Winters Oliver Insurance Agency
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Firm History

Winters-Oliver was founded in Richmond in 1945 by E. Ray Winters Sr. and Stuart Oliver.  Mr. Oliver was a banker and mostly a silent partner in the agency.  In the late 1950's, Mr. Winters purchased land in Hanover County and move his family from the city out to what was then very rural countryside.  In 1959, Mr. Winters relocated the agency from downtown Richmond to the corner of Atlee Road and Mechanicsville Tpke. where it remains today.  The agency is still family-owned.  Steve Winters, CIC, CLU is the third generation and agency principal.  Ben Winters joined the agency in 2010 to become the fourth generation to enter the insurance business. 


Winters-Oliver is a boutique insurance agency offering property & casualty insurance and employee benefits to small and middle market businesses.