North Bennington, VT Homes

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  /36

  $460,000

  • 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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  /26

  $1,750 per month

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Condo for Rent

  9 Mechanic St Unit B, North Bennington, VT 05257

  9 Mechanic St Unit B, North Bennington, VT 05257
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  /30

  $345,750 Sold Oct 21, 2025

  374 Overlea Rd, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft
  • Built 1948

  Last Sold Summary

  • 5% Below List Price
  • $197/SF
  • 58 Days On Market

  Last Listing Agent Gregory Cutler Four Seasons Sotheby's Int'l Realty

  374 Overlea Rd, North Bennington, VT 05257
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  /37

  Est $378,153 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft

  91 Mcguire St, North Bennington, VT 05257

  91 Mcguire St, North Bennington, VT 05257
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  /52

  $725,000

  • 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 50

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 810-8434

  2 Cold Spring Rd, North Bennington, VT 05257
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  /25

  $1,850 per month

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Condo for Rent

  9 Church St Unit 9 Church St, North Bennington, VT 05257

  Beautifully maintained 2 bedroom unit (half of a duplex) in desirable North Bennington. Heat included with rent.Credit and background checks required. First and security due at lease signing. Sorry no smoking, and no pets.

  9 Church St Unit 9 Church St, North Bennington, VT 05257
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  /42

  $252,000 Sold Jul 25, 2025

  935 Shaftsbury Hollow Rd, North Bennington, VT 05257

  • 2 Beds
  • 1 Bath
  • 1,221 Sq Ft
  • Built 1965

  Last Sold Summary

  • 15% Below List Price
  • $206/SF
  • 41 Days On Market

  Current Estimated Value $280,817

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  935 Shaftsbury Hollow Rd, North Bennington, VT 05257
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  /30

  Est $412,228 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,623 Sq Ft

  94 Lake Dr, North Bennington, VT 05257

  94 Lake Dr, North Bennington, VT 05257
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  /27

  $320,000

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft

  196 Granger Hollow Rd, North Bennington, VT 05257

  This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large living room. 3 bedrooms, including an addition with a large primary with 2 closets inlcuding one whick is a large walk-in closet. A large full bath with washer/dryer hookups completes the living area. The house has a partial concrete basement

  Steve Schoppmeyer BHG Masiello Brattleboro

  196 Granger Hollow Rd, North Bennington, VT 05257
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  /20

  $1,275 per month

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  18 Main St Unit C, North Bennington, VT 05257

  Centrally located 3 family house with awesome tenants and awesome neigbors.

  18 Main St Unit C, North Bennington, VT 05257
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  /24

  $42,000 Sold Oct 24, 2025

  26 Asa's Way, Bennington, VT 05257

  • Land
  • 0.48 Acre
  • $87,500 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 55 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Realty

  26 Asa's Way, Bennington, VT 05257
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  /37

  Est $384,660 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  181 Dunham Ave, North Bennington, VT 05257

  181 Dunham Ave, North Bennington, VT 05257
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  /39

  $269,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  77 Mcguire St, North Bennington, VT 05257

  Charming Ranch in the sought-after Paran Acres neighborhood, this tidy 3BR/1BA is a blank slate waiting for your personal touches. Photos have been virtually staged to help you visualize just how sweet this home can be. Step inside to find sun-filled rooms and an easy, open layout designed for comfortable, low-maintenance living. A clean, dry basement offers endless possibilities: create a cozy

  Angela Bevin Maple Leaf Realty

  77 Mcguire St, North Bennington, VT 05257
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  /16

  $130,000 Sold Nov 25, 2025

  76 Harvest Hills Dr, North Bennington, VT 05257

  • 3 Beds
  • 1 Bath
  • 1,290 Sq Ft
  • Built 1966

  Last Sold Summary

  • 16% Below List Price
  • $101/SF
  • 45 Days On Market

  Last Listing Agent Susan Bellville Bellville Realty

  76 Harvest Hills Dr, North Bennington, VT 05257
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  /39

  Est $239,898 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,413 Sq Ft

  61 Dunham Ave, North Bennington, VT 05257

  61 Dunham Ave, North Bennington, VT 05257
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  /44

  $294,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft

  211 Grandview St, North Bennington, VT 05257

  This inviting home combines classic Vermont charm with modern updates, set on a spacious corner lot that provides plenty of room for outdoor activities, gardening, and relaxation. Step inside to find a bright, open living space with hardwood floors and large windows that fill the rooms with natural light. Upstairs consists of comfortable bedrooms that offer generous closet space and a full bath.

  Flex Realty Group Flex Realty

  211 Grandview St, North Bennington, VT 05257
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  /49

  $313,000 Sold Jul 21, 2025

  1385 N Bennington Rd, North Bennington, VT 05257

  • 4 Beds
  • 2 Baths
  • 2,050 Sq Ft
  • Built 1910

  Last Sold Summary

  • 1% Below List Price
  • $153/SF
  • 53 Days On Market

  Current Estimated Value $349,913

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  1385 N Bennington Rd, North Bennington, VT 05257
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  /40

  Est $500,535 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,236 Sq Ft

  287 Hewitt Dr, North Bennington, VT 05257

  287 Hewitt Dr, North Bennington, VT 05257
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  /27

  $279,000 Under Contract

  • 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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  /2

  $450,000 Sold May 23, 2025

  20 Harvest Hills Dr, North Bennington, VT 05257

  • 4 Beds
  • 2.5 Baths
  • 1,660 Sq Ft
  • Built 1972

  Last Sold Summary

  • $271/SF
  • 0 Days On Market

  Current Estimated Value $443,967

  Last Listing Agent Floyd Amidon Maple Leaf Realty

  20 Harvest Hills Dr, North Bennington, VT 05257
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  /45

  Est $431,509 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,573 Sq Ft

  294 Tinkham Rd, North Bennington, VT 05257

  294 Tinkham Rd, North Bennington, VT 05257
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  /52

  $389,000

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

  263 Elm St, North Bennington, VT 05257

  New Price! 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 graces 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

  Margretta Fischer Wohler Realty Group

  263 Elm St, North Bennington, VT 05257
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  /60

  $420,000 Sold Jun 26, 2025

  123 Bank St, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 2,753 Sq Ft
  • Built 1952

  Last Sold Summary

  • 6% Below List Price
  • $153/SF
  • 31 Days On Market

  Current Estimated Value $418,935

  Last Listing Agent Margretta Fischer Wohler Realty Group

  123 Bank St, North Bennington, VT 05257
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  /29

  Est $367,912 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 2,400 Sq Ft

  604 Tinkham Rd, North Bennington, VT 05257

  604 Tinkham Rd, North Bennington, VT 05257
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  /36

  $399,000 Pending

  • 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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  /60

  $652,000 Sold Jul 21, 2025

  21 Main St, North Bennington, VT 05257

  • 6 Beds
  • 4.5 Baths
  • 4,708 Sq Ft
  • Built 1857

  Last Sold Summary

  • 7% Below List Price
  • $138/SF
  • 65 Days On Market

  Current Estimated Value $651,156

  Last Listing Agent Thomas Martins Maple Leaf Realty

  21 Main St, North Bennington, VT 05257
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  /24

  Est $502,912 Not Listed For Sale

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

  318 Eleanors Way, North Bennington, VT 05257

  318 Eleanors Way, North Bennington, VT 05257
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  /4

  $190,000

  • 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. Current tenants keep their units up well.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  32-34 Sage St, Bennington, VT 05257
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  /29

  $367,000 Sold Nov 21, 2025

  26 College Rd, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 1945

  Last Sold Summary

  • 7% Below List Price
  • $189/SF
  • 54 Days On Market

  Last Listing Agent Phil Lewis Mahar McCarthy Real Estate

  26 College Rd, North Bennington, VT 05257
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  /12

  Est $211,114 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 920 Sq Ft

  816 Shaftsbury Hollow Rd, North Bennington, VT 05257

  816 Shaftsbury Hollow Rd, North Bennington, VT 05257
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  /50

  $374,900 Under Contract

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

  927 Water St, North Bennington, VT 05257

  Charming Historic Home with Garden, Barn & Flexible Living Spaces This beautiful 100+ year-old home offers over 3,400 sq. ft. of warmth, character, and room to grow. Flooded with natural light, this home on 2+ acres has three sunny upstairs bedrooms and three baths. In addition to a large living room and full dining room, the main floor has a laundry/mudroom and front and rear parlors that can

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  927 Water St, North Bennington, VT 05257
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  /39

  $215,000 Sold Dec 30, 2024

  3 Church St, North Bennington, VT 05257

  • 3 Beds
  • 1.5 Baths
  • 1,238 Sq Ft
  • Built 1920

  Last Sold Summary

  • 14% Below List Price
  • $174/SF
  • 78 Days On Market

  Current Estimated Value $256,539

  Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

  3 Church St, North Bennington, VT 05257
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  /32

  Est $361,218 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft

  1041 Shaftsbury Hollow Rd, North Bennington, VT 05257

  1041 Shaftsbury Hollow Rd, North Bennington, VT 05257
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  /32

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,696 Sq Ft

  130 Ipan Rd, North Bennington, VT 05257

  Tucked away on a private road, this stunning brick colonial offers over 30 acres of peaceful Vermont countryside-yet is less than 2 miles from the Village of North Bennington and Bennington College. A classic barn and separate studio provide endless possibilities for hobbies, storage, or creative space. The main level features a spacious living room with a fireplace, warm pine floors, and plenty

  Kelley Mccarthy Mahar McCarthy Real Estate

  130 Ipan Rd, North Bennington, VT 05257
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  /53

  $614,000 Sold Sep 15, 2025

  23 Mechanic St, North Bennington, VT 05257

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft
  • Built 1870

  Last Sold Summary

  • 3% Above List Price
  • $250/SF
  • 40 Days On Market

  Current Estimated Value $627,742

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  23 Mechanic St, North Bennington, VT 05257
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  /38

  Est $732,380 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,560 Sq Ft

  1058 Granger Hollow Rd, North Bennington, VT 05257

  1058 Granger Hollow Rd, North Bennington, VT 05257
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  /31

  $400,000 Sold Aug 13, 2025

  2374 Shaftsbury Hollow Rd, North Bennington, VT 05257

  • 2 Beds
  • 1 Bath
  • 1,624 Sq Ft
  • Built 1961

  Last Sold Summary

  • 1% Above List Price
  • $246/SF
  • 10 Days On Market

  Current Estimated Value $435,056

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  2374 Shaftsbury Hollow Rd, North Bennington, VT 05257
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  /30

  Est $470,218 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,429 Sq Ft

  414 Matteson Rd, North Bennington, VT 05257

  414 Matteson Rd, North Bennington, VT 05257
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  /32

  Est $341,209 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,680 Sq Ft

  19 Royal St, North Bennington, VT 05257

  19 Royal St, North Bennington, VT 05257
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  /5

  Est $260,507 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,125 Sq Ft

  2 Royal St, North Bennington, VT 05257

  2 Royal St, North Bennington, VT 05257

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