View 18 Oakland Avenue Chester, NY MLS# 935124
  • Virtual Tour
1 of 33
$369,900
2

Beds

1.0

Baths

1,084

Sq.Ft.

18 Oakland Avenue

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 47 Greycourt Avenue Chester, NY MLS# 901280
$425,000
4

Beds

1.1

Baths

1,386

Sq.Ft.

47 Greycourt Avenue

Chester, NY

Courtesy of CURASI REALTY, INC.
View 84 Pine Hill Road Chester, NY MLS# 926175
$425,000
3

Beds

1.0

Baths

1,266

Sq.Ft.

84 Pine Hill Road

Chester, NY

Courtesy of EREALTY ADVISORS, INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 16 Oakland Avenue Chester, NY MLS# 939522
$425,000
4

Beds

2.1

Baths

2,090

Sq.Ft.

16 Oakland Avenue

Chester, NY

Courtesy of BHG REAL ESTATE GREEN TEAM
View 70 Main Street Chester, NY MLS# 914556
$475,000
4

Beds

2.1

Baths

1,357

Sq.Ft.

70 Main Street

Chester, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 6 Vista Drive Chester, NY MLS# 944968
  • Virtual Tour
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 Main Street Chester, NY MLS# H6204360
$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
  • Virtual Tour
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 391 Bull Mill Road Chester, NY MLS# 880804
  • Virtual Tour
1 of 32
$509,999
3

Beds

2.0

Baths

1,800

Sq.Ft.

391 Bull Mill Road

Chester, NY

Courtesy of CENTURY 21 REALTY CENTER
View 219 Bull Mill Road Chester, NY MLS# 924125
$525,000
4

Beds

2.0

Baths

1,928

Sq.Ft.

219 Bull Mill Road

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 80 Pewter Circle Chester, NY MLS# 913254
$534,900
3

Beds

2.1

Baths

1,946

Sq.Ft.

80 Pewter Circle

Chester, NY

Courtesy of BHG REAL ESTATE GREEN TEAM
View 3 DeRose Lane Chester, NY MLS# 924694
  • Virtual Tour
1 of 50
$650,000
5

Beds

3.1

Baths

2,550

Sq.Ft.

3 DeRose Lane

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 65 Oxford Springs Road Chester, NY MLS# 938744
$650,000
5

Beds

3.1

Baths

3,617

Sq.Ft.

65 Oxford Springs Road

Chester, NY

Courtesy of EXP REALTY
View 23 Pewter Circle Chester, NY MLS# 939836
  • Virtual Tour
1 of 37
$650,000
4

Beds

2.1

Baths

2,318

Sq.Ft.

23 Pewter Circle

Chester, NY

Courtesy of EXP REALTY
View 101 Oxford Road Chester, NY MLS# 943068
$669,000
3

Beds

1.1

Baths

1,816

Sq.Ft.

101 Oxford Road

Chester, NY

Courtesy of LOOP REALTY INC
View 507 Bull Mill Road Chester, NY MLS# 894259
  • Virtual Tour
1 of 45
$674,999
5

Beds

2.1

Baths

3,115

Sq.Ft.

507 Bull Mill Road

Chester, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 2 Dawn Court Chester, NY MLS# 905740
  • Virtual Tour
1 of 34
$689,900
4

Beds

2.1

Baths

3,092

Sq.Ft.

2 Dawn Court

Chester, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 220 Oxford Road Chester, NY MLS# 927454
$699,000
4

Beds

3.1

Baths

3,472

Sq.Ft.

220 Oxford Road

Chester, NY

Courtesy of EXIT REALTY VENTURE
View 360 Prospect Road Chester, NY MLS# 944607
  • Recently Listed
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 34 Mountainside Drive Chester, NY MLS# 895079
$699,990
4

Beds

3.0

Baths

1,867

Sq.Ft.

34 Mountainside Drive

Chester, NY

Courtesy of OUR HOUSE REAL ESTATE GROUP

About Chester

Listings in Chester, NY

60

Estimated median home price

$592,450
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

PriceCount
$0 - 100K1
$100K - 200K2
$200K - 300K5
$300K - 400K12
$400K - 500K7
$500K - 600K3
$600K - 700K9
$700K - 800K4
$800K - 900K3
$900K - 1M1
$1M - Max13

Homes for Sale by Type in Chester, NY

Property TypeCount
Single Family33
Townhouse0
Condo9
Commercial7
Rental27
Lots and Land9
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home0
Farms0

(Data as of 1/9/2026)

Information deemed reliable but not guaranteed.

All information provided is deemed reliable but is not guaranteed and should be independently verified.

Copyright 2026 by the Multiple Listing service of Ulster County, Inc. All Rights Reserved.

The data relating to real estate on this web site comes in part from the IDX of the Multiple Listing service of Ulster County, Inc. Real estate listings held by brokerage firms other that Weichert Realtors are marked with IDX logo and the detailed information about them includes the name of the listing broker.

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.