Attorney Stephen Chaplin focuses his practice primarily on business issues and on litigation involving businesses, real estate boundary and title issues, landlord-tenant disputes, trusts and estates of deceased persons.

He routinely practices in the Massachusetts Superior Court, District Court, Probate and Family Court, Housing Court and Land Court. Mr. Chaplin’s experience in various courts allows him to develop strategies to help clients achieve their goals in a cost-effective manner.

Mr. Chaplin graduated summa cum laude from Berklee College of Music in Boston and cum laude from Brooklyn Law School (in New York City). While studying in New York, he worked as a judicial intern for a federal judge in the Southern District of New York and received awards for academic achievement in international intellectual property law and the law of incorporated and unincorporated businesses. He began practicing on his own in his hometown of Milford in 2012, and joined Doherty, Dugan, Cannon, Raymond & Weil, P.C. in 2015. In 2021, he was selected, based on a vote of licensed attorneys in MA and a review by an independent blue ribbon panel, as a “Rising Star” in the annual “Super Lawyers” publication.

Mr. Chaplin is actively involved in the greater Milford community as president of the Milford Rotary Club (2017-18), as president of the Board of Directors of the Claflin Hill Music Performance Foundation (2017-present), and as Chairperson of the Hopedale Planning Board (2020-present). He is a former member of the Milford Area Humanitarian Coalition and a former assistant coach for the Hopedale Junior/Senior High School boys’ tennis team. Mr. Chaplin is a professional pianist who regularly appears at music venues and churches throughout central and eastern Massachusetts.