North Bennington, VT Homes

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  $725,000

  • 4 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) 810-8873

  2 Cold Spring Rd, North Bennington, VT 05257
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  /39

  $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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  /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

  Current Estimated Value $371,563

  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 $340,114 Not Listed For Sale

  91 Mcguire St, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • Built 1978

  91 Mcguire St, North Bennington, VT 05257

  Last Sold Summary

  • 10% Above List Price
  • $218/SF
  • 5 Days On Market

  Last Sold Price $309,000

  Last Listing Agent Justine Curry Maple Leaf Realty
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  /13

  $265,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,882 Sq Ft

  13 Hall St, North Bennington, VT 05257

  Full of potential, this 4-bedroom, 2-bath North Bennington home is a true hidden gem with space to grow and a location to love. Cozy up in the living room with its fireplace and hardwood floors, host dinners in the formal dining room, and enjoy the open flow from the kitchen into a large family room. The main floor primary suite offers comfort and privacy with its own bath and walk-in closet,

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  13 Hall St, North Bennington, VT 05257
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  /36

  $435,000 Sold Mar 24, 2026

  1061 Granger Hollow Rd, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 2,108 Sq Ft
  • Built 1990

  Last Sold Summary

  • 13% Below List Price
  • $206/SF
  • 215 Days On Market

  Current Estimated Value $453,102

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  1061 Granger Hollow Rd, North Bennington, VT 05257
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  /30

  Est $400,947 Not Listed For Sale

  94 Lake Dr, North Bennington, VT 05257

  • 3 Beds
  • 1.5 Baths
  • 2,623 Sq Ft
  • Built 1979

  94 Lake Dr, North Bennington, VT 05257

  Last Sold Summary

  • 15% Above List Price
  • $133/SF
  • 24 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Brenda Jones KW Vermont - Brenda Jones Real Estate Group
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  /27

  $290,000

  • 4 Beds
  • 2 Baths
  • 2,190 Sq Ft

  196 Granger Hollow Rd, North Bennington, VT 05257

  Currently being used as a primary home with in-law rental 2nd home, this property could easily transition into a 2 unit multifamily with 2 separate houses with your tenants paying all utilities responsible for their own plowing and yard upkeep. 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

  Steve Schoppmeyer BHG Masiello Brattleboro

  196 Granger Hollow Rd, 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 $254,689

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  935 Shaftsbury Hollow Rd, North Bennington, VT 05257
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  /37

  Est $365,933 Not Listed For Sale

  181 Dunham Ave, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1955

  181 Dunham Ave, North Bennington, VT 05257

  Last Sold Summary

  • 4% Below List Price
  • $339/SF
  • 12 Days On Market

  Last Sold Price $380,000

  Last Listing Agent Abi Gregorio
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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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  /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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  /39

  Est $228,749 Not Listed For Sale

  61 Dunham Ave, North Bennington, VT 05257

  • 3 Beds
  • 1 Bath
  • 1,413 Sq Ft
  • Built 1920

  61 Dunham Ave, North Bennington, VT 05257

  Last Sold Summary

  • 52% Above List Price
  • $106/SF
  • 29 Days On Market

  Last Sold Price $150,000

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
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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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  /39

  $255,500 Sold Jan 15, 2026

  77 Mcguire St, North Bennington, VT 05257

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $253/SF
  • 15 Days On Market

  Current Estimated Value $257,590

  Last Listing Agent Angela Bevin Maple Leaf Realty

  77 Mcguire St, North Bennington, VT 05257
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  /40

  Est $493,082 Not Listed For Sale

  287 Hewitt Dr, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 2,236 Sq Ft
  • Built 1974

  287 Hewitt Dr, North Bennington, VT 05257

  Last Sold Summary

  • 11% Above List Price
  • $199/SF
  • 68 Days On Market

  Last Sold Price $445,000

  Last Listing Agent Angela Bevin Maple Leaf Realty
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  $269,900

  • 3 Beds
  • 1.5 Baths
  • 900 Sq Ft

  2092 N Bennington Rd, North Bennington, VT 05257

  Waterfront Bungalow style house offering 3 bedrooms and 2 bathrooms. This home has 2 bedrooms upstairs and a pocket half bathroom. downstairs has a master bedroom with a newly remodeled ensuite, kitchen with breakfast table area, 4 seasons living space in the back and a front livingroom with new flooring. The previous owner used the 4 seasons room as a formal dining room since it has

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  2092 N Bennington Rd, 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

  Current Estimated Value $202,312

  Last Listing Agent Susan Bellville Bellville Realty

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

  Est $384,490 Not Listed For Sale

  294 Tinkham Rd, North Bennington, VT 05257

  • 2 Beds
  • 2 Baths
  • 1,573 Sq Ft
  • Built 1975

  294 Tinkham Rd, North Bennington, VT 05257

  Last Sold Summary

  • 7% Below List Price
  • $264/SF
  • 4 Days On Market

  Last Sold Price $415,000

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
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  /25

  $1,425,000

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

  1058 Granger Hollow Rd, North Bennington, VT 05257

  A private Vermont sanctuary set on over 40 acres of meadows, rolling hills, stone walls, and mature forest. This sophisticated modern farmhouse offers rare peace, privacy, and natural beauty, and sweeping seasonal views from every room.Designed to blend seamlessly into the land, the light-filled home features expansive Marvin windows and refined custom finishes throughout. The chef’s kitchen

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  1058 Granger Hollow Rd, 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 $321,049

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  1385 N Bennington Rd, North Bennington, VT 05257
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  /24

  Est $449,962 Not Listed For Sale

  318 Eleanors Way, North Bennington, VT 05257

  • 4 Beds
  • 3 Baths
  • 2,065 Sq Ft
  • Built 1968

  318 Eleanors Way, North Bennington, VT 05257

  Last Sold Summary

  • 18% Above List Price
  • $184/SF
  • 10 Days On Market

  Last Sold Price $380,000

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
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  /44

  $275,000 Sold Jan 23, 2026

  211 Grandview St, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Below List Price
  • $149/SF
  • 21 Days On Market

  Current Estimated Value $286,493

  Last Listing Agent Flex Realty Group Flex Realty

  211 Grandview St, North Bennington, VT 05257
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  /12

  Est $225,233 Not Listed For Sale

  816 Shaftsbury Hollow Rd, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 920 Sq Ft
  • Built 1935

  816 Shaftsbury Hollow Rd, North Bennington, VT 05257

  Last Sold Summary

  • 88% Above List Price
  • $130/SF
  • 111 Days On Market

  Last Sold Price $120,000

  Last Listing Agent Kevin Holmes Blue Slate Realty
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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 $463,895

  Last Listing Agent Floyd Amidon Maple Leaf Realty

  20 Harvest Hills Dr, North Bennington, VT 05257
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  /32

  Est $343,035 Not Listed For Sale

  1041 Shaftsbury Hollow Rd, North Bennington, VT 05257

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1986

  1041 Shaftsbury Hollow Rd, North Bennington, VT 05257

  Last Sold Summary

  • 8% Above List Price
  • $289/SF
  • 27 Days On Market

  Last Sold Price $319,000

  Last Listing Agent Abi Gregorio
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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 $424,846

  Last Listing Agent Margretta Fischer Wohler Realty Group

  123 Bank St, North Bennington, VT 05257
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  /30

  Est $445,652 Not Listed For Sale

  414 Matteson Rd, North Bennington, VT 05257

  • 3 Beds
  • 2.5 Baths
  • 1,429 Sq Ft
  • Built 1981

  414 Matteson Rd, North Bennington, VT 05257

  Last Sold Summary

  • 6% Above List Price
  • $294/SF
  • 4 Days On Market

  Last Sold Price $420,000

  Last Listing Agent Lindsey Martin Maple Leaf Realty
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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 $634,108

  Last Listing Agent Thomas Martins Maple Leaf Realty

  21 Main St, North Bennington, VT 05257
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  /32

  Est $349,703 Not Listed For Sale

  19 Royal St, North Bennington, VT 05257

  • 4 Beds
  • 1 Bath
  • 1,680 Sq Ft
  • Built 2002

  19 Royal St, North Bennington, VT 05257

  Last Sold Summary

  • 8% Above List Price
  • $193/SF
  • 16 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Lindsey Martin Maple Leaf Realty
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  /27

  $274,000 Sold Jan 22, 2026

  26 Sage St, Bennington, VT 05257

  • 9 Beds
  • 3 Baths
  • 3,176 Sq Ft
  • Built 1820

  Last Sold Summary

  • 8% Below List Price
  • $86/SF
  • 55 Days On Market

  Last Listing Agent Lilli West Maple Leaf Realty

  26 Sage St, Bennington, VT 05257
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  /29

  Est $388,000 Not Listed For Sale

  3 Polygraphic Ln, North Bennington, VT 05257

  • 4 Beds
  • 2 Baths
  • 2,247 Sq Ft
  • Built 1946

  3 Polygraphic Ln, North Bennington, VT 05257

  Last Sold Summary

  • 19% Above List Price
  • $145/SF
  • 20 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
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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

  Current Estimated Value $374,588

  Last Listing Agent Phil Lewis Mahar McCarthy Real Estate

  26 College Rd, North Bennington, VT 05257
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  /38

  Est $340,953 Not Listed For Sale

  683 Water St, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1934

  683 Water St, North Bennington, VT 05257

  Last Sold Summary

  • 14% Above List Price
  • $199/SF
  • 58 Days On Market

  Last Sold Price $299,000

  Last Listing Agent Angela Bevin Maple Leaf Realty
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  /52

  $378,500 Sold Mar 26, 2026

  263 Elm St, North Bennington, VT 05257

  • 4 Beds
  • 2 Baths
  • 2,368 Sq Ft
  • Built 1948

  Last Sold Summary

  • 3% Below List Price
  • $160/SF
  • 0 Days On Market

  Current Estimated Value $371,001

  Last Listing Agent Margretta Fischer Wohler Realty Group

  263 Elm St, North Bennington, VT 05257
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  /32

  Est $319,264 Not Listed For Sale

  159 Matteson Rd, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft
  • Built 1973

  159 Matteson Rd, North Bennington, VT 05257

  Last Sold Summary

  • 6% Above List Price
  • $193/SF
  • 34 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Vicki Wilson Maple Leaf Realty
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  /50

  $355,000 Sold Jan 29, 2026

  927 Water St, North Bennington, VT 05257

  • 5 Beds
  • 4 Baths
  • 3,400 Sq Ft
  • Built 1893

  Last Sold Summary

  • 11% Below List Price
  • $104/SF
  • 200 Days On Market

  Current Estimated Value $365,137

  Last Listing Agent Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  927 Water St, North Bennington, VT 05257
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  /40

  Est $427,981 Not Listed For Sale

  23 Church St, North Bennington, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1847

  23 Church St, North Bennington, VT 05257

  Last Sold Summary

  • 4% Below List Price
  • $235/SF
  • 6 Days On Market

  Last Sold Price $446,500

  Last Listing Agent Vicki Wilson Maple Leaf Realty
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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 $587,552

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

  23 Mechanic St, North Bennington, VT 05257
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  /30

  Est $312,396 Not Listed For Sale

  4 Church St, North Bennington, VT 05257

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1910

  4 Church St, North Bennington, VT 05257

  Last Sold Summary

  • 11% Above List Price
  • $217/SF
  • 7 Days On Market

  Last Sold Price $281,000

  Last Listing Agent Linda McLenithan SoVermont Realty

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