Bennington Vermont Homes for Sale

403 total properties
View 148 Barne Lane Pownal, VT MLS# 5104239
Save 148 Barne Lane Pownal, VT MLS# 5104239
1 of 35
$217,500
2

Beds

1.0

Baths

1,258

Sq.Ft.

148 Barne Lane

Pownal, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 75 Sylvan Ridge Road Winhall, VT MLS# 5104082
  • Virtual Tour
Save 75 Sylvan Ridge Road Winhall, VT MLS# 5104082
1 of 15
$115,000
0.0

Baths

75 Sylvan Ridge Road

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 84 Overlook Road Dorset, VT MLS# 5103836
Save 84 Overlook Road Dorset, VT MLS# 5103836
1 of 24
$1,250,000
3

Beds

2.1

Baths

2,035

Sq.Ft.

84 Overlook Road

Dorset, 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 159 Winhall Hollow Road Winhall, VT MLS# 5104104
Save 159 Winhall Hollow Road Winhall, VT MLS# 5104104
1 of 60
$5,575,000
7

Beds

9.1

Baths

9,915

Sq.Ft.

159 Winhall Hollow Road

Winhall, VT

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Courtesy of WOHLER REALTY GROUP
View 212 Taconic Road Manchester, VT MLS# 5104124
Save 212 Taconic Road Manchester, VT MLS# 5104124
1 of 37
$1,600,000
5

Beds

3.2

Baths

4,200

Sq.Ft.

212 Taconic Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 232 Depot Street Bennington, VT MLS# 5103372
Save 232 Depot Street Bennington, VT MLS# 5103372
1 of 44
$189,900
3

Beds

1.0

Baths

1,206

Sq.Ft.

232 Depot Street

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 1625 Barnumville Road Manchester, VT MLS# 5103524
Save 1625 Barnumville Road Manchester, VT MLS# 5103524
1 of 25
$550,000
3

Beds

2.0

Baths

2,009

Sq.Ft.

1625 Barnumville Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 4791-3 Main Street Manchester, VT MLS# 5103569
Save 4791-3 Main Street Manchester, VT MLS# 5103569
1 of 2
$100,000
800

Sq.Ft.

4791-3 Main Street

Manchester, VT

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Courtesy of EXP REALTY
View 37 Brookside Road Manchester, VT MLS# 5103575
Save 37 Brookside Road Manchester, VT MLS# 5103575
1 of 23
$469,000
3

Beds

2.0

Baths

1,188

Sq.Ft.

37 Brookside Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 11 Founders Hill Road Winhall, VT MLS# 5103259
Save 11 Founders Hill Road Winhall, VT MLS# 5103259
1 of 25
$1,200,000
6

Beds

3.1

Baths

4,017

Sq.Ft.

11 Founders Hill Road

Winhall, VT

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Courtesy of DEREK GREENE
View 710 Main Street Bennington, VT MLS# 5102985
Save 710 Main Street Bennington, VT MLS# 5102985
1 of 4
$349,000
8

Beds

4.0

Baths

3,637

Sq.Ft.

710 Main Street

Bennington, VT

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Courtesy of PERROTT REALTY
View 123 Nichols Road Peru, VT MLS# 5102892
Save 123 Nichols Road Peru, VT MLS# 5102892
1 of 60
$3,500,000
6

Beds

5.1

Baths

4,690

Sq.Ft.

123 Nichols Road

Peru, VT

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Courtesy of WOHLER REALTY GROUP
View 0 Mount Anthony Road Bennington, VT MLS# 5102718
Save 0 Mount Anthony Road Bennington, VT MLS# 5102718
1 of 1
$75,000
0.0

Baths

0 Mount Anthony Road

Bennington, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 207 Sycamore Road Woodford, VT MLS# 5102427
Save 207 Sycamore Road Woodford, VT MLS# 5102427
1 of 21
$150,000
4

Beds

1.0

Baths

1,536

Sq.Ft.

207 Sycamore Road

Woodford, VT

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Courtesy of EXP REALTY
View 36A Marisa Lane Dorset, VT MLS# 5102825
Save 36A Marisa Lane Dorset, VT MLS# 5102825
1 of 16
$520,000
3

Beds

2.1

Baths

1,847

Sq.Ft.

36A Marisa Lane

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 78 Bonnet Street Manchester, VT MLS# 5102036
Save 78 Bonnet Street Manchester, VT MLS# 5102036
1 of 50
$1,100,000
5,164

Sq.Ft.

78 Bonnet Street

Manchester, VT

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Courtesy of TPW REAL ESTATE
View 1131 Route 30 Dorset, VT MLS# 5102040
Save 1131 Route 30 Dorset, VT MLS# 5102040
1 of 52
$565,000
4

Beds

2.1

Baths

2,399

Sq.Ft.

1131 Route 30

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 432 South Street # A11 Bennington, VT MLS# 5102057
Save 432 South Street # A11 Bennington, VT MLS# 5102057
1 of 15
$162,500
2

Beds

1.1

Baths

819

Sq.Ft.

432 South Street # A11

Bennington, VT

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Courtesy of FLEX 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
View 6 Sunset Ridge Road Winhall, VT MLS# 5101868
Save 6 Sunset Ridge Road Winhall, VT MLS# 5101868
1 of 59
$2,350,000
5

Beds

3.1

Baths

4,752

Sq.Ft.

6 Sunset Ridge Road

Winhall, VT

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Courtesy of WOHLER REALTY GROUP

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 10/2/2026”

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