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Shelly Middlebrooks & O'Leary Since opening its doors 1952, Shelly, Middlebrooks & O'Leary, Inc. has served the insurance marketplace as a quality wholesaler with access to both admitted and non-admitted markets for independent agents. Protecting property is never limited to just four walls and a roof. Shelly, Middlebrooks and O'Leary provides comprehensive coverage that covers high value homes from the inside and out.

Today's companies face an ever-present threat of lawsuits. Safeguard your client's assets with innovative solutions backed by experience underwriting and insurer stability.
Services
Highways or byways, railways or airways. Whatever way you choose to travel, we're the driving force behind your transportation business. Commercial transportation continues to evolve to meet the needs of today's economy. Our work is to find innovative solutions for you and all of your business' moving parts.
Whether it's hauling produce from Orlando to Oakland, or moving cattle from Kissimmee to Kansas, there's a lot riding your trucking business. With more than 60 years of experience, Shelly, Middlebrooks & O'Leary is your trusted business partner for creating long term solutions for all your trucking needs.
Protecting your high-end assets - like a multi-million dollar home, custom sports car, or beachfront property - can come with unique challenges. But with an underwriting team that understands complex exposures and high risk lines, Shelly, Middlebrooks and O'Leary provides the custom coverage you can't find in the admitted market.
As a homeowner, boat owner or landowner, your clients have needs that are as unique as their property. From high end homes, to renters insurance and even personal artifacts - we build policies that cover the roof to the floor and everything in between. Minimum attachment of $250/500/100 or $300,000 CSL Automobile, Boats and Recreational Vehicles.
Reviews (1)
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Daniel Colucci
Jan 31, 2020
I have been dealing with Erin and the O'leary family for a long time. They are good old time MGA and a pleasure to work with.