Bennington Vermont Homes for Sale

404 total properties
View 112 Outwater Road Shaftsbury, VT MLS# 5108455
Save 112 Outwater Road Shaftsbury, VT MLS# 5108455
1 of 16
$204,000
3

Beds

2.0

Baths

1,460

Sq.Ft.

112 Outwater Road

Shaftsbury, VT

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Courtesy of BRATTLEBORO AREA 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 5549 Main Street Manchester, VT MLS# 5108274
Save 5549 Main Street Manchester, VT MLS# 5108274
1 of 30
$649,000
12,568

Sq.Ft.

5549 Main Street

Manchester, VT

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Courtesy of FLEX REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 5549 Main Street Manchester, VT MLS# 5108275
Save 5549 Main Street Manchester, VT MLS# 5108275
1 of 30
$649,000
13

Beds

11.1

Baths

5,572

Sq.Ft.

5549 Main Street

Manchester, VT

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Courtesy of FLEX REALTY
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 88 Sugar Brook Road # C1 Peru, VT MLS# 5108352
Save 88 Sugar Brook Road # C1 Peru, VT MLS# 5108352
1 of 52
$489,000
3

Beds

2.1

Baths

1,603

Sq.Ft.

88 Sugar Brook Road # C1

Peru, VT

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Courtesy of BROMLEY REAL ESTATE
View 327 Vermont Route 313 W Arlington, VT MLS# 5108370
Save 327 Vermont Route 313 W Arlington, VT MLS# 5108370
1 of 20
$225,000
3

Beds

2.0

Baths

1,490

Sq.Ft.

327 Vermont Route 313 W

Arlington, VT

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Courtesy of WINHALL REAL ESTATE
View 325 Twin Willows Lane Dorset, VT MLS# 5108010
Save 325 Twin Willows Lane Dorset, VT MLS# 5108010
1 of 60
$4,200,000
4

Beds

4.2

Baths

7,833

Sq.Ft.

325 Twin Willows Lane

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 18 Old Snow Valley Road Winhall, VT MLS# 5108069
Save 18 Old Snow Valley Road Winhall, VT MLS# 5108069
1 of 39
$350,000
3

Beds

2.0

Baths

1,040

Sq.Ft.

18 Old Snow Valley Road

Winhall, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 292 Forest Mountain Road Peru, VT MLS# 5108157
  • Virtual Tour
Save 292 Forest Mountain Road Peru, VT MLS# 5108157
1 of 37
$489,000
3

Beds

2.0

Baths

1,830

Sq.Ft.

292 Forest Mountain Road

Peru, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 93 Elizabeth Court Sunderland, VT MLS# 5108165
Save 93 Elizabeth Court Sunderland, VT MLS# 5108165
1 of 59
$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 7330 Main Street Manchester, VT MLS# 5108077
Save 7330 Main Street Manchester, VT MLS# 5108077
1 of 29
$425,000
2

Beds

2.1

Baths

1,490

Sq.Ft.

7330 Main Street

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 66 Crosier Private Road Shaftsbury, VT MLS# 5107608
  • Virtual Tour
Save 66 Crosier Private Road Shaftsbury, VT MLS# 5107608
1 of 35
$495,000
4

Beds

2.0

Baths

2,509

Sq.Ft.

66 Crosier Private Road

Shaftsbury, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 20 West Branch Road Winhall, VT MLS# 5107687
  • Virtual Tour
Save 20 West Branch Road Winhall, VT MLS# 5107687
1 of 43
$1,050,000
4

Beds

4.0

Baths

2,380

Sq.Ft.

20 West Branch Road

Winhall, VT

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Courtesy of STRATTON REAL ESTATE
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 0 Sunderland Hill Road Sunderland, VT MLS# 5107454
Save 0 Sunderland Hill Road Sunderland, VT MLS# 5107454
1 of 16
$60,000
0.0

Baths

0 Sunderland Hill Road

Sunderland, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 7 Woodrock Road Winhall, VT MLS# 5107482
  • Virtual Tour
Save 7 Woodrock Road Winhall, VT MLS# 5107482
1 of 26
$749,000
3

Beds

2.0

Baths

976

Sq.Ft.

7 Woodrock Road

Winhall, VT

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Courtesy of STRATTON REAL ESTATE
View 11 Round Tree Road Winhall, VT MLS# 5107395
Save 11 Round Tree Road Winhall, VT MLS# 5107395
1 of 40
$1,325,000
4

Beds

3.1

Baths

3,400

Sq.Ft.

11 Round Tree Road

Winhall, VT

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Courtesy of STRATTON REAL ESTATE
View 197 Bromley Brook Road Manchester, VT MLS# 5107321
Save 197 Bromley Brook Road Manchester, VT MLS# 5107321
1 of 29
$639,000
3

Beds

2.0

Baths

1,832

Sq.Ft.

197 Bromley Brook Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 148 VT Route 30 Winhall, VT MLS# 5107343
Save 148 VT Route 30 Winhall, VT MLS# 5107343
1 of 10
$190,000
0.0

Baths

148 VT Route 30

Winhall, VT

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Courtesy of TPW 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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