 3 bedroom 1 and a half bath home. Nice kitchen, dining room, living room, main level primary with half bath, main level laundry and more. Needs some TLC. Won't qualify for first time homebuyer programs.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 444-8936

  755 Main St, Bennington, VT 05201
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  /41

  $335,000

  • 3 Beds
  • 1.5 Baths
  • 1,682 Sq Ft

  23 Robinson Ave, Bennington, VT 05201

  Nestled on a quiet street just moments from the golf course, this beautiful two-story brick home offers timeless charm and modern updates. The inviting front porch and lush perennial gardens set the tone for this well-loved property, which also features a fenced-in yard, a small outbuilding, a brand-new shed, and a peaceful backyard water feature. Inside, you'll find 3 bedrooms and 1.5 baths with

  Kelley Mccarthy Mahar McCarthy Real Estate

  23 Robinson Ave, Bennington, VT 05201
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  /33

  $355,000

  • 4 Beds
  • 2 Baths
  • 2,072 Sq Ft

  60 Knoll Crest Ln, Bennington, VT 05201

  Step into this well maintained brick and clapboard residence, perfectly nestled in a lovely neighborhood. Just minutes from the hospital and a short, pleasant walk to downtown, this home offers the best of both convenience and community.Bathed in natural light, the interior boasts an inviting and functional layout highlighted by gleaming hardwood floors and timeless character throughout.

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  60 Knoll Crest Ln, Bennington, VT 05201
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  /25

  $305,000

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft

  120 Albe Dr, Bennington, VT 05201

  Comfortable, convenient and close to downtown Bennington and all its amenities. Built in 2001, in a quiet neighborhood, the home features 3 bedrooms and 2.5 baths,, which includes a primary suite with its own bath. The first floor offers a spacious eat-in kitchen with washer and dryer efficiently installed in a large closet. The kitchen also has glass doors that open to private deck and a level

  Ann Greenwood Alton + Westall Real Estate Agency, LLC

  120 Albe Dr, Bennington, VT 05201
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  /45

  $355,000

  • 4 Beds
  • 1 Bath
  • 1,680 Sq Ft

  19 Royal St, North Bennington, VT 05257

  Charming North Bennington Home in a Desirable Neighborhood.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

  Lindsey Martin Maple Leaf Realty

  19 Royal St, North Bennington, VT 05257
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  /41

  $524,900

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  245 Southshire Dr, Bennington, VT 05201

  Nestled in one of Bennington’s most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm—all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System (BATS).The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a

  Ann Greenwood Alton + Westall Real Estate Agency, LLC

  245 Southshire Dr, Bennington, VT 05201
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  /53

  $595,000

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  23 Mechanic St, North Bennington, VT 05257

  Modern Comfort Meets Historic Charm in North Bennington, VermontNestled within the heart of North Bennington's National Historic District, this thoroughly modern and light-filled home offers the perfect blend of timeless character and contemporary living. Situated on a beautifully landscaped 0.69-acre lot, the property includes a private backyard with ample space for perennial and vegetable

  Kelley Mccarthy Mahar McCarthy Real Estate

  23 Mechanic St, North Bennington, VT 05257
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  /50

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,941 Sq Ft

  97 Buck Hill Rd, Shaftsbury, VT 05262

  Two homes on 4.67 acres in Shaftsbury, VT! This village home offers a rare opportunity indeed by including a separate 2 bedroom ranch home as well. The main home is a charming New England farmhouse with 3 bedrooms and 2 bathrooms, living room, formal dining room, kitchen, main level laundry and so much more. The accessory dwelling unit offers 2 bedrooms, 1 bathroom, eat-in kitchen and living

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  97 Buck Hill Rd, Shaftsbury, VT 05262
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  /26

  $289,900

  • 3 Beds
  • 1.5 Baths
  • 1,576 Sq Ft

  519 South St, Bennington, VT 05201

  Welcome to this beautifully maintained 3-bedroom, 1.25-bath home nestled on a corner lot in Bennington. This inviting property blends classic charm with thoughtful updates, offering comfort and style both inside and out.Step into the spacious kitchen featuring stunning wood cabinetry, granite countertops, and a functional island with a bar sink-perfect for entertaining or everyday living. The

  Kelley Mccarthy Mahar McCarthy Real Estate

  519 South St, Bennington, VT 05201
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  /49

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,664 Sq Ft

  93 Pace Rd, Bennington, VT 05201

  Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about

  Harvey Roettinger RE/MAX North Professionals

  93 Pace Rd, Bennington, VT 05201
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  /50

  $398,900

  • 5 Beds
  • 4 Baths
  • 3,400 Sq Ft

  927 Water St, North Bennington, VT 05257

  Stately North Bennington Colonial with In-Law Suite & Barn on 2.6 Acres.Step into timeless elegance in this beautifully crafted colonial-style home located in the heart of charming North Bennington. Offering 5 spacious bedrooms and 4 bathrooms, this home features a flexible floor plan that includes a private in-law suite, formal living and dining rooms, a welcoming foyer, and both front and

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  927 Water St, North Bennington, VT 05257
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  /48

  $599,900

  • 4 Beds
  • 3.5 Baths
  • 3,742 Sq Ft

  34 Southshire Dr, Bennington, VT 05201

  Expansive Ranch on 2.4 Acres in Desirable Southshire Neighborhood – Bennington, VermontSet on a generous 2.4-acre lot in the sought-after Southshire neighborhood, this spacious ranch offers comfortable living with scenic privacy and versatile space. The main level features a well-appointed kitchen that opens to a cozy family room complete with a fireplace and built-in bookshelves, all

  Kelley Mccarthy Mahar McCarthy Real Estate

  34 Southshire Dr, Bennington, VT 05201
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  /52

  $775,000

  • 4 Beds
  • 3.5 Baths
  • 4,032 Sq Ft

  77 Monument Ave, Bennington, VT 05201

  Located in the prestigious Village of Old Bennington, this stately 4,000+ sq. ft. center hall Colonial sits on 1.6 beautifully landscaped acres with a year-round creek and charming footbridge. Thoughtfully maintained, it features updates including electrical, plumbing, new roofing, and rebuilt chimneys. A gracious foyer welcomes you, flanked by a formal parlor with fireplace and half bath,

  Moira Spivey Four Seasons Sotheby's Int'l Realty

  77 Monument Ave, Bennington, VT 05201
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  /36

  $199,900

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  1211 Carpenter Hill Rd, Bennington, VT 05201

  Charming, fully furnished woodland retreat on over 3.5 acres with sweeping mountain views. This private getaway features two cozy cabins, each with a sleeping loft, warm wood finishes, and rustic charm. The main cabin includes a vaulted living area with exposed beams, a wood stove, vintage-style kitchen, and a spacious deck with built-in seating.The second cabin offers flexible space for guests,

  Jesse Dimitropolis BISHOP WEST REAL ESTATE

  1211 Carpenter Hill Rd, Bennington, VT 05201
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  /14

  $43,000

  • Land
  • 0.48 Acre
  • $89,583 per Acre

  26 Asa's Way, Bennington, VT 05257

  Walking trails, a paved road, underground utilities, and water/sewer at the street, what more could you ask for? Situated high on Asa's Way, almost a half acre of slightly sloping and level lot is ready to build on. Over 200 feet of road frontage allows for many home designs; from a hillside house that maximizes the southerly sun, to a modern bungalow perched on a flat landing, bring your ideas!

  Angela Bevin Maple Leaf Realty

  26 Asa's Way, Bennington, VT 05257
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  /53

  $410,000

  • 3 Beds
  • 2 Baths
  • 1,309 Sq Ft

  495 Fairview St, Bennington, VT 05201

  This charming cape style home is close to town yet enjoys a sense of rural privacy. There is an open floor plan for entertaining on the first floor as well as two bedrooms and a bath. The wood stove keeps you cozy on those cold winter evenings. The second floor is a primary suite with large bath including a claw foot soaking tub and walk-in closet. Access to the full basement via the

  Catherine Cairns Maple Leaf Realty

  495 Fairview St, Bennington, VT 05201
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  /19

  $219,500

  • 3 Beds
  • 1 Bath
  • 1,254 Sq Ft

  14 Robinson Ave, Bennington, VT 05201

  Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

  Timothy Corcoran Mahar McCarthy Real Estate

  14 Robinson Ave, Bennington, VT 05201
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  /9

  $1,950,000

  • Land
  • 7 Acres
  • $278,571 per Acre

  720 N Branch St, Bennington, VT 05201

  Prime redevelopment opportunity in Bennington. 720 North Branch Street offers 6 acres of level land with frontage and easy access—ideal for residential or mixed-use development. Included in the sale is 702 North Branch Street, a two-unit duplex with a 3-bedroom apartment on the first floor and a 2-bedroom unit upstairs. Recent improvements include a new boiler, oil tank, and hot water heater.

  Paul Carroccio TPW Real Estate

  720 N Branch St, Bennington, VT 05201
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  /44

  $100,000

  • 5 Beds
  • 1 Bath
  • 1,952 Sq Ft

  273 Union St, Bennington, VT 05201

  This village property has great bones and potential!! First floor includes generously sized kitchen, formal dining room and living room as well as a small office offering the opportunity to expand the full bath to include laundry. The second floor includes four bedrooms including a primary that has a sitting area/dressing room/nursery, whatever suits your needs. Separate barn that while

  Catherine Cairns Maple Leaf Realty

  273 Union St, Bennington, VT 05201
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  /31

  $150,000

  • 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

  Zachary Zupan EXP Realty

  109 Evergreen Dr, Bennington, VT 05201
• 

  

  /22

  $139,000

  • 4 Beds
  • 1 Bath
  • 1,262 Sq Ft

  101 Morgan St, Bennington, VT 05201

  Motivated seller.!!! Move in asd add your finishing touches to this Antique House located in Downtown on a generous corner. This 2 story, 4 bedroom, 1 bath Bennington home has great character featuring a Dutch front door, enclosed front porch, and beautiful bay window. Property has an eat-in kitchen, dinning room, laundry room with washer and dryer, living room, basement, and den! Enjoy being

  Dan Mason Perrott Realty

  101 Morgan St, Bennington, VT 05201
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  /58

  $269,000

  • 7 Beds
  • 4 Baths
  • 4,417 Sq Ft

  200 Depot St, Bennington, VT 05201

  Own a piece of Bennington history! Alex Drysdale House, c. 1850. The grocery store (formerly 138 River Street) operated under the name "A. Drysdale & Son" and was built in 1876. Today this historic property is set up as a four-unit with great income potential. It currently houses three apartments: a freshly renovated four bedroom (used as an Airbnb), three bedroom, and efficiency, along with the

  Justine Curry Maple Leaf Realty

  200 Depot St, Bennington, VT 05201
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  /57

  $200,000

  • 3 Beds
  • 1 Bath
  • 1,416 Sq Ft

  100 Webb St, Bennington, VT 05201

  Enchanted Historic Home with Storybook Charm – A Hidden Gem Near Downtown!Step into a fairytale in this one-of-a-kind, lovingly maintained home — a true magical retreat nestled just minutes from downtown. Owned and cherished by the same family since 1951, this architectural treasure blends old-world artistry with everyday comfort.From the moment you arrive, you're greeted by the

  Lindsey Martin Maple Leaf Realty

  100 Webb St, Bennington, VT 05201
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  /42

  $1,950,000

  • 9 Beds
  • 7 Baths
  • 6,956 Sq Ft

  1086 West Rd, Bennington, VT 05201

  Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining

  Chris DeFelice Four Seasons Sotheby's Int'l Realty

  1086 West Rd, Bennington, VT 05201
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  /35

  $244,900

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft

  115 Jefferson Ave, Bennington, VT 05201

  Located in a charming Bennington neighborhood, this home offers both convenience and comfort, with shopping, schools, the post office, and the hospital just a short distance away. The welcoming three-season front porch is perfect for enjoying your morning coffee or winding down after a long day. Inside, the spacious, eat-in kitchen has brand-new flooring and newer appliances, adding a fresh and

  Kelley Mccarthy Mahar McCarthy Real Estate

  115 Jefferson Ave, Bennington, VT 05201
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  /7

  $175,000

  • Land
  • 15 Acres
  • $11,298 per Acre

  00 Silk Rd, Bennington, VT 05201

  Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision.Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here

  David White OwnerEntry.com

  00 Silk Rd, Bennington, VT 05201
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  /52

  $199,000

  • 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.

  Dan Mason Perrott Realty

  130 Morgan St, Bennington, VT 05201
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  /47

  $275,000

  • 4 Beds
  • 2.5 Baths
  • 2,404 Sq Ft

  120 Imperial Ave, Bennington, VT 05201

  Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find

  Kelley Mccarthy Mahar McCarthy Real Estate

  120 Imperial Ave, Bennington, VT 05201
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  /39

  $297,500

  • 5 Beds
  • 2 Baths
  • 2,294 Sq Ft

  218 Union St, Bennington, VT 05201

  Charming Downtown Victorian - Income Opportunity Meets Timeless StyleTucked behind the classic facade of this downtown Bennington gem lies an incredible opportunity-for homeowners and investors alike. Located in the heart of downtown on a street known for both professional and residential appeal, this Victorian-style duplex offers versatility, character, and reliable income potential. Each

  Kelley Mccarthy Mahar McCarthy Real Estate

  218 Union St, Bennington, VT 05201
• 

  

  /12

  $575,000

  • 6 Beds
  • 4 Baths
  • 15,179 Sq Ft

  423 Main St, Bennington, VT 05201

  Historic building in heart of downtown Bennington with solid income from existing commercial tenancy and a fantastic second floor begging to be utilized as residential space. This loft type space is approx. 8,000 sq. ft. and would be an amazing living space (or several) with varying exposure, views of mountains in the distance and of the downtown area. The building offers an abundance of indoor

  Chris Long BHG Masiello Brattleboro

  423 Main St, Bennington, VT 05201
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  /52

  $429,000

  • 4 Beds
  • 2 Baths
  • 2,368 Sq Ft

  263 Elm St, North Bennington, VT 05257

  Fabulous Four Bedroom Farmhouse. Updated kitchen with new stainless steel appliances. Take in the mountain view through your newer windows over the new stainless steel sink and subway tile backsplash. Natural light floods this spacious home. The first-floor primary bedroom has a private walk-out deck overlooking the large level backyard. The generous living room opens up to a dining area just off

  Margretta Fischer Wohler Realty Group

  263 Elm St, North Bennington, VT 05257

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