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 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. Stephen was instrumental in establishing O'Regan's National Leasing, an all makes leasing 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 has begun construction of an auto mall at 60 Baker Drive in Dartmouth.  This new state of the art facility will house three to four dealerships, including Toyota Dartmouth and O'Regan's second Used Car Centre and is scheduled to open early in 2008. 

O'Regan's is proud to employ over 550 employees.  O'Regan's is very active in the community and earned the Corporate Philanthropist of the Year Award from the Association of Fundraising Professionals of Nova Scotia in 2004.  In 2005, they were awarded the Ernst & Young Entrepreneur of the Year, for Business to Consumer Products (Atlantic).  In 2006, O'Regan's was named one of Canada's 50 Best Managed Companies, they continue to hold the highest ranking for an automotive group in the Progress Top 101 Companies in Atlantic Canada and won the Better Business Bureau Ethics Award for a company with over 100 employees.

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 Vice Presidents of the company, for Sales and Business Development respectively. Kathleen, Paul’s daughter, is the Director of Human Resources. Stephen’s son, Tim,  is a managing partner and the General Manager of O’Regan’s Bridgewater dealerships (Toyota, Hyundai and Subaru) and Stephen's daughter Mary Ellen is a Sales Manager at O'Regan's Mercedes-Benz & smart centre.