Bennington Vermont Homes for Sale

402 total properties
View 00 VT Route 11 Peru, VT MLS# 5072898
Save 00 VT Route 11 Peru, VT MLS# 5072898
1 of 14
$2,395,000
0.0

Baths

00 VT Route 11

Peru, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
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
View 241 High Hill Road Manchester, VT MLS# 5099394
Save 241 High Hill Road Manchester, VT MLS# 5099394
1 of 26
$2,300,000
5

Beds

3.1

Baths

3,332

Sq.Ft.

241 High Hill Road

Manchester, 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 543 Lower Hollow Road Dorset, VT MLS# 5089892
Save 543 Lower Hollow Road Dorset, VT MLS# 5089892
1 of 52
$2,285,000
5

Beds

4.1

Baths

4,647

Sq.Ft.

543 Lower Hollow Road

Dorset, VT

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Courtesy of WOHLER REALTY GROUP
View 288 Cedar Lane Peru, VT MLS# 5061819
Save 288 Cedar Lane Peru, VT MLS# 5061819
1 of 57
$2,275,000
9

Beds

6.2

Baths

5,512

Sq.Ft.

288 Cedar Lane

Peru, VT

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Courtesy of CUMMINGS & CO
View 165 High Meadow Road Winhall, VT MLS# 5111781
  • Recently Listed
Save 165 High Meadow Road Winhall, VT MLS# 5111781
1 of 40
$2,250,000
4

Beds

4.1

Baths

3,034

Sq.Ft.

165 High Meadow Road

Winhall, VT

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Courtesy of 42 NORTH LP
View 301 Northside Drive Bennington, VT MLS# 5072776
Save 301 Northside Drive Bennington, VT MLS# 5072776
1 of 1
$2,190,000
0.0

Baths

301 Northside Drive

Bennington, VT

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Courtesy of TPW REAL ESTATE
View 655 Squirrel Hollow Road Dorset, VT MLS# 5093536
  • Virtual Tour
Save 655 Squirrel Hollow Road Dorset, VT MLS# 5093536
1 of 25
$1,997,000
4

Beds

2.1

Baths

4,125

Sq.Ft.

655 Squirrel Hollow Road

Dorset, VT

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Courtesy of LANDVEST, INC/WOODSTOCK
View 209 Jack Cross Road Shaftsbury, VT MLS# 5109798
  • Recently Listed
Save 209 Jack Cross Road Shaftsbury, VT MLS# 5109798
1 of 48
$1,990,000
4

Beds

3.1

Baths

3,844

Sq.Ft.

209 Jack Cross Road

Shaftsbury, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 226-228 Northside Drive Bennington, VT MLS# 5074956
Save 226-228 Northside Drive Bennington, VT MLS# 5074956
1 of 30
$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
Save 00 VT Route 11 Peru, VT MLS# 5077219
1 of 8
$1,900,000
0.0

Baths

00 VT Route 11

Peru, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 751 Main Road Stamford, VT MLS# 5085047
Save 751 Main Road Stamford, VT MLS# 5085047
1 of 60
$1,900,000
6

Beds

4.2

Baths

5,704

Sq.Ft.

751 Main Road

Stamford, VT

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Courtesy of UNITED COUNTRY REAL ESTATE MIKE JARVIS GROUP INC
View 27 Mountain View Road Winhall, VT MLS# 5092802
  • Virtual Tour
Save 27 Mountain View Road Winhall, VT MLS# 5092802
1 of 54
$1,895,000
6

Beds

6.1

Baths

5,896

Sq.Ft.

27 Mountain View Road

Winhall, VT

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Courtesy of STRATTON REAL ESTATE
View 93 Elizabeth Court Sunderland, VT MLS# 5108165
Save 93 Elizabeth Court Sunderland, VT MLS# 5108165
1 of 59
OPEN HOUSE: Saturday 10/3 10:00 AM - 12:00 PM
$1,815,000
5

Beds

4.1

Baths

5,588

Sq.Ft.

93 Elizabeth Court

Sunderland, VT

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Courtesy of WOHLER REALTY GROUP
View 2167 Myers Road Shaftsbury, VT MLS# 5078597
Save 2167 Myers Road Shaftsbury, VT MLS# 5078597
1 of 51
$1,795,000
3

Beds

3.0

Baths

5,228

Sq.Ft.

2167 Myers Road

Shaftsbury, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 1310 Dorset Hill Road Dorset, VT MLS# 5090426
Save 1310 Dorset Hill Road Dorset, VT MLS# 5090426
1 of 38
$1,795,000
4

Beds

3.0

Baths

3,370

Sq.Ft.

1310 Dorset Hill Road

Dorset, VT

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Courtesy of REAL BROKER LLC
View 84 Frost Pond Road Dorset, VT MLS# 5098268
Save 84 Frost Pond Road Dorset, VT MLS# 5098268
1 of 32
$1,795,000
5

Beds

3.0

Baths

5,287

Sq.Ft.

84 Frost Pond Road

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 312 Beartown Road Manchester, VT MLS# 5094155
  • Virtual Tour
Save 312 Beartown Road Manchester, VT MLS# 5094155
1 of 56
$1,775,000
4

Beds

3.1

Baths

3,000

Sq.Ft.

312 Beartown Road

Manchester, VT

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Courtesy of TPW REAL ESTATE
View 1949 South Road Peru, VT MLS# 5100514
Save 1949 South Road Peru, VT MLS# 5100514
1 of 40
$1,699,000
4

Beds

4.0

Baths

2,951

Sq.Ft.

1949 South Road

Peru, VT

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Courtesy of THE HAVEN GROUP
View 1944 Monument Avenue Bennington, VT MLS# 5105174
  • Virtual Tour
Save 1944 Monument Avenue Bennington, VT MLS# 5105174
1 of 53
$1,695,000
3

Beds

2.1

Baths

4,120

Sq.Ft.

1944 Monument Avenue

Bennington, VT

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Courtesy of MAHAR MCCARTHY 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 10/2/2026”

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