Chester Connecticut Homes for Sale

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Turkey Hill Road # Chester, CT MLS# 24164488 - Image 1

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 2

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 3

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 4

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 5

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 6

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 7

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 8

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 9

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 10

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 11

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 12

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 13

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 14

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 15

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 16

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 17

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 18

Turkey Hill Road # Chester, CT MLS# 24164488 - Image 19

1 of 19

$75,000

0.0

Baths

Turkey Hill Road #

Chester, CT

90 Water Street Chester, CT MLS# 24198111 - Image 3

90 Water Street Chester, CT MLS# 24198111 - Image 4

90 Water Street Chester, CT MLS# 24198111 - Image 5

90 Water Street Chester, CT MLS# 24198111 - Image 6

90 Water Street Chester, CT MLS# 24198111 - Image 7

90 Water Street Chester, CT MLS# 24198111 - Image 8

90 Water Street Chester, CT MLS# 24198111 - Image 9

90 Water Street Chester, CT MLS# 24198111 - Image 10

90 Water Street Chester, CT MLS# 24198111 - Image 11

90 Water Street Chester, CT MLS# 24198111 - Image 12

90 Water Street Chester, CT MLS# 24198111 - Image 13

90 Water Street Chester, CT MLS# 24198111 - Image 14

90 Water Street Chester, CT MLS# 24198111 - Image 15

90 Water Street Chester, CT MLS# 24198111 - Image 16

90 Water Street Chester, CT MLS# 24198111 - Image 17

90 Water Street Chester, CT MLS# 24198111 - Image 18

90 Water Street Chester, CT MLS# 24198111 - Image 19

90 Water Street Chester, CT MLS# 24198111 - Image 20

90 Water Street Chester, CT MLS# 24198111 - Image 21

90 Water Street Chester, CT MLS# 24198111 - Image 22

90 Water Street Chester, CT MLS# 24198111 - Image 23

90 Water Street Chester, CT MLS# 24198111 - Image 24

1 of 24

$254,900

Beds

1.0

Baths

1,034

Sq.Ft.

90 Water Street

Chester, CT

92 Water Street Chester, CT MLS# 24198196 - Image 3

92 Water Street Chester, CT MLS# 24198196 - Image 4

92 Water Street Chester, CT MLS# 24198196 - Image 5

92 Water Street Chester, CT MLS# 24198196 - Image 6

92 Water Street Chester, CT MLS# 24198196 - Image 7

92 Water Street Chester, CT MLS# 24198196 - Image 8

92 Water Street Chester, CT MLS# 24198196 - Image 9

92 Water Street Chester, CT MLS# 24198196 - Image 10

92 Water Street Chester, CT MLS# 24198196 - Image 11

92 Water Street Chester, CT MLS# 24198196 - Image 12

92 Water Street Chester, CT MLS# 24198196 - Image 13

92 Water Street Chester, CT MLS# 24198196 - Image 14

92 Water Street Chester, CT MLS# 24198196 - Image 15

92 Water Street Chester, CT MLS# 24198196 - Image 16

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92 Water Street Chester, CT MLS# 24198196 - Image 18

92 Water Street Chester, CT MLS# 24198196 - Image 19

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92 Water Street Chester, CT MLS# 24198196 - Image 21

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92 Water Street Chester, CT MLS# 24198196 - Image 25

92 Water Street Chester, CT MLS# 24198196 - Image 26

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92 Water Street Chester, CT MLS# 24198196 - Image 28

92 Water Street Chester, CT MLS# 24198196 - Image 29

92 Water Street Chester, CT MLS# 24198196 - Image 30

1 of 30

OPEN HOUSE: Saturday 10/3 12:00 PM - 2:00 PM

$269,900

Beds

1.0

Baths

1,217

Sq.Ft.

92 Water Street

Chester, CT

THE TIME TO SELL IS NOW!

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 1

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 2

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 3

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 4

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 5

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 6

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 7

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 8

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 9

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 10

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 11

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 12

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 13

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 14

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 15

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 16

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 17

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 18

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 19

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 20

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 21

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 22

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 23

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 24

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 25

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 26

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 27

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 28

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 29

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 30

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 31

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 32

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 33

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 34

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 35

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 36

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 37

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 38

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 39

43 Goose Hill Road Chester, CT MLS# 24205998 - Image 40

1 of 40

$439,900

Beds

1.1

Baths

1,742

Sq.Ft.

43 Goose Hill Road

Chester, CT

6 Castle View Drive Chester, CT MLS# 24102694 - Image 3

6 Castle View Drive Chester, CT MLS# 24102694 - Image 4

6 Castle View Drive Chester, CT MLS# 24102694 - Image 5

6 Castle View Drive Chester, CT MLS# 24102694 - Image 6

6 Castle View Drive Chester, CT MLS# 24102694 - Image 7

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6 Castle View Drive Chester, CT MLS# 24102694 - Image 15

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6 Castle View Drive Chester, CT MLS# 24102694 - Image 30

6 Castle View Drive Chester, CT MLS# 24102694 - Image 31

6 Castle View Drive Chester, CT MLS# 24102694 - Image 32

Virtual Tour

1 of 32

$449,000

Beds

1.1

Baths

2,031

Sq.Ft.

6 Castle View Drive

Chester, CT

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 3

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 4

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 5

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 6

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 7

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 8

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 9

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 10

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 11

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 12

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 13

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 14

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 15

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 16

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 17

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 18

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 19

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135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 21

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135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 31

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135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 33

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 34

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 35

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 36

1 of 36

OPEN HOUSE: Saturday 10/3 12:00 PM - 2:00 PM

$475,000

Beds

2.0

Baths

1,188

Sq.Ft.

135 Middlesex Avenue

Chester, CT

11 Castle View Drive Chester, CT MLS# 24198796 - Image 3

11 Castle View Drive Chester, CT MLS# 24198796 - Image 4

11 Castle View Drive Chester, CT MLS# 24198796 - Image 5

11 Castle View Drive Chester, CT MLS# 24198796 - Image 6

11 Castle View Drive Chester, CT MLS# 24198796 - Image 7

11 Castle View Drive Chester, CT MLS# 24198796 - Image 8

11 Castle View Drive Chester, CT MLS# 24198796 - Image 9

11 Castle View Drive Chester, CT MLS# 24198796 - Image 10

11 Castle View Drive Chester, CT MLS# 24198796 - Image 11

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11 Castle View Drive Chester, CT MLS# 24198796 - Image 13

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11 Castle View Drive Chester, CT MLS# 24198796 - Image 15

11 Castle View Drive Chester, CT MLS# 24198796 - Image 16

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11 Castle View Drive Chester, CT MLS# 24198796 - Image 26

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11 Castle View Drive Chester, CT MLS# 24198796 - Image 28

11 Castle View Drive Chester, CT MLS# 24198796 - Image 29

1 of 29

$496,900

Beds

2.0

Baths

2,103

Sq.Ft.

11 Castle View Drive

Chester, CT

88 Winthrop Road Chester, CT MLS# 24204497 - Image 3

88 Winthrop Road Chester, CT MLS# 24204497 - Image 4

88 Winthrop Road Chester, CT MLS# 24204497 - Image 5

88 Winthrop Road Chester, CT MLS# 24204497 - Image 6

88 Winthrop Road Chester, CT MLS# 24204497 - Image 7

88 Winthrop Road Chester, CT MLS# 24204497 - Image 8

88 Winthrop Road Chester, CT MLS# 24204497 - Image 9

88 Winthrop Road Chester, CT MLS# 24204497 - Image 10

88 Winthrop Road Chester, CT MLS# 24204497 - Image 11

88 Winthrop Road Chester, CT MLS# 24204497 - Image 12

88 Winthrop Road Chester, CT MLS# 24204497 - Image 13

88 Winthrop Road Chester, CT MLS# 24204497 - Image 14

88 Winthrop Road Chester, CT MLS# 24204497 - Image 15

88 Winthrop Road Chester, CT MLS# 24204497 - Image 16

88 Winthrop Road Chester, CT MLS# 24204497 - Image 17

88 Winthrop Road Chester, CT MLS# 24204497 - Image 18

88 Winthrop Road Chester, CT MLS# 24204497 - Image 19

88 Winthrop Road Chester, CT MLS# 24204497 - Image 20

88 Winthrop Road Chester, CT MLS# 24204497 - Image 21

88 Winthrop Road Chester, CT MLS# 24204497 - Image 22

88 Winthrop Road Chester, CT MLS# 24204497 - Image 23

88 Winthrop Road Chester, CT MLS# 24204497 - Image 24

1 of 24

$499,000

Beds

2.1

Baths

2,240

Sq.Ft.

88 Winthrop Road

Chester, CT

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 3

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 4

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 5

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 6

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 7

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 8

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 9

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 10

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 11

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 12

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 13

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 14

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55 Wig Hill Road Chester, CT MLS# 24202647 - Image 16

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55 Wig Hill Road Chester, CT MLS# 24202647 - Image 28

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55 Wig Hill Road Chester, CT MLS# 24202647 - Image 31

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55 Wig Hill Road Chester, CT MLS# 24202647 - Image 35

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 36

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 37

55 Wig Hill Road Chester, CT MLS# 24202647 - Image 38

1 of 38

$499,900

Beds

2.0

Baths

1,774

Sq.Ft.

55 Wig Hill Road

Chester, CT

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 3

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 4

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 5

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 6

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 7

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 8

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 9

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 10

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 11

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 12

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 13

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 14

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 15

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 16

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 17

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 18

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 19

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 20

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 21

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28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 23

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28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 26

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 27

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28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 29

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28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 35

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 36

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 37

1 of 37

$559,000

Beds

1.2

Baths

1,740

Sq.Ft.

28 Deep Hollow Road

Chester, CT

84-86 Spring Street Chester, CT MLS# 24207359 - Image 3

84-86 Spring Street Chester, CT MLS# 24207359 - Image 4

84-86 Spring Street Chester, CT MLS# 24207359 - Image 5

84-86 Spring Street Chester, CT MLS# 24207359 - Image 6

84-86 Spring Street Chester, CT MLS# 24207359 - Image 7

84-86 Spring Street Chester, CT MLS# 24207359 - Image 8

84-86 Spring Street Chester, CT MLS# 24207359 - Image 9

84-86 Spring Street Chester, CT MLS# 24207359 - Image 10

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84-86 Spring Street Chester, CT MLS# 24207359 - Image 12

84-86 Spring Street Chester, CT MLS# 24207359 - Image 13

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84-86 Spring Street Chester, CT MLS# 24207359 - Image 36

Recently Listed

1 of 36

$579,900

Beds

2.1

Baths

3,506

Sq.Ft.

84-86 Spring Street

Chester, CT

112 Oakwood Trail 112 Chester, CT MLS# 24202649 - Image 3

112 Oakwood Trail 112 Chester, CT MLS# 24202649 - Image 4

112 Oakwood Trail 112 Chester, CT MLS# 24202649 - Image 5

112 Oakwood Trail 112 Chester, CT MLS# 24202649 - Image 6

112 Oakwood Trail 112 Chester, CT MLS# 24202649 - Image 7

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112 Oakwood Trail 112 Chester, CT MLS# 24202649 - Image 39

Adult Community

1 of 39

$599,900

Beds

2.1

Baths

2,000

Sq.Ft.

112 Oakwood Trail 112

Chester, CT

13 High Field Lane Chester, CT MLS# 24198973 - Image 3

13 High Field Lane Chester, CT MLS# 24198973 - Image 4

13 High Field Lane Chester, CT MLS# 24198973 - Image 5

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1 of 40

$764,900

Beds

2.1

Baths

2,662

Sq.Ft.

13 High Field Lane

Chester, CT

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 3

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 4

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15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 17

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15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 39

Recently Listed

1 of 39

$875,000

Beds

2.1

Baths

3,233

Sq.Ft.

15 Hickory Hill Drive

Chester, CT

$975,000

23,467

Sq.Ft.

132 Main Street

Chester, CT

$995,000

3,000

Sq.Ft.

21 Main Street #

Chester, CT

$995,000

1.0

Baths

3,000

Sq.Ft.

21 Main Street

Chester, CT

19 Denlar Drive Chester, CT MLS# 24205746 - Image 3

19 Denlar Drive Chester, CT MLS# 24205746 - Image 4

19 Denlar Drive Chester, CT MLS# 24205746 - Image 5

19 Denlar Drive Chester, CT MLS# 24205746 - Image 6

19 Denlar Drive Chester, CT MLS# 24205746 - Image 7

19 Denlar Drive Chester, CT MLS# 24205746 - Image 8

19 Denlar Drive Chester, CT MLS# 24205746 - Image 9

19 Denlar Drive Chester, CT MLS# 24205746 - Image 10

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19 Denlar Drive Chester, CT MLS# 24205746 - Image 40

1 of 40

$1,350,000

Beds

2.0

Baths

5,886

Sq.Ft.

19 Denlar Drive

Chester, CT

$1,450,000

28,525

Sq.Ft.

10 Denlar Drive

Chester, CT

47 East Kings Highway Chester, CT MLS# 24206419 - Image 3

47 East Kings Highway Chester, CT MLS# 24206419 - Image 4

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Recently Listed with Virtual Tour

1 of 40

$1,900,000

Beds

3.1

Baths

3,957

Sq.Ft.

47 East Kings Highway

Chester, CT

About Chester

Chester achieved fame as a center for inventors and manufacturing innovations. Today, Chester touts itself as “home to a stone mason with the eye of an artist, and artists with the industry of stone masons.” Many multinational businesses complete with New York for clients.

Listings in Chester, CT: 24
Estimated median home price: $682,400

Chester CT Homes for Sale & Properties

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

Homes for Sale by Price in Chester, CT

Price	Count
$0 - 100K	1
$100K - 200K	0
$200K - 300K	2
$300K - 400K	0
$400K - 500K	6
$500K - 600K	3
$600K - 700K	0
$700K - 800K	1
$800K - 900K	2
$900K - 1M	3
$1M - Max	6

Homes for Sale by Type in Chester, CT

Property Type	Count
Single Family	14
Townhouse	0
Condo	1
Commercial	5
Rental	7
Lots and Land	1
Condo/Town/CoOp	0
CoOp	0
Multi Family	3
Mobile Home	0
Farms	0

(Data as of 10/2/2026)

Find Properties in Chester, CT

Chester, CT Information

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06412

Information deemed reliable but not guaranteed.

Listing information has been assembled from various sources of varying degrees of reliability. Any information critical to a buying decision should be independently verified.

Information on this this page is provided by the Smart Multiple Listing Service, Inc. 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. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

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