Bennington Vermont Homes for Sale

402 total properties
View 142 Schenkar Road Pownal, VT MLS# 5087002
Save 142 Schenkar Road Pownal, VT MLS# 5087002
1 of 60
$625,000
3

Beds

2.1

Baths

3,295

Sq.Ft.

142 Schenkar Road

Pownal, VT

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Courtesy of KW VERMONT
View 23 Stonewall Lane Dorset, VT MLS# 5087463
Save 23 Stonewall Lane Dorset, VT MLS# 5087463
1 of 36
$609,900
3

Beds

2.0

Baths

2,250

Sq.Ft.

23 Stonewall Lane

Dorset, VT

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Courtesy of RE/MAX SUMMIT
View 1 Beaver Street Winhall, VT MLS# 5094344
Save 1 Beaver Street Winhall, VT MLS# 5094344
1 of 38
$605,000
3

Beds

2.0

Baths

2,288

Sq.Ft.

1 Beaver Street

Winhall, VT

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Courtesy of WINHALL REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
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 G6 Cobble Ridge Road # G6 Winhall, VT MLS# 5108248
Save G6 Cobble Ridge Road # G6 Winhall, VT MLS# 5108248
1 of 12
$599,000
3

Beds

3.0

Baths

1,830

Sq.Ft.

G6 Cobble Ridge Road # G6

Winhall, VT

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Courtesy of NATHAN AUCTION & REAL ESTATE INC.
View 81 Honeysuckle Lane Bennington, VT MLS# 5093651
  • Virtual Tour
Save 81 Honeysuckle Lane Bennington, VT MLS# 5093651
1 of 32
$595,000
5

Beds

3.0

Baths

5,524

Sq.Ft.

81 Honeysuckle Lane

Bennington, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 1278 Harrington Road Bennington, VT MLS# 5099405
Save 1278 Harrington Road Bennington, VT MLS# 5099405
1 of 30
$595,000
3

Beds

2.0

Baths

2,379

Sq.Ft.

1278 Harrington Road

Bennington, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 3213 West Road Bennington, VT MLS# 5104539
Save 3213 West Road Bennington, VT MLS# 5104539
1 of 31
$595,000
0.0

Baths

3213 West Road

Bennington, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
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 125 North Street Bennington, VT MLS# 5036917
Save 125 North Street Bennington, VT MLS# 5036917
1 of 30
$590,000
3,725

Sq.Ft.

125 North Street

Bennington, VT

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Courtesy of HARSCH ASSOCIATES
View 436 Matteson Road Bennington, VT MLS# 5108314
Save 436 Matteson Road Bennington, VT MLS# 5108314
1 of 50
$589,900
3

Beds

3.1

Baths

2,800

Sq.Ft.

436 Matteson Road

Bennington, VT

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Courtesy of KW VERMONT - BRENDA JONES REAL ESTATE GROUP
View 1649 E Manchester Road Manchester, VT MLS# 5100596
Save 1649 E Manchester Road Manchester, VT MLS# 5100596
1 of 40
$579,900
5

Beds

2.0

Baths

2,050

Sq.Ft.

1649 E Manchester Road

Manchester, VT

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Courtesy of HOMECOIN.COM
View 560 New Ireland Road Manchester, VT MLS# 5098151
Save 560 New Ireland Road Manchester, VT MLS# 5098151
1 of 22
$579,000
3

Beds

1.1

Baths

2,048

Sq.Ft.

560 New Ireland Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 856 Matteson Road Bennington, VT MLS# 5110554
Save 856 Matteson Road Bennington, VT MLS# 5110554
1 of 34
$579,000
3

Beds

2.0

Baths

2,501

Sq.Ft.

856 Matteson Road

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 1131 Route 30 Dorset, VT MLS# 5102040
Save 1131 Route 30 Dorset, VT MLS# 5102040
1 of 52
$565,000
4

Beds

2.1

Baths

2,399

Sq.Ft.

1131 Route 30

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 331 Hideaway Lane Sunderland, VT MLS# 5107439
Save 331 Hideaway Lane Sunderland, VT MLS# 5107439
1 of 33
$565,000
3

Beds

2.0

Baths

1,456

Sq.Ft.

331 Hideaway Lane

Sunderland, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 971 South Stream Road Bennington, VT MLS# 5088350
  • Virtual Tour
Save 971 South Stream Road Bennington, VT MLS# 5088350
1 of 41
$550,000
5

Beds

2.0

Baths

1,974

Sq.Ft.

971 South Stream Road

Bennington, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 1039 Berwal Road Arlington, VT MLS# 5099912
Save 1039 Berwal Road Arlington, VT MLS# 5099912
1 of 56
$550,000
4

Beds

2.1

Baths

3,394

Sq.Ft.

1039 Berwal Road

Arlington, VT

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Courtesy of WOHLER REALTY GROUP
View 1625 Barnumville Road Manchester, VT MLS# 5103524
Save 1625 Barnumville Road Manchester, VT MLS# 5103524
1 of 25
$550,000
3

Beds

2.0

Baths

2,009

Sq.Ft.

1625 Barnumville Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 27 Owls Head Hill Lane Dorset, VT MLS# 5062143
Save 27 Owls Head Hill Lane Dorset, VT MLS# 5062143
1 of 20
$549,000
3

Beds

2.0

Baths

1,344

Sq.Ft.

27 Owls Head Hill Lane

Dorset, 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 10/3/2026”

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