View 25 Sugarloaf Mountain Road Chester, NY MLS# 951920
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1 of 38
$635,000
3

Beds

2.1

Baths

1,954

Sq.Ft.

25 Sugarloaf Mountain Road

Chester, NY

Courtesy of CRONIN & COMPANY REAL ESTATE
View 4 Camelback Road Chester, NY MLS# 955725
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1 of 48
$999,000
5

Beds

2.2

Baths

5,080

Sq.Ft.

4 Camelback Road

Chester, NY

Courtesy of PROMINENT PROPERTIES SOTHEBY'S
View 50 Elkay Drive Chester, NY MLS# 954329
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1 of 3
$699,000
Studio

Beds

0.0

Baths

87,120

Sq.Ft.

50 Elkay Drive

Chester, NY

Courtesy of POINT REALTY USA
The time to sell is now! THE TIME TO SELL IS NOW!
View 1367 Kings Highway Chester, NY MLS# 951876
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1 of 8
$460,000
3

Beds

1.1

Baths

1,728

Sq.Ft.

1367 Kings Highway

Chester, NY

Courtesy of KARTEN REAL ESTATE SVCS LLC
View 5 Gabriels Drive Chester, NY MLS# 952148
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1 of 49
$899,000
4

Beds

2.1

Baths

2,722

Sq.Ft.

5 Gabriels Drive

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 12 Damian Court Chester, NY MLS# 950640
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1 of 34
$999,000
5

Beds

4.0

Baths

3,136

Sq.Ft.

12 Damian Court

Chester, NY

Courtesy of MS REALTY GROUP USA, INC
View 4508 Whispering Hills Chester, NY MLS# 951306
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1 of 20
$325,000
2

Beds

1.1

Baths

1,072

Sq.Ft.

4508 Whispering Hills

Chester, NY

Courtesy of EXP REALTY
View 2113 Whispering Hills Chester, NY MLS# 950534
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1 of 24
$295,000
2

Beds

1.0

Baths

1,084

Sq.Ft.

2113 Whispering Hills

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 3910 Whispering Hills Chester, NY MLS# 946789
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1 of 9
$369,900
3

Beds

2.1

Baths

1,331

Sq.Ft.

3910 Whispering Hills

Chester, NY

Courtesy of EXP REALTY
View 108 Pine Hill Road Chester, NY MLS# 944582
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Save 108 Pine Hill Road Chester, NY MLS# 944582
1 of 37
$449,000
4

Beds

1.1

Baths

1,780

Sq.Ft.

108 Pine Hill Road

Chester, NY

Courtesy of AVION
View 3308 Whispering Hills Drive Chester, NY MLS# 924165
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1 of 30
OPEN HOUSE: Saturday 1/31 11:00 AM - 1:00 PM
$299,000
2

Beds

1.1

Baths

1,072

Sq.Ft.

3308 Whispering Hills Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 2 Garnett Hill Road Chester, NY MLS# 931380
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1 of 35
$999,999
5

Beds

3.1

Baths

4,772

Sq.Ft.

2 Garnett Hill Road

Chester, NY

Courtesy of PLATINUM REALTY ASSOCIATES
View Oxford Road Chester, NY MLS# 946546
Save Oxford Road Chester, NY MLS# 946546
1 of 2
$199,000
Studio

Beds

0.0

Baths

313,632

Sq.Ft.

Oxford Road

Chester, NY

Courtesy of BLOOMING REALTY
View Oxford Road Chester, NY MLS# 945194
Save Oxford Road Chester, NY MLS# 945194
1 of 1
$199,000
Studio

Beds

0.0

Baths

113,256

Sq.Ft.

Oxford Road

Chester, NY

Courtesy of BLOOMING REALTY
View 360 Prospect Road Chester, NY MLS# 944607
Save 360 Prospect Road Chester, NY MLS# 944607
1 of 50
$699,000
3

Beds

3.0

Baths

3,000

Sq.Ft.

360 Prospect Road

Chester, NY

Courtesy of EREALTY ADVISORS, INC
View 23 White Oak Drive Chester, NY MLS# 943245
Save 23 White Oak Drive Chester, NY MLS# 943245
1 of 23
$3,000
1,150

Sq.Ft.

23 White Oak Drive

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 3120 Whispering Hills Chester, NY MLS# 941582
Save 3120 Whispering Hills Chester, NY MLS# 941582
1 of 18
$310,000
2

Beds

1.1

Baths

1,072

Sq.Ft.

3120 Whispering Hills

Chester, NY

Courtesy of JOHN J LEASE REALTORS INC
View 44 Cedar Pond Lane Chester, NY MLS# 942578
Save 44 Cedar Pond Lane Chester, NY MLS# 942578
1 of 42
$600,000
3

Beds

2.0

Baths

1,876

Sq.Ft.

44 Cedar Pond Lane

Chester, NY

Courtesy of EXP REALTY
View 101 Oxford Road Chester, NY MLS# 943068
  • Adult Community
Save 101 Oxford Road Chester, NY MLS# 943068
1 of 1
$669,000
3

Beds

1.1

Baths

1,816

Sq.Ft.

101 Oxford Road

Chester, NY

Courtesy of LOOP REALTY INC
View 3917 Whispering Hills Chester, NY MLS# 942965
Save 3917 Whispering Hills Chester, NY MLS# 942965
1 of 28
$319,000
2

Beds

1.1

Baths

1,072

Sq.Ft.

3917 Whispering Hills

Chester, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY

About Chester

Listings in Chester, NY

68

Estimated median home price

$567,450
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 1
$100K - 200K 2
$200K - 300K 7
$300K - 400K 12
$400K - 500K 8
$500K - 600K 5
$600K - 700K 9
$700K - 800K 6
$800K - 900K 3
$900K - 1M 3
$1M - Max 12

Homes for Sale by Type in Chester, NY

Property Type Count
Single Family 39
Townhouse 0
Condo 12
Commercial 6
Rental 29
Lots and Land 10
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 1/28/2026)

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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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