Home, Auto, Farm & Business Insurance From Elkton, MD

Serving Families & Businesses Since 1956

The Winstead Insurance Agency serves the insurance needs of the community at the most competitive prices.  We maintain levels of knowledge and professionalism that make us unique, but our commitment to providing information, resources, and effective products distinguish us the most.

We deliver a ‘broad brush’ of personal and commercial insurance solutions and we’re very happy to serve these diverse interests.  After almost 60 years, we know what our clients need and how to meet these needs: it’s a mix of practice and continuous learning.  Our reputation for fast and efficient services, solid products, and graciousness precedes us, and as we grow we’re happy to have this as our calling card. 

For home, auto, and other personal lines we’re a go-to shop for comprehensive coverage.  For commercial lines, we’re an agency that ‘walks the walk and talks the talk,’ as we thoroughly know our clients’ businesses and match their needs with coverages that provide the most protection.  Altogether our insurance plans reflect our clients’ best investments and are coupled with risk management services that keep these investments sound. 

We’re insurers, advisers, and advocates.  Working with insurance partners like Erie, Allied, Lititz, and Progressive gives us access to coverages that help us deliver optimal solutions.  These solutions are the things that our clients need most, and we deliver them with as much passion and dedication as we have for anything else in our lives.  If you’d like to know more, give us a call or contact us.  We’ll be happy to hear from you.






Accommodating, professional, helpful, and quick. Very comfortable experience and I was impressed by their capabilities. Highly recommended.
Brad M.
I feel lucky to have found an agent willing to provide this level of service. No need to look anywhere else!
Michelle D.
Over the years we’ve never once had to worry about our coverage. My husband and I are long-time customers and proud to be.
Carol S.
Surprisingly flexible and in-touch with my needs as a small business owner. Can’t ask for more.
Spencer F.
They have strong ties with the community, and it shows. It’s nice to do business with people that really show they care about you and your family.
Susan T.