View 34 Booth Road Chester, NY MLS# 961100
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1 of 42
$720,000
4

Beds

2.1

Baths

2,506

Sq.Ft.

34 Booth Road

Chester, NY

Courtesy of CENTURY 21 FULL SERVICE REALTY
View 2913 Whispering Hills Chester, NY MLS# 962709
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1 of 29
$279,900
2

Beds

1.0

Baths

1,084

Sq.Ft.

2913 Whispering Hills

Chester, NY

Courtesy of HOMESMART HOMES & ESTATES
View 4 Debbie Court Chester, NY MLS# 962813
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1 of 46
$849,999
5

Beds

5.1

Baths

5,403

Sq.Ft.

4 Debbie Court

Chester, NY

Courtesy of FLAG REALTY GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 20 Goshen Road Chester, NY MLS# 961236
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1 of 50
$1,725,000
4

Beds

2.1

Baths

3,348

Sq.Ft.

20 Goshen Road

Chester, NY

Courtesy of EXP REALTY
View 487 Black Meadow Road Chester, NY MLS# 960665
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1 of 30
$725,000
6

Beds

3.1

Baths

4,204

Sq.Ft.

487 Black Meadow Road

Chester, NY

Courtesy of JOSEPH BARATTA COMPANY REALTY
View 5 Bens Way Chester, NY MLS# 959390
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1 of 28
$744,999
4

Beds

2.1

Baths

2,544

Sq.Ft.

5 Bens Way

Chester, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 34 Mountainside Drive Chester, NY MLS# 956879
Save 34 Mountainside Drive Chester, NY MLS# 956879
1 of 8
$699,990
4

Beds

3.0

Baths

1,867

Sq.Ft.

34 Mountainside Drive

Chester, NY

Courtesy of OUR HOUSE REAL ESTATE GROUP
View 4 Camelback Road Chester, NY MLS# 955725
Save 4 Camelback Road Chester, NY MLS# 955725
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
Save 50 Elkay Drive Chester, NY MLS# 954329
1 of 3
$675,000
Studio

Beds

0.0

Baths

87,120

Sq.Ft.

50 Elkay Drive

Chester, NY

Courtesy of POINT REALTY USA
View 145 Kings Highway Bypass Chester, NY MLS# 953574
Save 145 Kings Highway Bypass Chester, NY MLS# 953574
1 of 15
$1,399,999
4

Beds

4.0

Baths

4,508

Sq.Ft.

145 Kings Highway Bypass

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 1367 Kings Highway Chester, NY MLS# 951876
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1 of 13
$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
Save 12 Damian Court Chester, NY MLS# 950640
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 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 108 Pine Hill Road Chester, NY MLS# 944582
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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
Save 3308 Whispering Hills Drive Chester, NY MLS# 924165
1 of 30
$289,000
2

Beds

1.1

Baths

1,072

Sq.Ft.

3308 Whispering Hills Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 25 Oakland Avenue Chester, NY MLS# 949886
Save 25 Oakland Avenue Chester, NY MLS# 949886
1 of 17
$28,000,000
270,000

Sq.Ft.

25 Oakland Avenue

Chester, NY

Courtesy of EREALTY ADVISORS, INC
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

About Chester

Listings in Chester, NY

57

Estimated median home price

$600,000
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 2
$200K - 300K 8
$300K - 400K 8
$400K - 500K 8
$500K - 600K 3
$600K - 700K 4
$700K - 800K 8
$800K - 900K 3
$900K - 1M 3
$1M - Max 10

Homes for Sale by Type in Chester, NY

Property Type Count
Single Family 32
Townhouse 0
Condo 9
Commercial 5
Rental 25
Lots and Land 10
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 2/22/2026)

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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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