Chester Connecticut Homes for Sale

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288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 1

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 2

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 3

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 4

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 5

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 6

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 7

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 8

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 9

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 10

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 11

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 12

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 13

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 14

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 15

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 16

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 17

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 18

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 19

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 20

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 21

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 22

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 23

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 24

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 25

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 26

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 27

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 28

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 29

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 30

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 31

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 32

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 33

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 34

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 35

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 36

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 37

288 Middlesex Avenue Chester, CT MLS# 24166793 - Image 38

Virtual Tour

1 of 38

$3,150,000

Beds

4.2

Baths

4,926

Sq.Ft.

288 Middlesex Avenue

Chester, CT

47 East Kings Highway Chester, CT MLS# 24180698 - Image 3

47 East Kings Highway Chester, CT MLS# 24180698 - Image 4

47 East Kings Highway Chester, CT MLS# 24180698 - Image 5

47 East Kings Highway Chester, CT MLS# 24180698 - Image 6

47 East Kings Highway Chester, CT MLS# 24180698 - Image 7

47 East Kings Highway Chester, CT MLS# 24180698 - Image 8

47 East Kings Highway Chester, CT MLS# 24180698 - Image 9

47 East Kings Highway Chester, CT MLS# 24180698 - Image 10

47 East Kings Highway Chester, CT MLS# 24180698 - Image 11

47 East Kings Highway Chester, CT MLS# 24180698 - Image 12

47 East Kings Highway Chester, CT MLS# 24180698 - Image 13

47 East Kings Highway Chester, CT MLS# 24180698 - Image 14

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47 East Kings Highway Chester, CT MLS# 24180698 - Image 16

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47 East Kings Highway Chester, CT MLS# 24180698 - Image 18

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47 East Kings Highway Chester, CT MLS# 24180698 - Image 21

47 East Kings Highway Chester, CT MLS# 24180698 - Image 22

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47 East Kings Highway Chester, CT MLS# 24180698 - Image 25

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47 East Kings Highway Chester, CT MLS# 24180698 - Image 27

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47 East Kings Highway Chester, CT MLS# 24180698 - Image 35

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47 East Kings Highway Chester, CT MLS# 24180698 - Image 37

47 East Kings Highway Chester, CT MLS# 24180698 - Image 38

47 East Kings Highway Chester, CT MLS# 24180698 - Image 39

47 East Kings Highway Chester, CT MLS# 24180698 - Image 40

Recently Listed

1 of 40

$2,200,000

Beds

3.1

Baths

3,957

Sq.Ft.

47 East Kings Highway

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 37

1 of 37

$2,100,000

Beds

10.2

Baths

8,500

Sq.Ft.

59-65 Maple Street

Chester, CT

THE TIME TO SELL IS NOW!

10 Denlar Drive Chester, CT MLS# 24149430 - Image 1

10 Denlar Drive Chester, CT MLS# 24149430 - Image 2

10 Denlar Drive Chester, CT MLS# 24149430 - Image 3

10 Denlar Drive Chester, CT MLS# 24149430 - Image 4

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10 Denlar Drive Chester, CT MLS# 24149430 - Image 30

1 of 30

$1,450,000

28,525

Sq.Ft.

10 Denlar Drive

Chester, CT

21 Main Street # Chester, CT MLS# 24144188 - Image 3

21 Main Street # Chester, CT MLS# 24144188 - Image 4

21 Main Street # Chester, CT MLS# 24144188 - Image 5

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1 of 37

$1,200,000

3,000

Sq.Ft.

21 Main Street #

Chester, CT

21 Main Street Chester, CT MLS# 24148717 - Image 3

21 Main Street Chester, CT MLS# 24148717 - Image 4

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1 of 35

$1,200,000

1.0

Baths

3,000

Sq.Ft.

21 Main Street

Chester, CT

$975,000

23,467

Sq.Ft.

132 Main Street

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 24

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

136 Goose Hill Road Chester, CT MLS# 24172811 - Image 26

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

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

1 of 41

$945,000

Beds

3.0

Baths

3,343

Sq.Ft.

136 Goose Hill Road

Chester, CT

26 Ferry Road Chester, CT MLS# 24148777 - Image 3

26 Ferry Road Chester, CT MLS# 24148777 - Image 4

26 Ferry Road Chester, CT MLS# 24148777 - Image 5

26 Ferry Road Chester, CT MLS# 24148777 - Image 6

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26 Ferry Road Chester, CT MLS# 24148777 - Image 21

1 of 21

$850,000

Beds

2.0

Baths

8,382

Sq.Ft.

26 Ferry Road

Chester, CT

6 Jagger Lane Chester, CT MLS# 24164157 - Image 3

6 Jagger Lane Chester, CT MLS# 24164157 - Image 4

6 Jagger Lane Chester, CT MLS# 24164157 - Image 5

6 Jagger Lane Chester, CT MLS# 24164157 - Image 6

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6 Jagger Lane Chester, CT MLS# 24164157 - Image 40

1 of 40

$805,000

Beds

2.1

Baths

2,428

Sq.Ft.

6 Jagger Lane

Chester, CT

59-61 Wig Hill Road Chester, CT MLS# 24166010 - Image 3

59-61 Wig Hill Road Chester, CT MLS# 24166010 - Image 4

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1 of 38

$695,000

Beds

2.1

Baths

3,862

Sq.Ft.

59-61 Wig Hill Road

Chester, CT

16 Sypher Road Chester, CT MLS# 24170124 - Image 3

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1 of 40

$585,000

Beds

2.1

Baths

1,726

Sq.Ft.

16 Sypher Road

Chester, CT

135 Middlesex Avenue Chester, CT MLS# 24169301 - Image 3

135 Middlesex Avenue Chester, CT MLS# 24169301 - Image 4

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1 of 37

OPEN HOUSE: Sunday 6/21 12:00 PM - 2:00 PM

$525,000

Beds

2.0

Baths

1,188

Sq.Ft.

135 Middlesex Avenue

Chester, CT

1 of 1

$282,225

Beds

2.0

Baths

1,344

Sq.Ft.

3 KIRTLAND Avenue

Chester, CT

Goose Hill Road # Chester, CT MLS# 24180404 - Image 3

Goose Hill Road # Chester, CT MLS# 24180404 - Image 4

Goose Hill Road # Chester, CT MLS# 24180404 - Image 5

Goose Hill Road # Chester, CT MLS# 24180404 - Image 6

1 of 6

$145,000

Studio

Beds

0.0

Baths

Goose Hill Road #

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

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

$99,900

Studio

Beds

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: 16
Estimated median home price: $897,500

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

Homes for Sale by Type in Chester, CT

Property Type	Count
Single Family	8
Townhouse	0
Condo	0
Commercial	4
Rental	3
Lots and Land	2
Condo/Town/CoOp	0
CoOp	0
Multi Family	2
Mobile Home	0
Farms	0

(Data as of 6/20/2026)

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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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