Bennington Vermont Homes for Sale

282 total properties
View 0 Barber Pond Road Pownal, VT MLS# 5073107
Save 0 Barber Pond Road Pownal, VT MLS# 5073107
1 of 8
$35,000
Studio

Beds

0.0

Baths

0 Barber Pond Road

Pownal, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 2023 North Road Sunderland, VT MLS# 5072829
  • Virtual Tour
Save 2023 North Road Sunderland, VT MLS# 5072829
1 of 28
$390,000
3

Beds

1.1

Baths

1,222

Sq.Ft.

2023 North Road

Sunderland, VT

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Courtesy of REAL BROKER LLC
View 12 Sunny Hill Road Winhall, VT MLS# 5072842
Save 12 Sunny Hill Road Winhall, VT MLS# 5072842
1 of 43
$1,399,000
4

Beds

3.1

Baths

5,397

Sq.Ft.

12 Sunny Hill Road

Winhall, VT

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Courtesy of WINHALL REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 301 Northside Drive Bennington, VT MLS# 5072776
Save 301 Northside Drive Bennington, VT MLS# 5072776
1 of 1
$2,190,000
Studio

Beds

0.0

Baths

301 Northside Drive

Bennington, VT

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Courtesy of TPW REAL ESTATE
View 726 Rice Lane Bennington, VT MLS# 5072594
Save 726 Rice Lane Bennington, VT MLS# 5072594
1 of 47
$245,000
2

Beds

2.0

Baths

911

Sq.Ft.

726 Rice Lane

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 281 Old County Lane Readsboro, VT MLS# 5072526
Save 281 Old County Lane Readsboro, VT MLS# 5072526
1 of 51
$399,000
3

Beds

2.0

Baths

1,816

Sq.Ft.

281 Old County Lane

Readsboro, VT

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Courtesy of REAL BROKER LLC
View 354 New Ireland Road Manchester, VT MLS# 5072524
Save 354 New Ireland Road Manchester, VT MLS# 5072524
1 of 28
$479,000
3

Beds

2.1

Baths

1,392

Sq.Ft.

354 New Ireland Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 0 Lower Taylor Hill Road Winhall, VT MLS# 5072280
Save 0 Lower Taylor Hill Road Winhall, VT MLS# 5072280
1 of 16
$139,000
Studio

Beds

0.0

Baths

0 Lower Taylor Hill Road

Winhall, VT

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Courtesy of MICHAEL ENGLAND REAL ESTATE
View 1844 Depot Street Manchester, VT MLS# 5072189
Save 1844 Depot Street Manchester, VT MLS# 5072189
1 of 33
$1,050,000
4,413

Sq.Ft.

1844 Depot Street

Manchester, VT

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Courtesy of WOHLER REALTY GROUP
View 5 Linscott Road Winhall, VT MLS# 5072170
Save 5 Linscott Road Winhall, VT MLS# 5072170
1 of 35
$650,000
3

Beds

2.1

Baths

2,370

Sq.Ft.

5 Linscott Road

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 196 Granger Hollow Road Shaftsbury, VT MLS# 5072211
Save 196 Granger Hollow Road Shaftsbury, VT MLS# 5072211
1 of 27
$290,000
4

Beds

2.0

Baths

2,190

Sq.Ft.

196 Granger Hollow Road

Shaftsbury, VT

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Courtesy of BHG MASIELLO BRATTLEBORO
View 124 Elm Street Bennington, VT MLS# 5072098
Save 124 Elm Street Bennington, VT MLS# 5072098
1 of 25
$975,000
Studio

Beds

0.0

Baths

8,888

Sq.Ft.

124 Elm Street

Bennington, VT

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Courtesy of TPW REAL ESTATE
View 17 Henry Hill Stamford, VT MLS# 5071700
Save 17 Henry Hill Stamford, VT MLS# 5071700
1 of 3
$219,000
2

Beds

1.0

Baths

1,872

Sq.Ft.

17 Henry Hill

Stamford, VT

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Courtesy of MORESI REAL ESTATE PARTNERS
View 7 Roundtree Road Winhall, VT MLS# 5071605
Save 7 Roundtree Road Winhall, VT MLS# 5071605
1 of 41
$950,000
4

Beds

3.1

Baths

3,031

Sq.Ft.

7 Roundtree Road

Winhall, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 318 North Street Bennington, VT MLS# 5071451
Save 318 North Street Bennington, VT MLS# 5071451
1 of 32
$295,000
1

Beds

1.1

Baths

1,680

Sq.Ft.

318 North Street

Bennington, VT

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Courtesy of HOFFMAN REAL ESTATE
View 318 North Street Bennington, VT MLS# 5071452
Save 318 North Street Bennington, VT MLS# 5071452
1 of 32
$295,000
1,680

Sq.Ft.

318 North Street

Bennington, VT

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Courtesy of HOFFMAN REAL ESTATE
View 8 Silver Birch Road # 8 Winhall, VT MLS# 5071313
Save 8 Silver Birch Road # 8 Winhall, VT MLS# 5071313
1 of 32
$430,000
3

Beds

2.0

Baths

1,215

Sq.Ft.

8 Silver Birch Road # 8

Winhall, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 44 Lake Road Winhall, VT MLS# 5071173
Save 44 Lake Road Winhall, VT MLS# 5071173
1 of 32
$450,000
5

Beds

3.0

Baths

2,303

Sq.Ft.

44 Lake Road

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 196 Granger Hollow Road Shaftsbury, VT MLS# 5070958
Save 196 Granger Hollow Road Shaftsbury, VT MLS# 5070958
1 of 27
$290,000
3

Beds

1.0

Baths

1,392

Sq.Ft.

196 Granger Hollow Road

Shaftsbury, VT

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Courtesy of BHG MASIELLO BRATTLEBORO
View 9 Pond View Road # 9 Winhall, VT MLS# 5071102
Save 9 Pond View Road # 9 Winhall, VT MLS# 5071102
1 of 46
$660,000
3

Beds

3.0

Baths

1,650

Sq.Ft.

9 Pond View Road # 9

Winhall, VT

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Courtesy of WOHLER REALTY GROUP

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 3/4/2026”

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