Bennington Vermont Homes for Sale

277 total properties
View 301 Northside Drive Bennington, VT MLS# 5072776
Save 301 Northside Drive Bennington, VT MLS# 5072776
1 of 1
$2,190,000
Studio

Beds

0.0

Baths

301 Northside Drive

Bennington, VT

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Courtesy of TPW REAL ESTATE
View 1228 Skiparee Road Pownal, VT MLS# 5008279
Save 1228 Skiparee Road Pownal, VT MLS# 5008279
1 of 43
$2,100,000
4

Beds

3.0

Baths

3,780

Sq.Ft.

1228 Skiparee Road

Pownal, VT

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Courtesy of TPW REAL ESTATE
View 2589 W. Sandgate Road Sandgate, VT MLS# 5047939
  • Virtual Tour
Save 2589 W. Sandgate Road Sandgate, VT MLS# 5047939
1 of 38
$1,995,000
5

Beds

3.0

Baths

6,323

Sq.Ft.

2589 W. Sandgate Road

Sandgate, VT

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Courtesy of LANDVEST, INC/WOODSTOCK
The time to sell is now! THE TIME TO SELL IS NOW!
View 720 North Branch Street Bennington, VT MLS# 5047411
Save 720 North Branch Street Bennington, VT MLS# 5047411
1 of 10
$1,950,000
Studio

Beds

0.0

Baths

720 North Branch Street

Bennington, VT

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Courtesy of TPW REAL ESTATE
View 1086 West Road Bennington, VT MLS# 5074314
  • Virtual Tour
Save 1086 West Road Bennington, VT MLS# 5074314
1 of 58
$1,950,000
9

Beds

5.2

Baths

6,956

Sq.Ft.

1086 West Road

Bennington, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 226-228 Northside Drive Bennington, VT MLS# 5074956
Save 226-228 Northside Drive Bennington, VT MLS# 5074956
1 of 25
$1,925,000
5,972

Sq.Ft.

226-228 Northside Drive

Bennington, VT

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Courtesy of HOFFMAN REAL ESTATE
View 00 VT Route 11 Peru, VT MLS# 5077219
  • Recently Listed
Save 00 VT Route 11 Peru, VT MLS# 5077219
1 of 8
$1,900,000
Studio

Beds

0.0

Baths

00 VT Route 11

Peru, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 14 Old Ridge Road Winhall, VT MLS# 4988110
  • Virtual Tour
Save 14 Old Ridge Road Winhall, VT MLS# 4988110
1 of 40
$1,899,000
4

Beds

4.0

Baths

4,270

Sq.Ft.

14 Old Ridge Road

Winhall, VT

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Courtesy of TPW 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 276 Wilcox Hollow Road Sandgate, VT MLS# 5073964
Save 276 Wilcox Hollow Road Sandgate, VT MLS# 5073964
1 of 51
$1,875,000
3

Beds

2.1

Baths

3,368

Sq.Ft.

276 Wilcox Hollow Road

Sandgate, VT

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Courtesy of WOHLER REALTY GROUP
View 139 Prospect Street Manchester, VT MLS# 5058891
Save 139 Prospect Street Manchester, VT MLS# 5058891
1 of 60
$1,849,000
3

Beds

2.1

Baths

3,450

Sq.Ft.

139 Prospect Street

Manchester, VT

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Courtesy of THE HAVEN GROUP
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 264 French Hollow Road Winhall, VT MLS# 5076014
  • Recently Listed
Save 264 French Hollow Road Winhall, VT MLS# 5076014
1 of 33
$1,650,000
4

Beds

3.1

Baths

2,813

Sq.Ft.

264 French Hollow Road

Winhall, VT

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Courtesy of WINHALL REAL ESTATE
View 3888-3904 VT Route 7A Arlington, VT MLS# 5046390
Save 3888-3904 VT Route 7A Arlington, VT MLS# 5046390
1 of 60
$1,595,000
14,861

Sq.Ft.

3888-3904 VT Route 7A

Arlington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 3888-3904 VT Route 7A Arlington, VT MLS# 5046479
  • Virtual Tour
Save 3888-3904 VT Route 7A Arlington, VT MLS# 5046479
1 of 60
$1,595,000
17

Beds

18.2

Baths

14,861

Sq.Ft.

3888-3904 VT Route 7A

Arlington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 20 Blackberry Lane Peru, VT MLS# 5075483
Save 20 Blackberry Lane Peru, VT MLS# 5075483
1 of 52
$1,550,000
5

Beds

5.0

Baths

4,650

Sq.Ft.

20 Blackberry Lane

Peru, VT

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Courtesy of RE/MAX FOUR SEASONS
View 1035 Holy Smoke Road Shaftsbury, VT MLS# 5077038
  • Recently Listed
Save 1035 Holy Smoke Road Shaftsbury, VT MLS# 5077038
1 of 46
$1,550,000
5

Beds

5.0

Baths

6,129

Sq.Ft.

1035 Holy Smoke Road

Shaftsbury, VT

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Courtesy of FOUR CORNER PROPERTIES LLC
View 932 McNamara Road Dorset, VT MLS# 5058749
Save 932 McNamara Road Dorset, VT MLS# 5058749
1 of 42
$1,525,000
4

Beds

3.0

Baths

3,931

Sq.Ft.

932 McNamara Road

Dorset, VT

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Courtesy of WOHLER REALTY GROUP
View 500 Nims Road # Lot #2 Dorset, VT MLS# 5049329
Save 500 Nims Road # Lot #2 Dorset, VT MLS# 5049329
1 of 47
$1,500,000
Studio

Beds

0.0

Baths

500 Nims Road # Lot #2

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 3568 Main Street Manchester, VT MLS# 5061491
Save 3568 Main Street Manchester, VT MLS# 5061491
1 of 8
$1,500,000
14,940

Sq.Ft.

3568 Main Street

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY

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 2/27/2026”

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