Thank you for stopping by.

We’re a family-owned insurance agency and brokerage based in Redlands, CA that provides specialized insurance services for specific types of businesses.  Our roots are in agriculture and we’re still grounded there, although we’ve branched out and learned how to properly insure a few other types of businesses as well.

We’ve been around since 1986 and are rolling with the changes as we get deeper in the 21st century with its unique challenges and ways of doing business.  We like to think of ourselves as classic, yet relevant.

You might be asking: those “specific types of businesses” mentioned above – what are they?”  That’s a great question.   Scroll down a few inches and find out!

Also, please browse around our site and get to know us!  Meet our team here.

Oh, and one more thing: in addition to insuring businesses, we also insure people and the things that matter most to them like their homes, cars, boats motorcycles, etc.  You can also read about them when you scroll down.

Have Questions?


 (800)793-1846 Toll Free

Our Specialties

The world’s first industry.   Just as risky and important as it ever was.

Today’s wineries are an exciting blend of farming, fun, and style.

You build, remodel, repair, and service our buildings.  For that we thank you.


It is because of you we all have gym memberships (that we don’t use).

Made in the USA.  Enough said.  Distributed and delivered in the USA too.

Workers Compensation

Even if you have only one part time seasonal employee, you have to have this.

One of the biggest risks you face as an employer… and growing.

Covering the water damage that’s not covered on your other policies.

The coverage almost no one has, but everyone should.

Houses, cars, and boats (and renters, condos… and umbrellas)


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I am very impressed with the quality service that Gillespie Insurance Services provides. By combining our homeowner and automobile insurance we not only saved money, but we also got better coverage. I was amazed at how much more automobile coverage we were able to get at a better price than we got from our previous insurance company. Because of the quality staff and the affordable insurance rates, we will be a customer for life.

Jeff Hamilton February 10, 2015