View 25 Oakland Avenue Chester, NY MLS# 949886
$28,000,000
270,000

Sq.Ft.

25 Oakland Avenue

Chester, NY

Courtesy of EREALTY ADVISORS, INC
View 42 Brookside Avenue Chester, NY MLS# H6204289
$1,750,000
4,020

Sq.Ft.

42 Brookside Avenue

Chester, NY

Courtesy of KELLER WILLIAMS 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 20 Goshen Road Chester, NY MLS# 961236
  • Recently Listed
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 37-39 Main Street Chester, NY MLS# 873541
$1,498,888
4

Beds

4.0

Baths

7,308

Sq.Ft.

37-39 Main Street

Chester, NY

Courtesy of EXP REALTY
View 145 Kings Highway Bypass Chester, NY MLS# 953574
$1,399,999
4

Beds

4.0

Baths

4,508

Sq.Ft.

145 Kings Highway Bypass

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 2948 State Route 94 Chester, NY MLS# 940751
$1,395,000
4

Beds

2.1

Baths

3,866

Sq.Ft.

2948 State Route 94

Chester, NY

Courtesy of TUXEDO HUDSON REALTY CORP
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 207 Greycourt Road Chester, NY MLS# 885483
$1,200,000
8,800

Sq.Ft.

207 Greycourt Road

Chester, NY

Courtesy of EXP REALTY
View 53 Odyssey Drive Chester, NY MLS# 881474
  • Virtual Tour
1 of 48
$1,100,000
4

Beds

3.1

Baths

4,467

Sq.Ft.

53 Odyssey Drive

Chester, NY

Courtesy of HOWARD HANNA RAND REALTY
View 2 Garnett Hill Road Chester, NY MLS# 931380
  • Virtual Tour
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 12 Damian Court Chester, NY MLS# 950640
$999,000
5

Beds

4.0

Baths

3,136

Sq.Ft.

12 Damian Court

Chester, NY

Courtesy of MS REALTY GROUP USA, INC
View 4 Camelback Road Chester, NY MLS# 955725
$999,000
5

Beds

2.2

Baths

5,080

Sq.Ft.

4 Camelback Road

Chester, NY

Courtesy of PROMINENT PROPERTIES SOTHEBY'S
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 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
$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

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)

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.