Bennington Vermont Homes for Sale

403 total properties
View 3711 Main Road Stamford, VT MLS# 5107516
  • Virtual Tour
Save 3711 Main Road Stamford, VT MLS# 5107516
1 of 37
$169,900
1

Beds

0.0

Baths

789

Sq.Ft.

3711 Main Road

Stamford, VT

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Courtesy of BISHOP WEST REAL ESTATE, INC.
View 0 Stratton Gardens Road # 10a, 10b, Winhall, VT MLS# 5107127
Save 0 Stratton Gardens Road # 10a, 10b, Winhall, VT MLS# 5107127
1 of 11
$240,000
0.0

Baths

0 Stratton Gardens Road # 10a, 10b,

Winhall, VT

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Courtesy of MICHAEL ENGLAND REAL ESTATE
View 3 Kimball Hill Road # 1 Winhall, VT MLS# 5107205
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Save 3 Kimball Hill Road # 1 Winhall, VT MLS# 5107205
1 of 22
$425,000
3

Beds

2.0

Baths

1,344

Sq.Ft.

3 Kimball Hill Road # 1

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
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 601 Riverbend Drive Manchester, VT MLS# 5107271
Save 601 Riverbend Drive Manchester, VT MLS# 5107271
1 of 54
$1,450,000
4

Beds

3.1

Baths

3,551

Sq.Ft.

601 Riverbend Drive

Manchester, VT

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Courtesy of TPW REAL ESTATE
View 0 West Mountain Road Shaftsbury, VT MLS# 5106931
Save 0 West Mountain Road Shaftsbury, VT MLS# 5106931
1 of 9
$85,000
0.0

Baths

0 West Mountain Road

Shaftsbury, VT

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Courtesy of EXP REALTY
View 1376 Shaftsbury Hollow Road Shaftsbury, VT MLS# 5106977
Save 1376 Shaftsbury Hollow Road Shaftsbury, VT MLS# 5106977
1 of 17
$469,000
2

Beds

1.0

Baths

1,144

Sq.Ft.

1376 Shaftsbury Hollow Road

Shaftsbury, VT

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Courtesy of FOUR CORNER PROPERTIES LLC
View 686 Route 30 Dorset, VT MLS# 5106993
Save 686 Route 30 Dorset, VT MLS# 5106993
1 of 27
$345,000
4

Beds

3.0

Baths

2,000

Sq.Ft.

686 Route 30

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View North Pownal Road # 002 232 Pownal, VT MLS# 5107042
Save North Pownal Road # 002 232 Pownal, VT MLS# 5107042
1 of 10
$695,000
0.0

Baths

North Pownal Road # 002 232

Pownal, VT

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Courtesy of ALTON + WESTALL REAL ESTATE AGENCY, LLC
View 40 Kelleher Road Dorset, VT MLS# 5106750
Save 40 Kelleher Road Dorset, VT MLS# 5106750
1 of 53
$949,000
3

Beds

3.0

Baths

1,823

Sq.Ft.

40 Kelleher Road

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 1474 Dorset West Road Dorset, VT MLS# 5106786
Save 1474 Dorset West Road Dorset, VT MLS# 5106786
1 of 60
$1,375,000
3

Beds

3.0

Baths

2,457

Sq.Ft.

1474 Dorset West Road

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 4910 Vaughn Farm Road # #10 Manchester, VT MLS# 5106809
Save 4910 Vaughn Farm Road # #10 Manchester, VT MLS# 5106809
1 of 30
$499,000
4

Beds

3.1

Baths

2,345

Sq.Ft.

4910 Vaughn Farm Road # #10

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 735 Granger Hollow Road Shaftsbury, VT MLS# 5106851
Save 735 Granger Hollow Road Shaftsbury, VT MLS# 5106851
1 of 46
$399,900
3

Beds

2.1

Baths

1,920

Sq.Ft.

735 Granger Hollow Road

Shaftsbury, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 57 Paran Road Shaftsbury, VT MLS# 5106873
Save 57 Paran Road Shaftsbury, VT MLS# 5106873
1 of 35
$349,000
3

Beds

2.0

Baths

1,616

Sq.Ft.

57 Paran Road

Shaftsbury, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 3149 West Hill Drive Readsboro, VT MLS# 5107298
Save 3149 West Hill Drive Readsboro, VT MLS# 5107298
1 of 46
$325,000
2

Beds

1.0

Baths

976

Sq.Ft.

3149 West Hill Drive

Readsboro, VT

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Courtesy of MONARCH REALTY
View 845 Bailey Hill Road Readsboro, VT MLS# 5106559
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Save 845 Bailey Hill Road Readsboro, VT MLS# 5106559
1 of 22
$74,500
1

Beds

0.0

Baths

586

Sq.Ft.

845 Bailey Hill Road

Readsboro, VT

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Courtesy of DEERFIELD VALLEY REAL ESTATE
View 219-221 Washington Avenue Bennington, VT MLS# 5106581
Save 219-221 Washington Avenue Bennington, VT MLS# 5106581
1 of 36
$349,900
6

Beds

4.0

Baths

2,584

Sq.Ft.

219-221 Washington Avenue

Bennington, VT

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Courtesy of HOFFMAN REAL ESTATE
View 134 Grapevine Lane Pownal, VT MLS# 5106582
Save 134 Grapevine Lane Pownal, VT MLS# 5106582
1 of 60
$999,000
4

Beds

3.1

Baths

7,102

Sq.Ft.

134 Grapevine Lane

Pownal, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 171 Garbrooke Drive Bennington, VT MLS# 5106631
Save 171 Garbrooke Drive Bennington, VT MLS# 5106631
1 of 25
$325,000
3

Beds

2.0

Baths

1,688

Sq.Ft.

171 Garbrooke Drive

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 301 Beech Street Bennington, VT MLS# 5106352
Save 301 Beech Street Bennington, VT MLS# 5106352
1 of 39
$179,900
2

Beds

1.0

Baths

462

Sq.Ft.

301 Beech Street

Bennington, 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 10/1/2026”

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