Jack Ashley

Since 1980, he has served as the broker and owner of Ashley Insurance, leading the agency through decades of growth and expansion. Licensed in Property & Casualty and Life & Health since 1979, he has nearly five decades of insurance experience and has successfully expanded Ashley Insurance through the acquisition of several independent agencies across Maryland’s Eastern Shore. He also holds a Series 6 Securities License and has earned multiple Certified Insurance Counselor (CIC) designations in Commercial Casualty, Commercial Property, Life & Health, and Personal Lines.

In addition to his insurance career, he has enjoyed a long and successful career in real estate. He has served as broker of Ashley Premier Properties since 2009 and previously led Prudential Premier Properties. Throughout his career, he has been recognized for his leadership within the real estate industry, including being named Bay Area Association of Realtors’ Realtor of the Year in 1996 and serving as President of the Queen Anne’s County Board of Realtors.

A graduate of Queen Anne’s County High School, he continued his education at Chesapeake College and completed the Catonsville Community College Real Estate Broker Program. He has remained actively involved in the community for decades through the Queen Anne’s County Chamber of Commerce and the Centreville Lions Club, where he has served in numerous leadership roles.