Bennington Vermont Homes for Sale

403 total properties
View 12 Hurley Lane Bennington, VT MLS# 5106353
Save 12 Hurley Lane Bennington, VT MLS# 5106353
1 of 59
$199,900
3

Beds

1.0

Baths

1,132

Sq.Ft.

12 Hurley Lane

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 262 Timber Trail Road Shaftsbury, VT MLS# 5106454
Save 262 Timber Trail Road Shaftsbury, VT MLS# 5106454
1 of 47
$685,000
3

Beds

3.0

Baths

3,153

Sq.Ft.

262 Timber Trail Road

Shaftsbury, VT

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Courtesy of WOHLER REALTY GROUP
View 2 Bromley Lane Bennington, VT MLS# 5106470
Save 2 Bromley Lane Bennington, VT MLS# 5106470
1 of 31
$395,000
4

Beds

1.1

Baths

1,816

Sq.Ft.

2 Bromley Lane

Bennington, VT

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Courtesy of PACELLI ZEPKA CORPORATION
The time to sell is now! THE TIME TO SELL IS NOW!
View 145 White Farm Lane Shaftsbury, VT MLS# 5107304
  • Virtual Tour
Save 145 White Farm Lane Shaftsbury, VT MLS# 5107304
1 of 59
OPEN HOUSE: Saturday 10/3 12:00 PM - 2:00 PM
$849,900
4

Beds

3.2

Baths

3,974

Sq.Ft.

145 White Farm Lane

Shaftsbury, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 33 Burnt Hill Road Winhall, VT MLS# 5106334
  • Virtual Tour
Save 33 Burnt Hill Road Winhall, VT MLS# 5106334
1 of 26
$599,000
3

Beds

2.0

Baths

1,890

Sq.Ft.

33 Burnt Hill Road

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 1141 Burgess Road Bennington, VT MLS# 5106263
Save 1141 Burgess Road Bennington, VT MLS# 5106263
1 of 50
$330,000
2

Beds

1.1

Baths

1,750

Sq.Ft.

1141 Burgess Road

Bennington, VT

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Courtesy of EXP REALTY
View 19 Winhall Condo Road # 4 Winhall, VT MLS# 5106209
Save 19 Winhall Condo Road # 4 Winhall, VT MLS# 5106209
1 of 34
$345,000
2

Beds

2.0

Baths

960

Sq.Ft.

19 Winhall Condo Road # 4

Winhall, VT

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Courtesy of THE HAVEN GROUP
View 0 Sylvan Ridge Road # Lot 25 Winhall, VT MLS# 5106244
Save 0 Sylvan Ridge Road # Lot 25 Winhall, VT MLS# 5106244
1 of 7
$108,000
0.0

Baths

0 Sylvan Ridge Road # Lot 25

Winhall, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 440 Marcia Lane Dorset, VT MLS# 5105868
  • Virtual Tour
Save 440 Marcia Lane Dorset, VT MLS# 5105868
1 of 60
$4,995,000
5

Beds

6.1

Baths

7,455

Sq.Ft.

440 Marcia Lane

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 2529 Main Street Manchester, VT MLS# 5105906
Save 2529 Main Street Manchester, VT MLS# 5105906
1 of 27
$995,000
5

Beds

2.0

Baths

3,522

Sq.Ft.

2529 Main Street

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 5187 VT Route 7A Arlington, VT MLS# 5105741
Save 5187 VT Route 7A Arlington, VT MLS# 5105741
1 of 12
$428,000
4,107

Sq.Ft.

5187 VT Route 7A

Arlington, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 133 Kent Hill Road Dorset, VT MLS# 5105753
  • Virtual Tour
Save 133 Kent Hill Road Dorset, VT MLS# 5105753
1 of 39
$1,185,000
4

Beds

2.1

Baths

2,078

Sq.Ft.

133 Kent Hill Road

Dorset, VT

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Courtesy of LANDVEST, INC/WOODSTOCK
View 493 Main Road Stamford, VT MLS# 5105488
Save 493 Main Road Stamford, VT MLS# 5105488
1 of 16
$159,900
5

Beds

1.0

Baths

1,534

Sq.Ft.

493 Main Road

Stamford, VT

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Courtesy of LAMACCHIA REALTY INC.
View 01 Old Depot Road Arlington, VT MLS# 5105515
Save 01 Old Depot Road Arlington, VT MLS# 5105515
1 of 8
$239,000
0.0

Baths

01 Old Depot Road

Arlington, VT

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Courtesy of TPW REAL ESTATE
View 0 Fox Lane # lot 3 Dorset, VT MLS# 5105566
Save 0 Fox Lane # lot 3 Dorset, VT MLS# 5105566
1 of 2
$245,000
0.0

Baths

0 Fox Lane # lot 3

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 3542 North Road Sunderland, VT MLS# 5105575
Save 3542 North Road Sunderland, VT MLS# 5105575
1 of 40
$989,000
3

Beds

2.0

Baths

1,680

Sq.Ft.

3542 North Road

Sunderland, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 16B Bromley Knolls Road # B Winhall, VT MLS# 5105387
Save 16B Bromley Knolls Road # B Winhall, VT MLS# 5105387
1 of 20
$399,000
3

Beds

2.0

Baths

1,225

Sq.Ft.

16B Bromley Knolls Road # B

Winhall, VT

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Courtesy of WWW.HOMEZU.COM
View 23 Loop Road # 10 Winhall, VT MLS# 5105544
Save 23 Loop Road # 10 Winhall, VT MLS# 5105544
1 of 40
$595,000
3

Beds

2.0

Baths

1,416

Sq.Ft.

23 Loop Road # 10

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 51 Pageant Street Bennington, VT MLS# 5105313
Save 51 Pageant Street Bennington, VT MLS# 5105313
1 of 38
$315,000
3

Beds

1.0

Baths

1,248

Sq.Ft.

51 Pageant Street

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
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 10/1/2026”

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