Sheryl J. Dennis

Sheryl J. Dennis


Wellesley Estate Planning Attorney

Attorney Sheryl Dennis has been practicing family law for more than 24 years. Over this time, she has helped scores of family members resolve complex legal issues with a high level of skill, professionalism and compassion.

One of the Firm’s founding partners, Sheryl Dennis is one of the most sought-after Massachusetts estate planning lawyers, and a leader in family law and special needs planning. She has an expertise in working with closely held family businesses and helping to set up business succession plans and estate plans. She is a member of WealthCounsel, ElderCounsel and the Academy of Special Needs Planners.

Ms. Dennis also brings significant litigation experience to the practice. Whether it is conducting a cross-examination, giving a closing statement, or arguing motions, Ms. Dennis feels at home in the courtroom.

Her expertise has been in demand at speaking events, in the media and in education: she has been a featured speaker at the annual Fall Conference of the Massachusetts Council for Family Mediation on the subject of prenuptial agreements along with partner Jonathan Fields. She was also invited to contribute to a lecture on discovery issues for a prestigious legal education series.

Ms. Dennis has appeared on Boston’s highest rated radio morning show, “Matty in the Morning,” on KISS-108 FM, to discuss prenuptial agreements. In recent years, she was admitted to the United States Court of Appeals for Veteran’s Claims.

She blogs frequently, contributes to social media, and has been quoted in Massachusetts Lawyers Weekly relating to digital legacy planning relating to a Facebook feature that allows individuals to choose a “legacy contact” to manage their count in the event of their death.

  • B.A. from Methodist College
  • J.D., cum laude, from the New England School of Law
  • Degree from the Western New England School of Law estate planning and elder law LL.M. program
  • Massachusetts Bar Admission
  • Member of WealthCounsel, ElderCounsel
  • Academy of Special Needs Planners
  • Admitted to the United States Court of Appeals for Veteran’s Claims.