Bennington Vermont Homes for Sale

402 total properties

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00 Heartwellville View Road # 38 Readsboro, VT MLS# 5104818 - Image 1

00 Heartwellville View Road # 38 Readsboro, VT MLS# 5104818 - Image 2

00 Heartwellville View Road # 38 Readsboro, VT MLS# 5104818 - Image 3

00 Heartwellville View Road # 38 Readsboro, VT MLS# 5104818 - Image 4

00 Heartwellville View Road # 38 Readsboro, VT MLS# 5104818 - Image 5

00 Heartwellville View Road # 38 Readsboro, VT MLS# 5104818 - Image 6

00 Heartwellville View Road # 38 Readsboro, VT MLS# 5104818 - Image 7

00 Heartwellville View Road # 38 Readsboro, VT MLS# 5104818 - Image 8

1 of 8

$15,500

0.0

Baths

00 Heartwellville View Road # 38

Readsboro, VT

Courtesy of FLEX REALTY

00 Heartwellville View Road # 39 Readsboro, VT MLS# 5104821 - Image 1

00 Heartwellville View Road # 39 Readsboro, VT MLS# 5104821 - Image 2

00 Heartwellville View Road # 39 Readsboro, VT MLS# 5104821 - Image 3

00 Heartwellville View Road # 39 Readsboro, VT MLS# 5104821 - Image 4

00 Heartwellville View Road # 39 Readsboro, VT MLS# 5104821 - Image 5

00 Heartwellville View Road # 39 Readsboro, VT MLS# 5104821 - Image 6

1 of 6

$15,500

0.0

Baths

00 Heartwellville View Road # 39

Readsboro, VT

Courtesy of FLEX REALTY

00 Heartwellville View Road # 69 Readsboro, VT MLS# 5104828 - Image 1

00 Heartwellville View Road # 69 Readsboro, VT MLS# 5104828 - Image 2

00 Heartwellville View Road # 69 Readsboro, VT MLS# 5104828 - Image 3

00 Heartwellville View Road # 69 Readsboro, VT MLS# 5104828 - Image 4

00 Heartwellville View Road # 69 Readsboro, VT MLS# 5104828 - Image 5

00 Heartwellville View Road # 69 Readsboro, VT MLS# 5104828 - Image 6

1 of 6

$19,500

0.0

Baths

00 Heartwellville View Road # 69

Readsboro, VT

Courtesy of FLEX REALTY

THE TIME TO SELL IS NOW!

00 Heartwellville View Road # 70 Readsboro, VT MLS# 5104829 - Image 1

00 Heartwellville View Road # 70 Readsboro, VT MLS# 5104829 - Image 2

00 Heartwellville View Road # 70 Readsboro, VT MLS# 5104829 - Image 3

00 Heartwellville View Road # 70 Readsboro, VT MLS# 5104829 - Image 4

1 of 4

$19,500

0.0

Baths

00 Heartwellville View Road # 70

Readsboro, VT

Courtesy of FLEX REALTY

Lebensdorf Lane Readsboro, VT MLS# 5068765 - Image 1

Lebensdorf Lane Readsboro, VT MLS# 5068765 - Image 2

Lebensdorf Lane Readsboro, VT MLS# 5068765 - Image 3

Lebensdorf Lane Readsboro, VT MLS# 5068765 - Image 4

Lebensdorf Lane Readsboro, VT MLS# 5068765 - Image 5

Lebensdorf Lane Readsboro, VT MLS# 5068765 - Image 6

Lebensdorf Lane Readsboro, VT MLS# 5068765 - Image 7

Lebensdorf Lane Readsboro, VT MLS# 5068765 - Image 8

Lebensdorf Lane Readsboro, VT MLS# 5068765 - Image 9

1 of 9

$19,999

0.0

Baths

Lebensdorf Lane

Readsboro, VT

Courtesy of OWNERENTRY.COM

0 Route 30 Winhall, VT MLS# 5099207 - Image 1

0 Route 30 Winhall, VT MLS# 5099207 - Image 2

0 Route 30 Winhall, VT MLS# 5099207 - Image 3

0 Route 30 Winhall, VT MLS# 5099207 - Image 4

1 of 4

$20,000

0.0

Baths

0 Route 30

Winhall, VT

Courtesy of MICHAEL ENGLAND REAL ESTATE

0 Bergrucken Lane # 6-377 Stamford, VT MLS# 5105218 - Image 1

0 Bergrucken Lane # 6-377 Stamford, VT MLS# 5105218 - Image 2

0 Bergrucken Lane # 6-377 Stamford, VT MLS# 5105218 - Image 3

0 Bergrucken Lane # 6-377 Stamford, VT MLS# 5105218 - Image 4

1 of 4

$20,000

0.0

Baths

0 Bergrucken Lane # 6-377

Stamford, VT

Courtesy of SOUTHERN VERMONT REALTY GROUP

00 Heartwellville View Road # 34/35 Readsboro, VT MLS# 5068956 - Image 1

00 Heartwellville View Road # 34/35 Readsboro, VT MLS# 5068956 - Image 2

00 Heartwellville View Road # 34/35 Readsboro, VT MLS# 5068956 - Image 3

00 Heartwellville View Road # 34/35 Readsboro, VT MLS# 5068956 - Image 4

00 Heartwellville View Road # 34/35 Readsboro, VT MLS# 5068956 - Image 5

00 Heartwellville View Road # 34/35 Readsboro, VT MLS# 5068956 - Image 6

00 Heartwellville View Road # 34/35 Readsboro, VT MLS# 5068956 - Image 7

00 Heartwellville View Road # 34/35 Readsboro, VT MLS# 5068956 - Image 8

1 of 8

$23,999

0.0

Baths

00 Heartwellville View Road # 34/35

Readsboro, VT

Courtesy of FLEX REALTY

00 Heartwellville View Road # 65 & 66 Readsboro, VT MLS# 5104824 - Image 1

00 Heartwellville View Road # 65 & 66 Readsboro, VT MLS# 5104824 - Image 2

00 Heartwellville View Road # 65 & 66 Readsboro, VT MLS# 5104824 - Image 3

00 Heartwellville View Road # 65 & 66 Readsboro, VT MLS# 5104824 - Image 4

00 Heartwellville View Road # 65 & 66 Readsboro, VT MLS# 5104824 - Image 5

00 Heartwellville View Road # 65 & 66 Readsboro, VT MLS# 5104824 - Image 6

1 of 6

$39,500

0.0

Baths

00 Heartwellville View Road # 65 & 66

Readsboro, VT

Courtesy of FLEX REALTY

0 Grapevine Lane Pownal, VT MLS# 5109674 - Image 1

0 Grapevine Lane Pownal, VT MLS# 5109674 - Image 2

0 Grapevine Lane Pownal, VT MLS# 5109674 - Image 3

1 of 3

$45,000

0.0

Baths

0 Grapevine Lane

Pownal, VT

Courtesy of MAHAR MCCARTHY REAL ESTATE

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 1

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 2

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 3

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 4

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 5

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 6

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 7

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 8

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 9

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 10

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 11

2 Belvedere Street Bennington, VT MLS# 5102053 - Image 12

1 of 12

$49,000

0.0

Baths

2 Belvedere Street

Bennington, VT

Courtesy of PERROTT REALTY

24 Asa's Way Bennington, VT MLS# 5086022 - Image 1

24 Asa's Way Bennington, VT MLS# 5086022 - Image 2

24 Asa's Way Bennington, VT MLS# 5086022 - Image 3

24 Asa's Way Bennington, VT MLS# 5086022 - Image 4

24 Asa's Way Bennington, VT MLS# 5086022 - Image 5

24 Asa's Way Bennington, VT MLS# 5086022 - Image 6

24 Asa's Way Bennington, VT MLS# 5086022 - Image 7

1 of 7

$53,000

0.0

Baths

24 Asa's Way

Bennington, VT

Courtesy of MAHAR MCCARTHY REAL ESTATE

29 Asa's Way Bennington, VT MLS# 5086024 - Image 1

29 Asa's Way Bennington, VT MLS# 5086024 - Image 2

29 Asa's Way Bennington, VT MLS# 5086024 - Image 3

29 Asa's Way Bennington, VT MLS# 5086024 - Image 4

29 Asa's Way Bennington, VT MLS# 5086024 - Image 5

1 of 5

$53,000

0.0

Baths

29 Asa's Way

Bennington, VT

Courtesy of MAHAR MCCARTHY REAL ESTATE

0 Route 153 Rupert, VT MLS# 5111140 - Image 1

Recently Listed

1 of 1

$55,000

0.0

Baths

0 Route 153

Rupert, VT

Courtesy of NEW ENGLAND LAKESIDE REALTY

33 Asa's Way # 16 Bennington, VT MLS# 5104588 - Image 1

1 of 1

$58,000

0.0

Baths

33 Asa's Way # 16

Bennington, VT

Courtesy of MAPLE LEAF REAL ESTATE

14 The Lane Stamford, VT MLS# 5098536 - Image 1

14 The Lane Stamford, VT MLS# 5098536 - Image 2

14 The Lane Stamford, VT MLS# 5098536 - Image 3

14 The Lane Stamford, VT MLS# 5098536 - Image 4

14 The Lane Stamford, VT MLS# 5098536 - Image 5

14 The Lane Stamford, VT MLS# 5098536 - Image 6

14 The Lane Stamford, VT MLS# 5098536 - Image 7

14 The Lane Stamford, VT MLS# 5098536 - Image 8

14 The Lane Stamford, VT MLS# 5098536 - Image 9

14 The Lane Stamford, VT MLS# 5098536 - Image 10

14 The Lane Stamford, VT MLS# 5098536 - Image 11

14 The Lane Stamford, VT MLS# 5098536 - Image 12

14 The Lane Stamford, VT MLS# 5098536 - Image 13

14 The Lane Stamford, VT MLS# 5098536 - Image 14

14 The Lane Stamford, VT MLS# 5098536 - Image 15

14 The Lane Stamford, VT MLS# 5098536 - Image 16

14 The Lane Stamford, VT MLS# 5098536 - Image 17

14 The Lane Stamford, VT MLS# 5098536 - Image 18

14 The Lane Stamford, VT MLS# 5098536 - Image 19

14 The Lane Stamford, VT MLS# 5098536 - Image 20

14 The Lane Stamford, VT MLS# 5098536 - Image 21

14 The Lane Stamford, VT MLS# 5098536 - Image 22

14 The Lane Stamford, VT MLS# 5098536 - Image 23

14 The Lane Stamford, VT MLS# 5098536 - Image 24

14 The Lane Stamford, VT MLS# 5098536 - Image 25

14 The Lane Stamford, VT MLS# 5098536 - Image 26

14 The Lane Stamford, VT MLS# 5098536 - Image 27

14 The Lane Stamford, VT MLS# 5098536 - Image 28

14 The Lane Stamford, VT MLS# 5098536 - Image 29

14 The Lane Stamford, VT MLS# 5098536 - Image 30

14 The Lane Stamford, VT MLS# 5098536 - Image 31

14 The Lane Stamford, VT MLS# 5098536 - Image 32

14 The Lane Stamford, VT MLS# 5098536 - Image 33

14 The Lane Stamford, VT MLS# 5098536 - Image 34

14 The Lane Stamford, VT MLS# 5098536 - Image 35

14 The Lane Stamford, VT MLS# 5098536 - Image 36

14 The Lane Stamford, VT MLS# 5098536 - Image 37

14 The Lane Stamford, VT MLS# 5098536 - Image 38

14 The Lane Stamford, VT MLS# 5098536 - Image 39

14 The Lane Stamford, VT MLS# 5098536 - Image 40

1 of 40

$59,900

0.0

Baths

14 The Lane

Stamford, VT

Courtesy of MONARCH REALTY

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 1

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 2

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 3

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 4

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 5

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 6

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 7

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 8

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 9

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 10

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 11

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 12

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 13

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 14

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 15

0 Sunderland Hill Road Sunderland, VT MLS# 5107454 - Image 16

1 of 16

$60,000

0.0

Baths

0 Sunderland Hill Road

Sunderland, VT

Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 1

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 2

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 3

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 4

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 5

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 6

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 7

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 8

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 9

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 10

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 11

3 W Hill Drive Readsboro, VT MLS# 5085630 - Image 12

1 of 12

$64,000

0.0

Baths

3 W Hill Drive

Readsboro, VT

Courtesy of DEREK GREENE

0 Brambley Lane Bennington, VT MLS# 5092066 - Image 1

0 Brambley Lane Bennington, VT MLS# 5092066 - Image 2

0 Brambley Lane Bennington, VT MLS# 5092066 - Image 3

1 of 3

$69,900

0.0

Baths

0 Brambley Lane

Bennington, VT

Courtesy of HOFFMAN REAL ESTATE

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 1

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 2

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 3

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 4

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 5

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 6

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 7

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 8

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 9

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 10

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 11

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 12

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 13

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 14

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 15

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 16

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 17

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 18

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 19

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 20

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 21

845 Bailey Hill Road Readsboro, VT MLS# 5106559 - Image 22

Virtual Tour

1 of 22

$74,500

Beds

0.0

Baths

586

Sq.Ft.

845 Bailey Hill Road

Readsboro, VT

Courtesy of DEERFIELD VALLEY REAL ESTATE

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”

Trends Information provided by ATTOM Data Solutions.

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