Bennington Vermont Homes for Sale

280 total properties
View 41 Moose Hollow Road Winhall, VT MLS# 5070793
Save 41 Moose Hollow Road Winhall, VT MLS# 5070793
1 of 12
$95,000
Studio

Beds

0.0

Baths

41 Moose Hollow Road

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 490 Barnumville Road Manchester, VT MLS# 5070798
Save 490 Barnumville Road Manchester, VT MLS# 5070798
1 of 52
$699,000
3

Beds

2.2

Baths

2,274

Sq.Ft.

490 Barnumville Road

Manchester, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 253 Owls Head Hill Lane South Dorset, VT MLS# 5070757
Save 253 Owls Head Hill Lane South Dorset, VT MLS# 5070757
1 of 29
$729,000
3

Beds

3.1

Baths

2,262

Sq.Ft.

253 Owls Head Hill Lane South

Dorset, VT

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Courtesy of REAL BROKER LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 207 Silver Street Bennington, VT MLS# 5070659
Save 207 Silver Street Bennington, VT MLS# 5070659
1 of 58
$299,000
4

Beds

2.0

Baths

2,000

Sq.Ft.

207 Silver Street

Bennington, VT

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Courtesy of PERROTT REALTY
View 8 Winhall Woods Road Winhall, VT MLS# 5070428
Save 8 Winhall Woods Road Winhall, VT MLS# 5070428
1 of 27
$359,000
3

Beds

1.1

Baths

1,144

Sq.Ft.

8 Winhall Woods Road

Winhall, VT

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Courtesy of WINHALL REAL ESTATE
View 311 Beechwood Lane # 19 Peru, VT MLS# 5070443
Save 311 Beechwood Lane # 19 Peru, VT MLS# 5070443
1 of 18
$125,000
Studio

Beds

0.0

Baths

311 Beechwood Lane # 19

Peru, VT

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Courtesy of BROMLEY REAL ESTATE
View 425 Main Street Bennington, VT MLS# 5070282
Save 425 Main Street Bennington, VT MLS# 5070282
1 of 45
$499,000
15,179

Sq.Ft.

425 Main Street

Bennington, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 108 Baker Drive Bennington, VT MLS# 5070452
Save 108 Baker Drive Bennington, VT MLS# 5070452
1 of 17
$79,900
2

Beds

2.0

Baths

980

Sq.Ft.

108 Baker Drive

Bennington, VT

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Courtesy of MONARCH REALTY
View 940 Gage Street Bennington, VT MLS# 5069924
Save 940 Gage Street Bennington, VT MLS# 5069924
1 of 18
$300,000
3

Beds

1.1

Baths

1,570

Sq.Ft.

940 Gage Street

Bennington, VT

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Courtesy of BRATTLEBORO AREA REALTY
View 4697 Main Street Manchester, VT MLS# 5069842
Save 4697 Main Street Manchester, VT MLS# 5069842
1 of 54
$675,000
1,264

Sq.Ft.

4697 Main Street

Manchester, VT

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Courtesy of WOHLER REALTY GROUP
View 1180 North Road Sunderland, VT MLS# 5069594
Save 1180 North Road Sunderland, VT MLS# 5069594
1 of 20
$524,900
4

Beds

2.1

Baths

2,240

Sq.Ft.

1180 North Road

Sunderland, VT

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Courtesy of WWW.HOMEZU.COM
View 211 ROD and GUN CLUB Road Shaftsbury, VT MLS# 5069551
Save 211 ROD and GUN CLUB Road Shaftsbury, VT MLS# 5069551
1 of 42
$565,000
3

Beds

2.0

Baths

1,748

Sq.Ft.

211 ROD and GUN CLUB Road

Shaftsbury, VT

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Courtesy of HOOSICK REALTY
View 146 Ridges Way # 1200-1 Peru, VT MLS# 5069206
Save 146 Ridges Way # 1200-1 Peru, VT MLS# 5069206
1 of 33
$700,000
4

Beds

3.1

Baths

1,829

Sq.Ft.

146 Ridges Way # 1200-1

Peru, VT

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Courtesy of CUMMINGS & CO
View 24 North Branch Road Winhall, VT MLS# 5069406
Save 24 North Branch Road Winhall, VT MLS# 5069406
1 of 55
$995,000
5

Beds

4.1

Baths

2,321

Sq.Ft.

24 North Branch Road

Winhall, VT

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Courtesy of WOHLER REALTY GROUP
View 74 Eagle Nest Road # 7 Manchester, VT MLS# 5069098
Save 74 Eagle Nest Road # 7 Manchester, VT MLS# 5069098
1 of 24
$595,000
3

Beds

2.1

Baths

2,210

Sq.Ft.

74 Eagle Nest Road # 7

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View Lot 21 Sunderland Hill Road Sunderland, VT MLS# 5069111
Save Lot 21 Sunderland Hill Road Sunderland, VT MLS# 5069111
1 of 17
$160,000
Studio

Beds

0.0

Baths

Lot 21 Sunderland Hill Road

Sunderland, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 11 Founders Hill Road Winhall, VT MLS# 5069133
Save 11 Founders Hill Road Winhall, VT MLS# 5069133
1 of 40
$1,150,000
5

Beds

3.1

Baths

4,017

Sq.Ft.

11 Founders Hill Road

Winhall, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 5406 - 5408 Main Street Manchester, VT MLS# 5069158
Save 5406 - 5408 Main Street Manchester, VT MLS# 5069158
1 of 60
$629,000
5

Beds

3.1

Baths

3,271

Sq.Ft.

5406 - 5408 Main Street

Manchester, VT

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Courtesy of WOHLER REALTY GROUP
View 682 E. Manchester Road Manchester, VT MLS# 5069161
Save 682 E. Manchester Road Manchester, VT MLS# 5069161
1 of 36
$699,000
4

Beds

3.0

Baths

2,400

Sq.Ft.

682 E. Manchester Road

Manchester, VT

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Courtesy of CUMMINGS & CO
View 00 Heartwellville View Road # 38/39 Readsboro, VT MLS# 5068949
Save 00 Heartwellville View Road # 38/39 Readsboro, VT MLS# 5068949
1 of 4
$28,000
Studio

Beds

0.0

Baths

00 Heartwellville View Road # 38/39

Readsboro, VT

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Courtesy of FLEX 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 3/5/2026”

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