Bennington Vermont Homes for Sale

293 total properties
View 17 Signal Hill Road Winhall, VT MLS# 5061426
Save 17 Signal Hill Road Winhall, VT MLS# 5061426
1 of 39
$599,000
5

Beds

3.1

Baths

2,468

Sq.Ft.

17 Signal Hill Road

Winhall, VT

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Courtesy of TPW REAL ESTATE
View 624 Main Street Bennington, VT MLS# 5061443
Save 624 Main Street Bennington, VT MLS# 5061443
1 of 15
$269,000
2

Beds

1.0

Baths

2,500

Sq.Ft.

624 Main Street

Bennington, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 143 Stratton Mountain Access Road Winhall, VT MLS# 5061221
  • New Construction
Save 143 Stratton Mountain Access Road Winhall, VT MLS# 5061221
1 of 40
$1,695,000
5

Beds

4.1

Baths

3,688

Sq.Ft.

143 Stratton Mountain Access Road

Winhall, 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 55 Monument Avenue Bennington, VT MLS# 5060833
  • Virtual Tour
Save 55 Monument Avenue Bennington, VT MLS# 5060833
1 of 50
$650,000
3

Beds

2.1

Baths

2,675

Sq.Ft.

55 Monument Avenue

Bennington, VT

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Courtesy of MAPLE LEAF REALTY
View 1059 Bailey Hill Road Readsboro, VT MLS# 5060762
Save 1059 Bailey Hill Road Readsboro, VT MLS# 5060762
1 of 38
$502,900
3

Beds

1.0

Baths

2,400

Sq.Ft.

1059 Bailey Hill Road

Readsboro, VT

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Courtesy of KW VERMONT
View 550 Finbars Forest Road Manchester, VT MLS# 5060396
Save 550 Finbars Forest Road Manchester, VT MLS# 5060396
1 of 28
$629,000
3

Beds

2.0

Baths

1,958

Sq.Ft.

550 Finbars Forest Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 1439 Main Street Manchester, VT MLS# 5060633
Save 1439 Main Street Manchester, VT MLS# 5060633
1 of 30
$550,000
2

Beds

2.0

Baths

2,218

Sq.Ft.

1439 Main Street

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 1568 Depot Street Manchester, VT MLS# 5059843
Save 1568 Depot Street Manchester, VT MLS# 5059843
1 of 27
$895,000
1,848

Sq.Ft.

1568 Depot Street

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 1594 Vermont Route 7A Shaftsbury, VT MLS# 5059756
Save 1594 Vermont Route 7A Shaftsbury, VT MLS# 5059756
1 of 60
$995,000

1594 Vermont Route 7A

Shaftsbury, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 3264 Route 153 Rupert, VT MLS# 5059970
Save 3264 Route 153 Rupert, VT MLS# 5059970
1 of 51
$269,000
2

Beds

1.0

Baths

1,400

Sq.Ft.

3264 Route 153

Rupert, VT

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Courtesy of MCCHESNEY RE, INC.
View 100 Depot Street Bennington, VT MLS# 5059469
Save 100 Depot Street Bennington, VT MLS# 5059469
1 of 4
$300,000
1,122

Sq.Ft.

100 Depot Street

Bennington, VT

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Courtesy of TPW REAL ESTATE
View 736 Main Street Bennington, VT MLS# 5060023
Save 736 Main Street Bennington, VT MLS# 5060023
1 of 54
$825,000
12,868

Sq.Ft.

736 Main Street

Bennington, VT

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Courtesy of MAPLE LEAF REALTY
View 215 Maple Street Bennington, VT MLS# 5059117
Save 215 Maple Street Bennington, VT MLS# 5059117
1 of 26
$189,900
4

Beds

2.0

Baths

1,278

Sq.Ft.

215 Maple Street

Bennington, VT

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Courtesy of HOFFMAN REAL ESTATE
View 0 Oberhugel Road Stamford, VT MLS# 5059139
Save 0 Oberhugel Road Stamford, VT MLS# 5059139
1 of 4
$39,500
Studio

Beds

0.0

Baths

0 Oberhugel Road

Stamford, VT

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Courtesy of MAPLE LEAF REALTY
View 3 Kimball Hill Road # 1 Winhall, VT MLS# 5059005
  • Virtual Tour
Save 3 Kimball Hill Road # 1 Winhall, VT MLS# 5059005
1 of 22
$375,000
3

Beds

2.0

Baths

1,344

Sq.Ft.

3 Kimball Hill Road # 1

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 139 Prospect Street Manchester, VT MLS# 5058891
Save 139 Prospect Street Manchester, VT MLS# 5058891
1 of 56
$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 1 & 2 Joy Lane Arlington, VT MLS# 5058622
Save 1 & 2 Joy Lane Arlington, VT MLS# 5058622
1 of 17
$85,000
Studio

Beds

0.0

Baths

1 & 2 Joy Lane

Arlington, VT

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Courtesy of WOHLER REALTY GROUP
View 932 McNamara Road Dorset, VT MLS# 5058749
Save 932 McNamara Road Dorset, VT MLS# 5058749
1 of 40
$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 4325 VT Route 7A Shaftsbury, VT MLS# 5058810
Save 4325 VT Route 7A Shaftsbury, VT MLS# 5058810
1 of 51
$599,900
4,500

Sq.Ft.

4325 VT Route 7A

Shaftsbury, VT

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Courtesy of KW VERMONT - BRENDA JONES REAL ESTATE GROUP
View 211 School Street Bennington, VT MLS# 5058301
Save 211 School Street Bennington, VT MLS# 5058301
1 of 38
$315,000
2,280

Sq.Ft.

211 School Street

Bennington, VT

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Courtesy of MAPLE LEAF REALTY

Information deemed reliable but not guaranteed.

“Copyright 2025 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 12/20/2025”

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