- Obstetricians & Gynecologists, Chestertown - Ob-Gyn Doctors, Physicians & Surgeons (Obstetrics & Gynecology)
- Occupational Health Care Professionals, Chestertown
- Occupational Therapy, Chestertown - Occupational Health Specialists
- Office Supplies, Equipment & Office Furniture Stores, Chestertown
- Oil Burners Services, Chestertown
- Oncologists, Chestertown - Cancer Doctors, Physicians & Surgeons (Oncology)
- Optical Stores - Eyeglasses, Lenses & Sunglasses, Chestertown
- Opticians, Chestertown
- Optometrists, Chestertown - Eye Doctors, Physicians & Surgeons (Optometry)
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- Organizing Services & Products – Household & Business, Chestertown
- Ornamental Greenhouses, Chestertown
- Ornamental Nursery, Chestertown
- Ornamental Nursery Services, Chestertown
- Orthodontist, Chestertown - Teeth Straightening, Invisalign & Dental Braces
- Other Building Materials & Supplies, Chestertown
- Outdoor & Lawn & Garden Equipment Repair & Service, Chestertown
- Outdoor Equipment & Accessories, Chestertown
- Outdoor Furniture & Patio Furniture, Chestertown - Garden Furniture Stores
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