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Winstead Insurance Agency Having been a "captive agent" with a large insurance company early in the history of my agency, it is very important to me, as an insurance professional, to be able to offer insurance products that specifically meet the needs and budget of my clients. Therefore, I'm now an independent agent and represent and sell only the products from companies who are financially strong and innovative in an ever-changing marketplace, all at competitive rates. I am happy to be able to offer more choices as an independent 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.
As a locally owned and operated insurance agency in Elkton, Maryland, Winstead Insurance Agency is committed to providing quality insurance products for individuals and businesses. We combine our strong insurance background and product knowledge to assist both current and future clients in managing and planning for all types of potential risk.
Be recognized for your safe driving skills with the YourTurn Rewards Program offered by Erie Insurance. Every year, distracted driving causes thousands of deaths in the U.S. By measuring certain criteria like speeding, braking and phone usage, the YourTurn Program helps to make drivers of all ages more aware of their driving behaviors and identifies areas for improvement.
Combining your home and auto policies can benefit you with discounts that help you save and additional coverage options to make your life easier. Choosing the right auto insurance is the key to keeping you and your car safe on the road in the event of an accident or other vehicle damage. Look after your biggest investment and everything in it with a proper policy that ensures its protection in the event of an accident or natural disaster. Keep your confidential information and personal assets secure with extended coverage options including personal umbrella insurance.
Reviews (9)
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Matthew Haack
May 28, 2022
I have been with Winstead Insurance Agency for about 10 months now and couldn't be happier. Reagan has done an excellent job of meeting my needs for both home and auto insurance.
Robert Smith
Feb 13, 2022
Winstead Insurance Agency was there for me every step of the way. I spoke with Reagan Fisher and found him to be polite and knowledgeable in his field. I don't have much of a clue about insurance, but he laid out my options very clearly and answered all my questions to put me on track to where I wanted to be. I originally contacted them a year ago for estimates but decided to stay on my Mom's plan.

In the year since they never pressured me or spammed me, but when I decided eventually to start my own plan, they were ready for me and speedily whipped up some options for me. Before switching to Winstead Insurance, I was given advice on how to get a spin-off policy from my Mom's policy (that would mean I might not need WIA.) That completely blew me away.

It turned out that through their network of providers, Winstead could still get me a much better deal than anywhere else, but that simple action proved to me that providing a service to the customer was their #1 priority more than bringing in money or anything else. I am a Winstead Insurance customer and trust them for all my insurance needs.
Connor Swalm
Feb 13, 2022
Reagan was awesome! He took the time to explain all my options and took the time to educate me on all the options that were available to me. If you're looking for a company that will treat you with respect and help you make the best decision, use Winstead Insurance Agency!
Bobbi Edwards
Dec 28, 2021
I have been with Winstead Agency for over 40 years I absolutely love Stephanie. I have never had an issue with any claims and everyone in the office is so helpful.
Rachel MSrvs
Dec 25, 2021
Excellent customer service! Stephanie is the best! I mean, everyone there is great, but I work with Stephanie the most. She is friendly, knowledgeable and lightening fast in getting me what I need. I recommend Winstead Insurance to everyone. Thank you guys!
Susan Waltrop
Nov 14, 2021
My husband and I had a wonderful experience with Reagan. He explained our options, got us a great deal and returned our calls promptly. We have told friends and neighbors about him and Winstead Insurance!
Michael M.
Nov 14, 2021
I have dealt with a number of insurance agencies over the years, however Winstead Insurance hands down is the BEST agency that I have dealt with. Their prices, service, staff and knowledge is wonderful!
Deborah Brooks
Mar 20, 2021
They are very friendly and always there to help you. If you're in an accident they are there to help you. And they're very understanding. If you don't understand something they do their best to explain it to you. And they are very patient with you. I've dropped in to talk to them and they were okay with that. The last agency I was with was upset that dropped in.

I told them I had made several phone calls on different days but got no answer. It was very chaotic in there and loud. Winstead is the extreme of that. They're organized, calm and caring. I've been there for about 20 years now. I don't plan on leaving them. I like everything about this agency.
Don Williams
Nov 29, 2020
As a fairly new Winstead Insurance Agency customer, I now constantly ask myself the question, "Why didn't I switch to this very professional agency sooner?" The entire staff makes me feel like I have been a part of their company for years instead of just 1 1/2 years. The agency exhibits true professionalism and strives to make its customers priorities and goals become realities because they take a vested interest in these goals.

For anyone who wants to feel like part of a family and not just another customer, let the Winstead Insurance Agency open their door to solve your insurance needs. Personalized service awaits you!