View 6 Main Street Chester, NY MLS# 1043650
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1 of 5
$25,000
700

Sq.Ft.

6 Main Street

Chester, NY

Courtesy of HOMESMART HOMES & ESTATES
View 1212 Whispering Hills Chester, NY MLS# 1048656
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$269,000
2

Beds

1.0

Baths

1,084

Sq.Ft.

1212 Whispering Hills

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 2113 Whispering Hills Chester, NY MLS# 950534
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1 of 24
$275,000
2

Beds

1.0

Baths

1,084

Sq.Ft.

2113 Whispering Hills

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
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 815 Craigville Road Chester, NY MLS# 1016060
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$280,000
3

Beds

1.0

Baths

2,016

Sq.Ft.

815 Craigville Road

Chester, NY

Courtesy of ELLIS SOTHEBY'S INTL REALTY
View 2124 Whispering Hills Chester, NY MLS# 1042658
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$289,000
2

Beds

1.0

Baths

1,084

Sq.Ft.

2124 Whispering Hills

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 4008 Whispering Hills Drive Chester, NY MLS# 1027838
Save 4008 Whispering Hills Drive Chester, NY MLS# 1027838
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 1005 Whispering Hills Chester, NY MLS# 1043197
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$290,000
2

Beds

1.1

Baths

1,053

Sq.Ft.

1005 Whispering Hills

Chester, NY

Courtesy of CENTURY 21 FULL SERVICE REALTY
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 552 Pine Hill Road Chester, NY MLS# 958740
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$299,000
0.0

Baths

248,292

Sq.Ft.

552 Pine Hill Road

Chester, NY

Courtesy of EREALTY ADVISORS, INC
View 151 Main Street Chester, NY MLS# 1031155
Save 151 Main Street Chester, NY MLS# 1031155
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$299,000
4

Beds

1.0

Baths

1,504

Sq.Ft.

151 Main Street

Chester, NY

Courtesy of HUDSON VALLEY GRIFFITH
View 2107 Whispering Hills Chester, NY MLS# 1050213
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1 of 34
$309,000
2

Beds

1.1

Baths

1,086

Sq.Ft.

2107 Whispering Hills

Chester, NY

Courtesy of WANSOR REALTY
View 2820 Whispering Hills Chester, NY MLS# 986005
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1 of 32
$319,900
2

Beds

1.1

Baths

1,072

Sq.Ft.

2820 Whispering Hills

Chester, NY

Courtesy of R2M REALTY INC
View 4118 Whispering Hills Drive Chester, NY MLS# 1018748
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$329,000
2

Beds

1.1

Baths

1,294

Sq.Ft.

4118 Whispering Hills Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 1311 Whispering Hills Chester, NY MLS# 983111
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1 of 32
$329,900
3

Beds

2.0

Baths

1,316

Sq.Ft.

1311 Whispering Hills

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 18 Schueler Road Chester, NY MLS# 1046033
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Save 18 Schueler Road Chester, NY MLS# 1046033
1 of 43
$339,900
2

Beds

1.0

Baths

960

Sq.Ft.

18 Schueler Road

Chester, NY

Courtesy of Weichert Realtors - Monroe
View 3706 Whispering Hills Chester, NY MLS# 1039289
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1 of 18
$339,900
2

Beds

1.1

Baths

1,086

Sq.Ft.

3706 Whispering Hills

Chester, NY

Courtesy of EXP REALTY
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 2 Virginia Lane Chester, NY MLS# H6215339
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1 of 4
$350,000
0.0

Baths

235,224

Sq.Ft.

2 Virginia Lane

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 2604 Whispering Hills Chester, NY MLS# 1025165
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1 of 35
$350,000
3

Beds

2.1

Baths

1,086

Sq.Ft.

2604 Whispering Hills

Chester, NY

Courtesy of HOMESMART HOMES & ESTATES

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 the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the NJMLS. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the Internet Data Exchange logo and information about them includes the name of the listing brokers. Some properties listed with the participating brokers do not appear on this website at the request of the seller. Listings of brokers that do not participate in Internet Data Exchange do not appear on this website.

All information deemed reliable but not guaranteed. Last date updated: 10/5/2026.

Source: New Jersey Multiple Listing Service, Inc.

© 2026 New Jersey Multiple Listing Service, Inc. All rights reserved.

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.

Information Copyright 2021, OneKey® MLS. All Rights Reserved.