View 18 Woodcliff Acres Chestertown, NY MLS# 202521026
$399,000
3

Beds

1.0

Baths

920

Sq.Ft.

18 Woodcliff Acres

Chestertown, NY

Courtesy of KW PLATFORM
View 36 Grove Street Chestertown, NY MLS# 202530425
$419,900
4

Beds

2.0

Baths

1,144

Sq.Ft.

36 Grove Street

Chestertown, NY

Courtesy of EXP REALTY
View 5387-5391 State Route 8 Chestertown, NY MLS# 202530223
$725,000
4

Beds

2.0

Baths

1,768

Sq.Ft.

5387-5391 State Route 8

Chestertown, NY

Courtesy of DAVIES-DAVIES & ASSOC REAL EST
The time to sell is now! THE TIME TO SELL IS NOW!
View 5204 State Route 9 Chestertown, NY MLS# 202529613
$119,000
2

Beds

1.1

Baths

1,862

Sq.Ft.

5204 State Route 9

Chestertown, NY

Courtesy of DAVIES-DAVIES & ASSOC REAL EST
View 5204 State Route 9 Chestertown, NY MLS# 202529615
$119,000
2.0

Baths

1,862

Sq.Ft.

5204 State Route 9

Chestertown, NY

Courtesy of DAVIES-DAVIES & ASSOC REAL EST
View 856 Olmstedville Road Chestertown, NY MLS# 202529390
$144,000
1

Beds

1.0

Baths

492

Sq.Ft.

856 Olmstedville Road

Chestertown, NY

Courtesy of GALLO REALTY ADK INC
View 15 Deer Run Chestertown, NY MLS# 202528852
$54,900
Studio

Beds

0.0

Baths

15 Deer Run

Chestertown, NY

Courtesy of PEARSALL REALTY
View L1.1 Elk Glade Road Chestertown, NY MLS# 202528647
$110,000
Studio

Beds

0.0

Baths

L1.1 Elk Glade Road

Chestertown, NY

Courtesy of GALLO REALTY ADK INC
View L7 MacGlashan Lane Chestertown, NY MLS# 202528376
$65,000
Studio

Beds

0.0

Baths

L7 MacGlashan Lane

Chestertown, NY

Courtesy of GALLO REALTY ADK INC
View 60 Dixon Road Chestertown, NY MLS# 202528178
$225,000
2

Beds

1.0

Baths

1,160

Sq.Ft.

60 Dixon Road

Chestertown, NY

Courtesy of GALLO REALTY ADK INC
View 71 Ferris Road Chestertown, NY MLS# 202528007
  • New Construction
1 of 48
$359,500
3

Beds

2.0

Baths

1,400

Sq.Ft.

71 Ferris Road

Chestertown, NY

Courtesy of GALLO REALTY ADK INC
View 161 E Shore Drive Chestertown, NY MLS# 202527808
$1,250,000
3

Beds

2.0

Baths

2,160

Sq.Ft.

161 E Shore Drive

Chestertown, NY

Courtesy of KW PLATFORM
View 73 Carl Turner Road Chestertown, NY MLS# 202527609
$299,000
2

Beds

1.0

Baths

877

Sq.Ft.

73 Carl Turner Road

Chestertown, NY

Courtesy of GALLO REALTY ADK INC
View 90 Dixon Road Chestertown, NY MLS# 202527496
$185,000
3

Beds

2.0

Baths

1,312

Sq.Ft.

90 Dixon Road

Chestertown, NY

Courtesy of HUNT ERA
View L31 Clarkson Road Chestertown, NY MLS# 202526758
$144,900
Studio

Beds

0.0

Baths

L31 Clarkson Road

Chestertown, NY

Courtesy of FOUR SEASONS SOTHEBY'S INTERNATIONAL REALTY
View 14 Granite Ridge Road Chestertown, NY MLS# 202526735
$49,000
Studio

Beds

0.0

Baths

14 Granite Ridge Road

Chestertown, NY

Courtesy of BIG HAT REALTY
View 367 Potter Brook Road Chestertown, NY MLS# 202526274
$589,900
3

Beds

1.1

Baths

2,752

Sq.Ft.

367 Potter Brook Road

Chestertown, NY

Courtesy of HOWARD HANNA
View 22 Memory Lane Chestertown, NY MLS# 202525940
$570,000
3

Beds

1.0

Baths

1,156

Sq.Ft.

22 Memory Lane

Chestertown, NY

Courtesy of HUNT ERA
View 199 Forest Lake Road Chestertown, NY MLS# 202525522
  • New Construction
1 of 16
$69,000
Studio

Beds

0.0

Baths

360

Sq.Ft.

199 Forest Lake Road

Chestertown, NY

Courtesy of COMPASS GREATER NY, LLC
View 484 Rock Ave Chestertown, NY MLS# 202525236
$374,000
3

Beds

1.1

Baths

1,344

Sq.Ft.

484 Rock Ave

Chestertown, NY

Courtesy of HUNT ERA

About Chestertown

Listings in Chestertown, NY

55

Estimated median home price

$85,000
Chestertown NY Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Chestertown, New York real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chestertown, NY.

Homes for Sale by Price in Chestertown, NY

Price Count
$0 - 100K 29
$100K - 200K 9
$200K - 300K 6
$300K - 400K 4
$400K - 500K 2
$500K - 600K 2
$600K - 700K 1
$700K - 800K 1
$800K - 900K 0
$900K - 1M 0
$1M - Max 1

Homes for Sale by Type in Chestertown, NY

Property Type Count
Single Family 15
Townhouse 0
Condo 1
Commercial 2
Rental 1
Lots and Land 35
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 12/10/2025)

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.

The data relating to real estate for sale on this web site comes in part from The Internet Data Exchange Program of ©2025 Global Multiple Listing Service, Inc. The data relating to real estate on this website comes in part from the Internet Data Exchange program of the GMLS. All information is deemed reliable but not guaranteed and should be independently verified. All properties subject to prior sale, change, or withdrawal. Neither listing broker(s), GMLS shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless from any damages arising from reliance upon these data. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties they may be interested in purchasing.

Data is updated as of 12/10/2025.