Homes for Sale near Mt. Anthony Union High School

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  /39

  $259,000

  • 3 Beds
  • 1.5 Baths
  • 1,264 Sq Ft

  139 Mckinley St, Bennington, VT 05201

  Welcome to 139 McKinley Street in Bennington! This charming 1920 New Englander blends character and convenience in a great village location. Inside, you'll find a first-floor primary bedroom with laundry and a half bath downstairs, a cozy living room with a beautiful woodstove, and hardwood floors upstairs with easy care laminate throughout the main level.A standout feature is the

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (607) 437-6795

  139 Mckinley 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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  /46

  $895,000

  • 5 Beds
  • 2 Baths
  • 2,424 Sq Ft

  2 Cold Spring Rd, North Bennington, VT 05257

  Welcome to 2 Cold Spring Road a cherished homestead steeped in history, beauty, and Vermont tradition. This 1785 Center Hall Colonial has been in the same family for generations and is now ready for its next chapter. With five spacious bedrooms, two full baths, and a classic layout that captures the warmth of country living, this property offers timeless charm with endless potential.Set on

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 810-8434

  2 Cold Spring Rd, North Bennington, VT 05257
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  /60

  $1,950,000

  • 4 Beds
  • 3.5 Baths
  • 3,333 Sq Ft

  1268 Myers Rd, Shaftsbury, VT 05262

  Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, a 2 car garage, top notch equestrian facilities, a trout and koi pond, and the list goes on and on. The winding driveway leads to a world away, as it opens to view of the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 441-6014

  1268 Myers Rd, Shaftsbury, VT 05262
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  /36

  $490,000

  • 3 Beds
  • 2 Baths
  • 2,108 Sq Ft

  1061 Granger Hollow Rd, North Bennington, VT 05257

  Dreaming of a peaceful Vermont lifestyle? This three bedroom, 2 bath home sits on 11.5 acres of beautiful land with rolling open mountain views, a stream, mature apple trees, and an inground pool all the ingredients for your perfect retreat.Step inside to this home that has had a complete refresh. The home offers a first floor bedroom and full bath with a step in shower, making it great

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 481-3292

  1061 Granger Hollow Rd, North Bennington, VT 05257
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  /62

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  679 Middle Pownal Rd, Pownal, VT 05261

  Nestled in the heart of rural Pownal, this beautifully renovated 4-bedroom, 3-bath home offers the perfect blend of modern comfort and peaceful countryside living. Set on 12.1 picturesque acres, the property features a mix of open level land and serene wooded areas, ideal for hobby farming, equestrian use, or simply enjoying nature. Inside, you'll find a spacious and thoughtfully designed layout

  

  Erin Vincent

  BISHOP WEST REAL ESTATE

  (802) 636-6092

  679 Middle Pownal Rd, Pownal, VT 05261
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  /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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  /60

  $1,150,000

  • 3 Beds
  • 3 Baths
  • 2,267 Sq Ft

  636 Dexter Rd, Shaftsbury, VT 05262

  In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic local backroads to write “Stopping by the Woods on a Snowy Evening." The Dexter Road Farmhouse, dating back 225 years, remains a testament to the enduring charm of Vermont and the simpler rhythms of country life. Nestled at the end of a serene, tree-lined town road, this charming 1800 farmhouse captures the

  

  Kristin Comeau

  TPW Real Estate

  (802) 520-1220

  636 Dexter Rd, Shaftsbury, VT 05262
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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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  /41

  $295,000

  • 5 Beds
  • 2 Baths
  • 1,588 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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  /13

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  2017 East Rd, Shaftsbury, VT 05262

  3 bedroom 2 bath, double wide on 1.49 acres in Shaftsbury. Offering good location, large yard, and convenient travel to town. Living room with new pellet stove, kitchen with modern appliances including newer stove and dining area. Outside a 2 car detached garage, storage sheds and front and rear porches. New carpet.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 798-5968

  2017 East Rd, Shaftsbury, VT 05262
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  /11

  $179,900

  • 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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  /21

  $175,000

  • Land
  • 18 Acres
  • $9,749 per Acre

  0 U S 7, Pownal, VT 05261

  Beautiful Pownal Valley views from almost wherever you stand on this 17.95 acre parcel. Zoned for commercial use along the road frontage and rural residential in back creates opportunities for different types of development.

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 327-8230

  0 U S 7, Pownal, VT 05261
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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. Great capitalization and income producer.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 210-1728

  123 Bradford St, Bennington, VT 05201
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  /2

  $20,000

  • Land
  • 3.00 Acres
  • $6,667 per Acre

  0 U S 7, Pownal, VT 05261

  3 acre parcel located behind other parcels. Would be a great place for a hunting "camp", blind or recreation. Right of Way is from 63 Metcalfe Road, Pownal.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 210-3911

  0 U S 7, Pownal, VT 05261
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  /41

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 1,792 Sq Ft

  882 East Rd, Bennington, VT 05201

  Welcome to 882 East Road! This spacious first-floor ranch, set on 1.97 acres, offers comfort, convenience, and room to grow. Built in 2002, the home features three bedrooms and two and half baths, all thoughtfully designed for easy single level living.The open kitchen provides plenty of working space, a beautiful pantry, and excellent flow into a large living room, perfect for gathering and

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 215-3662

  882 East Rd, Bennington, VT 05201
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  /26

  $295,000

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

  235 Elm St Unit 3, Bennington, VT 05201

  This three-unit building features one unit per floor and is ideally located downtown. Set back from the road, it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. Highlights include a large back deck, a spacious partially fenced yard, and a shared driveway with MLS #5057051. The seller prefers to sell both properties together. Listing agent is related to the seller.

  

  Erica Hale

  Ridgeline Real Estate

  (802) 210-4437

  235 Elm St Unit 3, Bennington, VT 05201
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  /17

  $270,000

  • 6 Beds
  • 3 Baths
  • 2,900 Sq Ft

  239 - 241 Elm St, Bennington, VT 05201

  Located downtown, this three-unit building it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. The property includes an unfinished space with the potential to add an additional unit, offering great investment upside. Recent updates include a brand-new roof installed this year. Shared driveway with MLS #5057052; seller is seeking to sell both properties together. Listing

  

  Erica Hale

  Ridgeline Real Estate

  (802) 278-6021

  239 - 241 Elm St, Bennington, VT 05201
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  /30

  $365,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft

  374 Overlea Rd, North Bennington, VT 05257

  A stunning three bedroom, two bath home on a wooded lot with mountain views and bordered on several sides by serene farm pastures! Just a few minutes from downtown Bennington and even closer to the village of North Bennington! Tons of natural light inside that compliments the updated kitchen and open dining / living room areas. First floor includes enclosed rear sun porch/mudroom, laundry and

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  374 Overlea Rd, North Bennington, VT 05257
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  /17

  $485,000

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262

  Discover a true Vermont lifestyle at this meticulously maintained charming farmhouse nestled on picturesque Shaftsbury Hollow Road. This property combines historic character with thoughtful modern updates, offering a serene retreat with breathtaking mountain views across a just shy of 10-acre lot where the White Creek gracefully runs along one side and the entire back boundary. Step out onto the

  Lori Hurley Four Corner Properties LLC

  1376 Shaftsbury Hollow Rd, Shaftsbury, VT 05262
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  /18

  $369,900

  • 4 Beds
  • 2.5 Baths
  • 2,529 Sq Ft

  2842 Vermont Route 7a, Shaftsbury, VT 05262

  Elegant Country Estate with Panoramic Mountain Views – Shaftsbury, VT.Welcome to 2842 VT-7A — an exceptional single-level luxury residence set on over 5 private, landscaped acres in the tranquil hills of Shaftsbury. This custom-designed ranch-style home blends timeless Vermont charm with modern comfort, offering 2,229± sq ft of refined interior space, thoughtfully crafted for both relaxed

  Derek Greene Derek Greene

  2842 Vermont Route 7a, Shaftsbury, VT 05262
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  /36

  $399,000

  • 5 Beds
  • 3 Baths
  • 3,118 Sq Ft

  100 McCarthy Acres, North Bennington, VT 05257

  Nearly Lakefront Living in the Heart of North Bennington!Come for the space—stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

  Nicholas Charest Maple Leaf Realty

  100 McCarthy Acres, North Bennington, VT 05257
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  /41

  $365,000

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft

  509 Thompson Pond Rd, Pownal, VT 05261

  Discover Your Perfect Getaway at Verdmont If you're a nature enthusiast, a rare and exclusive opportunity awaits at the Verdmont Outing Club. Nestled in the heart of the Green Mountain Preserve, this gated community spans nearly 500 acres of unspoiled wilderness-a true haven for outdoor living.As a shareholder, you'll enjoy a wealth of amenities: Water & Land Privileges: Two stunning

  Kelley Mccarthy Mahar McCarthy Real Estate

  509 Thompson Pond Rd, Pownal, VT 05261
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  /36

  $498,000

  • 3 Beds
  • 2 Baths
  • 1,671 Sq Ft

  6 Dwyers Camp Rd, Shaftsbury, VT 05262

  Discover quintessential Vermont living in this charming home, ideally situated on 6.9 serene acres in scenic Shaftsbury, a picturesque town in Southern Vermont. This meticulously maintained residence offers a blend of rustic charm and modern sophistication, providing a tranquil retreat with convenient access to area amenities and attractions. Thoughtful renovations have elevated its interior,

  Lori Hurley Four Corner Properties LLC

  6 Dwyers Camp Rd, Shaftsbury, VT 05262
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  /59

  $679,000

  • 3 Beds
  • 2.5 Baths
  • 3,637 Sq Ft

  272 Oak Hill Rd, Shaftsbury, VT 05262

  Built in 2001, this stunning contemporary home sits on just under 8 peaceful acres and offers a perfect blend of space, light, and comfort. The grand two-story living room features soaring ceilings and a cozy pellet stove, creating an impressive focal point. The first floor offers a spacious primary suite for ultimate convenience, along with a dedicated home office—perfect for remote work or

  Faith Rhodes Maple Leaf Realty

  272 Oak Hill Rd, Shaftsbury, VT 05262
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  /45

  $350,000

  • 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

  $499,900

  • 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 gracious

  Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  245 Southshire Dr, Bennington, VT 05201
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  /50

  $399,900

  • 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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  /33

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,666 Sq Ft

  379 Swallow Hill Rd, Pownal, VT 05261

  Welcome home! Tucked away on over 2.6 private and partially wooded acres in the exclusive and tight-knit Swallow Hill neighborhood, this stunning 3-bedroom, 1.5-bath home offers modern comfort and rustic charm in a serene natural setting in Southern Vermont.Step inside to soaring cathedral ceilings, exposed wood beams, and an abundance of Vermont beauty pouring in through large windows.

  Cassie Barbeau Mahar McCarthy Real Estate

  379 Swallow Hill Rd, Pownal, VT 05261
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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

  $425,000 Open Sun 10:30AM - 12:30PM

  • 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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  /49

  $425,000

  • 4 Beds
  • 4 Baths
  • 3,040 Sq Ft

  458 Fox Hill Rd, Bennington, VT 05201

  Beautiful Colonial-style home with an oversized two-car attached garage, set in one of Bennington’s most desirable neighborhoods. This inviting home features an open kitchen and family room, a bright sunroom, formal living and dining rooms, and 2.5 baths. The primary suite is complemented by three additional bedrooms, offering plenty of space for family and guests. A versatile, walkout finished

  Julie Glover Mahar McCarthy Real Estate

  458 Fox Hill Rd, Bennington, VT 05201
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  /45

  $79,000

  • 4 Beds
  • 1 Bath
  • 1,146 Sq Ft

  109 County St, Bennington, VT 05201

  Great potential to bring this cute antique home back to life! Step inside from the covered side porch to a large living room that connects to two first floor rooms ready for a variety of different uses. The kitchen has a small dining area and leads to a laundry room and 3/4 bath. Keep going and you'll find a useful attached shed/utility room. Upstairs are more bedrooms with plenty of storage,

  Justine Curry Maple Leaf Realty

  109 County St, Bennington, VT 05201
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  /8

  $59,000

  • Land
  • 0.29 Acre
  • $203,448 per Acre

  420 Burgess Rd, Bennington, VT 05201

  Level building lot with town sewer and water at the edge of town.Possible owner financing.

  Dan Mason Perrott Realty

  420 Burgess Rd, Bennington, VT 05201
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  /10

  $245,000

  • 4 Beds
  • 2 Baths
  • 1,652 Sq Ft

  209 Grove St Unit 11, Bennington, VT 05201

  Well-maintained 2-unit property offering flexibility for owner-occupants or investors. The main-level unit features 3 bedrooms, a full bath, an eat-in kitchen with new cabinets, and a laundry room with washer and dryer. The upstairs unit offers 1 bedroom, a full bath, eat-in kitchen, and a cozy living room with hardwood floors. Exterior features include a nice backyard, 2 covered parking spaces

  Julie Glover Mahar McCarthy Real Estate

  209 Grove St Unit 11, Bennington, VT 05201
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  /28

  $299,000

  • 9 Beds
  • 3 Baths
  • 3,176 Sq Ft

  26 Sage St, Bennington, VT 05257

  A wonderful investment opportunity in the desirable village of North Bennington! This income-producing property with three units has been well kept and updated over the years - most recently with a brand new roof. Two of the three-bedroom units have been freshly renovated and all are currently occupied with a strong rental history. Two of the units have two stories, giving it a townhouse feel,

  Lilli West Maple Leaf Realty

  26 Sage St, Bennington, VT 05257
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  /14

  $470,000

  • 3 Beds
  • 7 Baths
  • 2,148 Sq Ft

  106 School St, Bennington, VT 05201

  Investors take note. This 7 unit building features three one bedroom units and four studio units. Tenants pay their own electric and internet. The boiler servicing the building is an efficient pellet boiler. The hot water is also pre-heated with solar to help keep costs low. Five of the units have been updated in the past several years. At current rents and assumed 100% occupancy the building

  William Paquin Maple Leaf Realty

  106 School St, Bennington, VT 05201
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  /33

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  254 Union St, Bennington, VT 05201

  Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs.Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, Bennington, VT 05201

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