The O'Regan's family involvement in the automobile business dates back to 1915 when S.E. O'Regan established a Ford dealership in Parrsboro. In subsequent years, he operated Chrysler and Chevrolet Oldsmobile franchises in the community. Sons Stephen and Paul O'Regan worked at the family dealerships while growing up in Parrsboro in the 1940's and 50's. However, in 1956 the newly constructed Trans Canada Highway bypassed Parrsboro causing the O'Regan brothers to pursue their futures elsewhere. Stephen went on to pursue a degree in engineering and Paul a degree in education.

In 1974, Paul took a leave of absence from teaching and rented a gas station at corner of Thistle and Maple Street in Dartmouth and started selling and leasing used cars.  It was a lean time, with only two employees, former students of Paul's from Dartmouth High, and a pay phone their only telephone.  However, times were not lean for long, by 1981, Paul's corner lot was selling over 700 cars a year and it was time Stephen left his engineering position and joined his brother in the growing business.

In 1985, Paul and Stephen bought Scotia Chev Olds, now O'Regan's Chev Olds Cadillac on Robie Street in Halifax, transforming their successful team of twelve to an overwhelming team of 108. Managing a team this size would be crucial to their success and so O'Regan's became one of the first dealerships in Atlantic Canada to run their own human resources department. 

Their next venture came about in 1987 with the opportunity to purchase a Toyota franchise, now O'Regan's Lexus Toyota on Windmill Road, Dartmouth. They secured the Lexus franchise in 1990, along with a second Toyota franchise in Bridgewater, N.S., now O'Regan's South Shore Toyota. Toyota East was added in 1994, O'Regan's Subaru in Bridgewater in 1995 and O'Regan's Hyundai in Bridgewater in 1996.

O'Regan's debuted Kia for the HRM in 1999 with O'Regan's Kia on Wyse Road in Dartmouth. Kia started with only two models and has now expanded their offering to include everything from compacts to SUV's. In the fall of 2002, O'Regan's purchased Halifax Nissan and Infiniti Halifax, now O'Regan's Infiniti and O'Regan's Nissan on Kempt Road.

In the spring of 2003, O'Regan's opened a Used Car centre on Kempt Road and completed the construction of their state of the art O'Regan's Lexus and Toyota Halifax facility, also on Kempt Road.

In February 2004, O’Regan’s acquired Isnor Motors. In the fall of 2004 they acquired the smart franchise and opened a new facility, O’Regan’s Mercedes-Benz and smart Centre in the spring of 2005.

O'Regan's added two dealerships to the group in the summer of 2006, Dartmouth Hyundai in May and Heritage Nissan in June.  

O'Regan's largest project to date was completed in 2008.  This new state of the art facility houses four dealerships, including Toyota Dartmouth, O'Regan's Nissan Dartmouth, O'Regan's Dartmouth Hyundai and O'Regan's Green Light Used Cars.  O'Regan's received an award for Excellence in Business from the Eco-Effiiciency Centre for the Auto Mall project in June 2008.  O'Regan's was able to recycle or reuse approximately 80% of the building materials from the former location and implemented the latest in energy efficient, heating, cooling, plumbing and lighting for the new complex.

O'Regan's latest project is a new Kia Dealership on Windmill Road in Dartmouth. 

O'Regan's is now a third generation automobile company with five of Paul and Stephen's children active in the business. Paul’s son’s Sean and Patrick are now President & CEO and President of HRM Operations, respectively.  Stephen's son Tim is President of South Shore Operations. Kathleen, Paul’s daughter, is the Director of Human Resources and Stephen's daughter Mary Ellen is a Sales Manager at O'Regan's Toyota Halifax.  In 2009, Sean O'Regan was the winner of the Quantum Shift Award and in 2007, Patrick O'Regan was recognized as one of Canada's Top 40 Under 40.  

O’Regan’s is recognized as one of Canada’s 50 Best Managed Companies.  O'Regan's received the 2009 Award for Business of the Year from the Halifax Chamber of Commerce.  O'Regan's was the national winner of the 2008 Family Enterprise of the Year Award and named one of Nova Scotia's Top 10 Employers.  In 2007, O'Regan's was recognized as one of the Best Places to Work in Atlantic Canada.  In 2006, O’Regan’s received the Ethics Award from the Better Business Bureau (Maritimes) and in 2004 the Corporate Philanthropist of the Year Award (Atlantic).  With over 575 employees, O’Regan’s is one of the largest and most progressive automotive organizations in Canada.