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- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
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- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
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26 Properties Available In Chestertown
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)

$ 1,495,000
7961 QUAKER NECK RD, Chestertown, MD 21620
Single Family Home
MLS# MDKE2005090
Listed by Compass


$ 745,000
9050 POINT LN, Chestertown, MD 21620
Single Family Home
MLS# MDKE2005102
Listed by Coldwell Banker Chesapeake Real Estate Company


$ 1,799,000
21082 WYOMING AVE, Chestertown, MD 21620
Single Family Home
MLS# MDKE2005016
Listed by Doug Ashley Realtors, LLC


$ 700,000
5594 LANGFORD BAY RD, Chestertown, MD 21620
Single Family Home
MLS# MDKE2005118
Listed by TTR Sotheby's International Realty


$ 549,000
101 BIRCH RUN RD, Chestertown, MD 21620
Single Family Home
MLS# MDKE2005088
Listed by Cross Street Realtors LLC


$ 749,900
7988 ALDAN DR, Chestertown, MD 21620
Single Family Home
MLS# MDKE2004966
Listed by Doug Ashley Realtors, LLC


$ 579,900
5179 QUAKER NECK RD, Chestertown, MD 21620
Single Family Home
MLS# MDKE2005028
Listed by Hyatt & Company Real Estate, LLC


$ 1,200,000
22153 1ST POINT RD, Chestertown, MD 21620
Single Family Home
MLS# MDKE2004460
Listed by TTR Sotheby's International Realty


$ 364,900
216 SILVER HEEL RD, Chestertown, MD 21620
Single Family Home
MLS# MDKE2005024
Listed by CENTURY 21 New Millennium


$ 385,000
8605 CAMP RD, Chestertown, MD 21620
Single Family Home
MLS# MDKE2004952
Listed by RE/MAX Executive


$ 285,000
7483 SHORTALL ST, Chestertown, MD 21620
Single Family Home
MLS# MDKE2004948
Listed by RE/MAX Executive


$ 425,000
128 EDMORE RD, Chestertown, MD 21620
Single Family Home
MLS# MDQA2012546
Listed by Berkshire Hathaway HomeServices PenFed Realty


$ 319,000
306 CEDAR ST, Chestertown, MD 21620
Single Family Home
MLS# MDKE2004954
Listed by Doug Ashley Realtors, LLC


$ 515,000
314 DEVON DR, Chestertown, MD 21620
Single Family Home
MLS# MDKE2004946
Listed by The Parker Group


$ 289,500
116 OAK LEAF DR, Chestertown, MD 21620
Townhouse
MLS# MDKE2004942
Listed by Doug Ashley Realtors, LLC


$ 324,900
109 TAMARACK RD, Chestertown, MD 21620
Single Family Home
MLS# MDQA2012102
Listed by RE/MAX Executive


$ 349,900
110 FLYING CLOUD COURT, Chestertown, MD 21620
Single Family Home
MLS# MDKE2004850
Listed by Berkshire Hathaway HomeServices Homesale Realty


$ 349,900
109 WILTON RD, Chestertown, MD 21620
Single Family Home
MLS# MDQA2011782
Listed by Chesapeake Real Estate Associates, LLC


$ 1,450,000
23393 CACAWAY FARM LN, Chestertown, MD 21620
Condo
MLS# MDKE2004002
Listed by Gunther-McClary Real Estate


$ 1,870,000
870 HIGH ST, Chestertown, MD 21620
Commercial
MLS# MDKE2004140
Listed by Taylor Properties


$ 860,000
860 HIGH ST, Chestertown, MD 21620
Commercial
MLS# MDKE2004138
Listed by Taylor Properties


$ 2,400,000
860 & 870 HIGH ST, Chestertown, MD 21620
Commercial
MLS# MDKE2003850
Listed by Taylor Properties


$ 425
870 HIGH ST #INDIVIDUAL OFFICES, Chestertown, MD 21620
Commercial
MLS# MDKE2004432
Listed by Taylor Properties


$ 18
870 HIGH ST #2-3, Chestertown, MD 21620
Commercial
MLS# MDKE2003776
Listed by Taylor Properties
