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Contact Us | (727) 321-1212

RW Caldwell Insurance
The Service that Satisfies

You’re not going to hit a ridiculously long phone menu when you call us. Your email isn’t going to the inbox abyss, never to be seen or heard from again. At RW Caldwell, we provide the exceptional service we’d want to experience ourselves!

5201 Gulfport Boulevard
Gulfport, FL 33707

Phone: (727) 321-1212
Fax: (727) 321-4548

Request your FREE Insurance Quote

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Our team of independent auto insurance agents have been serving families in the Gulfport, Greater Tampa and the Beaches of Florida since 1937.

Let’s get started.  Please take a moment and fill out the form below to receive your free “No Hassle” quote. We’ll get back to you shortly to help you find the right insurance at the right price.



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RW Caldwell Insurance - Horsnleth/Sepulveda family
Robert William ‘Rob’ Caldwell, our company founder, began insurance in1935 before opening R.W. Caldwell Realty and Insurance in 1937. Now in its fourth generation as a trusted family business, we at Caldwell’s have been governed by the simple philosophy of trying to help people.

Don't just take our word for it...

I've been with RW Caldwell for our Home and Auto Insurance for several years. Rob Sepulveda has been extremely helpful in navigating the ever-changing property insurance laws and getting us discounts. On the auto side, we recently had claims and I can honestly say I don't know how people handle insurance claims without an agent to advise them. In an era when customer service is a lost art, Rob and the rest of the team take care of their customers and they support the community.

Great insurance services! Very friendly and efficient, helped up to find the best policy and the best price. Amazing service from start to finish.

We are very thankful that you are in this business because it makes our lives so much easier!

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