Prior to entering private practice in Brookline, Attorney Lipson had served as a legal services  attorney for Neighborhood Legal Services in Lynn, a non-profit organization of which he also  had served as President. In this role, he provided legal assistance in a variety of civil matters to low income clients who were unable to afford the cost of hiring a private attorney.

The next phase of Attorney Lipson’s career was in public service. The Town of Brookline
chose Attorney Lipson to become the Director-Counsel of the Brookline Rent Control Board.  The cities of Santa Monica, West Hollywood and Berkeley, California, sought his assistance  after reading an interview about him and the Brookline Rent Control Board in the Los Angeles Times. As his title indicates, he not only directed a staff which included several attorney/hearing officers, he also successfully defended the Board’s decisions, when they were appealed to the  courts. Many of his appellate decisions are reported in the official published court reports and are cited by appellate courts in cases concerning administrative law and condominium law.

After serving for 16 years in public service, Attorney Lipson resigned to go into private practice with the Boston law firm of Israel and Goldenberg, while, at the same time, attending Boston University School of Law on a part-time basis to earn his LL.M in tax law. Many years earlier, he had received his J.D. cum laude from New England School of Law and his A.B. in Political Science from Boston University where he was elected to the national political science honor society.

After 4 years in Boston, he returned to Brookline to start a private practice as part of the former law firm of Goldenberg, Walters and Lipson, a professional association of attorneys who were located at 7 Harvard Street. On August 1, 2011, the Law Office of Roger R. Lipson moved a few doors down the street to 27 Harvard Street, maintaining its presence in Brookline Village.