Bennington Vermont Homes for Sale

280 total properties
View 4928 Main Street # #2 Manchester, VT MLS# 5066452
Save 4928 Main Street # #2 Manchester, VT MLS# 5066452
1 of 27
$675,000
2

Beds

2.0

Baths

1,432

Sq.Ft.

4928 Main Street # #2

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 114 Colebrook Road Arlington, VT MLS# 5066245
Save 114 Colebrook Road Arlington, VT MLS# 5066245
1 of 34
$375,000
3

Beds

2.1

Baths

2,800

Sq.Ft.

114 Colebrook Road

Arlington, VT

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Courtesy of OWNERENTRY.COM
View 00 Heartwellville View Road # 64/65/66/69/70 Readsboro, VT MLS# 5066003
Save 00 Heartwellville View Road # 64/65/66/69/70 Readsboro, VT MLS# 5066003
1 of 6
$74,900
Studio

Beds

0.0

Baths

00 Heartwellville View Road # 64/65/66/69/70

Readsboro, VT

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Courtesy of FLEX REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 3746-3738 Main Street # 1 Manchester, VT MLS# 5065565
  • New Construction
Save 3746-3738 Main Street # 1 Manchester, VT MLS# 5065565
1 of 9
$1,350,000
3

Beds

4.1

Baths

3,415

Sq.Ft.

3746-3738 Main Street # 1

Manchester, VT

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Courtesy of WOHLER REALTY GROUP
View 9 Lower Taylor Hill Road Winhall, VT MLS# 5065319
Save 9 Lower Taylor Hill Road Winhall, VT MLS# 5065319
1 of 45
$1,195,000
4

Beds

3.1

Baths

4,200

Sq.Ft.

9 Lower Taylor Hill Road

Winhall, VT

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Courtesy of STRATTON REAL ESTATE
View 317 Pleasant Street Bennington, VT MLS# 5065393
Save 317 Pleasant Street Bennington, VT MLS# 5065393
1 of 40
$198,000
5

Beds

2.0

Baths

2,201

Sq.Ft.

317 Pleasant Street

Bennington, VT

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Courtesy of 3GEN REAL ESTATE INC
View 134 Monument Avenue Bennington, VT MLS# 5065403
Save 134 Monument Avenue Bennington, VT MLS# 5065403
1 of 40
$695,000
3

Beds

2.1

Baths

2,868

Sq.Ft.

134 Monument Avenue

Bennington, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 158 Upland Downs Road Manchester, VT MLS# 5065178
Save 158 Upland Downs Road Manchester, VT MLS# 5065178
1 of 33
$815,000
3

Beds

2.0

Baths

1,743

Sq.Ft.

158 Upland Downs Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 848 Coleville Road Bennington, VT MLS# 5065182
Save 848 Coleville Road Bennington, VT MLS# 5065182
1 of 45
$425,000
4

Beds

3.0

Baths

2,030

Sq.Ft.

848 Coleville Road

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 466 Three Maple Drive Manchester, VT MLS# 5065200
Save 466 Three Maple Drive Manchester, VT MLS# 5065200
1 of 56
$3,350,000
3

Beds

4.1

Baths

3,059

Sq.Ft.

466 Three Maple Drive

Manchester, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 00 Oberdorf Road # Lot 276 Stamford, VT MLS# 5064834
Save 00 Oberdorf Road # Lot 276 Stamford, VT MLS# 5064834
1 of 7
$29,000
Studio

Beds

0.0

Baths

00 Oberdorf Road # Lot 276

Stamford, VT

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Courtesy of SOUTHERN VERMONT REALTY GROUP
View 21 County Road Pownal, VT MLS# 5064470
Save 21 County Road Pownal, VT MLS# 5064470
1 of 43
$450,000
4

Beds

2.0

Baths

2,884

Sq.Ft.

21 County Road

Pownal, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 144 Taconic Avenue Manchester, VT MLS# 5064505
Save 144 Taconic Avenue Manchester, VT MLS# 5064505
1 of 43
$1,895,000
6

Beds

5.1

Baths

5,178

Sq.Ft.

144 Taconic Avenue

Manchester, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, MANCHESTER BRANCH OFFICE
View 215 & 221 VT Route 30 Dorset, VT MLS# 5064340
Save 215 & 221 VT Route 30 Dorset, VT MLS# 5064340
1 of 56
$1,750,000
6

Beds

3.0

Baths

3,340

Sq.Ft.

215 & 221 VT Route 30

Dorset, VT

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Courtesy of WOHLER REALTY GROUP
View 114 Cemetery Avenue Manchester, VT MLS# 5064256
Save 114 Cemetery Avenue Manchester, VT MLS# 5064256
1 of 51
$3,250,000
8,288

Sq.Ft.

114 Cemetery Avenue

Manchester, VT

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Courtesy of WOHLER REALTY GROUP
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 89 Merson Street Bennington, VT MLS# 5064108
Save 89 Merson Street Bennington, VT MLS# 5064108
1 of 34
$349,000
3

Beds

1.1

Baths

1,829

Sq.Ft.

89 Merson Street

Bennington, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 130 Ipan Road Shaftsbury, VT MLS# 5064228
Save 130 Ipan Road Shaftsbury, VT MLS# 5064228
1 of 32
$795,000
3

Beds

2.1

Baths

2,696

Sq.Ft.

130 Ipan Road

Shaftsbury, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 236-240 Grandview Street Bennington, VT MLS# 5063668
Save 236-240 Grandview Street Bennington, VT MLS# 5063668
1 of 21
$75,000
Studio

Beds

0.0

Baths

236-240 Grandview Street

Bennington, VT

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Courtesy of FOUR CORNER PROPERTIES LLC

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 3/10/2026”

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