Bennington Vermont Homes for Sale

407 total properties
View 261 Skyboro Road Pownal, VT MLS# 5110100
Save 261 Skyboro Road Pownal, VT MLS# 5110100
1 of 39
$350,000
3

Beds

1.1

Baths

1,256

Sq.Ft.

261 Skyboro Road

Pownal, VT

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Courtesy of HOFFMAN REAL ESTATE
View 291 Spring Hill Road Bennington, VT MLS# 5104363
Save 291 Spring Hill Road Bennington, VT MLS# 5104363
1 of 43
$355,000
3

Beds

2.0

Baths

2,016

Sq.Ft.

291 Spring Hill Road

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 230 North Street Bennington, VT MLS# 5097265
Save 230 North Street Bennington, VT MLS# 5097265
1 of 43
$360,000
1,968

Sq.Ft.

230 North Street

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 7252 Main Street Manchester, VT MLS# 5096948
Save 7252 Main Street Manchester, VT MLS# 5096948
1 of 15
$365,000

7252 Main Street

Manchester, VT

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Courtesy of CHRIS FUCCI ASSOCIATES, LTD
View 143 Mattison Road Pownal, VT MLS# 5113030
  • Recently Listed
Save 143 Mattison Road Pownal, VT MLS# 5113030
1 of 35
$369,900
3

Beds

2.0

Baths

2,556

Sq.Ft.

143 Mattison Road

Pownal, VT

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Courtesy of KW VERMONT - BRENDA JONES REAL ESTATE GROUP
View 0 Wall Street # Lot 2 & 3 Winhall, VT MLS# 5093473
Save 0 Wall Street # Lot 2 & 3 Winhall, VT MLS# 5093473
1 of 9
$374,900
0.0

Baths

0 Wall Street # Lot 2 & 3

Winhall, VT

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Courtesy of THE HAVEN GROUP
View 0 Winhall Hollow Road # Lot 23 Ravenwood Winhall, VT MLS# 5073717
Save 0 Winhall Hollow Road # Lot 23 Ravenwood Winhall, VT MLS# 5073717
1 of 38
$375,000
0.0

Baths

0 Winhall Hollow Road # Lot 23 Ravenwood

Winhall, VT

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Courtesy of WOHLER REALTY GROUP
View 527 Jennings Brook Drive Bennington, VT MLS# 5080868
Save 527 Jennings Brook Drive Bennington, VT MLS# 5080868
1 of 25
$375,000
2

Beds

2.0

Baths

1,190

Sq.Ft.

527 Jennings Brook Drive

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 446 Highland Avenue Manchester, VT MLS# 5079187
Save 446 Highland Avenue Manchester, VT MLS# 5079187
1 of 37
$379,000
3

Beds

1.0

Baths

1,663

Sq.Ft.

446 Highland Avenue

Manchester, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 515 Buck Hill Road Arlington, VT MLS# 5093425
Save 515 Buck Hill Road Arlington, VT MLS# 5093425
1 of 31
$379,000
3

Beds

1.0

Baths

1,535

Sq.Ft.

515 Buck Hill Road

Arlington, VT

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Courtesy of FOUR CORNER PROPERTIES LLC
View 1580 Main Road Stamford, VT MLS# 5107230
Save 1580 Main Road Stamford, VT MLS# 5107230
1 of 25
$379,000
2

Beds

1.0

Baths

1,276

Sq.Ft.

1580 Main Road

Stamford, VT

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Courtesy of MORESI REAL ESTATE PARTNERS
View 319 Chester Knoll Drive Bennington, VT MLS# 5113804
  • Recently Listed
Save 319 Chester Knoll Drive Bennington, VT MLS# 5113804
1 of 33
$389,000
4

Beds

2.0

Baths

2,516

Sq.Ft.

319 Chester Knoll Drive

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 2 Bromley Lane Bennington, VT MLS# 5106470
Save 2 Bromley Lane Bennington, VT MLS# 5106470
1 of 31
$395,000
4

Beds

1.1

Baths

1,816

Sq.Ft.

2 Bromley Lane

Bennington, VT

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Courtesy of PACELLI ZEPKA CORPORATION
View 126 Washington Avenue Bennington, VT MLS# 5064429
Save 126 Washington Avenue Bennington, VT MLS# 5064429
1 of 30
$399,000
5,208

Sq.Ft.

126 Washington Avenue

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 126 Washington Avenue Bennington, VT MLS# 5064754
Save 126 Washington Avenue Bennington, VT MLS# 5064754
1 of 29
$399,000
6

Beds

3.0

Baths

5,208

Sq.Ft.

126 Washington Avenue

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 253 Perkins Road Rupert, VT MLS# 5098562
Save 253 Perkins Road Rupert, VT MLS# 5098562
1 of 36
$399,000
4

Beds

2.0

Baths

2,768

Sq.Ft.

253 Perkins Road

Rupert, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 16B Bromley Knolls Road # B Winhall, VT MLS# 5105387
Save 16B Bromley Knolls Road # B Winhall, VT MLS# 5105387
1 of 20
$399,000
3

Beds

2.0

Baths

1,225

Sq.Ft.

16B Bromley Knolls Road # B

Winhall, VT

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Courtesy of WWW.HOMEZU.COM
View 928 Main Road Stamford, VT MLS# 5106013
Save 928 Main Road Stamford, VT MLS# 5106013
1 of 48
$399,000
4

Beds

2.0

Baths

3,096

Sq.Ft.

928 Main Road

Stamford, VT

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Courtesy of LAMACCHIA REALTY INC.
View 2937 Dorset West Road Dorset, VT MLS# 5013651
Save 2937 Dorset West Road Dorset, VT MLS# 5013651
1 of 12
$399,500
0.0

Baths

2937 Dorset West Road

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 87 B Hill Road Pownal, VT MLS# 5102082
Save 87 B Hill Road Pownal, VT MLS# 5102082
1 of 41
$399,900
3

Beds

2.1

Baths

2,760

Sq.Ft.

87 B Hill Road

Pownal, VT

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Courtesy of MAPLE LEAF REAL ESTATE

Information deemed reliable but not guaranteed.

“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 10/10/2026”

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