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 1401 Whispering Hills Chester, NY MLS# 935471
$295,000
2

Beds

1.0

Baths

1,084

Sq.Ft.

1401 Whispering Hills

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 65 Hudson Street Chester, NY MLS# 934146
$345,000
3

Beds

1.0

Baths

1,120

Sq.Ft.

65 Hudson Street

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 2 Pine Hill Road Chester, NY MLS# 933779
  • Virtual Tour
1 of 31
$875,000
3

Beds

2.1

Baths

2,302

Sq.Ft.

2 Pine Hill Road

Chester, NY

Courtesy of SHAHAR MANAGEMENT LLC
View 2915 Whispering Hills Chester, NY MLS# 927990
  • Virtual Tour
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 80 Black Meadow Road Chester, NY MLS# 929619
$1,725,000
12,500

Sq.Ft.

80 Black Meadow Road

Chester, NY

Courtesy of MK REALTY INC
View 10 Damian Court Chester, NY MLS# 930372
$1,375,000
11

Beds

6.1

Baths

4,327

Sq.Ft.

10 Damian Court

Chester, NY

Courtesy of MS REALTY GROUP USA, INC
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 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 7 Park Place Chester, NY MLS# 927218
$740,000
4

Beds

3.1

Baths

2,780

Sq.Ft.

7 Park Place

Chester, NY

Courtesy of CENTURY 21 FULL SERVICE REALTY
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 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
View 9 Country Woods Drive Chester, NY MLS# 925049
  • Virtual Tour
1 of 30
$725,000
5

Beds

2.1

Baths

3,124

Sq.Ft.

9 Country Woods Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
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 69 Cedar Pond Lane Chester, NY MLS# 920071
$1,875,000
6

Beds

7.1

Baths

7,034

Sq.Ft.

69 Cedar Pond Lane

Chester, NY

Courtesy of FOUR SEASONS SOTHEBYS INTL
View 69 Cedar Pond Lane Chester, NY MLS# 20254768
$1,875,000
6

Beds

7.1

Baths

7,034

Sq.Ft.

69 Cedar Pond Lane

Chester, NY

UlsterCountyNY
Courtesy of FOUR SEASONS SOTHEBY'S INT.
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 8 Camelback Road Chester, NY MLS# 912372
$349,999
Studio

Beds

0.0

Baths

213,444

Sq.Ft.

8 Camelback Road

Chester, NY

Courtesy of EXP REALTY
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 4703 Whispering Hills Drive Chester, NY MLS# 904289
$369,000
3

Beds

2.1

Baths

1,331

Sq.Ft.

4703 Whispering Hills Drive

Chester, NY

Courtesy of ARTISAN REALTY

About Chester

Listings in Chester, NY

63

Estimated median home price

$534,900
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 1
$200K - 300K 5
$300K - 400K 13
$400K - 500K 8
$500K - 600K 4
$600K - 700K 9
$700K - 800K 4
$800K - 900K 3
$900K - 1M 0
$1M - Max 15

Homes for Sale by Type in Chester, NY

Property Type Count
Single Family 34
Townhouse 0
Condo 9
Commercial 7
Rental 23
Lots and Land 11
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 12/29/2025)

Information deemed reliable but not guaranteed.

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

Copyright 2025 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.