Chester Connecticut Homes for Sale

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275 West Main Street Chester, CT MLS# 24213774 - Image 1

275 West Main Street Chester, CT MLS# 24213774 - Image 2

275 West Main Street Chester, CT MLS# 24213774 - Image 3

275 West Main Street Chester, CT MLS# 24213774 - Image 4

275 West Main Street Chester, CT MLS# 24213774 - Image 5

275 West Main Street Chester, CT MLS# 24213774 - Image 6

275 West Main Street Chester, CT MLS# 24213774 - Image 7

275 West Main Street Chester, CT MLS# 24213774 - Image 8

275 West Main Street Chester, CT MLS# 24213774 - Image 9

275 West Main Street Chester, CT MLS# 24213774 - Image 10

275 West Main Street Chester, CT MLS# 24213774 - Image 11

275 West Main Street Chester, CT MLS# 24213774 - Image 12

275 West Main Street Chester, CT MLS# 24213774 - Image 13

275 West Main Street Chester, CT MLS# 24213774 - Image 14

275 West Main Street Chester, CT MLS# 24213774 - Image 15

275 West Main Street Chester, CT MLS# 24213774 - Image 16

275 West Main Street Chester, CT MLS# 24213774 - Image 17

275 West Main Street Chester, CT MLS# 24213774 - Image 18

275 West Main Street Chester, CT MLS# 24213774 - Image 19

275 West Main Street Chester, CT MLS# 24213774 - Image 20

275 West Main Street Chester, CT MLS# 24213774 - Image 21

275 West Main Street Chester, CT MLS# 24213774 - Image 22

275 West Main Street Chester, CT MLS# 24213774 - Image 23

275 West Main Street Chester, CT MLS# 24213774 - Image 24

275 West Main Street Chester, CT MLS# 24213774 - Image 25

275 West Main Street Chester, CT MLS# 24213774 - Image 26

275 West Main Street Chester, CT MLS# 24213774 - Image 27

275 West Main Street Chester, CT MLS# 24213774 - Image 28

275 West Main Street Chester, CT MLS# 24213774 - Image 29

275 West Main Street Chester, CT MLS# 24213774 - Image 30

275 West Main Street Chester, CT MLS# 24213774 - Image 31

275 West Main Street Chester, CT MLS# 24213774 - Image 32

275 West Main Street Chester, CT MLS# 24213774 - Image 33

275 West Main Street Chester, CT MLS# 24213774 - Image 34

275 West Main Street Chester, CT MLS# 24213774 - Image 35

275 West Main Street Chester, CT MLS# 24213774 - Image 36

275 West Main Street Chester, CT MLS# 24213774 - Image 37

275 West Main Street Chester, CT MLS# 24213774 - Image 38

275 West Main Street Chester, CT MLS# 24213774 - Image 39

Recently Listed

1 of 39

$715,000

Beds

3.1

Baths

2,706

Sq.Ft.

275 West Main Street

Chester, CT

40 Castle View Drive Chester, CT MLS# 24210808 - Image 3

40 Castle View Drive Chester, CT MLS# 24210808 - Image 4

40 Castle View Drive Chester, CT MLS# 24210808 - Image 5

40 Castle View Drive Chester, CT MLS# 24210808 - Image 6

40 Castle View Drive Chester, CT MLS# 24210808 - Image 7

40 Castle View Drive Chester, CT MLS# 24210808 - Image 8

40 Castle View Drive Chester, CT MLS# 24210808 - Image 9

40 Castle View Drive Chester, CT MLS# 24210808 - Image 10

40 Castle View Drive Chester, CT MLS# 24210808 - Image 11

40 Castle View Drive Chester, CT MLS# 24210808 - Image 12

40 Castle View Drive Chester, CT MLS# 24210808 - Image 13

40 Castle View Drive Chester, CT MLS# 24210808 - Image 14

40 Castle View Drive Chester, CT MLS# 24210808 - Image 15

40 Castle View Drive Chester, CT MLS# 24210808 - Image 16

40 Castle View Drive Chester, CT MLS# 24210808 - Image 17

40 Castle View Drive Chester, CT MLS# 24210808 - Image 18

40 Castle View Drive Chester, CT MLS# 24210808 - Image 19

40 Castle View Drive Chester, CT MLS# 24210808 - Image 20

40 Castle View Drive Chester, CT MLS# 24210808 - Image 21

40 Castle View Drive Chester, CT MLS# 24210808 - Image 22

40 Castle View Drive Chester, CT MLS# 24210808 - Image 23

40 Castle View Drive Chester, CT MLS# 24210808 - Image 24

40 Castle View Drive Chester, CT MLS# 24210808 - Image 25

Recently Listed

1 of 25

$379,900

Beds

1.1

Baths

1,142

Sq.Ft.

40 Castle View Drive

Chester, CT

42 Straits Road Chester, CT MLS# 24212291 - Image 3

42 Straits Road Chester, CT MLS# 24212291 - Image 4

42 Straits Road Chester, CT MLS# 24212291 - Image 5

42 Straits Road Chester, CT MLS# 24212291 - Image 6

42 Straits Road Chester, CT MLS# 24212291 - Image 7

42 Straits Road Chester, CT MLS# 24212291 - Image 8

42 Straits Road Chester, CT MLS# 24212291 - Image 9

42 Straits Road Chester, CT MLS# 24212291 - Image 10

42 Straits Road Chester, CT MLS# 24212291 - Image 11

42 Straits Road Chester, CT MLS# 24212291 - Image 12

42 Straits Road Chester, CT MLS# 24212291 - Image 13

42 Straits Road Chester, CT MLS# 24212291 - Image 14

42 Straits Road Chester, CT MLS# 24212291 - Image 15

42 Straits Road Chester, CT MLS# 24212291 - Image 16

42 Straits Road Chester, CT MLS# 24212291 - Image 17

42 Straits Road Chester, CT MLS# 24212291 - Image 18

42 Straits Road Chester, CT MLS# 24212291 - Image 19

42 Straits Road Chester, CT MLS# 24212291 - Image 20

42 Straits Road Chester, CT MLS# 24212291 - Image 21

42 Straits Road Chester, CT MLS# 24212291 - Image 22

42 Straits Road Chester, CT MLS# 24212291 - Image 23

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42 Straits Road Chester, CT MLS# 24212291 - Image 25

42 Straits Road Chester, CT MLS# 24212291 - Image 26

42 Straits Road Chester, CT MLS# 24212291 - Image 27

42 Straits Road Chester, CT MLS# 24212291 - Image 28

42 Straits Road Chester, CT MLS# 24212291 - Image 29

42 Straits Road Chester, CT MLS# 24212291 - Image 30

42 Straits Road Chester, CT MLS# 24212291 - Image 31

42 Straits Road Chester, CT MLS# 24212291 - Image 32

42 Straits Road Chester, CT MLS# 24212291 - Image 33

42 Straits Road Chester, CT MLS# 24212291 - Image 34

42 Straits Road Chester, CT MLS# 24212291 - Image 35

42 Straits Road Chester, CT MLS# 24212291 - Image 36

42 Straits Road Chester, CT MLS# 24212291 - Image 37

42 Straits Road Chester, CT MLS# 24212291 - Image 38

42 Straits Road Chester, CT MLS# 24212291 - Image 39

42 Straits Road Chester, CT MLS# 24212291 - Image 40

42 Straits Road Chester, CT MLS# 24212291 - Image 41

42 Straits Road Chester, CT MLS# 24212291 - Image 42

42 Straits Road Chester, CT MLS# 24212291 - Image 43

42 Straits Road Chester, CT MLS# 24212291 - Image 44

42 Straits Road Chester, CT MLS# 24212291 - Image 45

42 Straits Road Chester, CT MLS# 24212291 - Image 46

42 Straits Road Chester, CT MLS# 24212291 - Image 47

Recently Listed

1 of 47

$699,000

Beds

2.1

Baths

2,882

Sq.Ft.

42 Straits Road

Chester, CT

THE TIME TO SELL IS NOW!

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

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

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

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

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

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

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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

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

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

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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

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

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

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

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

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

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

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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 23

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

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28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 31

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28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 33

28 Deep Hollow Road Chester, CT MLS# 24199280 - Image 34

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

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

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

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

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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

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

47 East Kings Highway Chester, CT MLS# 24206419 - Image 6

47 East Kings Highway Chester, CT MLS# 24206419 - Image 7

47 East Kings Highway Chester, CT MLS# 24206419 - Image 8

47 East Kings Highway Chester, CT MLS# 24206419 - Image 9

47 East Kings Highway Chester, CT MLS# 24206419 - Image 10

47 East Kings Highway Chester, CT MLS# 24206419 - Image 11

47 East Kings Highway Chester, CT MLS# 24206419 - Image 12

47 East Kings Highway Chester, CT MLS# 24206419 - Image 13

47 East Kings Highway Chester, CT MLS# 24206419 - Image 14

47 East Kings Highway Chester, CT MLS# 24206419 - Image 15

47 East Kings Highway Chester, CT MLS# 24206419 - Image 16

47 East Kings Highway Chester, CT MLS# 24206419 - Image 17

47 East Kings Highway Chester, CT MLS# 24206419 - Image 18

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47 East Kings Highway Chester, CT MLS# 24206419 - Image 20

47 East Kings Highway Chester, CT MLS# 24206419 - Image 21

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47 East Kings Highway Chester, CT MLS# 24206419 - Image 23

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47 East Kings Highway Chester, CT MLS# 24206419 - Image 25

47 East Kings Highway Chester, CT MLS# 24206419 - Image 26

47 East Kings Highway Chester, CT MLS# 24206419 - Image 27

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47 East Kings Highway Chester, CT MLS# 24206419 - Image 31

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47 East Kings Highway Chester, CT MLS# 24206419 - Image 33

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47 East Kings Highway Chester, CT MLS# 24206419 - Image 37

47 East Kings Highway Chester, CT MLS# 24206419 - Image 38

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

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

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

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

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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

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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

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

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

1 of 40

OPEN HOUSE: Sunday 10/18 2:00 PM - 4:00 PM

$764,900

Beds

2.1

Baths

2,662

Sq.Ft.

13 High Field Lane

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

288 Middlesex Avenue Chester, CT MLS# 24201816 - Image 5

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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

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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

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1 of 30

$269,900

Beds

1.0

Baths

1,217

Sq.Ft.

92 Water Street

Chester, CT

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

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1 of 36

$475,000

Beds

2.0

Baths

1,188

Sq.Ft.

135 Middlesex Avenue

Chester, CT

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

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1 of 7

$3,300,000

21,905

Sq.Ft.

189 Middlesex Avenue

Chester, CT

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

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1 of 37

$1,995,000

Beds

7.0

Baths

8,500

Sq.Ft.

59-65 Maple Street

Chester, CT

$1,450,000

28,525

Sq.Ft.

10 Denlar Drive

Chester, CT

$995,000

3,000

Sq.Ft.

21 Main Street #

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: 23
Estimated median home price: $699,000

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	0
$100K - 200K	0
$200K - 300K	2
$300K - 400K	1
$400K - 500K	5
$500K - 600K	3
$600K - 700K	1
$700K - 800K	2
$800K - 900K	1
$900K - 1M	3
$1M - Max	5

Homes for Sale by Type in Chester, CT

Property Type	Count
Single Family	15
Townhouse	0
Condo	1
Commercial	5
Rental	9
Lots and Land	0
Condo/Town/CoOp	0
CoOp	0
Multi Family	2
Mobile Home	0
Farms	0

(Data as of 10/13/2026)

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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