Our Insurance Agents

Meet our Winstead Insurance Agents

Barry Winstead, LUTCF

Barry Winstead, LUTCF

Owner, Insurance Agent

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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.

Stephanie Helsel

Stephanie Helsel

Office Manager, Licensed Insurance Agent

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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.

Reagan Fisher

Reagan Fisher

Customer Service Representative

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Reagan recently joined Winstead Insurance after working at a local TV station in Raleigh NC for 5 years. Reagan is Barry Winstead’s son-in-law and is excited to work with the family business. He’s licensed in Property and Casualty.

 Andy Parrett

Andy Parrett

Financial Planner, Life Insurance Agent

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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.

Missy Logan

Missy Logan

Customer Service Representative

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Melissa has been in the Insurance industry for over 15 years. She has come to specialize in Personal Insurance. Born and raised in Cecil County, she has one grown son and enjoys photography and reading in her spare time.

Amy Chapman

Amy Chapman

Customer Service Representative

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Amy joined the Winstead Agency in 2018 with a background in various Administrative Duties.  She licensed in Property & Casualty and is eager to contribute to the Winstead Customer Service. She moved to Elkton in 2016 after spending 10 years in Pennsylvania. She enjoys swing dancing, camping, and gardening.

Visit Our Office

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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