Bennington County Real Estate

3,735Results

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Bennington is the oldest county in Vermont. Bennington not only has abundant cultural resources like the Bennington Museum and Southern Vermont Art Center but is also served by well respected institutions such as Southern Vermont College and Bennington College. The largest towns in Bennington County are Bennington and Shaftsbury. Browse available Bennington County real estate below.

Newest

New Listing

$255,000

Sandgate, VT

2650 Rupert Road

2 Beds
1 Bath
17 Acres
1,458 SqFt
1 Day on Market

Listed by Margretta Fischer of Wohler Realty Group

MLS#: 5093708

New Listing

$395,000

Shaftsbury, VT

1111 Old Depot Road

4 Beds
2 Baths
4 Acres
1,593 SqFt
1 Day on Market

Listed by Bob Maisey of Berkshire Hathaway HomeServices Stratton Home

MLS#: 5093706

New Listing

$429,000

Pownal, VT

3310 Vt Route 346

2 Beds
2 Baths
0.86 Acres
6,686 SqFt
1 Day on Market

Listed by Paul Harsch of Harsch Associates

MLS#: 5093596

New Listing

$1,997,000

Dorset, VT

655 Squirrel Hollow Road

4 Beds
3 Baths
23.09 Acres
4,125 SqFt
1 Day on Market

Listed by Laura Kottler of LandVest,Inc/Woodstock

MLS#: 5093536

New Listing

$374,900

Winhall, VT

Wall Street

Land
2.31 Acres
1 Day on Market

Listed by Cheyanne Pugliese of The Haven Group

MLS#: 5093473

New Listing

$875,000

Peru, VT

447 Rock Bottom Lane

3 Beds
2 Baths
20.5 Acres
1,600 SqFt
2 Days on Market

Listed by Andy Reed of Four Seasons Sotheby's Int'l Realty

MLS#: 5093451

New Listing

$399,000

Arlington, VT

515 Buck Hill Road

3 Beds
1 Bath
0.25 Acres
1,535 SqFt
2 Days on Market

Listed by Lori Hurley of Four Corner Properties LLC

MLS#: 5093425

New Listing

$650,000

Manchester, VT

635 Equinox On The Battenkill, Unit Unit L1

4 Beds
2 Baths
2,364 SqFt
5 Days on Market

Listed by Margretta Fischer of Wohler Realty Group

MLS#: 5093125

New Listing

$1,990,000

Winhall, VT

27 Mountain View Road

6 Beds
7 Baths
1.49 Acre
5,896 SqFt
6 Days on Market

Listed by Jamie Wylie of Stratton Real Estate

MLS#: 5092802

New Listing

$325,000

Manchester, VT

80 Murray Hill South Road, Unit 13

2 Beds
3 Baths
1,199 SqFt
7 Days on Market

Listed by Tatsiana Clark of Four Seasons Sotheby's Int'l Realty

MLS#: 5092625

New Listing

$1,295,000

Pownal, VT

00 Montgomery Road

Land
52.61 Acres
9 Days on Market

Listed by Ann Greenwood of Alton + Westall Real Estate Agency,LLC

MLS#: 5092084

New Listing

$198,900

Pownal, VT

348 Center Street

2 Beds
1 Bath
4.15 Acres
1,332 SqFt
11 Days on Market

Listed by Sheryl Morehouse of Bishop West Real Estate,Inc.

MLS#: 5091890

Bennington County VT Homes for Sale

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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 June 9, 2026 10:10 PM EDT