View 151 Main Street Chester, NY MLS# 1031155
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1 of 16
$299,000
4

Beds

1.0

Baths

1,504

Sq.Ft.

151 Main Street

Chester, NY

Courtesy of HUDSON VALLEY GRIFFITH
View 2007 Whispering Hills Chester, NY MLS# 1030827
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1 of 44
$279,999
2

Beds

1.1

Baths

1,086

Sq.Ft.

2007 Whispering Hills

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 68 Conklingtown Road 1&2 Chester, NY MLS# 992189
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1 of 38
$575,000
6

Beds

2.0

Baths

43,560

Sq.Ft.

68 Conklingtown Road 1&2

Chester, NY

Courtesy of MS REALTY GROUP USA, INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 4008 Whispering Hills Drive Chester, NY MLS# 1027838
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1 of 33
$290,000
2

Beds

1.1

Baths

1,072

Sq.Ft.

4008 Whispering Hills Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 1 Hilltop Lane Chester, NY MLS# 1031045
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$750,000
5

Beds

2.1

Baths

2,700

Sq.Ft.

1 Hilltop Lane

Chester, NY

Courtesy of MK REALTY INC
View 7 Lakeview Drive Chester, NY MLS# 1028872
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$549,999
4

Beds

2.1

Baths

2,098

Sq.Ft.

7 Lakeview Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 197 Oxford Road Chester, NY MLS# 1012284
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$799,000
4

Beds

2.1

Baths

3,070

Sq.Ft.

197 Oxford Road

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 4114 Whispering Hills Chester, NY MLS# 1027245
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1 of 29
$389,900
3

Beds

2.0

Baths

1,393

Sq.Ft.

4114 Whispering Hills

Chester, NY

Courtesy of COLDWELL BANKER REALTY
View 2604 Whispering Hills Chester, NY MLS# 1025165
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$350,000
3

Beds

2.1

Baths

1,086

Sq.Ft.

2604 Whispering Hills

Chester, NY

Courtesy of HOMESMART HOMES & ESTATES
View 2 Hemlock Court Chester, NY MLS# 1025992
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1 of 3
$750,000
5

Beds

2.1

Baths

2,700

Sq.Ft.

2 Hemlock Court

Chester, NY

Courtesy of MK REALTY INC
View 1 Arborvitae Court Chester, NY MLS# 1024518
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1 of 1
$725,000
3

Beds

2.1

Baths

2,677

Sq.Ft.

1 Arborvitae Court

Chester, NY

Courtesy of MK REALTY INC
View 3414 Whispering Hills Chester, NY MLS# 974398
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$349,999
3

Beds

2.0

Baths

1,316

Sq.Ft.

3414 Whispering Hills

Chester, NY

Courtesy of KW HUDSON VALLEY UNITED
View 11 Chandler Drive Chester, NY MLS# 1018371
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OPEN HOUSE: Sunday 10/4 12:30 PM - 2:30 PM
$499,999
3

Beds

2.1

Baths

1,908

Sq.Ft.

11 Chandler Drive

Chester, NY

Courtesy of COLDWELL BANKER REALTY
View 4118 Whispering Hills Drive Chester, NY MLS# 1018748
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1 of 22
$329,000
2

Beds

1.1

Baths

1,294

Sq.Ft.

4118 Whispering Hills Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 5 Hilltop Lane Chester, NY MLS# 1020076
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$850,000
5

Beds

2.1

Baths

3,200

Sq.Ft.

5 Hilltop Lane

Chester, NY

Courtesy of MK REALTY INC
View 3 Hemlock Court Chester, NY MLS# 1020128
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1 of 50
$750,000
5

Beds

2.1

Baths

2,700

Sq.Ft.

3 Hemlock Court

Chester, NY

Courtesy of MK REALTY INC
View 2119 Whispering Hills Chester, NY MLS# 1019548
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1 of 32
$295,000
2

Beds

1.1

Baths

1,086

Sq.Ft.

2119 Whispering Hills

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 815 Craigville Road Chester, NY MLS# 1016060
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1 of 50
$280,000
3

Beds

1.0

Baths

2,016

Sq.Ft.

815 Craigville Road

Chester, NY

Courtesy of ELLIS SOTHEBY'S INTL REALTY
View 19 Grand View Terrace Chester, NY MLS# 1012919
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OPEN HOUSE: Saturday 10/3 11:00 AM - 3:00 PM
$789,900
5

Beds

4.0

Baths

4,697

Sq.Ft.

19 Grand View Terrace

Chester, NY

Courtesy of EXP REALTY
View 49 Stone Mountain Trail Chester, NY MLS# 1011165
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$875,000
4

Beds

2.1

Baths

3,656

Sq.Ft.

49 Stone Mountain Trail

Chester, NY

Courtesy of EREALTY ADVISORS, INC

About Chester

Listings in Chester, NY

101

Estimated median home price

$675,000
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 0
$200K - 300K 10
$300K - 400K 18
$400K - 500K 8
$500K - 600K 9
$600K - 700K 11
$700K - 800K 17
$800K - 900K 10
$900K - 1M 6
$1M - Max 11

Homes for Sale by Type in Chester, NY

Property Type Count
Single Family 67
Townhouse 0
Condo 21
Commercial 6
Rental 22
Lots and Land 4
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 10/3/2026)

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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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