Homes in ZIP Code 05257

• 

  

  

  /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

  (802) 215-5280

  29 Asa Way, Bennington, VT 05257
• 

  

  

  /11

  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

  (802) 733-9260

  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 $369,539

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

  374 Overlea Rd, North Bennington, VT 05257
• 

  

  

  /37

  Est $347,504

  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

  • 5 Days On Market
• 

  

  

  /52

  $725,000

  $170K PRICE DROP

  • 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
• 

  

  /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 $442,090

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  1061 Granger Hollow Rd, North Bennington, VT 05257
• 

  

  /30

  Est $410,560

  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

  • 24 Days On Market
• 

  

  /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

  (802) 471-2764

  24 Asa Way, Bennington, VT 05257
• 

  

  /7

  $1,500

  Total Monthly Price

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

  11 Route 67 W Unit 2, North Bennington, VT 05257

  Large main room is a real eye grabber! Tall ceilings and large open space. No pets, no smoking, credit and background check is required. Owners live on premise. Water/sewer, and garbage included in the rent. Heat is oil.

  11 Route 67 W Unit 2, North Bennington, VT 05257
• 

  

  /20

  $242,500

  Sold May 06, 2026

  1645 Vermont Route 67 E, Shaftsbury, VT 05257

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 2003

  Last Sold Summary

  • $160/SF
  • 6 Days On Market

  Last Listing Agent Morriah Adams BHG Masiello Brattleboro

  1645 Vermont Route 67 E, Shaftsbury, VT 05257
• 

  

  /37

  Est $389,751

  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
• 

  

  /45

  $365,000

  • 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
• 

  

  /8

  $1,100 Per Month

  • 1 Bed
  • 1 Bath
  • 642 Sq Ft
  • 12-16 Sage St.

  12-16-16 Sage St Unit 1, Bennington, VT 05257

  12-16-16 Sage St Unit 1, Bennington, VT 05257
• 

  

  /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 $254,301

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  935 Shaftsbury Hollow Rd, North Bennington, VT 05257
• 

  

  /40

  Est $502,032

  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
• 

  

  /43

  $339,900

  • 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
• 

  

  /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
• 

  

  /45

  Est $380,920

  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
• 

  

  /43

  $579,000

  • 3 Beds
  • 2 Baths
  • 2,501 Sq Ft

  856 Matteson Rd, North Bennington, VT 05257

  Nestled on 5 private acres, this custom-built log home offers the perfect blend of rustic charm and refined comfort. Surrounded by beautifully curated gardens, mature apple trees, lilacs, maples, plum trees, oaks, and stone walls, the setting is both tranquil and picturesque—yet just minutes from town conveniences. There is even a targeting golf green! Inside, the home showcases a stunning great

  Faith Rhodes Maple Leaf Real Estate

  856 Matteson Rd, 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 $251,657

  Last Listing Agent Angela Bevin Maple Leaf Real Estate

  77 Mcguire St, North Bennington, VT 05257
• 

  

  /24

  Est $435,843

  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

  • 10 Days On Market
• 

  

  /27

  $290,000

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 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
• 

  

  /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 $261,051

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

  13 Hall St, North Bennington, VT 05257
• 

  

  /12

  Est $180,541

  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
• 

  

  /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
• 

  

  /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 $205,002

  Last Listing Agent Susan Bellville Bellville Realty

  76 Harvest Hills Dr, North Bennington, VT 05257
• 

  

  /32

  Est $342,232

  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
• 

  

  /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
• 

  

  /50

  $449,000

  Sold Jun 08, 2026

  1284 Granger Hollow Rd, Shaftsbury, VT 05262

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1979

  Last Sold Summary

  • 3% Below List Price
  • $320/SF
  • 19 Days On Market

  Last Listing Agent Jenifer Prouty Hoffman Hoffman Real Estate

  1284 Granger Hollow Rd, Shaftsbury, VT 05262
• 

  

  /30

  Est $460,127

  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
• 

  

  /12

  $825,000

  $40K PRICE DROP

  • 5,568 Sq Ft

  1931 Vermont Route 67 E, Shaftsbury, VT 05262

  Rare investment opportunity in one of the area’s most desirable neighborhoods! This unique offering includes two historic buildings set on a spacious 1-acre lot, featuring a total of 8 well-maintained units—comprised of (4) two-bedroom apartments and (4) one-bedroom apartments. Each building offers shared covered front porches, perfect for enjoying the charm of this pleasant street setting. The

  Julie Glover Mahar McCarthy Real Estate

  1931 Vermont Route 67 E, Shaftsbury, VT 05262
• 

  

  /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 $314,777

  Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

  1385 N Bennington Rd, North Bennington, VT 05257
• 

  

  /29

  Est $357,106

  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
• 

  

  /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
• 

  

  /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 $282,027

  Last Listing Agent Colt Hazell Flex Realty

  211 Grandview St, North Bennington, VT 05257
• 

  

  /40

  Est $434,845

  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
• 

  

  /30

  $209,000

  $10K PRICE DROP

  • 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
• 

  

  /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 $423,989

  Last Listing Agent Margretta Fischer Wohler Realty Group

  123 Bank St, North Bennington, VT 05257
• 

  

  /39

  Est $266,412

  Not Listed For Sale

  3 Church St, North Bennington, VT 05257

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

  3 Church St, North Bennington, VT 05257

  Last Sold Summary

  • 78 Days On Market

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