Our Insurance Agents

Meet our Winstead Insurance Agents

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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.

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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.

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Ron was born in Wilmington, Delaware. Since 1988, he has been a resident of Cecil County Maryland. He graduated from the University of Delaware in 1985 with a Bachelor’s and Master’s Degree in Mechanical Engineering. Ron worked as a Senior Project Engineer for Thiokol Corporation designing rocket motors. After leaving the Engineering field, he has spent the last 24 years working in Sales and Management. His Sales and Management experience includes being General Manager for a local automotive dealership, 11 years in Real Estate Sales, and most recently 2 years as an Insurance Sale Producer specializing in personal lines. He became a licensed insurance agent in 2014 for Property and Casualty. Ron began his insurance career as a Sales Producer for Allstate Insurance Company. Ron recently joined Winstead Insurance Company and looks forward to assisting you with all your insurance needs in Cecil County. Ron currently resides in Elkton, MD and loves spending time with his wife and three sons.

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404 W. Pulaski Highway
Elkton, MD 21921


Our experienced insurance agents here at Winstead Insurance Agency have years of work put into the Elkton, MD community and surrounding areas in NE 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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