Chester New York Homes for Sale

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17 Woodridge Drive Chester, NY MLS# 972648 - Image 1

17 Woodridge Drive Chester, NY MLS# 972648 - Image 2

17 Woodridge Drive Chester, NY MLS# 972648 - Image 3

17 Woodridge Drive Chester, NY MLS# 972648 - Image 4

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17 Woodridge Drive Chester, NY MLS# 972648 - Image 7

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17 Woodridge Drive Chester, NY MLS# 972648 - Image 11

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17 Woodridge Drive Chester, NY MLS# 972648 - Image 13

17 Woodridge Drive Chester, NY MLS# 972648 - Image 14

17 Woodridge Drive Chester, NY MLS# 972648 - Image 15

17 Woodridge Drive Chester, NY MLS# 972648 - Image 16

17 Woodridge Drive Chester, NY MLS# 972648 - Image 17

17 Woodridge Drive Chester, NY MLS# 972648 - Image 18

17 Woodridge Drive Chester, NY MLS# 972648 - Image 19

17 Woodridge Drive Chester, NY MLS# 972648 - Image 20

17 Woodridge Drive Chester, NY MLS# 972648 - Image 21

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17 Woodridge Drive Chester, NY MLS# 972648 - Image 23

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17 Woodridge Drive Chester, NY MLS# 972648 - Image 26

17 Woodridge Drive Chester, NY MLS# 972648 - Image 27

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17 Woodridge Drive Chester, NY MLS# 972648 - Image 46

17 Woodridge Drive Chester, NY MLS# 972648 - Image 47

17 Woodridge Drive Chester, NY MLS# 972648 - Image 48

17 Woodridge Drive Chester, NY MLS# 972648 - Image 49

17 Woodridge Drive Chester, NY MLS# 972648 - Image 50

1 of 50

$749,000

Beds

2.1

Baths

2,524

Sq.Ft.

17 Woodridge Drive

Chester, NY

Courtesy of EXP REALTY

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 2

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 3

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 4

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 5

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 6

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 7

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 8

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145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 11

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145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 13

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145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 16

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145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 18

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 19

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145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 41

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 42

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145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 44

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 45

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 46

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 47

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 48

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 49

145 Kings Highway Bypass Chester, NY MLS# 982708 - Image 50

Recently Listed with Virtual Tour

1 of 50

OPEN HOUSE: Saturday 4/18 1:00 PM - 3:00 PM

$1,450,000

Beds

4.0

Baths

4,508

Sq.Ft.

145 Kings Highway Bypass

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

53 Gibson Hill Road Chester, NY MLS# 986225 - Image 2

53 Gibson Hill Road Chester, NY MLS# 986225 - Image 3

53 Gibson Hill Road Chester, NY MLS# 986225 - Image 4

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53 Gibson Hill Road Chester, NY MLS# 986225 - Image 7

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53 Gibson Hill Road Chester, NY MLS# 986225 - Image 37

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53 Gibson Hill Road Chester, NY MLS# 986225 - Image 42

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53 Gibson Hill Road Chester, NY MLS# 986225 - Image 45

53 Gibson Hill Road Chester, NY MLS# 986225 - Image 46

53 Gibson Hill Road Chester, NY MLS# 986225 - Image 47

53 Gibson Hill Road Chester, NY MLS# 986225 - Image 48

Recently Listed

1 of 48

OPEN HOUSE: Sunday 4/19 12:00 PM - 2:00 PM

$1,100,000

Beds

4.0

Baths

5,312

Sq.Ft.

53 Gibson Hill Road

Chester, NY

Courtesy of EXP REALTY

THE TIME TO SELL IS NOW!

5 Roggia Road Chester, NY MLS# 978824 - Image 1

5 Roggia Road Chester, NY MLS# 978824 - Image 2

5 Roggia Road Chester, NY MLS# 978824 - Image 3

5 Roggia Road Chester, NY MLS# 978824 - Image 4

5 Roggia Road Chester, NY MLS# 978824 - Image 5

5 Roggia Road Chester, NY MLS# 978824 - Image 6

5 Roggia Road Chester, NY MLS# 978824 - Image 7

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5 Roggia Road Chester, NY MLS# 978824 - Image 11

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5 Roggia Road Chester, NY MLS# 978824 - Image 13

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5 Roggia Road Chester, NY MLS# 978824 - Image 31

5 Roggia Road Chester, NY MLS# 978824 - Image 32

Recently Listed with Virtual Tour

1 of 32

OPEN HOUSE: Saturday 4/18 1:00 PM - 3:00 PM

$450,000

Beds

2.0

Baths

1,882

Sq.Ft.

5 Roggia Road

Chester, NY

Courtesy of NAZMA REAL ESTATE LLC

85 Surrey Road Chester, NY MLS# 984933 - Image 2

85 Surrey Road Chester, NY MLS# 984933 - Image 3

85 Surrey Road Chester, NY MLS# 984933 - Image 4

85 Surrey Road Chester, NY MLS# 984933 - Image 5

85 Surrey Road Chester, NY MLS# 984933 - Image 6

85 Surrey Road Chester, NY MLS# 984933 - Image 7

85 Surrey Road Chester, NY MLS# 984933 - Image 8

85 Surrey Road Chester, NY MLS# 984933 - Image 9

85 Surrey Road Chester, NY MLS# 984933 - Image 10

85 Surrey Road Chester, NY MLS# 984933 - Image 11

85 Surrey Road Chester, NY MLS# 984933 - Image 12

85 Surrey Road Chester, NY MLS# 984933 - Image 13

85 Surrey Road Chester, NY MLS# 984933 - Image 14

85 Surrey Road Chester, NY MLS# 984933 - Image 15

85 Surrey Road Chester, NY MLS# 984933 - Image 16

85 Surrey Road Chester, NY MLS# 984933 - Image 17

85 Surrey Road Chester, NY MLS# 984933 - Image 18

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85 Surrey Road Chester, NY MLS# 984933 - Image 20

85 Surrey Road Chester, NY MLS# 984933 - Image 21

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85 Surrey Road Chester, NY MLS# 984933 - Image 29

85 Surrey Road Chester, NY MLS# 984933 - Image 30

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85 Surrey Road Chester, NY MLS# 984933 - Image 32

85 Surrey Road Chester, NY MLS# 984933 - Image 33

85 Surrey Road Chester, NY MLS# 984933 - Image 34

85 Surrey Road Chester, NY MLS# 984933 - Image 35

Recently Listed

1 of 35

OPEN HOUSE: Saturday 4/18 12:00 PM - 2:00 PM

$524,900

Beds

2.0

Baths

2,076

Sq.Ft.

85 Surrey Road

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

16 Lori Lane Chester, NY MLS# 982679 - Image 2

16 Lori Lane Chester, NY MLS# 982679 - Image 3

16 Lori Lane Chester, NY MLS# 982679 - Image 4

16 Lori Lane Chester, NY MLS# 982679 - Image 5

16 Lori Lane Chester, NY MLS# 982679 - Image 6

16 Lori Lane Chester, NY MLS# 982679 - Image 7

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16 Lori Lane Chester, NY MLS# 982679 - Image 11

16 Lori Lane Chester, NY MLS# 982679 - Image 12

16 Lori Lane Chester, NY MLS# 982679 - Image 13

16 Lori Lane Chester, NY MLS# 982679 - Image 14

16 Lori Lane Chester, NY MLS# 982679 - Image 15

16 Lori Lane Chester, NY MLS# 982679 - Image 16

16 Lori Lane Chester, NY MLS# 982679 - Image 17

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16 Lori Lane Chester, NY MLS# 982679 - Image 21

16 Lori Lane Chester, NY MLS# 982679 - Image 22

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16 Lori Lane Chester, NY MLS# 982679 - Image 36

16 Lori Lane Chester, NY MLS# 982679 - Image 37

16 Lori Lane Chester, NY MLS# 982679 - Image 38

16 Lori Lane Chester, NY MLS# 982679 - Image 39

16 Lori Lane Chester, NY MLS# 982679 - Image 40

16 Lori Lane Chester, NY MLS# 982679 - Image 41

Recently Listed with Virtual Tour

1 of 41

OPEN HOUSE: Saturday 4/18 1:00 PM - 3:00 PM

$1,159,900

Beds

3.2

Baths

4,624

Sq.Ft.

16 Lori Lane

Chester, NY

Courtesy of EXP REALTY

1071 Craigville Road Chester, NY MLS# 976307 - Image 2

1071 Craigville Road Chester, NY MLS# 976307 - Image 3

1071 Craigville Road Chester, NY MLS# 976307 - Image 4

1071 Craigville Road Chester, NY MLS# 976307 - Image 5

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1071 Craigville Road Chester, NY MLS# 976307 - Image 21

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1071 Craigville Road Chester, NY MLS# 976307 - Image 39

1071 Craigville Road Chester, NY MLS# 976307 - Image 40

1071 Craigville Road Chester, NY MLS# 976307 - Image 41

1071 Craigville Road Chester, NY MLS# 976307 - Image 42

1071 Craigville Road Chester, NY MLS# 976307 - Image 43

1071 Craigville Road Chester, NY MLS# 976307 - Image 44

1071 Craigville Road Chester, NY MLS# 976307 - Image 45

1071 Craigville Road Chester, NY MLS# 976307 - Image 46

1071 Craigville Road Chester, NY MLS# 976307 - Image 47

1071 Craigville Road Chester, NY MLS# 976307 - Image 48

Recently Listed with Virtual Tour

1 of 48

$795,000

Beds

2.1

Baths

2,780

Sq.Ft.

1071 Craigville Road

Chester, NY

Courtesy of MS REALTY GROUP USA, INC

5 Gabriels Drive Chester, NY MLS# 983687 - Image 2

5 Gabriels Drive Chester, NY MLS# 983687 - Image 3

5 Gabriels Drive Chester, NY MLS# 983687 - Image 4

5 Gabriels Drive Chester, NY MLS# 983687 - Image 5

5 Gabriels Drive Chester, NY MLS# 983687 - Image 6

5 Gabriels Drive Chester, NY MLS# 983687 - Image 7

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5 Gabriels Drive Chester, NY MLS# 983687 - Image 11

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5 Gabriels Drive Chester, NY MLS# 983687 - Image 45

Recently Listed

1 of 45

OPEN HOUSE: Sunday 4/19 12:00 PM - 2:00 PM

$850,000

Beds

2.1

Baths

2,722

Sq.Ft.

5 Gabriels Drive

Chester, NY

Courtesy of Q HOME SALES

2 Pine Hill Road Chester, NY MLS# 974429 - Image 2

2 Pine Hill Road Chester, NY MLS# 974429 - Image 3

2 Pine Hill Road Chester, NY MLS# 974429 - Image 4

2 Pine Hill Road Chester, NY MLS# 974429 - Image 5

2 Pine Hill Road Chester, NY MLS# 974429 - Image 6

2 Pine Hill Road Chester, NY MLS# 974429 - Image 7

2 Pine Hill Road Chester, NY MLS# 974429 - Image 8

2 Pine Hill Road Chester, NY MLS# 974429 - Image 9

2 Pine Hill Road Chester, NY MLS# 974429 - Image 10

2 Pine Hill Road Chester, NY MLS# 974429 - Image 11

2 Pine Hill Road Chester, NY MLS# 974429 - Image 12

2 Pine Hill Road Chester, NY MLS# 974429 - Image 13

2 Pine Hill Road Chester, NY MLS# 974429 - Image 14

2 Pine Hill Road Chester, NY MLS# 974429 - Image 15

2 Pine Hill Road Chester, NY MLS# 974429 - Image 16

2 Pine Hill Road Chester, NY MLS# 974429 - Image 17

2 Pine Hill Road Chester, NY MLS# 974429 - Image 18

2 Pine Hill Road Chester, NY MLS# 974429 - Image 19

2 Pine Hill Road Chester, NY MLS# 974429 - Image 20

2 Pine Hill Road Chester, NY MLS# 974429 - Image 21

2 Pine Hill Road Chester, NY MLS# 974429 - Image 22

2 Pine Hill Road Chester, NY MLS# 974429 - Image 23

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2 Pine Hill Road Chester, NY MLS# 974429 - Image 26

2 Pine Hill Road Chester, NY MLS# 974429 - Image 27

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2 Pine Hill Road Chester, NY MLS# 974429 - Image 33

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2 Pine Hill Road Chester, NY MLS# 974429 - Image 35

2 Pine Hill Road Chester, NY MLS# 974429 - Image 36

Recently Listed with Virtual Tour

1 of 36

OPEN HOUSE: Sunday 4/19 2:30 PM - 4:30 PM

$875,000

Beds

2.1

Baths

2,302

Sq.Ft.

2 Pine Hill Road

Chester, NY

Courtesy of ELLIS SOTHEBY'S INTL REALTY

58 Oxford Springs Road Chester, NY MLS# 982136 - Image 2

58 Oxford Springs Road Chester, NY MLS# 982136 - Image 3

58 Oxford Springs Road Chester, NY MLS# 982136 - Image 4

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58 Oxford Springs Road Chester, NY MLS# 982136 - Image 38

Recently Listed with Virtual Tour

1 of 38

$349,900

Beds

1.0

Baths

783

Sq.Ft.

58 Oxford Springs Road

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

101 Whitetail Run Chester, NY MLS# 983196 - Image 2

101 Whitetail Run Chester, NY MLS# 983196 - Image 3

101 Whitetail Run Chester, NY MLS# 983196 - Image 4

101 Whitetail Run Chester, NY MLS# 983196 - Image 5

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101 Whitetail Run Chester, NY MLS# 983196 - Image 8

101 Whitetail Run Chester, NY MLS# 983196 - Image 9

101 Whitetail Run Chester, NY MLS# 983196 - Image 10

101 Whitetail Run Chester, NY MLS# 983196 - Image 11

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Recently Listed

1 of 35

$589,000

Beds

2.1

Baths

1,854

Sq.Ft.

101 Whitetail Run

Chester, NY

Courtesy of CRONIN & COMPANY REAL ESTATE

1311 Whispering Hills Chester, NY MLS# 983111 - Image 2

1311 Whispering Hills Chester, NY MLS# 983111 - Image 3

1311 Whispering Hills Chester, NY MLS# 983111 - Image 4

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Recently Listed

1 of 32

$349,900

Beds

2.0

Baths

1,316

Sq.Ft.

1311 Whispering Hills

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

78 Goshen Road Chester, NY MLS# 968517 - Image 2

78 Goshen Road Chester, NY MLS# 968517 - Image 3

78 Goshen Road Chester, NY MLS# 968517 - Image 4

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Recently Listed

1 of 50

$725,000

Beds

2.2

Baths

3,908

Sq.Ft.

78 Goshen Road

Chester, NY

Courtesy of CRONIN & COMPANY REAL ESTATE

4 Oak Street Chester, NY MLS# 973625 - Image 2

4 Oak Street Chester, NY MLS# 973625 - Image 3

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Recently Listed

1 of 42

$499,900

Beds

2.1

Baths

1,888

Sq.Ft.

4 Oak Street

Chester, NY

Courtesy of CRONIN & COMPANY REAL ESTATE

90 Pewter Circle Chester, NY MLS# 981270 - Image 2

90 Pewter Circle Chester, NY MLS# 981270 - Image 3

90 Pewter Circle Chester, NY MLS# 981270 - Image 4

90 Pewter Circle Chester, NY MLS# 981270 - Image 5

Recently Listed

1 of 5

$759,900

Beds

2.1

Baths

2,250

Sq.Ft.

90 Pewter Circle

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

5 N Hudson Street Chester, NY MLS# 976521 - Image 2

5 N Hudson Street Chester, NY MLS# 976521 - Image 3

5 N Hudson Street Chester, NY MLS# 976521 - Image 4

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Recently Listed

1 of 28

$500,000

Beds

2.0

Baths

2,688

Sq.Ft.

5 N Hudson Street

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

55 Beverly Road Chester, NY MLS# 977281 - Image 2

55 Beverly Road Chester, NY MLS# 977281 - Image 3

55 Beverly Road Chester, NY MLS# 977281 - Image 4

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Recently Listed with Virtual Tour

1 of 49

$735,000

Beds

3.1

Baths

3,356

Sq.Ft.

55 Beverly Road

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY

4116 Whispering Hills Chester, NY MLS# 975277 - Image 2

4116 Whispering Hills Chester, NY MLS# 975277 - Image 3

4116 Whispering Hills Chester, NY MLS# 975277 - Image 4

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1 of 25

$375,000

Beds

2.1

Baths

1,355

Sq.Ft.

4116 Whispering Hills

Chester, NY

Courtesy of WILLIAM RAVEIS-NEW YORK, LLC

21 Bull Mine Road Chester, NY MLS# 973228 - Image 2

21 Bull Mine Road Chester, NY MLS# 973228 - Image 3

21 Bull Mine Road Chester, NY MLS# 973228 - Image 4

21 Bull Mine Road Chester, NY MLS# 973228 - Image 5

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Virtual Tour

1 of 48

$925,000

Beds

3.1

Baths

3,680

Sq.Ft.

21 Bull Mine Road

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY

1 of 1

$1,000,000

Address not provided

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

About Chester

Listings in Chester, NY: 70
Estimated median home price: $674,500

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	0
$100K - 200K	3
$200K - 300K	8
$300K - 400K	11
$400K - 500K	8
$500K - 600K	2
$600K - 700K	7
$700K - 800K	11
$800K - 900K	6
$900K - 1M	4
$1M - Max	10

Homes for Sale by Type in Chester, NY

Property Type	Count
Single Family	43
Townhouse	0
Condo	10
Commercial	5
Rental	26
Lots and Land	12
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	0
Farms	0

(Data as of 4/17/2026)

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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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