Our Insurance Agents
Meet our Winstead Insurance Agents
Barry Winstead, LUTCF
Owner, Insurance Agent
Agency Principal Barry Winstead, LUTCF, began his insurance career in 1980 following in the footsteps of his father, Grayson Winstead. His agency specializes in auto, home, business, life insurance, and great service! He has earned his Life Underwriting Council Fellow (LUTCF) and has completed seven parts of the Chartered Life Underwriters (CLU) professional designations, and has a bachelor of business degree from Salisbury University. Barry is the father of eight children and an active member of the community serving as a deacon at Christ Presbyterian Church of Elkton, Md.
Office Manager, Licensed Insurance Agent
I have been with the Winstead Agency since 1988. I am licensed to sell Property and Casualty insurance. I earned my CISR designation (Certified Insurance Service Representative) in May 2010. I specialize in personal and small business clients.
Licensed Insurance Agent
Reagan joined Winstead Insurance in 2019 after working in a career Media and Digital Marketing. Reagan is Barry Winstead’s son-in-law and is excited to work with the family business. He’s licensed in Property and Casualty as well as Life Insurance. He enjoys spending time at his homestead raising pigs and chickens and a large garden.
Andy Parrett is our life specialist at Winstead agency. He has 16 years experience with the Winstead team helping clients in Cecil county with investment planning and life/health insurance needs. Andy helps small business’ in the area with group health insurance, key man life insurance, buy sell agreements etc.
Customer Service Representative
Licensed Insurance Agent
Grayson joined Winstead Insurance Agency in 2024 after working for a decade in software sales. He has a bachelor’s degree from Wake Forest University and was an Armor officer in the National Guard. Grayson is the third generation of Winsteads to join the agency. He is licensed in Property, Casualty, Life, and Health Insurance. He enjoys spending his time on the golf course or on the water.
Our experienced insurance agents here at Winstead Insurance Agency have years of work put into the Elkton, MD community and surrounding areas in North East Maryland. Contact us for information and quotes on farm insurance, home insurance, auto insurance, business & commercial insurance, bundled insurance and more.
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