Bennington Vermont Homes for Sale

405 total properties
View 0 Mount Anthony Road Bennington, VT MLS# 5102718
Save 0 Mount Anthony Road Bennington, VT MLS# 5102718
1 of 1
$75,000
0.0

Baths

0 Mount Anthony Road

Bennington, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 00 Bill T Drive Readsboro, VT MLS# 5068152
  • Virtual Tour
Save 00 Bill T Drive Readsboro, VT MLS# 5068152
1 of 18
$79,000
0.0

Baths

00 Bill T Drive

Readsboro, VT

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Courtesy of DEERFIELD VALLEY REAL ESTATE
View 107 Lyons Street Bennington, VT MLS# 5096159
Save 107 Lyons Street Bennington, VT MLS# 5096159
1 of 4
$80,000
4

Beds

2.0

Baths

1,465

Sq.Ft.

107 Lyons Street

Bennington, VT

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Courtesy of KW VERMONT - BRENDA JONES REAL ESTATE GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 23 Moose Hollow Road # 40 Winhall, VT MLS# 5083719
Save 23 Moose Hollow Road # 40 Winhall, VT MLS# 5083719
1 of 15
$85,000
0.0

Baths

23 Moose Hollow Road # 40

Winhall, VT

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Courtesy of WINHALL REAL ESTATE
View 0 West Mountain Road Shaftsbury, VT MLS# 5106931
Save 0 West Mountain Road Shaftsbury, VT MLS# 5106931
1 of 9
$85,000
0.0

Baths

0 West Mountain Road

Shaftsbury, VT

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Courtesy of EXP REALTY
View 0 Ladd Road Pownal, VT MLS# 5111157
  • Recently Listed
Save 0 Ladd Road Pownal, VT MLS# 5111157
1 of 29
$85,000
0.0

Baths

0 Ladd Road

Pownal, VT

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Courtesy of HOFFMAN REAL ESTATE
View 0 East Road Shaftsbury, VT MLS# 5094032
Save 0 East Road Shaftsbury, VT MLS# 5094032
1 of 19
$88,000
0.0

Baths

0 East Road

Shaftsbury, VT

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Courtesy of HOFFMAN REAL ESTATE
View 41 Moose Hollow Road Winhall, VT MLS# 5070793
Save 41 Moose Hollow Road Winhall, VT MLS# 5070793
1 of 12
$90,000
0.0

Baths

41 Moose Hollow Road

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
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 32 Cassie Lane Bennington, VT MLS# 5050696
Save 32 Cassie Lane Bennington, VT MLS# 5050696
1 of 16
$96,906
2

Beds

2.0

Baths

777

Sq.Ft.

32 Cassie Lane

Bennington, VT

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Courtesy of EXP REALTY
View 0 Kesick Swamp Road Sunderland, VT MLS# 5085683
Save 0 Kesick Swamp Road Sunderland, VT MLS# 5085683
1 of 1
$99,900
0.0

Baths

0 Kesick Swamp Road

Sunderland, VT

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Courtesy of KW VERMONT - BRENDA JONES REAL ESTATE GROUP
View 4791-3 Main Street Manchester, VT MLS# 5103569
Save 4791-3 Main Street Manchester, VT MLS# 5103569
1 of 2
$100,000
800

Sq.Ft.

4791-3 Main Street

Manchester, VT

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Courtesy of EXP REALTY
View 347 Hickory Road Woodford, VT MLS# 5084654
Save 347 Hickory Road Woodford, VT MLS# 5084654
1 of 14
$104,900
3

Beds

1.0

Baths

768

Sq.Ft.

347 Hickory Road

Woodford, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 0 Sylvan Ridge Road # Lot 25 Winhall, VT MLS# 5106244
Save 0 Sylvan Ridge Road # Lot 25 Winhall, VT MLS# 5106244
1 of 7
$108,000
0.0

Baths

0 Sylvan Ridge Road # Lot 25

Winhall, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View Lot 3 Route 11/30 # 3 Winhall, VT MLS# 4963233
Save Lot 3 Route 11/30 # 3 Winhall, VT MLS# 4963233
1 of 15
$115,000
0.0

Baths

Lot 3 Route 11/30 # 3

Winhall, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 311 Beechwood Lane # 19 Peru, VT MLS# 5070443
Save 311 Beechwood Lane # 19 Peru, VT MLS# 5070443
1 of 34
$115,000
0.0

Baths

311 Beechwood Lane # 19

Peru, VT

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Courtesy of BROMLEY REAL ESTATE
View 75 Sylvan Ridge Road Winhall, VT MLS# 5104082
  • Virtual Tour
Save 75 Sylvan Ridge Road Winhall, VT MLS# 5104082
1 of 15
$115,000
0.0

Baths

75 Sylvan Ridge Road

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 818 Old Depot Road Shaftsbury, VT MLS# 5074845
Save 818 Old Depot Road Shaftsbury, VT MLS# 5074845
1 of 23
$120,000
2

Beds

1.0

Baths

880

Sq.Ft.

818 Old Depot Road

Shaftsbury, VT

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Courtesy of GREAT AMERICAN DREAM REALTY
View 510 Center Street Pownal, VT MLS# 5097453
Save 510 Center Street Pownal, VT MLS# 5097453
1 of 15
$125,000
0.0

Baths

510 Center Street

Pownal, VT

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Courtesy of MAPLE LEAF REAL ESTATE
View 60 Tori Lane Bennington, VT MLS# 5101539
Save 60 Tori Lane Bennington, VT MLS# 5101539
1 of 21
$132,900
2

Beds

1.0

Baths

784

Sq.Ft.

60 Tori Lane

Bennington, VT

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Courtesy of KW VERMONT - BRENDA JONES REAL ESTATE 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 10/4/2026”

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