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Welcome to Winston Insurance Group,

Madison's most trusted insurance brokers. 

What sets us apart from other insurance brokers?

We are a husband wife duo with a strong team working towards the same goal. Winning for our clients! We aim to provide insurance to our clients based on their needs and what makes the most sense for them. Winston Insurance Group is looking forward to helping you gain peace of mind. 

Jason Craig, Winston, and Cindy Kiley Craig from Winston Insurance Group family photo.

SERVICES

Interested in learning more? Book a consultation at no cost to you!

MEDICARE

LIFE

HEALTH

MORTGAGE PROTECTION

DENTAL, VISION, & HEARING

RETIREMENT

LEADING CARRIERS WE WORK WITH 

Humana
SSM Health
Delta Dental
Cigna
Quartz
United Healthcare
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