Bennington Vermont Homes for Sale

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1384 Route 153 Rupert, VT MLS# 5089545 - Image 1

1384 Route 153 Rupert, VT MLS# 5089545 - Image 2

1384 Route 153 Rupert, VT MLS# 5089545 - Image 3

1384 Route 153 Rupert, VT MLS# 5089545 - Image 4

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1384 Route 153 Rupert, VT MLS# 5089545 - Image 7

1384 Route 153 Rupert, VT MLS# 5089545 - Image 8

1384 Route 153 Rupert, VT MLS# 5089545 - Image 9

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1384 Route 153 Rupert, VT MLS# 5089545 - Image 11

1384 Route 153 Rupert, VT MLS# 5089545 - Image 12

1384 Route 153 Rupert, VT MLS# 5089545 - Image 13

1384 Route 153 Rupert, VT MLS# 5089545 - Image 14

1384 Route 153 Rupert, VT MLS# 5089545 - Image 15

1384 Route 153 Rupert, VT MLS# 5089545 - Image 16

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1384 Route 153 Rupert, VT MLS# 5089545 - Image 18

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1384 Route 153 Rupert, VT MLS# 5089545 - Image 20

1384 Route 153 Rupert, VT MLS# 5089545 - Image 21

1384 Route 153 Rupert, VT MLS# 5089545 - Image 22

1384 Route 153 Rupert, VT MLS# 5089545 - Image 23

1384 Route 153 Rupert, VT MLS# 5089545 - Image 24

1384 Route 153 Rupert, VT MLS# 5089545 - Image 25

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1384 Route 153 Rupert, VT MLS# 5089545 - Image 28

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1384 Route 153 Rupert, VT MLS# 5089545 - Image 30

1384 Route 153 Rupert, VT MLS# 5089545 - Image 31

1384 Route 153 Rupert, VT MLS# 5089545 - Image 32

1 of 32

$275,000

Beds

1.0

Baths

1,668

Sq.Ft.

1384 Route 153

Rupert, VT

Courtesy of WOHLER REALTY GROUP

155 Brookman Road Pownal, VT MLS# 5089724 - Image 1

155 Brookman Road Pownal, VT MLS# 5089724 - Image 2

155 Brookman Road Pownal, VT MLS# 5089724 - Image 3

155 Brookman Road Pownal, VT MLS# 5089724 - Image 4

155 Brookman Road Pownal, VT MLS# 5089724 - Image 5

155 Brookman Road Pownal, VT MLS# 5089724 - Image 6

155 Brookman Road Pownal, VT MLS# 5089724 - Image 7

155 Brookman Road Pownal, VT MLS# 5089724 - Image 8

155 Brookman Road Pownal, VT MLS# 5089724 - Image 9

155 Brookman Road Pownal, VT MLS# 5089724 - Image 10

155 Brookman Road Pownal, VT MLS# 5089724 - Image 11

155 Brookman Road Pownal, VT MLS# 5089724 - Image 12

155 Brookman Road Pownal, VT MLS# 5089724 - Image 13

155 Brookman Road Pownal, VT MLS# 5089724 - Image 14

155 Brookman Road Pownal, VT MLS# 5089724 - Image 15

155 Brookman Road Pownal, VT MLS# 5089724 - Image 16

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155 Brookman Road Pownal, VT MLS# 5089724 - Image 18

155 Brookman Road Pownal, VT MLS# 5089724 - Image 19

155 Brookman Road Pownal, VT MLS# 5089724 - Image 20

155 Brookman Road Pownal, VT MLS# 5089724 - Image 21

155 Brookman Road Pownal, VT MLS# 5089724 - Image 22

155 Brookman Road Pownal, VT MLS# 5089724 - Image 23

155 Brookman Road Pownal, VT MLS# 5089724 - Image 24

155 Brookman Road Pownal, VT MLS# 5089724 - Image 25

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155 Brookman Road Pownal, VT MLS# 5089724 - Image 28

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155 Brookman Road Pownal, VT MLS# 5089724 - Image 30

155 Brookman Road Pownal, VT MLS# 5089724 - Image 31

155 Brookman Road Pownal, VT MLS# 5089724 - Image 32

155 Brookman Road Pownal, VT MLS# 5089724 - Image 33

155 Brookman Road Pownal, VT MLS# 5089724 - Image 34

155 Brookman Road Pownal, VT MLS# 5089724 - Image 35

155 Brookman Road Pownal, VT MLS# 5089724 - Image 36

155 Brookman Road Pownal, VT MLS# 5089724 - Image 37

Virtual Tour

1 of 37

$875,000

Beds

2.0

Baths

2,000

Sq.Ft.

155 Brookman Road

Pownal, VT

Courtesy of MAHAR MCCARTHY REAL ESTATE

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 1

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 2

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 3

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 4

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 5

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26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 8

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 9

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26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 11

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26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 13

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 14

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 15

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26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 17

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 18

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 19

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 20

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 21

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 22

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 23

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 24

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 25

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26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 28

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 29

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 30

26 Knoll Crest Lane Bennington, VT MLS# 5089377 - Image 31

1 of 31

$274,900

Beds

1.0

Baths

1,210

Sq.Ft.

26 Knoll Crest Lane

Bennington, VT

Courtesy of HOFFMAN REAL ESTATE

THE TIME TO SELL IS NOW!

166 Cardinal Lane Bennington, VT MLS# 5089120 - Image 1

166 Cardinal Lane Bennington, VT MLS# 5089120 - Image 2

166 Cardinal Lane Bennington, VT MLS# 5089120 - Image 3

166 Cardinal Lane Bennington, VT MLS# 5089120 - Image 4

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166 Cardinal Lane Bennington, VT MLS# 5089120 - Image 13

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166 Cardinal Lane Bennington, VT MLS# 5089120 - Image 42

166 Cardinal Lane Bennington, VT MLS# 5089120 - Image 43

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166 Cardinal Lane Bennington, VT MLS# 5089120 - Image 45

166 Cardinal Lane Bennington, VT MLS# 5089120 - Image 46

166 Cardinal Lane Bennington, VT MLS# 5089120 - Image 47

166 Cardinal Lane Bennington, VT MLS# 5089120 - Image 48

1 of 48

$295,000

Beds

2.0

Baths

2,753

Sq.Ft.

166 Cardinal Lane

Bennington, VT

Courtesy of MAHAR MCCARTHY REAL ESTATE

515 Quarry Road Bennington, VT MLS# 5089246 - Image 1

515 Quarry Road Bennington, VT MLS# 5089246 - Image 2

515 Quarry Road Bennington, VT MLS# 5089246 - Image 3

515 Quarry Road Bennington, VT MLS# 5089246 - Image 4

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515 Quarry Road Bennington, VT MLS# 5089246 - Image 7

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515 Quarry Road Bennington, VT MLS# 5089246 - Image 21

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515 Quarry Road Bennington, VT MLS# 5089246 - Image 46

515 Quarry Road Bennington, VT MLS# 5089246 - Image 47

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515 Quarry Road Bennington, VT MLS# 5089246 - Image 49

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515 Quarry Road Bennington, VT MLS# 5089246 - Image 53

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515 Quarry Road Bennington, VT MLS# 5089246 - Image 55

515 Quarry Road Bennington, VT MLS# 5089246 - Image 56

515 Quarry Road Bennington, VT MLS# 5089246 - Image 57

515 Quarry Road Bennington, VT MLS# 5089246 - Image 58

515 Quarry Road Bennington, VT MLS# 5089246 - Image 59

515 Quarry Road Bennington, VT MLS# 5089246 - Image 60

Virtual Tour

1 of 60

$695,000

Beds

2.0

Baths

1,614

Sq.Ft.

515 Quarry Road

Bennington, VT

Courtesy of MAPLE LEAF REAL ESTATE

178 High Meadow Road Winhall, VT MLS# 5088923 - Image 1

178 High Meadow Road Winhall, VT MLS# 5088923 - Image 2

178 High Meadow Road Winhall, VT MLS# 5088923 - Image 3

178 High Meadow Road Winhall, VT MLS# 5088923 - Image 4

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178 High Meadow Road Winhall, VT MLS# 5088923 - Image 59

1 of 59

$899,000

Beds

3.1

Baths

4,000

Sq.Ft.

178 High Meadow Road

Winhall, VT

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME

32 Aspen Lane Winhall, VT MLS# 5089041 - Image 1

32 Aspen Lane Winhall, VT MLS# 5089041 - Image 2

32 Aspen Lane Winhall, VT MLS# 5089041 - Image 3

32 Aspen Lane Winhall, VT MLS# 5089041 - Image 4

32 Aspen Lane Winhall, VT MLS# 5089041 - Image 5

32 Aspen Lane Winhall, VT MLS# 5089041 - Image 6

32 Aspen Lane Winhall, VT MLS# 5089041 - Image 7

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32 Aspen Lane Winhall, VT MLS# 5089041 - Image 11

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32 Aspen Lane Winhall, VT MLS# 5089041 - Image 13

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32 Aspen Lane Winhall, VT MLS# 5089041 - Image 15

32 Aspen Lane Winhall, VT MLS# 5089041 - Image 16

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32 Aspen Lane Winhall, VT MLS# 5089041 - Image 21

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Virtual Tour

1 of 32

$449,000

Beds

2.1

Baths

1,460

Sq.Ft.

32 Aspen Lane

Winhall, VT

Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY

886 Hidden Valley Road Shaftsbury, VT MLS# 5088511 - Image 1

886 Hidden Valley Road Shaftsbury, VT MLS# 5088511 - Image 2

886 Hidden Valley Road Shaftsbury, VT MLS# 5088511 - Image 3

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886 Hidden Valley Road Shaftsbury, VT MLS# 5088511 - Image 45

1 of 45

$299,900

Beds

2.1

Baths

2,716

Sq.Ft.

886 Hidden Valley Road

Shaftsbury, VT

Courtesy of MAHAR MCCARTHY REAL ESTATE

104 Johnny Cake Hill Lane Readsboro, VT MLS# 5088576 - Image 1

104 Johnny Cake Hill Lane Readsboro, VT MLS# 5088576 - Image 2

104 Johnny Cake Hill Lane Readsboro, VT MLS# 5088576 - Image 3

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Virtual Tour

1 of 35

$409,000

Beds

3.0

Baths

1,696

Sq.Ft.

104 Johnny Cake Hill Lane

Readsboro, VT

Courtesy of BHG MASIELLO BRATTLEBORO

302 Us Rte 7 Pownal, VT MLS# 5088264 - Image 1

302 Us Rte 7 Pownal, VT MLS# 5088264 - Image 2

302 Us Rte 7 Pownal, VT MLS# 5088264 - Image 3

302 Us Rte 7 Pownal, VT MLS# 5088264 - Image 4

302 Us Rte 7 Pownal, VT MLS# 5088264 - Image 5

302 Us Rte 7 Pownal, VT MLS# 5088264 - Image 6

302 Us Rte 7 Pownal, VT MLS# 5088264 - Image 7

302 Us Rte 7 Pownal, VT MLS# 5088264 - Image 8

302 Us Rte 7 Pownal, VT MLS# 5088264 - Image 9

302 Us Rte 7 Pownal, VT MLS# 5088264 - Image 10

302 Us Rte 7 Pownal, VT MLS# 5088264 - Image 11

1 of 11

$179,900

Beds

1.0

Baths

848

Sq.Ft.

302 Us Rte 7

Pownal, VT

Courtesy of BRATTLEBORO AREA REALTY

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 1

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 2

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 3

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 4

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 5

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 6

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 7

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 8

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 9

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 10

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 11

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 12

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 13

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 14

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 15

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 16

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 17

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 18

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 19

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 20

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 21

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 22

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 23

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 24

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 25

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 26

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 27

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 28

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 29

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 30

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 31

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 32

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 33

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 34

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 35

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 36

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 37

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 38

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 39

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 40

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 41

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 42

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 43

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 44

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 45

1677 Barnumville Road Manchester, VT MLS# 5088273 - Image 46

Virtual Tour

1 of 46

$1,275,000

Beds

2.1

Baths

4,084

Sq.Ft.

1677 Barnumville Road

Manchester, VT

Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY

971 South Stream Road Bennington, VT MLS# 5088350 - Image 1

971 South Stream Road Bennington, VT MLS# 5088350 - Image 2

971 South Stream Road Bennington, VT MLS# 5088350 - Image 3

971 South Stream Road Bennington, VT MLS# 5088350 - Image 4

971 South Stream Road Bennington, VT MLS# 5088350 - Image 5

971 South Stream Road Bennington, VT MLS# 5088350 - Image 6

971 South Stream Road Bennington, VT MLS# 5088350 - Image 7

971 South Stream Road Bennington, VT MLS# 5088350 - Image 8

971 South Stream Road Bennington, VT MLS# 5088350 - Image 9

971 South Stream Road Bennington, VT MLS# 5088350 - Image 10

971 South Stream Road Bennington, VT MLS# 5088350 - Image 11

971 South Stream Road Bennington, VT MLS# 5088350 - Image 12

971 South Stream Road Bennington, VT MLS# 5088350 - Image 13

971 South Stream Road Bennington, VT MLS# 5088350 - Image 14

971 South Stream Road Bennington, VT MLS# 5088350 - Image 15

971 South Stream Road Bennington, VT MLS# 5088350 - Image 16

971 South Stream Road Bennington, VT MLS# 5088350 - Image 17

971 South Stream Road Bennington, VT MLS# 5088350 - Image 18

971 South Stream Road Bennington, VT MLS# 5088350 - Image 19

971 South Stream Road Bennington, VT MLS# 5088350 - Image 20

971 South Stream Road Bennington, VT MLS# 5088350 - Image 21

971 South Stream Road Bennington, VT MLS# 5088350 - Image 22

971 South Stream Road Bennington, VT MLS# 5088350 - Image 23

971 South Stream Road Bennington, VT MLS# 5088350 - Image 24

971 South Stream Road Bennington, VT MLS# 5088350 - Image 25

971 South Stream Road Bennington, VT MLS# 5088350 - Image 26

971 South Stream Road Bennington, VT MLS# 5088350 - Image 27

971 South Stream Road Bennington, VT MLS# 5088350 - Image 28

971 South Stream Road Bennington, VT MLS# 5088350 - Image 29

971 South Stream Road Bennington, VT MLS# 5088350 - Image 30

971 South Stream Road Bennington, VT MLS# 5088350 - Image 31

971 South Stream Road Bennington, VT MLS# 5088350 - Image 32

971 South Stream Road Bennington, VT MLS# 5088350 - Image 33

971 South Stream Road Bennington, VT MLS# 5088350 - Image 34

971 South Stream Road Bennington, VT MLS# 5088350 - Image 35

971 South Stream Road Bennington, VT MLS# 5088350 - Image 36

971 South Stream Road Bennington, VT MLS# 5088350 - Image 37

971 South Stream Road Bennington, VT MLS# 5088350 - Image 38

971 South Stream Road Bennington, VT MLS# 5088350 - Image 39

971 South Stream Road Bennington, VT MLS# 5088350 - Image 40

971 South Stream Road Bennington, VT MLS# 5088350 - Image 41

Virtual Tour

1 of 41

$550,000

Beds

2.0

Baths

1,974

Sq.Ft.

971 South Stream Road

Bennington, VT

Courtesy of MAHAR MCCARTHY REAL ESTATE

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 1

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 2

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 3

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 4

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 5

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 6

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 7

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 8

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 9

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 10

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 11

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 12

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 13

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 14

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 15

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 16

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 17

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 18

176 Glen Avenue Readsboro, VT MLS# 5088410 - Image 19

1 of 19

$182,000

Beds

1.0

Baths

1,590

Sq.Ft.

176 Glen Avenue

Readsboro, VT

Courtesy of BHG MASIELLO BRATTLEBORO

67 Valley Pass Manchester, VT MLS# 5088067 - Image 1

67 Valley Pass Manchester, VT MLS# 5088067 - Image 2

67 Valley Pass Manchester, VT MLS# 5088067 - Image 3

67 Valley Pass Manchester, VT MLS# 5088067 - Image 4

67 Valley Pass Manchester, VT MLS# 5088067 - Image 5

67 Valley Pass Manchester, VT MLS# 5088067 - Image 6

67 Valley Pass Manchester, VT MLS# 5088067 - Image 7

67 Valley Pass Manchester, VT MLS# 5088067 - Image 8

67 Valley Pass Manchester, VT MLS# 5088067 - Image 9

67 Valley Pass Manchester, VT MLS# 5088067 - Image 10

67 Valley Pass Manchester, VT MLS# 5088067 - Image 11

67 Valley Pass Manchester, VT MLS# 5088067 - Image 12

67 Valley Pass Manchester, VT MLS# 5088067 - Image 13

67 Valley Pass Manchester, VT MLS# 5088067 - Image 14

67 Valley Pass Manchester, VT MLS# 5088067 - Image 15

67 Valley Pass Manchester, VT MLS# 5088067 - Image 16

67 Valley Pass Manchester, VT MLS# 5088067 - Image 17

67 Valley Pass Manchester, VT MLS# 5088067 - Image 18

67 Valley Pass Manchester, VT MLS# 5088067 - Image 19

67 Valley Pass Manchester, VT MLS# 5088067 - Image 20

67 Valley Pass Manchester, VT MLS# 5088067 - Image 21

67 Valley Pass Manchester, VT MLS# 5088067 - Image 22

67 Valley Pass Manchester, VT MLS# 5088067 - Image 23

67 Valley Pass Manchester, VT MLS# 5088067 - Image 24

67 Valley Pass Manchester, VT MLS# 5088067 - Image 25

67 Valley Pass Manchester, VT MLS# 5088067 - Image 26

1 of 26

$479,000

Beds

2.1

Baths

2,688

Sq.Ft.

67 Valley Pass

Manchester, VT

Courtesy of JOSIAH ALLEN REAL ESTATE, INC.

935 Gage Street Bennington, VT MLS# 5088129 - Image 1

935 Gage Street Bennington, VT MLS# 5088129 - Image 2

935 Gage Street Bennington, VT MLS# 5088129 - Image 3

935 Gage Street Bennington, VT MLS# 5088129 - Image 4

935 Gage Street Bennington, VT MLS# 5088129 - Image 5

935 Gage Street Bennington, VT MLS# 5088129 - Image 6

935 Gage Street Bennington, VT MLS# 5088129 - Image 7

935 Gage Street Bennington, VT MLS# 5088129 - Image 8

935 Gage Street Bennington, VT MLS# 5088129 - Image 9

935 Gage Street Bennington, VT MLS# 5088129 - Image 10

935 Gage Street Bennington, VT MLS# 5088129 - Image 11

935 Gage Street Bennington, VT MLS# 5088129 - Image 12

935 Gage Street Bennington, VT MLS# 5088129 - Image 13

935 Gage Street Bennington, VT MLS# 5088129 - Image 14

935 Gage Street Bennington, VT MLS# 5088129 - Image 15

935 Gage Street Bennington, VT MLS# 5088129 - Image 16

935 Gage Street Bennington, VT MLS# 5088129 - Image 17

935 Gage Street Bennington, VT MLS# 5088129 - Image 18

935 Gage Street Bennington, VT MLS# 5088129 - Image 19

935 Gage Street Bennington, VT MLS# 5088129 - Image 20

935 Gage Street Bennington, VT MLS# 5088129 - Image 21

935 Gage Street Bennington, VT MLS# 5088129 - Image 22

935 Gage Street Bennington, VT MLS# 5088129 - Image 23

935 Gage Street Bennington, VT MLS# 5088129 - Image 24

935 Gage Street Bennington, VT MLS# 5088129 - Image 25

935 Gage Street Bennington, VT MLS# 5088129 - Image 26

935 Gage Street Bennington, VT MLS# 5088129 - Image 27

935 Gage Street Bennington, VT MLS# 5088129 - Image 28

935 Gage Street Bennington, VT MLS# 5088129 - Image 29

935 Gage Street Bennington, VT MLS# 5088129 - Image 30

935 Gage Street Bennington, VT MLS# 5088129 - Image 31

935 Gage Street Bennington, VT MLS# 5088129 - Image 32

935 Gage Street Bennington, VT MLS# 5088129 - Image 33

935 Gage Street Bennington, VT MLS# 5088129 - Image 34

935 Gage Street Bennington, VT MLS# 5088129 - Image 35

935 Gage Street Bennington, VT MLS# 5088129 - Image 36

935 Gage Street Bennington, VT MLS# 5088129 - Image 37

935 Gage Street Bennington, VT MLS# 5088129 - Image 38

935 Gage Street Bennington, VT MLS# 5088129 - Image 39

935 Gage Street Bennington, VT MLS# 5088129 - Image 40

935 Gage Street Bennington, VT MLS# 5088129 - Image 41

935 Gage Street Bennington, VT MLS# 5088129 - Image 42

935 Gage Street Bennington, VT MLS# 5088129 - Image 43

935 Gage Street Bennington, VT MLS# 5088129 - Image 44

1 of 44

$269,000

Beds

2.0

Baths

1,265

Sq.Ft.

935 Gage Street

Bennington, VT

Courtesy of MAPLE LEAF REAL ESTATE

23 Pageant Street Bennington, VT MLS# 5088223 - Image 1

23 Pageant Street Bennington, VT MLS# 5088223 - Image 2

23 Pageant Street Bennington, VT MLS# 5088223 - Image 3

23 Pageant Street Bennington, VT MLS# 5088223 - Image 4

23 Pageant Street Bennington, VT MLS# 5088223 - Image 5

23 Pageant Street Bennington, VT MLS# 5088223 - Image 6

23 Pageant Street Bennington, VT MLS# 5088223 - Image 7

23 Pageant Street Bennington, VT MLS# 5088223 - Image 8

23 Pageant Street Bennington, VT MLS# 5088223 - Image 9

23 Pageant Street Bennington, VT MLS# 5088223 - Image 10

23 Pageant Street Bennington, VT MLS# 5088223 - Image 11

23 Pageant Street Bennington, VT MLS# 5088223 - Image 12

23 Pageant Street Bennington, VT MLS# 5088223 - Image 13

23 Pageant Street Bennington, VT MLS# 5088223 - Image 14

23 Pageant Street Bennington, VT MLS# 5088223 - Image 15

23 Pageant Street Bennington, VT MLS# 5088223 - Image 16

23 Pageant Street Bennington, VT MLS# 5088223 - Image 17

23 Pageant Street Bennington, VT MLS# 5088223 - Image 18

23 Pageant Street Bennington, VT MLS# 5088223 - Image 19

23 Pageant Street Bennington, VT MLS# 5088223 - Image 20

23 Pageant Street Bennington, VT MLS# 5088223 - Image 21

23 Pageant Street Bennington, VT MLS# 5088223 - Image 22

23 Pageant Street Bennington, VT MLS# 5088223 - Image 23

23 Pageant Street Bennington, VT MLS# 5088223 - Image 24

23 Pageant Street Bennington, VT MLS# 5088223 - Image 25

23 Pageant Street Bennington, VT MLS# 5088223 - Image 26

23 Pageant Street Bennington, VT MLS# 5088223 - Image 27

23 Pageant Street Bennington, VT MLS# 5088223 - Image 28

23 Pageant Street Bennington, VT MLS# 5088223 - Image 29

23 Pageant Street Bennington, VT MLS# 5088223 - Image 30

23 Pageant Street Bennington, VT MLS# 5088223 - Image 31

23 Pageant Street Bennington, VT MLS# 5088223 - Image 32

23 Pageant Street Bennington, VT MLS# 5088223 - Image 33

23 Pageant Street Bennington, VT MLS# 5088223 - Image 34

23 Pageant Street Bennington, VT MLS# 5088223 - Image 35

23 Pageant Street Bennington, VT MLS# 5088223 - Image 36

23 Pageant Street Bennington, VT MLS# 5088223 - Image 37

23 Pageant Street Bennington, VT MLS# 5088223 - Image 38

23 Pageant Street Bennington, VT MLS# 5088223 - Image 39

23 Pageant Street Bennington, VT MLS# 5088223 - Image 40

23 Pageant Street Bennington, VT MLS# 5088223 - Image 41

23 Pageant Street Bennington, VT MLS# 5088223 - Image 42

23 Pageant Street Bennington, VT MLS# 5088223 - Image 43

23 Pageant Street Bennington, VT MLS# 5088223 - Image 44

23 Pageant Street Bennington, VT MLS# 5088223 - Image 45

23 Pageant Street Bennington, VT MLS# 5088223 - Image 46

23 Pageant Street Bennington, VT MLS# 5088223 - Image 47

23 Pageant Street Bennington, VT MLS# 5088223 - Image 48

23 Pageant Street Bennington, VT MLS# 5088223 - Image 49

23 Pageant Street Bennington, VT MLS# 5088223 - Image 50

23 Pageant Street Bennington, VT MLS# 5088223 - Image 51

23 Pageant Street Bennington, VT MLS# 5088223 - Image 52

23 Pageant Street Bennington, VT MLS# 5088223 - Image 53

23 Pageant Street Bennington, VT MLS# 5088223 - Image 54

23 Pageant Street Bennington, VT MLS# 5088223 - Image 55

23 Pageant Street Bennington, VT MLS# 5088223 - Image 56

23 Pageant Street Bennington, VT MLS# 5088223 - Image 57

23 Pageant Street Bennington, VT MLS# 5088223 - Image 58

23 Pageant Street Bennington, VT MLS# 5088223 - Image 59

1 of 59

$399,900

Beds

2.0

Baths

1,896

Sq.Ft.

23 Pageant Street

Bennington, VT

Courtesy of MAPLE LEAF REAL ESTATE

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 1

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 2

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 3

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 4

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 5

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 6

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 7

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 8

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 9

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 10

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 11

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 12

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 13

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 14

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 15

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 16

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 17

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 18

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 19

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 20

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 21

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 22

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 23

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 24

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 25

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 26

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 27

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 28

103 Jennings Brook Drive # 103 Bennington, VT MLS# 5088382 - Image 29

1 of 29

$250,000

Beds

2.0

Baths

1,824

Sq.Ft.

103 Jennings Brook Drive # 103

Bennington, VT

Courtesy of MAHAR MCCARTHY REAL ESTATE

123 Bradford Street Bennington, VT MLS# 5088385 - Image 1

123 Bradford Street Bennington, VT MLS# 5088385 - Image 2

123 Bradford Street Bennington, VT MLS# 5088385 - Image 3

123 Bradford Street Bennington, VT MLS# 5088385 - Image 4

1 of 4

$249,900

Beds

4.0

Baths

2,080

Sq.Ft.

123 Bradford Street

Bennington, VT

Courtesy of KW VERMONT - BRENDA JONES REAL ESTATE GROUP

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 1

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 2

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 3

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 4

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 5

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 6

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 7

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 8

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 9

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 10

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 11

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 12

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 13

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 14

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 15

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 16

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 17

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 18

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 19

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 20

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 21

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 22

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 23

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 24

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 25

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 26

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 27

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 28

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 29

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 30

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 31

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 32

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 33

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 34

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 35

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 36

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 37

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 38

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 39

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 40

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 41

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 42

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 43

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 44

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 45

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 46

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 47

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 48

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 49

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 50

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 51

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 52

99 Coolidge Avenue Bennington, VT MLS# 5088016 - Image 53

1 of 53

$219,000

Beds

1.0

Baths

1,047

Sq.Ft.

99 Coolidge Avenue

Bennington, VT

Courtesy of MAPLE LEAF REAL ESTATE

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 1

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 2

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 3

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 4

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 5

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 6

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 7

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 8

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 9

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 10

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 11

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 12

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 13

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 14

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 15

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 16

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 17

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 18

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 19

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 20

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 21

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 22

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 23

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 24

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 25

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 26

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 27

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 28

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 29

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 30

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 31

19 Maple Hill Road Winhall, VT MLS# 5087927 - Image 32

Virtual Tour

1 of 32

$1,275,000

Beds

2.1

Baths

2,814

Sq.Ft.

19 Maple Hill Road

Winhall, VT

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 7/1/2026”

Trends Information provided by ATTOM Data Solutions.

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