Bennington, VT

Houses for Sale in Bennington, VT

44Results

Bennington is the largest town in southwestern Vermont and the most searched town on our site outside the Manchester and Dorset area. See all Bennington real estate, create a free account to save this search and receive alerts, or call Josiah Allen Real Estate at 802-867-5555 to speak with an agent.

Newest
New Listing
200 Weeks Street Bennington VT 05201

$215,000

Bennington, VT

200 Weeks Street

  • 3 Beds
  • 2 Baths
  • 0.13 Acres
  • 1,680 SqFt
  • 4 Days on Market
MLS#: 5115662
Active Under Contract

$345,000

Bennington, VT

882 Matteson Road

  • 3 Beds
  • 2 Baths
  • 1.05 Acre
  • 2,232 SqFt
  • 8 Days on Market
MLS#: 5115368
New Listing

$299,000

Bennington, VT

48 Autumn Acres Road

  • 3 Beds
  • 2 Baths
  • 0.44 Acres
  • 1,618 SqFt
  • 11 Days on Market
MLS#: 5114802
New Listing

$389,000

Bennington, VT

319 Chester Knoll Drive

  • 4 Beds
  • 2 Baths
  • 2,516 SqFt
  • 20 Days on Market
MLS#: 5113804
Active Under Contract

$285,000

Bennington, VT

38 Center Street

  • 3 Beds
  • 2 Baths
  • 0.32 Acres
  • 3,000 SqFt
  • 21 Days on Market
MLS#: 5113739
New Listing

$480,000

Bennington, VT

55 Mcintosh Lane

  • 4 Beds
  • 3 Baths
  • 1.13 Acre
  • 3,120 SqFt
  • 21 Days on Market
MLS#: 5113685
Active Under Contract

$425,000

Bennington, VT

78 Astrachan Drive

  • 3 Beds
  • 2 Baths
  • 1.06 Acre
  • 1,788 SqFt
  • 24 Days on Market
MLS#: 5113018

$329,000

Bennington, VT

110 Coulter Street

  • 3 Beds
  • 2 Baths
  • 0.24 Acres
  • 1,563 SqFt
  • 33 Days on Market
MLS#: 5111698

$975,000

Bennington, VT

2100 Monument Avenue

  • 4 Beds
  • 3 Baths
  • 1.97 Acre
  • 3,326 SqFt
  • 34 Days on Market
MLS#: 5111680

$695,000

Bennington, VT

370 Southshire Drive

  • 4 Beds
  • 4 Baths
  • 2.37 Acres
  • 5,769 SqFt
  • 35 Days on Market
MLS#: 5111572

$199,000

Bennington, VT

2 North Street

  • 2 Beds
  • 1 Bath
  • 0.89 Acres
  • 1,397 SqFt
  • 36 Days on Market
MLS#: 5111442
Active Under Contract

$249,500

Bennington, VT

230 Beech Street

  • 3 Beds
  • 2 Baths
  • 0.41 Acres
  • 1,271 SqFt
  • 36 Days on Market
MLS#: 5111369

Single-Family Homes in Bennington, Vermont

Bennington's single-family homes range from Federal and Victorian houses in Old Bennington near the Battle Monument to capes, ranches and colonials in the neighborhoods around downtown and North Bennington. Bennington College, three historic covered bridges and quick access to the Green Mountain National Forest give the area a mix of village life and open country. Route 7 runs north to Manchester and Route 9 heads east toward Brattleboro and west to New York. This search lists every single-family house currently for sale in Bennington. Josiah Allen Real Estate works throughout Bennington County. See Bennington homes under $350K or browse colonial homes in Bennington.

Frequently Asked Questions

What is Bennington, VT known for?
Bennington is known for the Bennington Battle Monument, Bennington College, its historic covered bridges and the village of Old Bennington.
What highways serve Bennington?
Route 7 runs north to Manchester and Rutland, and Route 9 connects Bennington to Brattleboro and to New York State.
Broker Reciprocity 

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated October 30, 2026 7:37 AM EDT