Bennington Vermont Homes for Sale

408 total properties
View 1112 Main Road Stamford, VT MLS# 5112111
  • Recently Listed
Save 1112 Main Road Stamford, VT MLS# 5112111
1 of 41
$279,500
3

Beds

2.0

Baths

1,747

Sq.Ft.

1112 Main Road

Stamford, VT

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Courtesy of BISHOP WEST REAL ESTATE, INC.
View 300 Nims Road Dorset, VT MLS# 5112024
  • Recently Listed
Save 300 Nims Road Dorset, VT MLS# 5112024
1 of 6
$6,250,000
6

Beds

6.3

Baths

14,480

Sq.Ft.

300 Nims Road

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 4378 Route 30 Dorset, VT MLS# 5112032
  • Recently Listed
Save 4378 Route 30 Dorset, VT MLS# 5112032
1 of 44
$349,900
2

Beds

1.1

Baths

1,122

Sq.Ft.

4378 Route 30

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 81 Pond View Road Winhall, VT MLS# 5112039
  • Recently Listed
Save 81 Pond View Road Winhall, VT MLS# 5112039
1 of 52
$700,000
3

Beds

3.0

Baths

1,650

Sq.Ft.

81 Pond View Road

Winhall, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 180 High Meadow Road Winhall, VT MLS# 5111779
  • Recently Listed
Save 180 High Meadow Road Winhall, VT MLS# 5111779
1 of 34
$1,500,000
5

Beds

4.0

Baths

4,173

Sq.Ft.

180 High Meadow Road

Winhall, VT

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Courtesy of 42 NORTH LP
View 165 High Meadow Road Winhall, VT MLS# 5111781
  • Recently Listed
Save 165 High Meadow Road Winhall, VT MLS# 5111781
1 of 40
$2,250,000
4

Beds

4.1

Baths

3,034

Sq.Ft.

165 High Meadow Road

Winhall, VT

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Courtesy of 42 NORTH LP
View 45 Benson Fuller Drive Winhall, VT MLS# 5111782
  • Recently Listed
Save 45 Benson Fuller Drive Winhall, VT MLS# 5111782
1 of 30
$899,000
4

Beds

3.0

Baths

2,421

Sq.Ft.

45 Benson Fuller Drive

Winhall, VT

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Courtesy of 42 NORTH LP
View 15 Nearing Road Winhall, VT MLS# 5111784
  • Recently Listed
Save 15 Nearing Road Winhall, VT MLS# 5111784
1 of 33
$799,000
3

Beds

3.1

Baths

2,366

Sq.Ft.

15 Nearing Road

Winhall, VT

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Courtesy of 42 NORTH LP
View 691 Indian Paint Brush Road # E-13R and E-14R Winhall, VT MLS# 5111789
  • Recently Listed
Save 691 Indian Paint Brush Road # E-13R and E-14R Winhall, VT MLS# 5111789
1 of 2
$500,000
0.0

Baths

691 Indian Paint Brush Road # E-13R and E-14R

Winhall, VT

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Courtesy of 42 NORTH LP
View 110 Coulter Street Bennington, VT MLS# 5111698
  • Recently Listed
Save 110 Coulter Street Bennington, VT MLS# 5111698
1 of 48
$329,000
3

Beds

1.1

Baths

1,563

Sq.Ft.

110 Coulter Street

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 2100 Monument Avenue Bennington, VT MLS# 5111680
  • Recently Listed
Save 2100 Monument Avenue Bennington, VT MLS# 5111680
1 of 55
$975,000
3

Beds

3.0

Baths

3,326

Sq.Ft.

2100 Monument Avenue

Bennington, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 51 Eleanors Way Shaftsbury, VT MLS# 5111490
Save 51 Eleanors Way Shaftsbury, VT MLS# 5111490
1 of 43
$240,000
2

Beds

2.0

Baths

1,536

Sq.Ft.

51 Eleanors Way

Shaftsbury, VT

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Courtesy of HOFFMAN REAL ESTATE
View 370 Southshire Drive Bennington, VT MLS# 5111572
  • Recently Listed
Save 370 Southshire Drive Bennington, VT MLS# 5111572
1 of 40
$695,000
4

Beds

3.1

Baths

5,769

Sq.Ft.

370 Southshire Drive

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 363 Alden Road # 9 Sunderland, VT MLS# 5111590
  • Recently Listed
Save 363 Alden Road # 9 Sunderland, VT MLS# 5111590
1 of 60
$1,075,000
3

Beds

2.1

Baths

1,536

Sq.Ft.

363 Alden Road # 9

Sunderland, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 34 Sugar Brook Road # Unit F3 Peru, VT MLS# 5111591
  • Recently Listed
Save 34 Sugar Brook Road # Unit F3 Peru, VT MLS# 5111591
1 of 27
$425,000
3

Beds

2.1

Baths

1,377

Sq.Ft.

34 Sugar Brook Road # Unit F3

Peru, VT

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Courtesy of CUMMINGS & CO
View 230 Beech Street Bennington, VT MLS# 5111369
Save 230 Beech Street Bennington, VT MLS# 5111369
1 of 37
$249,500
3

Beds

2.0

Baths

1,271

Sq.Ft.

230 Beech Street

Bennington, VT

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Courtesy of HOFFMAN REAL ESTATE
View 390 Fairview Street Bennington, VT MLS# 5111395
  • Recently Listed
Save 390 Fairview Street Bennington, VT MLS# 5111395
1 of 1
$95,000
0.0

Baths

390 Fairview Street

Bennington, VT

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Courtesy of FOUR CORNER PROPERTIES LLC
View 2 North Street Bennington, VT MLS# 5111442
  • Recently Listed
Save 2 North Street Bennington, VT MLS# 5111442
1 of 57
$219,000
2

Beds

1.0

Baths

1,397

Sq.Ft.

2 North Street

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 515 Buck Hill Arlington, VT MLS# 5111464
  • Recently Listed
Save 515 Buck Hill Arlington, VT MLS# 5111464
1 of 39
$379,000
3

Beds

1.0

Baths

2,135

Sq.Ft.

515 Buck Hill

Arlington, VT

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Courtesy of FOUR CORNER PROPERTIES LLC
View 257 Watrous Road Rupert, VT MLS# 5111601
  • Recently Listed
Save 257 Watrous Road Rupert, VT MLS# 5111601
1 of 50
$279,500
2

Beds

2.0

Baths

1,128

Sq.Ft.

257 Watrous Road

Rupert, VT

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Courtesy of MCCHESNEY RE, INC.

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 9/30/2026”

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