View 5 Gabriels Drive Chester, NY MLS# 952148
  • Virtual Tour
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 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 558 Pine Hill Road Chester, NY MLS# 958731
1 of 50
OPEN HOUSE: Sunday 3/1 1:00 PM - 3:00 PM
$850,000
4

Beds

2.1

Baths

3,120

Sq.Ft.

558 Pine Hill Road

Chester, NY

Courtesy of EREALTY ADVISORS, INC
The time to sell is now! THE TIME TO SELL IS NOW!
View 4 Debbie Court Chester, NY MLS# 962813
  • Recently Listed
1 of 46
$849,999
5

Beds

5.1

Baths

5,403

Sq.Ft.

4 Debbie Court

Chester, NY

Courtesy of FLAG REALTY GROUP
View 148 Brookside Avenue Chester, NY MLS# H6146719
$799,000

148 Brookside Avenue

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 16 Oxford Springs Road Chester, NY MLS# 935115
  • Virtual Tour
1 of 48
$750,000
3

Beds

3.0

Baths

2,870

Sq.Ft.

16 Oxford Springs Road

Chester, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 5 Bens Way Chester, NY MLS# 959390
  • Recently Listed
1 of 28
OPEN HOUSE: Sunday 3/1 1:00 PM - 3:00 PM
$744,999
4

Beds

2.1

Baths

2,544

Sq.Ft.

5 Bens Way

Chester, NY

Courtesy of KELLER WILLIAMS HUDSON VALLEY
View 7 Park Place Chester, NY MLS# 927218
$730,000
4

Beds

3.1

Baths

2,780

Sq.Ft.

7 Park Place

Chester, NY

Courtesy of CENTURY 21 FULL SERVICE REALTY
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 487 Black Meadow Road Chester, NY MLS# 960665
  • Recently Listed
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 34 Booth Road Chester, NY MLS# 961100
  • Recently Listed with Virtual Tour
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 34 Mountainside Drive Chester, NY MLS# 956879
$699,990
4

Beds

3.0

Baths

1,867

Sq.Ft.

34 Mountainside Drive

Chester, NY

Courtesy of OUR HOUSE REAL ESTATE GROUP
View 360 Prospect Road Chester, NY MLS# 944607
$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
$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
$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
$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
$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
  • 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 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

About Chester

Listings in Chester, NY

57

Estimated median home price

$515,000
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 3
$200K - 300K 8
$300K - 400K 7
$400K - 500K 9
$500K - 600K 3
$600K - 700K 4
$700K - 800K 8
$800K - 900K 4
$900K - 1M 3
$1M - Max 8

Homes for Sale by Type in Chester, NY

Property Type Count
Single Family 33
Townhouse 0
Condo 8
Commercial 4
Rental 25
Lots and Land 11
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 2/25/2026)

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.

Information Copyright 2021, OneKey® MLS. All Rights Reserved.