About Sheri
Guidance rooted in trust, clarity, and compassion.
For more than two decades, Sheri Montecalvo has helped families across Rhode Island, Massachusetts, and Connecticut protect their legacy by making planned decisions concerning their most challenging life transitions. Sheri provides her clients with protection, clarity, and peace of mind through her compassionate legal counsel and customized estate planning strategies.
Sheri L. Montecalvo · Estate Planning & Elder Law
Why this work
Why Sheri does this work.
Sheri came to estate planning and elder law the way most people who care deeply about it do: through family. Watching loved ones navigate aging, illness, and the weight of decisions that nobody had planned for, she saw the value in a thoughtful, well-prepared plan and how often families were left without one.
That experience shaped everything about how she practices today. She is not interested in the cold, document-first approach that many people associate with attorneys. She is interested in the conversation that comes before the documents, the one where a family figures out, together, what matters most and how to protect it.
For her clients, that means a relationship rather than a transaction. It means time taken to understand who is in the family, who is helping, what is feared, and what is hoped for. It means strategies built around real lives, not pulled from a template. It also means a familiar, reliable voice they can call again as life changes, not just at the moment a document is signed.
More than anything, Sheri believes families deserve to feel prepared rather than overwhelmed. That belief is the steadfast engine behind every conversation she has.
Approach
A reassuring presence in important decisions.
Sheri's practice is built on four convictions: the ideas that shape every conversation, every plan, and every family relationship she takes on.
Advisor first, attorney second.
Most families do not need a lawyer in the traditional sense. They need a thoughtful advisor who can help them see the road ahead and walk it together.
Education before paperwork.
Decisions made with full understanding hold up over time. Sheri takes the time to explain, without legal jargon, what each choice actually means for your family.
Compassion is not optional.
These conversations touch the most tender parts of family life. They deserve patience, warmth, and care, not a checklist.
Thoughtful planning prevents crisis.
Almost every difficult moment families face later could have been softened by a thoughtful conversation earlier. That conversation is the work.
What families appreciate most
What clients tend to mention.
When families describe what working with Sheri has meant to them, the same handful of words come up again and again.
01
Clear explanations
Plain language, no jargon, and the patience to answer the same question twice if that is what helps.
02
Clear communication
An unhurried, reassuring presence, especially in moments when life feels anything but steady.
03
Genuine responsiveness
Phone calls returned. Questions answered. Families never left wondering where things stand.
04
Thoughtful planning
Strategies built around your family's real life, not a template pulled from a drawer.
05
Compassionate guidance
Difficult topics handled with dignity, warmth, and respect for everyone in the family.
06
Long-term partnership
A familiar voice families can call again as life changes, for years, not just a single matter.
Experience & credentials
Two decades of trusted guidance.
Credentials matter, but they sit beneath the relationship, not above it.
Bar Admissions
- State of Rhode Island
- Commonwealth of Massachusetts
- State of Connecticut
- United States District Court for the District of Rhode Island
- United States District Court for the District of Massachusetts
- United States Court of Appeals for the First Circuit
- United States Supreme Court
Education
- Roger Williams University School of Law — Juris Doctor, cum laude
- Pupillage, Chambers of Michael Parroy, Q.C., London, England
- Rhode Island College — B.A., magna cum laude
Affiliations
- Rhode Island Bar Association
- Massachusetts Bar Association
- Connecticut Bar Association — Windham County Chapter
- National Academy of Elder Law Attorneys (National and Rhode Island Chapter)
- Animal Legal Defense Fund
Areas of Focus
- Estate & Tax Planning
- Elder Law & Medicaid Planning
- Probate & Trust Administration
- Asset Protection & Long-Term Care Planning
- Special Needs Planning & Guardianship
- Corporate & Business Succession Planning
- Pet Estate Planning
Educator & community resource
Teaching is part of the practice.
Education is central to Sheri’s work. Through workshops, seminars, and ongoing resources, she helps families, professionals, and communities understand the practical work of planning ahead, in clear terms and long before anyone needs it.
- Community workshops on estate planning essentials for families
- Continuing education sessions for financial advisors and care professionals
- Library and senior center seminars on Medicaid planning and long-term care
- Featured author, Leading Elder Law and Estate Planning Attorneys (Remarkable Press, 2021)
A clear direction
“A trusted advisor helping families find their way, clearly, thoughtfully, and with care.”
A note from Sheri
You don’t have to figure this out alone.
Whether you’re just beginning to think about a plan, helping an aging parent, or carrying a decision you’ve been putting off, you’re welcome here. Whenever you’re ready, we’ll begin with a simple conversation.
No pressure. No obligation. Just a conversation.