Bennington Vermont Homes for Sale

367 total properties
View LOT 354 Oberhugel Road Stamford, VT MLS# 5114712
Save LOT 354 Oberhugel Road Stamford, VT MLS# 5114712
1 of 7
$30,000
0.0

Baths

LOT 354 Oberhugel Road

Stamford, VT

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Courtesy of REAL BROKER LLC
View 168 Stones Throw Lane Manchester, VT MLS# 5114727
Save 168 Stones Throw Lane Manchester, VT MLS# 5114727
1 of 36
$374,000
3

Beds

1.0

Baths

931

Sq.Ft.

168 Stones Throw Lane

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 2848 US Route 7 Pownal, VT MLS# 5114639
Save 2848 US Route 7 Pownal, VT MLS# 5114639
1 of 3
$125,000
3,800

Sq.Ft.

2848 US Route 7

Pownal, VT

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Courtesy of HARSCH ASSOCIATES
The time to sell is now! THE TIME TO SELL IS NOW!
View 1035 Holy Smoke Road Shaftsbury, VT MLS# 5114724
Save 1035 Holy Smoke Road Shaftsbury, VT MLS# 5114724
1 of 60
$1,450,000
5

Beds

5.0

Baths

6,129

Sq.Ft.

1035 Holy Smoke Road

Shaftsbury, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 228 Jepson Road Stamford, VT MLS# 5114700
Save 228 Jepson Road Stamford, VT MLS# 5114700
1 of 9
$269,000
3

Beds

1.1

Baths

2,200

Sq.Ft.

228 Jepson Road

Stamford, VT

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Courtesy of MORESI REAL ESTATE PARTNERS
View 127-133 Webb Street Bennington, VT MLS# 5113984
Save 127-133 Webb Street Bennington, VT MLS# 5113984
1 of 22
$835,000
20

Beds

8.0

Baths

9,664

Sq.Ft.

127-133 Webb Street

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 127-133 Webb Street Bennington, VT MLS# 5114075
Save 127-133 Webb Street Bennington, VT MLS# 5114075
1 of 24
$835,000
9,664

Sq.Ft.

127-133 Webb Street

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 122 Blue Heron Lane Dorset, VT MLS# 5113863
Save 122 Blue Heron Lane Dorset, VT MLS# 5113863
1 of 60
$2,250,000
4

Beds

3.1

Baths

4,831

Sq.Ft.

122 Blue Heron Lane

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 327 Bahan Road Shaftsbury, VT MLS# 5113867
Save 327 Bahan Road Shaftsbury, VT MLS# 5113867
1 of 57
$799,000
3

Beds

2.1

Baths

3,514

Sq.Ft.

327 Bahan Road

Shaftsbury, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 319 Chester Knoll Drive Bennington, VT MLS# 5113804
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 0 White Road Readsboro, VT MLS# 5113810
Save 0 White Road Readsboro, VT MLS# 5113810
1 of 1
$280,000
0.0

Baths

0 White Road

Readsboro, VT

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Courtesy of HARSCH ASSOCIATES
View 310 Longview Drive Manchester, VT MLS# 5113615
Save 310 Longview Drive Manchester, VT MLS# 5113615
1 of 49
$1,090,000
5

Beds

4.0

Baths

4,450

Sq.Ft.

310 Longview Drive

Manchester, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 55 McIntosh Lane Bennington, VT MLS# 5113685
Save 55 McIntosh Lane Bennington, VT MLS# 5113685
1 of 36
$465,000
4

Beds

2.1

Baths

3,120

Sq.Ft.

55 McIntosh Lane

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 38 Center Street Bennington, VT MLS# 5113739
  • Virtual Tour
Save 38 Center Street Bennington, VT MLS# 5113739
1 of 48
$285,000
3

Beds

2.0

Baths

3,000

Sq.Ft.

38 Center Street

Bennington, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 1958 Mt. Anthony Road Pownal, VT MLS# 5113781
Save 1958 Mt. Anthony Road Pownal, VT MLS# 5113781
1 of 60
$1,100,000
3

Beds

3.0

Baths

2,117

Sq.Ft.

1958 Mt. Anthony Road

Pownal, VT

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Courtesy of MONARCH REALTY
View 224-226 Branch Street Bennington, VT MLS# 5113809
Save 224-226 Branch Street Bennington, VT MLS# 5113809
1 of 25
$219,000
4

Beds

2.0

Baths

1,298

Sq.Ft.

224-226 Branch Street

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 432 South Street # C3 Bennington, VT MLS# 5113833
Save 432 South Street # C3 Bennington, VT MLS# 5113833
1 of 15
$149,000
2

Beds

1.1

Baths

819

Sq.Ft.

432 South Street # C3

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 2313 Barnumville Road Manchester, VT MLS# 5113440
Save 2313 Barnumville Road Manchester, VT MLS# 5113440
1 of 58
$1,200,000
5

Beds

5.0

Baths

5,092

Sq.Ft.

2313 Barnumville Road

Manchester, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 3936 North Road Sunderland, VT MLS# 5113459
Save 3936 North Road Sunderland, VT MLS# 5113459
1 of 51
$695,000
4

Beds

2.1

Baths

1,647

Sq.Ft.

3936 North Road

Sunderland, VT

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Courtesy of WOHLER REALTY GROUP
View 33 Old Ridge Road Winhall, VT MLS# 5113794
Save 33 Old Ridge Road Winhall, VT MLS# 5113794
1 of 58
$1,235,000
4

Beds

4.1

Baths

3,060

Sq.Ft.

33 Old 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 11/15/2026”

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