North Bennington, VT Homes

• 

  

  

  /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
• 

  

  

  /10

  Starting at $1,500

  Total Monthly Price

  • 1 - 5 Beds

  940 Water St, North Bennington, VT 05257

  940 Water Street evolved from a late-19th-century factory complex into a modern mixed-use historic property, preserving a key piece of North Bennington’s industrial heritage. Housing renovations began in 2010 and continue through today and into 2017.Available Units We are currently expanding our selection of units and now offer 1+, 2, 3, 4, and 5-bedroom units. I am available to work

  940 Water St, North Bennington, VT 05257
• 

  

  

  /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 $403,722

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

  374 Overlea Rd, North Bennington, VT 05257
• 

  

  

  /60

  Est $446,549

  Not Listed For Sale

  123 Bank St, North Bennington, VT 05257

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

  123 Bank St, North Bennington, VT 05257

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Margretta Fischer Wohler Realty Group
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  /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
• 

  

  /39

  $1,275

  Total Monthly Price

  • 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
• 

  

  /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 $448,825

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  1061 Granger Hollow Rd, North Bennington, VT 05257
• 

  

  /37

  Est $404,641

  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

  • 12 Days On Market

  Last Listing Agent Abi Gregorio
• 

  

  /45

  $357,500

  $8K PRICE DROP Under Contract

  • 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
• 

  

  /39

  $1,275

  Total Monthly Price

  • 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
• 

  

  /24

  $42,000

  Sold Oct 24, 2025

  26 Asa's Way, Bennington, VT 05257

  • Land
  • 20,908 Sq Ft
  • $87,500 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 55 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  26 Asa's Way, Bennington, VT 05257
• 

  

  /40

  Est $542,918

  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

  • 68 Days On Market

  Last Listing Agent Angela Bevin Maple Leaf Real Estate
• 

  

  /43

  $319,900

  $20K PRICE DROP Under Contract

  • 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
• 

  

  /26

  $1,750

  Total Monthly Price

  • 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
• 

  

  /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 $237,055

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  77 Mcguire St, North Bennington, VT 05257
• 

  

  /45

  Est $381,789

  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

  • 4 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /31

  $365,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft

  12 Hall St, North Bennington, VT 05257

  Located in the heart of the charming North Bennington Village, this beautifully renovated home offers the perfect blend of classic character and modern convenience. Completely renovated interior in 2022, including a new roof, this move-in-ready home features three bedrooms and two beautifully updated bathrooms, with the added convenience of a first-floor bedroom and main-level laundry. The

  Kelley Mccarthy Mahar McCarthy Real Estate

  12 Hall St, North Bennington, VT 05257
• 

  

  /22

  $1,795

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  4 Mechanic St Unit A, North Bennington, VT 05257

  Waterfront two bedroom duplex in superb location* RARELY AVAILABLE DUPLEX* Two bedrooms and a full bathroom upstairs* Living room, dining room, laundry room and kitchen on the first floor* Washer/dryer hookups in their own laundry room (there are no W/D units in the apartment) with a closet* Rear deck, new stove and fridge, new windows and doors, nice clean apartment with

  4 Mechanic St Unit A, North Bennington, VT 05257
• 

  

  /13

  $265,000

  Sold May 08, 2026

  13 Hall St, North Bennington, VT 05257

  • 4 Beds
  • 2 Baths
  • 1,882 Sq Ft
  • Built 1907

  Last Sold Summary

  • $141/SF
  • 3 Days On Market

  Current Estimated Value $269,328

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

  13 Hall St, North Bennington, VT 05257
• 

  

  /12

  Est $202,636

  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

  • 111 Days On Market

  Last Listing Agent Kevin Holmes Blue Slate Realty
• 

  

  /27

  $269,900

  $50K PRICE DROP

  • 2,190 Sq Ft

  196 Granger Hollow Rd, North Bennington, VT 05257

  Currently being used as a primary home a vacant 2nd home, this property could be either a single family residence with/without an in-law house or as 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

  Steve Schoppmeyer BHG Masiello Brattleboro

  196 Granger Hollow Rd, North Bennington, VT 05257
• 

  

  /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 $212,805

  Last Listing Agent Susan Bellville Bellville Realty

  76 Harvest Hills Dr, North Bennington, VT 05257
• 

  

  /32

  Est $360,723

  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

  • 27 Days On Market

  Last Listing Agent Abi Gregorio
• 

  

  /49

  $650,000

  • 5 Beds
  • 3 Baths
  • 5,524 Sq Ft

  81 Honeysuckle Ln, North Bennington, VT 05257

  Nestled on 9.89 secluded acres in North Bennington, this exceptional 4-bedroom, 3-bath home offers the perfect blend of character, comfort, and versatility. The sprawling residence features a beautiful interior highlighted by stunning post-and-beam cathedral ceilings and inviting living spaces designed for both everyday living and entertaining. The heart of the home is the large open space

  Kelley Mccarthy Mahar McCarthy Real Estate

  81 Honeysuckle Ln, North Bennington, VT 05257
• 

  

  /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 $290,253

  Last Listing Agent Colt Hazell Flex Realty

  211 Grandview St, North Bennington, VT 05257
• 

  

  /42

  Est $259,041

  Not Listed For Sale

  935 Shaftsbury Hollow Rd, North Bennington, VT 05257

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

  935 Shaftsbury Hollow Rd, North Bennington, VT 05257

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate
• 

  

  /37

  $439,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,389 Sq Ft

  15 Polygraphic Ln, North Bennington, VT 05257

  At the end of a quiet road in North Bennington, this beloved 1979 home is being offered for the first time by its original owner. Set on over an acre with a large private backyard, garden beds, wild blackberries, and a peaceful wooded backdrop, the property feels beautifully tucked away while remaining just a short walk to the Henry Bridge and the Walloomsac River. Inside, the home is timeless,

  Jenifer Prouty Hoffman Hoffman Real Estate

  15 Polygraphic Ln, North Bennington, VT 05257
• 

  

  /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 Real Estate

  26 Sage St, Bennington, VT 05257
• 

  

  /38

  Not Listed For Sale

  1058 Granger Hollow Rd, North Bennington, VT 05257

  • 3 Beds
  • 2.5 Baths
  • 2,560 Sq Ft
  • Built 2006

  1058 Granger Hollow Rd, North Bennington, VT 05257

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Carol O`Connor Four Seasons Sotheby's Int'l Realty
• 

  

  /36

  $359,000

  $40K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,938 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 Real Estate

  100 McCarthy Acres, North Bennington, VT 05257
• 

  

  /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 $372,655

  Last Listing Agent Phil Lewis Mahar McCarthy Real Estate

  26 College Rd, North Bennington, VT 05257
• 

  

  /30

  Est $468,115

  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

  • 4 Days On Market

  Last Listing Agent Lindsey Martin Maple Leaf Real Estate
• 

  

  /4

  $190,000

  $35K PRICE DROP Pending

  • 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
• 

  

  /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 $362,032

  Last Listing Agent Margretta Fischer Wohler Realty Group

  263 Elm St, North Bennington, VT 05257
• 

  

  /29

  Est $362,427

  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

  • 20 Days On Market

  Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate
• 

  /2

  $58,000

  • Land
  • 20,908 Sq Ft
  • $120,833 per Acre

  33 Asa's Way, Bennington, VT 05257

  This lot in beautiful North Bennington is ready to go! Building plans have been drawn up and available to come with the property for an approx. 2200 sq ft 3 bed, 2 bath home with decks facing the mountains. This lot has the electric, water, and sewer available at the street. Beyond having school choice for the elementary it also boasts being the second highest elevation lot in the development,

  William Paquin Maple Leaf Real Estate

  33 Asa's Way, Bennington, VT 05257
• 

  

  /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 $375,281

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

  927 Water St, North Bennington, VT 05257
• 

  

  /40

  Est $456,321

  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

  • 6 Days On Market

  Last Listing Agent Vicki Wilson Maple Leaf Real Estate
• 

  

  /30

  $209,000

  $10K PRICE DROP Under Contract

  • 4 Beds
  • 1 Bath
  • 1,127 Sq Ft

  20 Sage St, North Bennington, VT 05257

  Charming home in the heart of the Village of North Bennington, set on a beautiful village lot and offering solid bones with great potential. This well-maintained property features 4 bedrooms and a 3/4 bath, along with a first-floor bonus room. Wood floors lie beneath the carpet, ready to be revealed. Laundry hookups are in place for added convenience. Some updates are needed, providing an

  Abi Gregorio

  20 Sage St, North Bennington, VT 05257
• 

  

  /52

  $525,000

  Sold Aug 08, 2026

  2 Cold Spring Rd, North Bennington, VT 05257

  • 4 Beds
  • 2 Baths
  • 2,424 Sq Ft
  • Built 1785

  Last Sold Summary

  • 41% Below List Price
  • $217/SF
  • 348 Days On Market

  Current Estimated Value $736,121

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  2 Cold Spring Rd, North Bennington, VT 05257

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