View 3107 Whispering Hills Chester, NY MLS# 879298
$325,000
2

Beds

1.1

Baths

1,086

Sq.Ft.

3107 Whispering Hills

Chester, NY

Courtesy of MASTER REALTY GROUP INC.
View 20 Goshen Road Chester, NY MLS# 875731
$1,775,000
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
The time to sell is now! THE TIME TO SELL IS NOW!
View 5 Gabriels Drive Chester, NY MLS# 863852
  • Virtual Tour
1 of 48
$1,099,000
4

Beds

2.1

Baths

2,722

Sq.Ft.

5 Gabriels Drive

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 576 Bull Mill Road Chester, NY MLS# 859210
$399,000
2

Beds

1.0

Baths

1,484

Sq.Ft.

576 Bull Mill Road

Chester, NY

Courtesy of BLOOMING REALTY
View Odyssey Drive Chester, NY MLS# 858370
$350,000
Studio

Beds

0.0

Baths

222,156

Sq.Ft.

Odyssey Drive

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 206 Greycourt Road 190 Chester, NY MLS# 859813
$1,500,000
3,000

Sq.Ft.

206 Greycourt Road 190

Chester, NY

Courtesy of EXP REALTY
View 206 Greycourt Road 190 Chester, NY MLS# 836663
$1,500,000
Studio

Beds

0.0

Baths

139,392

Sq.Ft.

206 Greycourt Road 190

Chester, NY

Courtesy of EXP REALTY
View 25 Oakland Avenue Chester, NY MLS# 821132
$28,000,000
270,000

Sq.Ft.

25 Oakland Avenue

Chester, NY

Courtesy of EREALTY ADVISORS, INC
View 1 Winkler Place Chester, NY MLS# H6333708
$949,000
7,493

Sq.Ft.

1 Winkler Place

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 32 Mountainside Drive Chester, NY MLS# H6328761
$259,000
Studio

Beds

0.0

Baths

879,041

Sq.Ft.

32 Mountainside Drive

Chester, NY

Courtesy of OUR HOUSE REAL ESTATE GROUP
View 34 Mountainside Drive Chester, NY MLS# H6326715
$225,000
Studio

Beds

0.0

Baths

43,560

Sq.Ft.

34 Mountainside Drive

Chester, NY

Courtesy of OUR HOUSE REAL ESTATE GROUP
View Oxford Road Chester, NY MLS# H6287716
$325,000
Studio

Beds

0.0

Baths

235,224

Sq.Ft.

Oxford Road

Chester, NY

Courtesy of RE/MAX BENCHMARK REALTY GROUP
View 1414 Kings Highway Chester, NY MLS# H6282627
$499,000
Studio

Beds

0.0

Baths

196,020

Sq.Ft.

1414 Kings Highway

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
View 2 Virginia Lane Chester, NY MLS# H6215339
$350,000
Studio

Beds

0.0

Baths

235,224

Sq.Ft.

2 Virginia Lane

Chester, NY

Courtesy of KELLER WILLIAMS REALTY
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 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 148 Brookside Avenue Chester, NY MLS# H6146719
$799,000

148 Brookside Avenue

Chester, NY

Courtesy of KELLER WILLIAMS REALTY

About Chester

Listings in Chester, NY

58

Estimated median home price

$682,450
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 - 100K0
$100K - 200K0
$200K - 300K3
$300K - 400K12
$400K - 500K8
$500K - 600K4
$600K - 700K5
$700K - 800K6
$800K - 900K3
$900K - 1M1
$1M - Max16

Homes for Sale by Type in Chester, NY

Property TypeCount
Single Family31
Townhouse0
Condo6
Commercial9
Rental29
Lots and Land9
Condo/Town/CoOp0
CoOp0
Multi Family3
Mobile Home0
Farms0

(Data as of 11/11/2025)

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.