Bennington Vermont Homes for Sale

402 total properties
View 777 McCooey Drive Manchester, VT MLS# 5096878
Save 777 McCooey Drive Manchester, VT MLS# 5096878
1 of 26
$1,390,000
3

Beds

2.1

Baths

3,264

Sq.Ft.

777 McCooey Drive

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 39 Eagle Ridge Dorset, VT MLS# 5090534
Save 39 Eagle Ridge Dorset, VT MLS# 5090534
1 of 49
$1,375,000
5

Beds

4.1

Baths

4,376

Sq.Ft.

39 Eagle Ridge

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 1474 Dorset West Road Dorset, VT MLS# 5106786
Save 1474 Dorset West Road Dorset, VT MLS# 5106786
1 of 60
$1,375,000
3

Beds

3.0

Baths

2,457

Sq.Ft.

1474 Dorset West Road

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 400 Spring Brook Road Arlington, VT MLS# 5112267
  • Recently Listed
Save 400 Spring Brook Road Arlington, VT MLS# 5112267
1 of 60
$1,375,000
4

Beds

3.1

Baths

3,828

Sq.Ft.

400 Spring Brook Road

Arlington, VT

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Courtesy of HOFFMAN REAL ESTATE
View 11 Round Tree Road Winhall, VT MLS# 5107395
Save 11 Round Tree Road Winhall, VT MLS# 5107395
1 of 40
$1,325,000
4

Beds

3.1

Baths

3,400

Sq.Ft.

11 Round Tree Road

Winhall, VT

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Courtesy of STRATTON REAL ESTATE
View 4566 Main Street Manchester, VT MLS# 5101373
  • Virtual Tour
Save 4566 Main Street Manchester, VT MLS# 5101373
1 of 33
$1,300,000
8,991

Sq.Ft.

4566 Main Street

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 126 Elm Street Bennington, VT MLS# 5042623
Save 126 Elm Street Bennington, VT MLS# 5042623
1 of 25
$1,299,000
7,126

Sq.Ft.

126 Elm Street

Bennington, VT

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Courtesy of TPW REAL ESTATE
View 00 Montgomery Road Pownal, VT MLS# 5092084
Save 00 Montgomery Road Pownal, VT MLS# 5092084
1 of 4
$1,295,000
0.0

Baths

00 Montgomery Road

Pownal, VT

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Courtesy of ALTON + WESTALL REAL ESTATE AGENCY, LLC
View 1677 Barnumville Road Manchester, VT MLS# 5088273
  • Virtual Tour
Save 1677 Barnumville Road Manchester, VT MLS# 5088273
1 of 46
$1,275,000
4

Beds

2.1

Baths

4,084

Sq.Ft.

1677 Barnumville Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 50 Grouse Lane Dorset, VT MLS# 5083578
Save 50 Grouse Lane Dorset, VT MLS# 5083578
1 of 43
$1,250,000
4

Beds

4.1

Baths

5,170

Sq.Ft.

50 Grouse Lane

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 84 Overlook Road Dorset, VT MLS# 5103836
Save 84 Overlook Road Dorset, VT MLS# 5103836
1 of 24
$1,250,000
3

Beds

2.1

Baths

2,035

Sq.Ft.

84 Overlook Road

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 215 VT Route 30 Dorset, VT MLS# 5056222
Save 215 VT Route 30 Dorset, VT MLS# 5056222
1 of 43
$1,200,000
0.0

Baths

215 VT Route 30

Dorset, VT

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Courtesy of WOHLER REALTY GROUP
View 215 & 221 VT Route 30 Dorset, VT MLS# 5064340
Save 215 & 221 VT Route 30 Dorset, VT MLS# 5064340
1 of 56
$1,200,000
6

Beds

3.0

Baths

3,340

Sq.Ft.

215 & 221 VT Route 30

Dorset, VT

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Courtesy of WOHLER REALTY GROUP
View 109 Winhall Hollow Road Winhall, VT MLS# 5081867
  • Virtual Tour
Save 109 Winhall Hollow Road Winhall, VT MLS# 5081867
1 of 31
$1,200,000
1.0

Baths

950

Sq.Ft.

109 Winhall Hollow Road

Winhall, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 233 Squires Road Manchester, VT MLS# 5090840
Save 233 Squires Road Manchester, VT MLS# 5090840
1 of 27
$1,200,000
2

Beds

1.0

Baths

1,056

Sq.Ft.

233 Squires Road

Manchester, VT

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Courtesy of REAL BROKER LLC
View 81 Fern Hill Dorset, VT MLS# 5100399
Save 81 Fern Hill Dorset, VT MLS# 5100399
1 of 40
$1,200,000
2

Beds

2.1

Baths

1,950

Sq.Ft.

81 Fern Hill

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 1996 North Pownal Road Pownal, VT MLS# 5100794
Save 1996 North Pownal Road Pownal, VT MLS# 5100794
1 of 60
$1,200,000
3

Beds

2.1

Baths

2,911

Sq.Ft.

1996 North Pownal Road

Pownal, VT

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Courtesy of HARSCH ASSOCIATES
View 11 Founders Hill Road Winhall, VT MLS# 5103259
Save 11 Founders Hill Road Winhall, VT MLS# 5103259
1 of 25
$1,200,000
6

Beds

3.1

Baths

4,017

Sq.Ft.

11 Founders Hill Road

Winhall, VT

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Courtesy of DEREK GREENE
View 133 Kent Hill Road Dorset, VT MLS# 5105753
  • Virtual Tour
Save 133 Kent Hill Road Dorset, VT MLS# 5105753
1 of 39
$1,185,000
4

Beds

2.1

Baths

2,078

Sq.Ft.

133 Kent Hill Road

Dorset, VT

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Courtesy of LANDVEST, INC/WOODSTOCK
View 88 Windward South Dorset, VT MLS# 5108534
Save 88 Windward South Dorset, VT MLS# 5108534
1 of 38
$1,175,000
3

Beds

2.1

Baths

3,094

Sq.Ft.

88 Windward South

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L 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 10/2/2026”

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