Chester New York Homes for Sale

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5 Gabriels Drive Chester, NY MLS# 952148 - Image 1

5 Gabriels Drive Chester, NY MLS# 952148 - Image 2

5 Gabriels Drive Chester, NY MLS# 952148 - Image 3

5 Gabriels Drive Chester, NY MLS# 952148 - Image 4

5 Gabriels Drive Chester, NY MLS# 952148 - Image 5

5 Gabriels Drive Chester, NY MLS# 952148 - Image 6

5 Gabriels Drive Chester, NY MLS# 952148 - Image 7

5 Gabriels Drive Chester, NY MLS# 952148 - Image 8

5 Gabriels Drive Chester, NY MLS# 952148 - Image 9

5 Gabriels Drive Chester, NY MLS# 952148 - Image 10

5 Gabriels Drive Chester, NY MLS# 952148 - Image 11

5 Gabriels Drive Chester, NY MLS# 952148 - Image 12

5 Gabriels Drive Chester, NY MLS# 952148 - Image 13

5 Gabriels Drive Chester, NY MLS# 952148 - Image 14

5 Gabriels Drive Chester, NY MLS# 952148 - Image 15

5 Gabriels Drive Chester, NY MLS# 952148 - Image 16

5 Gabriels Drive Chester, NY MLS# 952148 - Image 17

5 Gabriels Drive Chester, NY MLS# 952148 - Image 18

5 Gabriels Drive Chester, NY MLS# 952148 - Image 19

5 Gabriels Drive Chester, NY MLS# 952148 - Image 20

5 Gabriels Drive Chester, NY MLS# 952148 - Image 21

5 Gabriels Drive Chester, NY MLS# 952148 - Image 22

5 Gabriels Drive Chester, NY MLS# 952148 - Image 23

5 Gabriels Drive Chester, NY MLS# 952148 - Image 24

5 Gabriels Drive Chester, NY MLS# 952148 - Image 25

5 Gabriels Drive Chester, NY MLS# 952148 - Image 26

5 Gabriels Drive Chester, NY MLS# 952148 - Image 27

5 Gabriels Drive Chester, NY MLS# 952148 - Image 28

5 Gabriels Drive Chester, NY MLS# 952148 - Image 29

5 Gabriels Drive Chester, NY MLS# 952148 - Image 30

5 Gabriels Drive Chester, NY MLS# 952148 - Image 31

5 Gabriels Drive Chester, NY MLS# 952148 - Image 32

5 Gabriels Drive Chester, NY MLS# 952148 - Image 33

5 Gabriels Drive Chester, NY MLS# 952148 - Image 34

5 Gabriels Drive Chester, NY MLS# 952148 - Image 35

5 Gabriels Drive Chester, NY MLS# 952148 - Image 36

5 Gabriels Drive Chester, NY MLS# 952148 - Image 37

5 Gabriels Drive Chester, NY MLS# 952148 - Image 38

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5 Gabriels Drive Chester, NY MLS# 952148 - Image 40

5 Gabriels Drive Chester, NY MLS# 952148 - Image 41

5 Gabriels Drive Chester, NY MLS# 952148 - Image 42

5 Gabriels Drive Chester, NY MLS# 952148 - Image 43

5 Gabriels Drive Chester, NY MLS# 952148 - Image 44

5 Gabriels Drive Chester, NY MLS# 952148 - Image 45

5 Gabriels Drive Chester, NY MLS# 952148 - Image 46

5 Gabriels Drive Chester, NY MLS# 952148 - Image 47

5 Gabriels Drive Chester, NY MLS# 952148 - Image 48

5 Gabriels Drive Chester, NY MLS# 952148 - Image 49

Recently Listed with Virtual Tour

1 of 49

$899,000

Beds

2.1

Baths

2,722

Sq.Ft.

5 Gabriels Drive

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

2 Pine Hill Road Chester, NY MLS# 933779 - Image 2

2 Pine Hill Road Chester, NY MLS# 933779 - Image 3

2 Pine Hill Road Chester, NY MLS# 933779 - Image 4

2 Pine Hill Road Chester, NY MLS# 933779 - Image 5

2 Pine Hill Road Chester, NY MLS# 933779 - Image 6

2 Pine Hill Road Chester, NY MLS# 933779 - Image 7

2 Pine Hill Road Chester, NY MLS# 933779 - Image 8

2 Pine Hill Road Chester, NY MLS# 933779 - Image 9

2 Pine Hill Road Chester, NY MLS# 933779 - Image 10

2 Pine Hill Road Chester, NY MLS# 933779 - Image 11

2 Pine Hill Road Chester, NY MLS# 933779 - Image 12

2 Pine Hill Road Chester, NY MLS# 933779 - Image 13

2 Pine Hill Road Chester, NY MLS# 933779 - Image 14

2 Pine Hill Road Chester, NY MLS# 933779 - Image 15

2 Pine Hill Road Chester, NY MLS# 933779 - Image 16

2 Pine Hill Road Chester, NY MLS# 933779 - Image 17

2 Pine Hill Road Chester, NY MLS# 933779 - Image 18

2 Pine Hill Road Chester, NY MLS# 933779 - Image 19

2 Pine Hill Road Chester, NY MLS# 933779 - Image 20

2 Pine Hill Road Chester, NY MLS# 933779 - Image 21

2 Pine Hill Road Chester, NY MLS# 933779 - Image 22

2 Pine Hill Road Chester, NY MLS# 933779 - Image 23

2 Pine Hill Road Chester, NY MLS# 933779 - Image 24

2 Pine Hill Road Chester, NY MLS# 933779 - Image 25

2 Pine Hill Road Chester, NY MLS# 933779 - Image 26

2 Pine Hill Road Chester, NY MLS# 933779 - Image 27

2 Pine Hill Road Chester, NY MLS# 933779 - Image 28

2 Pine Hill Road Chester, NY MLS# 933779 - Image 29

2 Pine Hill Road Chester, NY MLS# 933779 - Image 30

2 Pine Hill Road Chester, NY MLS# 933779 - Image 31

Virtual Tour

1 of 31

$875,000

Beds

2.1

Baths

2,302

Sq.Ft.

2 Pine Hill Road

Chester, NY

Courtesy of SHAHAR MANAGEMENT LLC

32 Mountainside Drive Chester, NY MLS# 901144 - Image 2

32 Mountainside Drive Chester, NY MLS# 901144 - Image 3

32 Mountainside Drive Chester, NY MLS# 901144 - Image 4

32 Mountainside Drive Chester, NY MLS# 901144 - Image 5

32 Mountainside Drive Chester, NY MLS# 901144 - Image 6

32 Mountainside Drive Chester, NY MLS# 901144 - Image 7

32 Mountainside Drive Chester, NY MLS# 901144 - Image 8

1 of 8

$849,900

Beds

2.1

Baths

2,603

Sq.Ft.

32 Mountainside Drive

Chester, NY

Courtesy of OUR HOUSE REAL ESTATE GROUP

THE TIME TO SELL IS NOW!

148 Brookside Avenue Chester, NY MLS# H6146719 - Image 1

148 Brookside Avenue Chester, NY MLS# H6146719 - Image 2

148 Brookside Avenue Chester, NY MLS# H6146719 - Image 3

1 of 3

$799,000

148 Brookside Avenue

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 2

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 3

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 4

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 5

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16 Oxford Springs Road Chester, NY MLS# 935115 - Image 8

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16 Oxford Springs Road Chester, NY MLS# 935115 - Image 40

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 41

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 42

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 43

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 44

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 45

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 46

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 47

16 Oxford Springs Road Chester, NY MLS# 935115 - Image 48

Virtual Tour

1 of 48

$750,000

Beds

3.0

Baths

2,870

Sq.Ft.

16 Oxford Springs Road

Chester, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP

3 Grand View Terrace Chester, NY MLS# 925401 - Image 2

3 Grand View Terrace Chester, NY MLS# 925401 - Image 3

3 Grand View Terrace Chester, NY MLS# 925401 - Image 4

3 Grand View Terrace Chester, NY MLS# 925401 - Image 5

3 Grand View Terrace Chester, NY MLS# 925401 - Image 6

3 Grand View Terrace Chester, NY MLS# 925401 - Image 7

3 Grand View Terrace Chester, NY MLS# 925401 - Image 8

3 Grand View Terrace Chester, NY MLS# 925401 - Image 9

3 Grand View Terrace Chester, NY MLS# 925401 - Image 10

3 Grand View Terrace Chester, NY MLS# 925401 - Image 11

3 Grand View Terrace Chester, NY MLS# 925401 - Image 12

3 Grand View Terrace Chester, NY MLS# 925401 - Image 13

3 Grand View Terrace Chester, NY MLS# 925401 - Image 14

3 Grand View Terrace Chester, NY MLS# 925401 - Image 15

3 Grand View Terrace Chester, NY MLS# 925401 - Image 16

3 Grand View Terrace Chester, NY MLS# 925401 - Image 17

3 Grand View Terrace Chester, NY MLS# 925401 - Image 18

3 Grand View Terrace Chester, NY MLS# 925401 - Image 19

3 Grand View Terrace Chester, NY MLS# 925401 - Image 20

3 Grand View Terrace Chester, NY MLS# 925401 - Image 21

3 Grand View Terrace Chester, NY MLS# 925401 - Image 22

3 Grand View Terrace Chester, NY MLS# 925401 - Image 23

3 Grand View Terrace Chester, NY MLS# 925401 - Image 24

3 Grand View Terrace Chester, NY MLS# 925401 - Image 25

3 Grand View Terrace Chester, NY MLS# 925401 - Image 26

3 Grand View Terrace Chester, NY MLS# 925401 - Image 27

3 Grand View Terrace Chester, NY MLS# 925401 - Image 28

3 Grand View Terrace Chester, NY MLS# 925401 - Image 29

3 Grand View Terrace Chester, NY MLS# 925401 - Image 30

3 Grand View Terrace Chester, NY MLS# 925401 - Image 31

3 Grand View Terrace Chester, NY MLS# 925401 - Image 32

3 Grand View Terrace Chester, NY MLS# 925401 - Image 33

3 Grand View Terrace Chester, NY MLS# 925401 - Image 34

3 Grand View Terrace Chester, NY MLS# 925401 - Image 35

3 Grand View Terrace Chester, NY MLS# 925401 - Image 36

3 Grand View Terrace Chester, NY MLS# 925401 - Image 37

1 of 37

$749,000

Beds

3.0

Baths

3,066

Sq.Ft.

3 Grand View Terrace

Chester, NY

Courtesy of EREALTY ADVISORS, INC

7 Park Place Chester, NY MLS# 927218 - Image 2

7 Park Place Chester, NY MLS# 927218 - Image 3

7 Park Place Chester, NY MLS# 927218 - Image 4

7 Park Place Chester, NY MLS# 927218 - Image 5

7 Park Place Chester, NY MLS# 927218 - Image 6

7 Park Place Chester, NY MLS# 927218 - Image 7

7 Park Place Chester, NY MLS# 927218 - Image 8

7 Park Place Chester, NY MLS# 927218 - Image 9

7 Park Place Chester, NY MLS# 927218 - Image 10

7 Park Place Chester, NY MLS# 927218 - Image 11

7 Park Place Chester, NY MLS# 927218 - Image 12

7 Park Place Chester, NY MLS# 927218 - Image 13

7 Park Place Chester, NY MLS# 927218 - Image 14

7 Park Place Chester, NY MLS# 927218 - Image 15

7 Park Place Chester, NY MLS# 927218 - Image 16

7 Park Place Chester, NY MLS# 927218 - Image 17

7 Park Place Chester, NY MLS# 927218 - Image 18

7 Park Place Chester, NY MLS# 927218 - Image 19

7 Park Place Chester, NY MLS# 927218 - Image 20

7 Park Place Chester, NY MLS# 927218 - Image 21

7 Park Place Chester, NY MLS# 927218 - Image 22

7 Park Place Chester, NY MLS# 927218 - Image 23

7 Park Place Chester, NY MLS# 927218 - Image 24

7 Park Place Chester, NY MLS# 927218 - Image 25

7 Park Place Chester, NY MLS# 927218 - Image 26

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7 Park Place Chester, NY MLS# 927218 - Image 28

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7 Park Place Chester, NY MLS# 927218 - Image 32

7 Park Place Chester, NY MLS# 927218 - Image 33

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7 Park Place Chester, NY MLS# 927218 - Image 35

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7 Park Place Chester, NY MLS# 927218 - Image 37

7 Park Place Chester, NY MLS# 927218 - Image 38

7 Park Place Chester, NY MLS# 927218 - Image 39

7 Park Place Chester, NY MLS# 927218 - Image 40

7 Park Place Chester, NY MLS# 927218 - Image 41

7 Park Place Chester, NY MLS# 927218 - Image 42

7 Park Place Chester, NY MLS# 927218 - Image 43

7 Park Place Chester, NY MLS# 927218 - Image 44

7 Park Place Chester, NY MLS# 927218 - Image 45

7 Park Place Chester, NY MLS# 927218 - Image 46

7 Park Place Chester, NY MLS# 927218 - Image 47

7 Park Place Chester, NY MLS# 927218 - Image 48

1 of 48

$740,000

Beds

3.1

Baths

2,780

Sq.Ft.

7 Park Place

Chester, NY

Courtesy of CENTURY 21 FULL SERVICE REALTY

9 Country Woods Drive Chester, NY MLS# 925049 - Image 2

9 Country Woods Drive Chester, NY MLS# 925049 - Image 3

9 Country Woods Drive Chester, NY MLS# 925049 - Image 4

9 Country Woods Drive Chester, NY MLS# 925049 - Image 5

9 Country Woods Drive Chester, NY MLS# 925049 - Image 6

9 Country Woods Drive Chester, NY MLS# 925049 - Image 7

9 Country Woods Drive Chester, NY MLS# 925049 - Image 8

9 Country Woods Drive Chester, NY MLS# 925049 - Image 9

9 Country Woods Drive Chester, NY MLS# 925049 - Image 10

9 Country Woods Drive Chester, NY MLS# 925049 - Image 11

9 Country Woods Drive Chester, NY MLS# 925049 - Image 12

9 Country Woods Drive Chester, NY MLS# 925049 - Image 13

9 Country Woods Drive Chester, NY MLS# 925049 - Image 14

9 Country Woods Drive Chester, NY MLS# 925049 - Image 15

9 Country Woods Drive Chester, NY MLS# 925049 - Image 16

9 Country Woods Drive Chester, NY MLS# 925049 - Image 17

9 Country Woods Drive Chester, NY MLS# 925049 - Image 18

9 Country Woods Drive Chester, NY MLS# 925049 - Image 19

9 Country Woods Drive Chester, NY MLS# 925049 - Image 20

9 Country Woods Drive Chester, NY MLS# 925049 - Image 21

9 Country Woods Drive Chester, NY MLS# 925049 - Image 22

9 Country Woods Drive Chester, NY MLS# 925049 - Image 23

9 Country Woods Drive Chester, NY MLS# 925049 - Image 24

9 Country Woods Drive Chester, NY MLS# 925049 - Image 25

9 Country Woods Drive Chester, NY MLS# 925049 - Image 26

9 Country Woods Drive Chester, NY MLS# 925049 - Image 27

9 Country Woods Drive Chester, NY MLS# 925049 - Image 28

9 Country Woods Drive Chester, NY MLS# 925049 - Image 29

9 Country Woods Drive Chester, NY MLS# 925049 - Image 30

Virtual Tour

1 of 30

$725,000

Beds

2.1

Baths

3,124

Sq.Ft.

9 Country Woods Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY

34 Mountainside Drive Chester, NY MLS# 895079 - Image 2

34 Mountainside Drive Chester, NY MLS# 895079 - Image 3

34 Mountainside Drive Chester, NY MLS# 895079 - Image 4

34 Mountainside Drive Chester, NY MLS# 895079 - Image 5

34 Mountainside Drive Chester, NY MLS# 895079 - Image 6

34 Mountainside Drive Chester, NY MLS# 895079 - Image 7

34 Mountainside Drive Chester, NY MLS# 895079 - Image 8

1 of 8

$699,990

Beds

3.0

Baths

1,867

Sq.Ft.

34 Mountainside Drive

Chester, NY

Courtesy of OUR HOUSE REAL ESTATE GROUP

220 Oxford Road Chester, NY MLS# 927454 - Image 2

220 Oxford Road Chester, NY MLS# 927454 - Image 3

220 Oxford Road Chester, NY MLS# 927454 - Image 4

220 Oxford Road Chester, NY MLS# 927454 - Image 5

220 Oxford Road Chester, NY MLS# 927454 - Image 6

220 Oxford Road Chester, NY MLS# 927454 - Image 7

220 Oxford Road Chester, NY MLS# 927454 - Image 8

220 Oxford Road Chester, NY MLS# 927454 - Image 9

220 Oxford Road Chester, NY MLS# 927454 - Image 10

220 Oxford Road Chester, NY MLS# 927454 - Image 11

220 Oxford Road Chester, NY MLS# 927454 - Image 12

220 Oxford Road Chester, NY MLS# 927454 - Image 13

220 Oxford Road Chester, NY MLS# 927454 - Image 14

220 Oxford Road Chester, NY MLS# 927454 - Image 15

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220 Oxford Road Chester, NY MLS# 927454 - Image 17

220 Oxford Road Chester, NY MLS# 927454 - Image 18

220 Oxford Road Chester, NY MLS# 927454 - Image 19

220 Oxford Road Chester, NY MLS# 927454 - Image 20

220 Oxford Road Chester, NY MLS# 927454 - Image 21

220 Oxford Road Chester, NY MLS# 927454 - Image 22

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220 Oxford Road Chester, NY MLS# 927454 - Image 24

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220 Oxford Road Chester, NY MLS# 927454 - Image 28

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220 Oxford Road Chester, NY MLS# 927454 - Image 40

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220 Oxford Road Chester, NY MLS# 927454 - Image 42

220 Oxford Road Chester, NY MLS# 927454 - Image 43

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220 Oxford Road Chester, NY MLS# 927454 - Image 49

220 Oxford Road Chester, NY MLS# 927454 - Image 50

1 of 50

$699,000

Beds

3.1

Baths

3,472

Sq.Ft.

220 Oxford Road

Chester, NY

Courtesy of EXIT REALTY VENTURE

360 Prospect Road Chester, NY MLS# 944607 - Image 2

360 Prospect Road Chester, NY MLS# 944607 - Image 3

360 Prospect Road Chester, NY MLS# 944607 - Image 4

360 Prospect Road Chester, NY MLS# 944607 - Image 5

360 Prospect Road Chester, NY MLS# 944607 - Image 6

360 Prospect Road Chester, NY MLS# 944607 - Image 7

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360 Prospect Road Chester, NY MLS# 944607 - Image 50

1 of 50

$699,000

Beds

3.0

Baths

3,000

Sq.Ft.

360 Prospect Road

Chester, NY

Courtesy of EREALTY ADVISORS, INC

50 Elkay Drive Chester, NY MLS# 954329 - Image 2

50 Elkay Drive Chester, NY MLS# 954329 - Image 3

Recently Listed

1 of 3

$699,000

Studio

Beds

0.0

Baths

87,120

Sq.Ft.

50 Elkay Drive

Chester, NY

Courtesy of POINT REALTY USA

507 Bull Mill Road Chester, NY MLS# 894259 - Image 2

507 Bull Mill Road Chester, NY MLS# 894259 - Image 3

507 Bull Mill Road Chester, NY MLS# 894259 - Image 4

507 Bull Mill Road Chester, NY MLS# 894259 - Image 5

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507 Bull Mill Road Chester, NY MLS# 894259 - Image 43

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507 Bull Mill Road Chester, NY MLS# 894259 - Image 45

Virtual Tour

1 of 45

$674,999

Beds

2.1

Baths

3,115

Sq.Ft.

507 Bull Mill Road

Chester, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY

Adult Community

1 of 1

$669,000

Beds

1.1

Baths

1,816

Sq.Ft.

101 Oxford Road

Chester, NY

Courtesy of LOOP REALTY INC

3 DeRose Lane Chester, NY MLS# 924694 - Image 2

3 DeRose Lane Chester, NY MLS# 924694 - Image 3

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3 DeRose Lane Chester, NY MLS# 924694 - Image 34

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3 DeRose Lane Chester, NY MLS# 924694 - Image 50

Virtual Tour

1 of 50

$650,000

Beds

3.1

Baths

2,550

Sq.Ft.

3 DeRose Lane

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY

65 Oxford Springs Road Chester, NY MLS# 938744 - Image 2

65 Oxford Springs Road Chester, NY MLS# 938744 - Image 3

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1 of 50

$650,000

Beds

3.1

Baths

3,617

Sq.Ft.

65 Oxford Springs Road

Chester, NY

Courtesy of EXP REALTY

23 Pewter Circle Chester, NY MLS# 939836 - Image 2

23 Pewter Circle Chester, NY MLS# 939836 - Image 3

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Virtual Tour

1 of 37

$650,000

Beds

2.1

Baths

2,318

Sq.Ft.

23 Pewter Circle

Chester, NY

Courtesy of EXP REALTY

25 Sugarloaf Mountain Road Chester, NY MLS# 951920 - Image 2

25 Sugarloaf Mountain Road Chester, NY MLS# 951920 - Image 3

25 Sugarloaf Mountain Road Chester, NY MLS# 951920 - Image 4

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Recently Listed

1 of 38

$635,000

Beds

2.1

Baths

1,954

Sq.Ft.

25 Sugarloaf Mountain Road

Chester, NY

Courtesy of CRONIN & COMPANY REAL ESTATE

44 Cedar Pond Lane Chester, NY MLS# 942578 - Image 2

44 Cedar Pond Lane Chester, NY MLS# 942578 - Image 3

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1 of 42

$600,000

Beds

2.0

Baths

1,876

Sq.Ft.

44 Cedar Pond Lane

Chester, NY

Courtesy of EXP REALTY

80 Pewter Circle Chester, NY MLS# 913254 - Image 2

80 Pewter Circle Chester, NY MLS# 913254 - Image 3

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1 of 49

$534,900

Beds

2.1

Baths

1,946

Sq.Ft.

80 Pewter Circle

Chester, NY

Courtesy of BHG REAL ESTATE GREEN TEAM

About Chester

Listings in Chester, NY: 69
Estimated median home price: $600,000

Chester NY Homes for Sale & Properties

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

Homes for Sale by Price in Chester, NY

Price	Count
$0 - 100K	1
$100K - 200K	2
$200K - 300K	8
$300K - 400K	11
$400K - 500K	8
$500K - 600K	5
$600K - 700K	10
$700K - 800K	6
$800K - 900K	3
$900K - 1M	3
$1M - Max	12

Homes for Sale by Type in Chester, NY

Property Type	Count
Single Family	40
Townhouse	0
Condo	12
Commercial	6
Rental	27
Lots and Land	10
Condo/Town/CoOp	0
CoOp	0
Multi Family	1
Mobile Home	0
Farms	0

(Data as of 1/30/2026)

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10918

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey® MLS.

The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use.

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