Bennington Vermont Homes for Sale

282 total properties
View 40 Bourn Brook Road # 50 Manchester, VT MLS# 5074946
  • Recently Listed
Save 40 Bourn Brook Road # 50 Manchester, VT MLS# 5074946
1 of 16
$225,000
1

Beds

1.0

Baths

616

Sq.Ft.

40 Bourn Brook Road # 50

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 226-228 Northside Drive Bennington, VT MLS# 5074956
  • Recently Listed
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 818 Old Depot Road Shaftsbury, VT MLS# 5074845
  • Recently Listed
Save 818 Old Depot Road Shaftsbury, VT MLS# 5074845
1 of 23
$120,000
2

Beds

1.0

Baths

880

Sq.Ft.

818 Old Depot Road

Shaftsbury, VT

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Courtesy of GREAT AMERICAN DREAM REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 109 Evergreen Drive Bennington, VT MLS# 5074746
  • Recently Listed
Save 109 Evergreen Drive Bennington, VT MLS# 5074746
1 of 31
$125,000
3

Beds

1.0

Baths

1,508

Sq.Ft.

109 Evergreen Drive

Bennington, VT

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Courtesy of EXP REALTY
View 13 Betty Johnson Lane Winhall, VT MLS# 5074830
  • Recently Listed
Save 13 Betty Johnson Lane Winhall, VT MLS# 5074830
1 of 39
$849,000
4

Beds

3.0

Baths

2,797

Sq.Ft.

13 Betty Johnson Lane

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 56 Lower Taylor Hill Road Winhall, VT MLS# 5074721
  • Recently Listed
Save 56 Lower Taylor Hill Road Winhall, VT MLS# 5074721
1 of 15
$500,000
Studio

Beds

0.0

Baths

56 Lower Taylor Hill Road

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 141 Hillvale Road Manchester, VT MLS# 5074392
Save 141 Hillvale Road Manchester, VT MLS# 5074392
1 of 24
$435,000
2

Beds

3.0

Baths

1,689

Sq.Ft.

141 Hillvale Road

Manchester, VT

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Courtesy of RE/MAX FOUR SEASONS
View 61 East Branch Farms # 1 Manchester, VT MLS# 5074305
  • Recently Listed
Save 61 East Branch Farms # 1 Manchester, VT MLS# 5074305
1 of 40
$305,000
3

Beds

2.1

Baths

1,378

Sq.Ft.

61 East Branch Farms # 1

Manchester, VT

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Courtesy of CUMMINGS & CO
View 1086 West Road Bennington, VT MLS# 5074314
  • Recently Listed with 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 57 Pearl Buck Drive # 33 Winhall, VT MLS# 5074260
  • Recently Listed
Save 57 Pearl Buck Drive # 33 Winhall, VT MLS# 5074260
1 of 50
$750,000
3

Beds

2.0

Baths

2,000

Sq.Ft.

57 Pearl Buck Drive # 33

Winhall, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 2092 N Bennington Road Bennington, VT MLS# 5074418
  • Recently Listed
Save 2092 N Bennington Road Bennington, VT MLS# 5074418
1 of 35
$269,900
3

Beds

1.1

Baths

900

Sq.Ft.

2092 N Bennington Road

Bennington, VT

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Courtesy of KW VERMONT - BRENDA JONES REAL ESTATE GROUP
View #7 Stratton West Road # #7 Winhall, VT MLS# 5074011
  • Recently Listed
Save #7 Stratton West Road # #7 Winhall, VT MLS# 5074011
1 of 49
$510,000
4

Beds

3.0

Baths

1,680

Sq.Ft.

#7 Stratton West Road # #7

Winhall, VT

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Courtesy of MICHAEL ENGLAND REAL ESTATE
View 3637 Vermont Rte 7A Arlington, VT MLS# 5074065
  • Recently Listed
Save 3637 Vermont Rte 7A Arlington, VT MLS# 5074065
1 of 46
$345,000
2

Beds

2.0

Baths

1,680

Sq.Ft.

3637 Vermont Rte 7A

Arlington, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 67 High Meadow Road Winhall, VT MLS# 5074118
  • Recently Listed
Save 67 High Meadow Road Winhall, VT MLS# 5074118
1 of 58
$3,075,000
6

Beds

4.2

Baths

6,437

Sq.Ft.

67 High Meadow Road

Winhall, VT

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Courtesy of WOHLER REALTY GROUP
View 97 North Branch Road # H4 Winhall, VT MLS# 5073906
  • Recently Listed
Save 97 North Branch Road # H4 Winhall, VT MLS# 5073906
1 of 1
$450,000
Studio

Beds

0.0

Baths

97 North Branch Road # H4

Winhall, VT

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Courtesy of STRATTON REAL ESTATE
View 276 Wilcox Hollow Road Sandgate, VT MLS# 5073964
  • Recently Listed
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 341 Dewey Street Bennington, VT MLS# 5073867
Save 341 Dewey Street Bennington, VT MLS# 5073867
1 of 58
$259,900
3

Beds

2.0

Baths

1,432

Sq.Ft.

341 Dewey Street

Bennington, VT

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Courtesy of MAPLE LEAF REALTY
View 5481 Main Street Manchester, VT MLS# 5073746
Save 5481 Main Street Manchester, VT MLS# 5073746
1 of 50
$565,000
5

Beds

2.2

Baths

2,150

Sq.Ft.

5481 Main Street

Manchester, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, MANCHESTER BRANCH OFFICE
View 78 Ethans Way Bennington, VT MLS# 5073749
  • Recently Listed
Save 78 Ethans Way Bennington, VT MLS# 5073749
1 of 25
$98,999
2

Beds

2.0

Baths

825

Sq.Ft.

78 Ethans Way

Bennington, VT

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Courtesy of EXP REALTY
View 1160 Bergrucken Lane Stamford, VT MLS# 5073757
Save 1160 Bergrucken Lane Stamford, VT MLS# 5073757
1 of 41
$259,000
2

Beds

1.0

Baths

816

Sq.Ft.

1160 Bergrucken Lane

Stamford, VT

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Courtesy of BHG MASIELLO BRATTLEBORO

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 1/29/2026”

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