View 3409 Whispering Hills Chester, NY MLS# 1032618
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1 of 1
$360,000
3

Beds

2.1

Baths

1,331

Sq.Ft.

3409 Whispering Hills

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 63 Hubshop Road Chester, NY MLS# 1039933
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1 of 19
$459,000
4

Beds

2.1

Baths

2,060

Sq.Ft.

63 Hubshop Road

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 32 Surrey Road Chester, NY MLS# 1040785
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1 of 39
OPEN HOUSE: Sunday 8/23 12:00 PM - 2:00 PM
$489,000
4

Beds

1.1

Baths

1,820

Sq.Ft.

32 Surrey Road

Chester, NY

Courtesy of EXP REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1367 Kings Highway Chester, NY MLS# 1036770
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1 of 16
$440,000
3

Beds

1.1

Baths

1,728

Sq.Ft.

1367 Kings Highway

Chester, NY

Courtesy of GREENE REALTY GROUP
View 166 Bull Mill Road Chester, NY MLS# 1030923
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1 of 37
$340,000
2

Beds

1.0

Baths

1,004

Sq.Ft.

166 Bull Mill Road

Chester, NY

Courtesy of KELLER WILLIAMS VALLEY REALTY
View 21 Trotting Drive Chester, NY MLS# 1030740
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1 of 50
$475,000
3

Beds

2.0

Baths

1,624

Sq.Ft.

21 Trotting Drive

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 70 Main Street Chester, NY MLS# 1034449
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1 of 27
$469,000
3

Beds

1.2

Baths

1,357

Sq.Ft.

70 Main Street

Chester, NY

Courtesy of CURASI REALTY, INC.
View 66 Whitetail Run Chester, NY MLS# 1033721
Save 66 Whitetail Run Chester, NY MLS# 1033721
1 of 50
$449,000
3

Beds

1.1

Baths

1,500

Sq.Ft.

66 Whitetail Run

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 2522 Whispering Hills Chester, NY MLS# 1027103
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1 of 35
$369,000
3

Beds

2.1

Baths

1,331

Sq.Ft.

2522 Whispering Hills

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 151 Main Street Chester, NY MLS# 1031155
Save 151 Main Street Chester, NY MLS# 1031155
1 of 16
$325,000
4

Beds

1.0

Baths

1,504

Sq.Ft.

151 Main Street

Chester, NY

Courtesy of HUDSON VALLEY GRIFFITH
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 185 Oxford Road Chester, NY MLS# 1019170
Save 185 Oxford Road Chester, NY MLS# 1019170
1 of 49
$389,000
3

Beds

1.0

Baths

1,062

Sq.Ft.

185 Oxford Road

Chester, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 4114 Whispering Hills Chester, NY MLS# 1027245
Save 4114 Whispering Hills Chester, NY MLS# 1027245
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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1 of 35
$350,000
3

Beds

2.1

Baths

1,086

Sq.Ft.

2604 Whispering Hills

Chester, NY

Courtesy of HOMESMART HOMES & ESTATES
View 76 Surrey Road Chester, NY MLS# 1022518
Save 76 Surrey Road Chester, NY MLS# 1022518
1 of 44
$489,900
3

Beds

2.0

Baths

1,912

Sq.Ft.

76 Surrey Road

Chester, NY

Courtesy of EXP REALTY
View 3414 Whispering Hills Chester, NY MLS# 974398
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1 of 34
$349,999
3

Beds

2.0

Baths

1,316

Sq.Ft.

3414 Whispering Hills

Chester, NY

Courtesy of KW HUDSON VALLEY UNITED
View 4118 Whispering Hills Drive Chester, NY MLS# 1018748
Save 4118 Whispering Hills Drive Chester, NY MLS# 1018748
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 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
Save 815 Craigville Road Chester, NY MLS# 1016060
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 2703 Whispering Hills Chester, NY MLS# 1016415
Save 2703 Whispering Hills Chester, NY MLS# 1016415
1 of 39
$365,000
3

Beds

2.1

Baths

1,331

Sq.Ft.

2703 Whispering Hills

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

About Chester

Listings in Chester, NY

108

Estimated median home price

$699,450
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 5
$300K - 400K 18
$400K - 500K 14
$500K - 600K 9
$600K - 700K 12
$700K - 800K 20
$800K - 900K 12
$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 22
Lots and Land 5
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 8/22/2026)

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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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