Tiffany M. Bentley


F: (617) 849 7238
Overview Insights News Education and Credentials Recognition and Community


Tiffany Bentley counsels high net worth individuals and families, as well as professional fiduciaries, through estate and trust disputes, probate issues, and divorce and related matters. Her practice includes all aspects of fiduciary litigation and family law.

As a probate and family court litigator, Tiffany works to identify each client's best possible outcome and then charts the necessary path through discovery, settlement negotiations, and all the way to trial where necessary. As this line of work often centers around traumatic and deeply personal life events, such as the death of a loved one or the end of a marriage, she takes great pride in guiding clients with both experience and empathy.

On the trust and estate side, Tiffany's practice includes contested probates, guardianships, and conservatorships; as well as postmortem challenges to the validity of trusts, deeds, beneficiary designations and lifetime transfers, and various challenges to the administration of estates and trusts. In the area of family law, she assists clients through divorce and custody matters; prenuptial and postnuptial planning; and post-divorce contempt and modification actions.

In addition to her regular practice, Tiffany volunteers as a conciliator in Middlesex and Worcester County to help resolve cases and unclog court dockets. She also dedicates a substantial amount of time on pro bono matters, representing children in custody disputes through the Attorneys Representing Children program.



Education and Credentials

University of Colorado Law School, J.D., Order of Coif, 2008; Rothgerber Moot Court, Honor Board; Colorado Journal of International Environmental Law and Policy, Lead Articles Editor
Curry College, B.A., summa cum laude, 2002
Commonwealth of Massachusetts
Massachusetts Bar Association
Boston Bar Association
Worcester Bar Association
Massachusetts Association of Guardians ad Litem
Greater Boston Fiduciary Law American Inn of Court, Board Member
Greater Boston Family Law American Inn of Court
American Association for Certified Financial Litigators
Women's Bar Association

Recognition and Community


No aspect of these advertisements has been approved by the highest court of any state. See Awards Methodology.

Selected to Boston Magazine's Top Lawyers List, Family Law, 2022

Selected to the list of Massachusetts Super Lawyers (Thomson Reuters), Estate and Trust Litigation, 2022-2023, Family Law, 2022-2023, Estate Planning and Probate, 2022-2023

Selected to the list of Massachusetts Super Lawyers Rising Stars (Thomson Reuters), Estate and Trust Litigation, 2011-2018

No aspect of these advertisements have been approved by the highest court of any state. See Awards Methodology.


Greater Boston Legal Services, Board of Directors

Attorneys Representing Children

Discovering Justice's Stand Up for Your Rights, Attorney Volunteer/Teacher, 2009-2015