Chester New York Homes for Sale

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3414 Whispering Hills Chester, NY MLS# 974398 - Image 1

3414 Whispering Hills Chester, NY MLS# 974398 - Image 2

3414 Whispering Hills Chester, NY MLS# 974398 - Image 3

3414 Whispering Hills Chester, NY MLS# 974398 - Image 4

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3414 Whispering Hills Chester, NY MLS# 974398 - Image 21

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3414 Whispering Hills Chester, NY MLS# 974398 - Image 23

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3414 Whispering Hills Chester, NY MLS# 974398 - Image 25

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3414 Whispering Hills Chester, NY MLS# 974398 - Image 31

3414 Whispering Hills Chester, NY MLS# 974398 - Image 32

3414 Whispering Hills Chester, NY MLS# 974398 - Image 33

3414 Whispering Hills Chester, NY MLS# 974398 - Image 34

Virtual Tour

1 of 34

$349,999

Beds

2.0

Baths

1,316

Sq.Ft.

3414 Whispering Hills

Chester, NY

Courtesy of KW HUDSON VALLEY UNITED

11 Chandler Drive Chester, NY MLS# 1018371 - Image 2

11 Chandler Drive Chester, NY MLS# 1018371 - Image 3

11 Chandler Drive Chester, NY MLS# 1018371 - Image 4

11 Chandler Drive Chester, NY MLS# 1018371 - Image 5

11 Chandler Drive Chester, NY MLS# 1018371 - Image 6

11 Chandler Drive Chester, NY MLS# 1018371 - Image 7

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11 Chandler Drive Chester, NY MLS# 1018371 - Image 9

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11 Chandler Drive Chester, NY MLS# 1018371 - Image 11

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11 Chandler Drive Chester, NY MLS# 1018371 - Image 15

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11 Chandler Drive Chester, NY MLS# 1018371 - Image 18

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11 Chandler Drive Chester, NY MLS# 1018371 - Image 21

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11 Chandler Drive Chester, NY MLS# 1018371 - Image 31

11 Chandler Drive Chester, NY MLS# 1018371 - Image 32

1 of 32

OPEN HOUSE: Sunday 8/30 1:00 PM - 3:00 PM

$545,000

Beds

2.1

Baths

1,908

Sq.Ft.

11 Chandler Drive

Chester, NY

Courtesy of COLDWELL BANKER REALTY

4118 Whispering Hills Drive Chester, NY MLS# 1018748 - Image 2

4118 Whispering Hills Drive Chester, NY MLS# 1018748 - Image 3

4118 Whispering Hills Drive Chester, NY MLS# 1018748 - Image 4

4118 Whispering Hills Drive Chester, NY MLS# 1018748 - Image 5

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4118 Whispering Hills Drive Chester, NY MLS# 1018748 - Image 22

1 of 22

$329,000

Beds

1.1

Baths

1,294

Sq.Ft.

4118 Whispering Hills Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY

THE TIME TO SELL IS NOW!

985 Craigville Road Chester, NY MLS# 1020165 - Image 1

985 Craigville Road Chester, NY MLS# 1020165 - Image 2

985 Craigville Road Chester, NY MLS# 1020165 - Image 3

985 Craigville Road Chester, NY MLS# 1020165 - Image 4

985 Craigville Road Chester, NY MLS# 1020165 - Image 5

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985 Craigville Road Chester, NY MLS# 1020165 - Image 7

985 Craigville Road Chester, NY MLS# 1020165 - Image 8

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985 Craigville Road Chester, NY MLS# 1020165 - Image 35

985 Craigville Road Chester, NY MLS# 1020165 - Image 36

Virtual Tour

1 of 36

$750,000

Beds

3.1

Baths

3,100

Sq.Ft.

985 Craigville Road

Chester, NY

Courtesy of SERHANT LLC

3 Hemlock Court Chester, NY MLS# 1020128 - Image 2

3 Hemlock Court Chester, NY MLS# 1020128 - Image 3

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3 Hemlock Court Chester, NY MLS# 1020128 - Image 49

3 Hemlock Court Chester, NY MLS# 1020128 - Image 50

1 of 50

$750,000

Beds

2.1

Baths

2,700

Sq.Ft.

3 Hemlock Court

Chester, NY

Courtesy of MK REALTY INC

2119 Whispering Hills Chester, NY MLS# 1019548 - Image 2

2119 Whispering Hills Chester, NY MLS# 1019548 - Image 3

2119 Whispering Hills Chester, NY MLS# 1019548 - Image 4

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2119 Whispering Hills Chester, NY MLS# 1019548 - Image 32

1 of 32

$295,000

Beds

1.1

Baths

1,086

Sq.Ft.

2119 Whispering Hills

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY

815 Craigville Road Chester, NY MLS# 1016060 - Image 2

815 Craigville Road Chester, NY MLS# 1016060 - Image 3

815 Craigville Road Chester, NY MLS# 1016060 - Image 4

815 Craigville Road Chester, NY MLS# 1016060 - Image 5

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1 of 50

$280,000

Beds

1.0

Baths

2,016

Sq.Ft.

815 Craigville Road

Chester, NY

Courtesy of ELLIS SOTHEBY'S INTL REALTY

2703 Whispering Hills Chester, NY MLS# 1016415 - Image 2

2703 Whispering Hills Chester, NY MLS# 1016415 - Image 3

2703 Whispering Hills Chester, NY MLS# 1016415 - Image 4

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2703 Whispering Hills Chester, NY MLS# 1016415 - Image 39

1 of 39

$365,000

Beds

2.1

Baths

1,331

Sq.Ft.

2703 Whispering Hills

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

26 Bridle Lane Chester, NY MLS# 1011224 - Image 2

26 Bridle Lane Chester, NY MLS# 1011224 - Image 3

26 Bridle Lane Chester, NY MLS# 1011224 - Image 4

26 Bridle Lane Chester, NY MLS# 1011224 - Image 5

26 Bridle Lane Chester, NY MLS# 1011224 - Image 6

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26 Bridle Lane Chester, NY MLS# 1011224 - Image 11

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26 Bridle Lane Chester, NY MLS# 1011224 - Image 21

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1 of 29

$685,000

Beds

2.1

Baths

1,718

Sq.Ft.

26 Bridle Lane

Chester, NY

Courtesy of OWNER ENTRY.COM

335 Laroe Road Chester, NY MLS# 1009848 - Image 2

335 Laroe Road Chester, NY MLS# 1009848 - Image 3

335 Laroe Road Chester, NY MLS# 1009848 - Image 4

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1 of 35

$675,000

Beds

2.1

Baths

2,784

Sq.Ft.

335 Laroe Road

Chester, NY

Courtesy of COLDWELL BANKER CHOICE PROP.

3318 State Route 94 Chester, NY MLS# 1008703 - Image 2

3318 State Route 94 Chester, NY MLS# 1008703 - Image 3

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1 of 29

$549,900

Beds

2.0

Baths

2,138

Sq.Ft.

3318 State Route 94

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY

37 Surrey Road Chester, NY MLS# 1007164 - Image 2

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37 Surrey Road Chester, NY MLS# 1007164 - Image 37

37 Surrey Road Chester, NY MLS# 1007164 - Image 38

37 Surrey Road Chester, NY MLS# 1007164 - Image 39

37 Surrey Road Chester, NY MLS# 1007164 - Image 40

Virtual Tour

1 of 40

$500,000

Beds

2.0

Baths

1,730

Sq.Ft.

37 Surrey Road

Chester, NY

Courtesy of EXP REALTY

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 2

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 3

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 4

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 5

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 6

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 7

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 8

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 9

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 10

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 11

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 12

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 13

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 14

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 15

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 16

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 17

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 18

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 19

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 20

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 21

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 22

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 23

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 24

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 25

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 26

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 27

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 28

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 29

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 30

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 31

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 32

107 Pine Hill Road Chester, NY MLS# 1003546 - Image 33

1 of 33

$549,000

Beds

2.1

Baths

1,730

Sq.Ft.

107 Pine Hill Road

Chester, NY

Courtesy of HUDSON VALLEY GRIFFITH

94 Booth Road Chester, NY MLS# 898870 - Image 2

94 Booth Road Chester, NY MLS# 898870 - Image 3

94 Booth Road Chester, NY MLS# 898870 - Image 4

94 Booth Road Chester, NY MLS# 898870 - Image 5

94 Booth Road Chester, NY MLS# 898870 - Image 6

94 Booth Road Chester, NY MLS# 898870 - Image 7

94 Booth Road Chester, NY MLS# 898870 - Image 8

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94 Booth Road Chester, NY MLS# 898870 - Image 11

94 Booth Road Chester, NY MLS# 898870 - Image 12

94 Booth Road Chester, NY MLS# 898870 - Image 13

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94 Booth Road Chester, NY MLS# 898870 - Image 15

94 Booth Road Chester, NY MLS# 898870 - Image 16

94 Booth Road Chester, NY MLS# 898870 - Image 17

94 Booth Road Chester, NY MLS# 898870 - Image 18

94 Booth Road Chester, NY MLS# 898870 - Image 19

94 Booth Road Chester, NY MLS# 898870 - Image 20

94 Booth Road Chester, NY MLS# 898870 - Image 21

94 Booth Road Chester, NY MLS# 898870 - Image 22

94 Booth Road Chester, NY MLS# 898870 - Image 23

1 of 23

$520,000

Beds

2.1

Baths

2,083

Sq.Ft.

94 Booth Road

Chester, NY

Courtesy of COMPASS GREATER NY, LLC

24 Walnut Street Chester, NY MLS# 1004369 - Image 2

24 Walnut Street Chester, NY MLS# 1004369 - Image 3

24 Walnut Street Chester, NY MLS# 1004369 - Image 4

24 Walnut Street Chester, NY MLS# 1004369 - Image 5

24 Walnut Street Chester, NY MLS# 1004369 - Image 6

24 Walnut Street Chester, NY MLS# 1004369 - Image 7

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24 Walnut Street Chester, NY MLS# 1004369 - Image 11

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24 Walnut Street Chester, NY MLS# 1004369 - Image 13

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24 Walnut Street Chester, NY MLS# 1004369 - Image 15

24 Walnut Street Chester, NY MLS# 1004369 - Image 16

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24 Walnut Street Chester, NY MLS# 1004369 - Image 18

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24 Walnut Street Chester, NY MLS# 1004369 - Image 20

24 Walnut Street Chester, NY MLS# 1004369 - Image 21

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24 Walnut Street Chester, NY MLS# 1004369 - Image 28

1 of 28

$539,000

Beds

2.1

Baths

2,698

Sq.Ft.

24 Walnut Street

Chester, NY

Courtesy of KELLER WILLIAMS VILLAGE SQ RLT

11 Oxford Depot Chester, NY MLS# 1002651 - Image 2

11 Oxford Depot Chester, NY MLS# 1002651 - Image 3

11 Oxford Depot Chester, NY MLS# 1002651 - Image 4

11 Oxford Depot Chester, NY MLS# 1002651 - Image 5

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11 Oxford Depot Chester, NY MLS# 1002651 - Image 26

1 of 26

$425,000

Beds

2.0

Baths

1,748

Sq.Ft.

11 Oxford Depot

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

492 Black Meadow Road Chester, NY MLS# 1002697 - Image 2

492 Black Meadow Road Chester, NY MLS# 1002697 - Image 3

492 Black Meadow Road Chester, NY MLS# 1002697 - Image 4

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492 Black Meadow Road Chester, NY MLS# 1002697 - Image 15

492 Black Meadow Road Chester, NY MLS# 1002697 - Image 16

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492 Black Meadow Road Chester, NY MLS# 1002697 - Image 18

1 of 18

$399,000

Studio

Beds

0.0

Baths

2,003,760

Sq.Ft.

492 Black Meadow Road

Chester, NY

Courtesy of EXP REALTY

3815 Whispering Hills Drive Chester, NY MLS# 1000359 - Image 2

3815 Whispering Hills Drive Chester, NY MLS# 1000359 - Image 3

3815 Whispering Hills Drive Chester, NY MLS# 1000359 - Image 4

3815 Whispering Hills Drive Chester, NY MLS# 1000359 - Image 5

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3815 Whispering Hills Drive Chester, NY MLS# 1000359 - Image 48

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3815 Whispering Hills Drive Chester, NY MLS# 1000359 - Image 50

1 of 50

$370,000

Beds

2.1

Baths

1,331

Sq.Ft.

3815 Whispering Hills Drive

Chester, NY

Courtesy of MK REALTY INC

58 Nancy Lane Chester, NY MLS# 995624 - Image 2

58 Nancy Lane Chester, NY MLS# 995624 - Image 3

58 Nancy Lane Chester, NY MLS# 995624 - Image 4

58 Nancy Lane Chester, NY MLS# 995624 - Image 5

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58 Nancy Lane Chester, NY MLS# 995624 - Image 13

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58 Nancy Lane Chester, NY MLS# 995624 - Image 15

58 Nancy Lane Chester, NY MLS# 995624 - Image 16

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58 Nancy Lane Chester, NY MLS# 995624 - Image 49

1 of 49

OPEN HOUSE: Sunday 8/30 11:00 AM - 1:00 PM

$749,999

Beds

2.1

Baths

2,718

Sq.Ft.

58 Nancy Lane

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY

151 Laroe Road Chester, NY MLS# 995916 - Image 2

151 Laroe Road Chester, NY MLS# 995916 - Image 3

151 Laroe Road Chester, NY MLS# 995916 - Image 4

151 Laroe Road Chester, NY MLS# 995916 - Image 5

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151 Laroe Road Chester, NY MLS# 995916 - Image 7

151 Laroe Road Chester, NY MLS# 995916 - Image 8

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151 Laroe Road Chester, NY MLS# 995916 - Image 11

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151 Laroe Road Chester, NY MLS# 995916 - Image 15

151 Laroe Road Chester, NY MLS# 995916 - Image 16

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1 of 43

$430,000

Beds

1.1

Baths

1,177

Sq.Ft.

151 Laroe Road

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

About Chester

Listings in Chester, NY: 108
Estimated median home price: $699,000

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	0
$100K - 200K	0
$200K - 300K	6
$300K - 400K	17
$400K - 500K	14
$500K - 600K	9
$600K - 700K	13
$700K - 800K	20
$800K - 900K	11
$900K - 1M	6
$1M - Max	12

Homes for Sale by Type in Chester, NY

Property Type	Count
Single Family	81
Townhouse	0
Condo	15
Commercial	5
Rental	23
Lots and Land	5
Condo/Town/CoOp	0
CoOp	0
Multi Family	2
Mobile Home	0
Farms	0

(Data as of 8/26/2026)

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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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