Bennington Vermont Homes for Sale

402 total properties
View 609-617 Depot Street Manchester, VT MLS# 5094388
$850,000
0.0

Baths

2,060

Sq.Ft.

609-617 Depot Street

Manchester, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 145 White Farm Lane Shaftsbury, VT MLS# 5107304
  • Virtual Tour
1 of 59
OPEN HOUSE: Saturday 10/3 12:00 PM - 2:00 PM
$849,900
4

Beds

3.2

Baths

3,974

Sq.Ft.

145 White Farm Lane

Shaftsbury, VT

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME
View 232 Powderhorn Road Manchester, VT MLS# 5108930
$835,000
3

Beds

2.1

Baths

2,780

Sq.Ft.

232 Powderhorn Road

Manchester, VT

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Courtesy of OWNERENTRY.COM
The time to sell is now! THE TIME TO SELL IS NOW!
View Winhall Hollow Road Winhall, VT MLS# 5079556
$825,000
0.0

Baths

Winhall Hollow Road

Winhall, VT

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Courtesy of WOHLER REALTY GROUP
View 159 Phyllis Lane Bennington, VT MLS# 5081088
$800,000

159 Phyllis Lane

Bennington, VT

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Courtesy of TPW REAL ESTATE
View 99 Holly's Way Rupert, VT MLS# 5094950
$800,000
3

Beds

2.0

Baths

2,403

Sq.Ft.

99 Holly's Way

Rupert, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 636 Dexter Road Shaftsbury, VT MLS# 5083102
$799,000
4

Beds

3.0

Baths

2,462

Sq.Ft.

636 Dexter Road

Shaftsbury, VT

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Courtesy of TPW REAL ESTATE
View 15 Nearing Road Winhall, VT MLS# 5111784
  • Recently Listed
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 1629 North Mann Hill Road Pownal, VT MLS# 5083490
  • Virtual Tour
1 of 47
$795,000
5

Beds

5.1

Baths

3,875

Sq.Ft.

1629 North Mann Hill Road

Pownal, VT

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Courtesy of MAHAR MCCARTHY REAL ESTATE
View 25 Benson Fuller Road Winhall, VT MLS# 5098019
  • Virtual Tour
1 of 38
$795,000
4

Beds

3.1

Baths

4,104

Sq.Ft.

25 Benson Fuller Road

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 2572 Morse Hill Road Dorset, VT MLS# 5090583
$775,000
4

Beds

3.0

Baths

4,112

Sq.Ft.

2572 Morse Hill Road

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 72 Benson Fuller Road Winhall, VT MLS# 5105009
$765,000
3

Beds

3.0

Baths

2,322

Sq.Ft.

72 Benson Fuller Road

Winhall, VT

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Courtesy of THE HAVEN GROUP
View 3622 Dorset West Road Dorset, VT MLS# 5015850
$750,000
3

Beds

2.0

Baths

2,610

Sq.Ft.

3622 Dorset West Road

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 0 Klondike Road Stamford, VT MLS# 5085248
$750,000
0.0

Baths

0 Klondike Road

Stamford, VT

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Courtesy of UNITED COUNTRY REAL ESTATE MIKE JARVIS GROUP INC
View 3373 Main Street Manchester, VT MLS# 5090752
$750,000
4

Beds

5.1

Baths

4,502

Sq.Ft.

3373 Main Street

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View C-4 Ridge Road # C-4 Winhall, VT MLS# 5094616
$750,000
3

Beds

3.0

Baths

2,598

Sq.Ft.

C-4 Ridge Road # C-4

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 7 Woodrock Road Winhall, VT MLS# 5107482
  • Virtual Tour
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 392 Powderhorn Road Manchester, VT MLS# 5095313
$735,000
4

Beds

2.1

Baths

2,220

Sq.Ft.

392 Powderhorn Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 2734 Mad Tom Road Dorset, VT MLS# 5100758
$735,000
2

Beds

2.0

Baths

1,420

Sq.Ft.

2734 Mad Tom Road

Dorset, VT

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Courtesy of RE/MAX FOUR SEASONS
View 456 Lower Hollow Road # 1 Dorset, VT MLS# 5110955
  • Recently Listed
1 of 25
$725,000
3

Beds

3.0

Baths

2,106

Sq.Ft.

456 Lower Hollow Road # 1

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY

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“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 10/2/2026”

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