Chester Connecticut Homes for Sale

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15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 1

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 2

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

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

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 5

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 6

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 7

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 8

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 9

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 10

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 11

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 12

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 13

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 14

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

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 16

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

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 18

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 19

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 20

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 21

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 22

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 23

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 24

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 25

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 26

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 27

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 28

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 29

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 30

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 31

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 32

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 33

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 34

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 35

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 36

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 37

15 Hickory Hill Drive Chester, CT MLS# 24210144 - Image 38

1 of 38

$875,000

Beds

2.1

Baths

3,233

Sq.Ft.

15 Hickory Hill Drive

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

84-86 Spring Street Chester, CT MLS# 24207359 - Image 11

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

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

84-86 Spring Street Chester, CT MLS# 24207359 - Image 14

84-86 Spring Street Chester, CT MLS# 24207359 - Image 15

84-86 Spring Street Chester, CT MLS# 24207359 - Image 16

84-86 Spring Street Chester, CT MLS# 24207359 - Image 17

84-86 Spring Street Chester, CT MLS# 24207359 - Image 18

84-86 Spring Street Chester, CT MLS# 24207359 - Image 19

84-86 Spring Street Chester, CT MLS# 24207359 - Image 20

84-86 Spring Street Chester, CT MLS# 24207359 - Image 21

84-86 Spring Street Chester, CT MLS# 24207359 - Image 22

84-86 Spring Street Chester, CT MLS# 24207359 - Image 23

84-86 Spring Street Chester, CT MLS# 24207359 - Image 24

84-86 Spring Street Chester, CT MLS# 24207359 - Image 25

84-86 Spring Street Chester, CT MLS# 24207359 - Image 26

84-86 Spring Street Chester, CT MLS# 24207359 - Image 27

84-86 Spring Street Chester, CT MLS# 24207359 - Image 28

84-86 Spring Street Chester, CT MLS# 24207359 - Image 29

84-86 Spring Street Chester, CT MLS# 24207359 - Image 30

84-86 Spring Street Chester, CT MLS# 24207359 - Image 31

84-86 Spring Street Chester, CT MLS# 24207359 - Image 32

84-86 Spring Street Chester, CT MLS# 24207359 - Image 33

84-86 Spring Street Chester, CT MLS# 24207359 - Image 34

84-86 Spring Street Chester, CT MLS# 24207359 - Image 35

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

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

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

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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

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

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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

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

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

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

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

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

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

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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

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

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

47 East Kings Highway Chester, CT MLS# 24206419 - Image 5

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47 East Kings Highway Chester, CT MLS# 24206419 - Image 39

47 East Kings Highway Chester, CT MLS# 24206419 - Image 40

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

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

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

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

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

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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

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

6 Castle View Drive Chester, CT MLS# 24102694 - Image 8

6 Castle View Drive Chester, CT MLS# 24102694 - Image 9

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6 Castle View Drive Chester, CT MLS# 24102694 - Image 11

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6 Castle View Drive Chester, CT MLS# 24102694 - Image 13

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6 Castle View Drive Chester, CT MLS# 24102694 - Image 16

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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

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

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

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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

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

13 High Field Lane Chester, CT MLS# 24198973 - Image 6

13 High Field Lane Chester, CT MLS# 24198973 - Image 7

13 High Field Lane Chester, CT MLS# 24198973 - Image 8

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13 High Field Lane Chester, CT MLS# 24198973 - Image 40

1 of 40

$764,900

Beds

2.1

Baths

2,662

Sq.Ft.

13 High Field Lane

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

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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

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

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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

288 Middlesex Avenue Chester, CT MLS# 24201816 - Image 3

288 Middlesex Avenue Chester, CT MLS# 24201816 - Image 4

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288 Middlesex Avenue Chester, CT MLS# 24201816 - Image 31

288 Middlesex Avenue Chester, CT MLS# 24201816 - Image 32

288 Middlesex Avenue Chester, CT MLS# 24201816 - Image 33

288 Middlesex Avenue Chester, CT MLS# 24201816 - Image 34

288 Middlesex Avenue Chester, CT MLS# 24201816 - Image 35

288 Middlesex Avenue Chester, CT MLS# 24201816 - Image 36

288 Middlesex Avenue Chester, CT MLS# 24201816 - Image 37

288 Middlesex Avenue Chester, CT MLS# 24201816 - Image 38

Virtual Tour

1 of 38

$2,995,000

Beds

4.2

Baths

4,926

Sq.Ft.

288 Middlesex Avenue

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

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

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

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

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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

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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

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

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

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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

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

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135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 20

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

135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 22

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135 Middlesex Avenue Chester, CT MLS# 24189125 - Image 29

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

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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

189 Middlesex Avenue Chester, CT MLS# 24188369 - Image 3

189 Middlesex Avenue Chester, CT MLS# 24188369 - Image 4

189 Middlesex Avenue Chester, CT MLS# 24188369 - Image 5

189 Middlesex Avenue Chester, CT MLS# 24188369 - Image 6

189 Middlesex Avenue Chester, CT MLS# 24188369 - Image 7

1 of 7

$3,300,000

21,905

Sq.Ft.

189 Middlesex Avenue

Chester, CT

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 3

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 4

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 5

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 6

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 7

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 8

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 9

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 10

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 11

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 12

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 13

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 14

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 15

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 16

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 17

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 18

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 19

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 20

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 21

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 22

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136 Goose Hill Road Chester, CT MLS# 24172811 - Image 25

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136 Goose Hill Road Chester, CT MLS# 24172811 - Image 27

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 28

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136 Goose Hill Road Chester, CT MLS# 24172811 - Image 31

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 32

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 33

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 34

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 35

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 36

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 37

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 38

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 39

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 40

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 41

1 of 41

$825,000

Beds

3.0

Baths

3,343

Sq.Ft.

136 Goose Hill Road

Chester, CT

59-65 Maple Street Chester, CT MLS# 24170551 - Image 3

59-65 Maple Street Chester, CT MLS# 24170551 - Image 4

59-65 Maple Street Chester, CT MLS# 24170551 - Image 5

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59-65 Maple Street Chester, CT MLS# 24170551 - Image 16

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59-65 Maple Street Chester, CT MLS# 24170551 - Image 37

1 of 37

$1,995,000

Beds

10.2

Baths

8,500

Sq.Ft.

59-65 Maple Street

Chester, CT

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

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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

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: 25
Estimated median home price: $764,900

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	2
$800K - 900K	2
$900K - 1M	3
$1M - Max	6

Homes for Sale by Type in Chester, CT

Property Type	Count
Single Family	15
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 10/1/2026)

Find Properties in Chester, CT

Chester, CT Information

Find Properties by Zip

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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