View 487 Black Meadow Road Chester, NY MLS# 960665
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$725,000
6

Beds

3.1

Baths

4,204

Sq.Ft.

487 Black Meadow Road

Chester, NY

Courtesy of JOSEPH BARATTA COMPANY REALTY
View 34 Booth Road Chester, NY MLS# 961100
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$720,000
4

Beds

2.1

Baths

2,506

Sq.Ft.

34 Booth Road

Chester, NY

Courtesy of CENTURY 21 FULL SERVICE REALTY
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 101 Oxford Road Chester, NY MLS# 943068
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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 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 25 High Street Chester, NY MLS# 883804
Save 25 High Street Chester, NY MLS# 883804
1 of 28
$515,000
4

Beds

2.1

Baths

2,898

Sq.Ft.

25 High Street

Chester, NY

Courtesy of CHRISTIE'S INT. REAL ESTATE
View 391 Bull Mill Road Chester, NY MLS# 880804
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$509,999
3

Beds

2.0

Baths

1,800

Sq.Ft.

391 Bull Mill Road

Chester, NY

Courtesy of CENTURY 21 REALTY CENTER
View Main Street Chester, NY MLS# H6204360
Save Main Street Chester, NY MLS# H6204360
1 of 2
$500,000
Studio

Beds

0.0

Baths

36,098

Sq.Ft.

Main Street

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 16 Mari Road Chester, NY MLS# 926859
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1 of 38
$500,000
4

Beds

3.0

Baths

2,098

Sq.Ft.

16 Mari Road

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 6 Vista Drive Chester, NY MLS# 944968
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1 of 45
$499,900
3

Beds

2.1

Baths

1,934

Sq.Ft.

6 Vista Drive

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 70 Main Street Chester, NY MLS# 914556
Save 70 Main Street Chester, NY MLS# 914556
1 of 23
$475,000
4

Beds

2.1

Baths

1,357

Sq.Ft.

70 Main Street

Chester, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 1367 Kings Highway Chester, NY MLS# 951876
Save 1367 Kings Highway Chester, NY MLS# 951876
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 71 Greycourt Road Chester, NY MLS# 942503
Save 71 Greycourt Road Chester, NY MLS# 942503
1 of 38
$449,000
3

Beds

1.1

Baths

1,056

Sq.Ft.

71 Greycourt Road

Chester, NY

Courtesy of BLOOMING 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 16 Oakland Avenue Chester, NY MLS# 939522
Save 16 Oakland Avenue Chester, NY MLS# 939522
1 of 49
$425,000
4

Beds

2.1

Baths

2,090

Sq.Ft.

16 Oakland Avenue

Chester, NY

Courtesy of BHG REAL ESTATE GREEN TEAM
View 7 Hambletonian Avenue Chester, NY MLS# 964090
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Save 7 Hambletonian Avenue Chester, NY MLS# 964090
1 of 20
$425,000
2

Beds

1.0

Baths

1,026

Sq.Ft.

7 Hambletonian Avenue

Chester, NY

Courtesy of HOMESMART HOMES & ESTATES
View 2915 Whispering Hills Chester, NY MLS# 927990
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1 of 23
$369,000
3

Beds

2.1

Baths

1,331

Sq.Ft.

2915 Whispering Hills

Chester, NY

Courtesy of CENTURY 21 FULL SERVICE REALTY
View 2 Virginia Lane Chester, NY MLS# H6215339
Save 2 Virginia Lane Chester, NY MLS# H6215339
1 of 4
$350,000
Studio

Beds

0.0

Baths

235,224

Sq.Ft.

2 Virginia Lane

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

About Chester

Listings in Chester, NY

57

Estimated median home price

$509,999
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 3
$200K - 300K 9
$300K - 400K 7
$400K - 500K 9
$500K - 600K 3
$600K - 700K 4
$700K - 800K 7
$800K - 900K 4
$900K - 1M 3
$1M - Max 8

Homes for Sale by Type in Chester, NY

Property Type Count
Single Family 32
Townhouse 0
Condo 9
Commercial 4
Rental 28
Lots and Land 11
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 2/26/2026)

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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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