Chester Vermont Homes for Sale

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3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 1

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 2

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 3

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 4

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 5

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 6

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 7

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 8

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 9

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 10

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 11

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 12

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 13

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 14

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 15

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 16

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 17

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 18

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 19

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 20

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 21

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 22

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 23

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 24

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 25

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 26

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 27

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 28

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 29

3630 Vt Rt 103 N Chester, VT MLS# 5044894 - Image 30

1 of 30

$650,000

4,324

Sq.Ft.

3630 Vt Rt 103 N

Chester, VT

Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 1

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 2

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 3

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 4

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 5

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 6

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 7

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 8

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 9

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 10

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 11

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 12

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 13

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 14

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 15

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 16

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 17

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 18

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 19

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 20

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 21

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 22

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 23

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 24

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 25

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 26

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 27

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 28

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 29

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 30

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 31

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 32

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 33

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 34

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 35

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 36

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 37

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 38

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 39

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 40

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 41

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 42

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 43

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 44

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 45

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 46

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 47

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 48

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 49

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 50

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 51

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 52

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 53

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 54

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 55

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 56

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 57

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 58

955 Smokeshire Road Chester, VT MLS# 5097722 - Image 59

1 of 59

$750,000

Beds

2.0

Baths

1,695

Sq.Ft.

955 Smokeshire Road

Chester, VT

Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES

223 Coach Road Chester, VT MLS# 5097600 - Image 1

223 Coach Road Chester, VT MLS# 5097600 - Image 2

223 Coach Road Chester, VT MLS# 5097600 - Image 3

223 Coach Road Chester, VT MLS# 5097600 - Image 4

223 Coach Road Chester, VT MLS# 5097600 - Image 5

223 Coach Road Chester, VT MLS# 5097600 - Image 6

223 Coach Road Chester, VT MLS# 5097600 - Image 7

223 Coach Road Chester, VT MLS# 5097600 - Image 8

223 Coach Road Chester, VT MLS# 5097600 - Image 9

223 Coach Road Chester, VT MLS# 5097600 - Image 10

223 Coach Road Chester, VT MLS# 5097600 - Image 11

223 Coach Road Chester, VT MLS# 5097600 - Image 12

223 Coach Road Chester, VT MLS# 5097600 - Image 13

223 Coach Road Chester, VT MLS# 5097600 - Image 14

223 Coach Road Chester, VT MLS# 5097600 - Image 15

223 Coach Road Chester, VT MLS# 5097600 - Image 16

223 Coach Road Chester, VT MLS# 5097600 - Image 17

223 Coach Road Chester, VT MLS# 5097600 - Image 18

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223 Coach Road Chester, VT MLS# 5097600 - Image 20

223 Coach Road Chester, VT MLS# 5097600 - Image 21

223 Coach Road Chester, VT MLS# 5097600 - Image 22

223 Coach Road Chester, VT MLS# 5097600 - Image 23

223 Coach Road Chester, VT MLS# 5097600 - Image 24

223 Coach Road Chester, VT MLS# 5097600 - Image 25

223 Coach Road Chester, VT MLS# 5097600 - Image 26

223 Coach Road Chester, VT MLS# 5097600 - Image 27

223 Coach Road Chester, VT MLS# 5097600 - Image 28

223 Coach Road Chester, VT MLS# 5097600 - Image 29

223 Coach Road Chester, VT MLS# 5097600 - Image 30

223 Coach Road Chester, VT MLS# 5097600 - Image 31

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223 Coach Road Chester, VT MLS# 5097600 - Image 33

223 Coach Road Chester, VT MLS# 5097600 - Image 34

223 Coach Road Chester, VT MLS# 5097600 - Image 35

223 Coach Road Chester, VT MLS# 5097600 - Image 36

223 Coach Road Chester, VT MLS# 5097600 - Image 37

223 Coach Road Chester, VT MLS# 5097600 - Image 38

223 Coach Road Chester, VT MLS# 5097600 - Image 39

223 Coach Road Chester, VT MLS# 5097600 - Image 40

223 Coach Road Chester, VT MLS# 5097600 - Image 41

223 Coach Road Chester, VT MLS# 5097600 - Image 42

223 Coach Road Chester, VT MLS# 5097600 - Image 43

223 Coach Road Chester, VT MLS# 5097600 - Image 44

1 of 44

$789,000

Beds

3.0

Baths

4,388

Sq.Ft.

223 Coach Road

Chester, VT

Courtesy of BARRETT AND VALLEY ASSOCIATES INC.

THE TIME TO SELL IS NOW!

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 1

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 2

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 3

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 4

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 5

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 6

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 7

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 8

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 9

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 10

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 11

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1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 13

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 14

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 15

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 16

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1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 33

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1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 36

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 37

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 38

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 39

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 40

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 41

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 42

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 43

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 44

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 45

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 46

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 47

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 48

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 49

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 50

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 51

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 52

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 53

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 54

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 55

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 56

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 57

1470 Popple Dungeon Road Chester, VT MLS# 5099745 - Image 58

1 of 58

$925,000

Beds

2.1

Baths

2,800

Sq.Ft.

1470 Popple Dungeon Road

Chester, VT

Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 1

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 2

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 3

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 4

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 5

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 6

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 7

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 8

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 9

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 10

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 11

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 12

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 13

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 14

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 15

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 16

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 17

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 18

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 19

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 20

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 21

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 22

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 23

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 24

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 25

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 26

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 27

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 28

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 29

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 30

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 31

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 32

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 33

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 34

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 35

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 36

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 37

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 38

76 Goldthwaite Road Chester, VT MLS# 5088175 - Image 39

Virtual Tour

1 of 39

$1,200,000

Beds

3.0

Baths

3,308

Sq.Ft.

76 Goldthwaite Road

Chester, VT

Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 1

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 2

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 3

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 4

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1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 7

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1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 21

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1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 35

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1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 37

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 38

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 39

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 40

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 41

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 42

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 43

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1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 45

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 46

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 47

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 48

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 49

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 50

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 51

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 52

1302 Popple Dungeon Road Chester, VT MLS# 5087874 - Image 53

Virtual Tour

1 of 53

$1,490,000

Beds

5.0

Baths

5,400

Sq.Ft.

1302 Popple Dungeon Road

Chester, VT

Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY

40 The Common Chester, VT MLS# 5078509 - Image 1

40 The Common Chester, VT MLS# 5078509 - Image 2

40 The Common Chester, VT MLS# 5078509 - Image 3

40 The Common Chester, VT MLS# 5078509 - Image 4

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40 The Common Chester, VT MLS# 5078509 - Image 60

1 of 60

$1,495,000

40 The Common

Chester, VT

Courtesy of REAL BROKER LLC

About Chester

Listings in Chester, VT: 48
Estimated median home price: $277,500

Chester VT Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Chester, Vermont real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chester, VT.

Homes for Sale by Price in Chester, VT

Price	Count
$0 - 100K	8
$100K - 200K	9
$200K - 300K	10
$300K - 400K	5
$400K - 500K	5
$500K - 600K	1
$600K - 700K	4
$700K - 800K	2
$800K - 900K	0
$900K - 1M	1
$1M - Max	3

Homes for Sale by Type in Chester, VT

Property Type	Count
Single Family	24
Townhouse	0
Condo	0
Commercial	5
Rental	2
Lots and Land	16
Condo/Town/CoOp	0
CoOp	0
Multi Family	2
Mobile Home	1
Farms	0

(Data as of 8/4/2026)

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Chester, VT Information

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05143

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 8/7/2026”

Trends Information provided by ATTOM Data Solutions.

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Chester Vermont Homes for Sale

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Chester Vermont Homes for Sale

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