| Business | Phone |
| Allstate Insurance 100 Philosophers Ter, Chestertown 21620 | (410) 810-2600 |
| Anthony Insurance Svc 109 East St, Chestertown 21620 | (410) 778-6380 |
| Chesapeake Benefit Svc 151 Dixon Dr # 3, Chestertown 21620 | (410) 778-9008 |
| Dukes-Moore Insurance 205 High St, Chestertown 21620 | (410) 778-2346 |
| Fleetwood Athey & Mc Beth 100 Talbot Blvd, Chestertown 21620 | (410) 778-0676 |
| Fleetwood Athey Macbeth Mccown 100 Talbot Blvd, Chestertown 21620 | (410) 778-0666 |
| Hill Management Co Insurance 315 High St, Chestertown 21620 | (410) 778-6470 |
| Hogans Real Estate 515 Washington Ave, Chestertown 21620 | (410) 778-1665 |
| Kent Insurance Inc 7332 Church Hill Rd, Chestertown 21620 | (410) 778-5700 |
| Massachusetts Mutual-Blue Chip 305 Washington Ave, Chestertown 21620 | (410) 758-8500 |
| Nationwide Insurance 7332 Church Hill Rd, Chestertown 21620 | (410) 778-2882 |
| Newcomb Group 521 N Kent St, Chestertown 21620 | (410) 810-3028 |
| Prudential Insurance Co 315 High St, Chestertown 21620 | (410) 758-4781 |
| State Farm Insurance 948 Washington Ave, Chestertown 21620 | (410) 778-0647 |