A trusted family advisor
Protecting your family,
your future, and your peace of mind.
Helping families protect what matters most, for today and for generations to come. Thoughtful, personal guidance across Rhode Island, Massachusetts, and Connecticut.
(401) 600-0146·No obligation. No pressure. Just clarity.
Where you are matters
What stage of life are you in right now?
Estate planning begins with life moments. Wherever you are today, there is a thoughtful next step, and a steady hand to help you take it.
My parent may need nursing home care
Medicaid planning, long-term care, and protecting what your family has built.
Learn About Medicaid PlanningWe have young children
Naming guardians and protecting your children if the unthinkable happens.
Learn About Estate PlanningMy spouse recently passed away
Patient guidance through probate and what comes next.
Learn About ProbateI care for a loved one with special needs
Lifelong planning that preserves benefits and protects their future.
Learn About Special Needs PlanningI own a family business
Succession, continuity, and preparing the next generation thoughtfully.
Learn About Business SuccessionOur family situation has changed
Remarriage, a diagnosis, blended family — your plan should change with you.
Explore All Practice Areas
Sheri L. Montecalvo, Esq.Principal, Estate Planning with Sheri L. Montecalvo, LLC
Meet Sheri
Helping families make important decisions with confidence and clarity.
For more than two decades, Sheri Montecalvo has helped families across Rhode Island, Massachusetts, and Connecticut plan with clarity, care, and confidence through every stage of life.
Her practice is built on long-term relationships. Many of her clients return again and again, and now bring their children and grandchildren to her too. That trust is the truest measure of her work.
The Elder Law Collaborative, LLC, provides hands-on support for families, from bill pay and trust administration to elder care coordination and advocacy.
Practice Areas
Support for the decisions that matter most to your family.
From planning ahead to navigating a loss, Sheri walks alongside families through every chapter, with patience, presence, and answers in terms families can understand.
Elder Law & Medicaid Planning
Caring for Aging Parents
Compassionate Medicaid planning, long-term care guidance, and asset protection that preserves dignity and family resources.
Learn About Medicaid Planning
Wills, Trusts & Estate Planning
Planning for the Life You Are Building
A thoughtful plan that reflects your family, your values, and what matters most.
Learn About Estate Planning
Powers of Attorney & Healthcare Directives
Protecting the People You Love
Make sure the right people can speak for you — financially and medically — when it matters.
Learn About Estate Planning
Probate & Trust Administration
Guidance After the Loss of a Loved One
Patient, practical help walking your family through what comes next.
Learn About Probate
Special Needs Planning
Supporting a Child With Special Needs
Lifelong protection that preserves benefits and ensures your child is cared for.
Learn About Special Needs Planning
Business Succession Planning
Continuing What You Have Built
Preparing your business — and your family — for what comes next.
Learn About Business Succession
Second Marriages & Multi-Generational Planning
Planning for Blended Families
Honoring everyone's interests with clarity, fairness, and care.
Learn About Estate Planning
Estate Plan Reviews
Updating an Existing Plan
Life changes, and your plan should too. We will provide a detailed review of your plan with a fresh perspective.
Learn About Estate PlanningA common question
When should you start estate planning?
Most people wait too long. The truth is simple: the right time to plan is whenever something meaningful is changing, or about to. If any of these feel familiar, it’s time for a conversation.
Schedule a Conversation- You are turning 18
- You are entering college
- You just got married
- You are starting a family
- You bought a home
- You started or sold a business
- Your parents are getting older
- You are approaching retirement
- You have a child with special needs
- You are navigating a blended family
- Someone you love received a diagnosis
- You have not updated your plan in 5+ years
Why families choose Sheri
Counsel that feels like family.
The right plan begins with the right relationship, one grounded in trust, patience, and a deep respect for the people you are planning for.
Compassionate Guidance
Thoughtful, patient counsel during the moments that matter most to your family.
“She brought a sense of calm we didn't know we needed.”
Personalized Planning
Customized, tailored planning. Every plan is shaped to your family, your values, and your goals.
“It felt like she designed our plan around our family — not the other way around.”
Multi-State Experience
Licensed across Rhode Island, Massachusetts, and Connecticut — guidance that follows your family.
“She handled both our RI home and our MA property with ease.”
Long-Term Relationships
Many families have trusted Sheri for decades — and now bring their children too.
“Three generations of our family work with Sheri now.”
Educational Approach
You will always understand what we are doing and why. Clarity is the goal.
“For the first time, estate planning actually made sense.”
Clear, Honest Communication
Plain language. No jargon. Honest answers, even on the hard questions.
“She told us the truth gently — and we trusted every word.”
What working with Sheri is like
You don’t need to have everything figured out.
Estate planning is not about having all the answers. It is about having someone you trust to help you think through difficult decisions at your own pace. Sheri helps families navigate uncertainty with patience, clarity, and practical guidance.
- We start by understanding your family, not your paperwork.
- You will always know what we are doing and why.
- We move at your pace. There’s no pressure.
- When life changes, we’ll be here to update the plan.
What happens next?
A simple three-step path forward.
Schedule a conversation
A relaxed, no-pressure call to share what is on your mind and what your family needs.
Plan together
We map out a plan that fits your family, your assets, and your goals, explained step by step.
Live with peace of mind
Your plan is in place, and we stay with your family as life unfolds.
In families' own words
Guidance when families need it most.
Stories from families across Rhode Island, Massachusetts, and Connecticut who came to Sheri during pivotal moments, and walked away with clarity and peace of mind.
After my mother's diagnosis, Sheri walked us through every option with such patience. Her calm during a very hard season made all the difference for our family.
Long-term care planning
We finally felt peace of mind after years of putting this off. Sheri explained everything clearly and helped us move forward with confidence.
Estate planning · first-time clients
Three generations of our family have now sat at Sheri's table. That tells you everything you need to know about how she takes care of people.
Multi-generational planning
Names abbreviated to protect family privacy. Reviews drawn from client correspondence and verified Google reviews.
Read more family storiesEducational guidance
Four common mistakes families make.
After two decades of advising Rhode Island, Massachusetts, and Connecticut families, Sheri has seen the same handful of missteps create the most worry. Most of them are entirely avoidable with a thoughtful conversation, started early.
Visit the Resource Center- 01
Waiting until a crisis forces the conversation
By the time a diagnosis or sudden loss arrives, many of the most protective options are no longer available. The earlier you plan, the more your family can preserve.
- 02
Assuming a will is enough
A will tells the court your wishes, but it does not avoid probate, plan for incapacity, or protect privacy. Most families need a more thoughtful structure.
- 03
Forgetting to update the plan as life changes
Marriages, grandchildren, moves, and new assets all matter. A plan written ten years ago may no longer reflect the family you are protecting today.
- 04
Putting off long-term care planning
Medicaid and elder law strategies work best with time. Acting early protects your dignity, your savings, and your family from impossible decisions later.
Educational resources
Learn at your own pace.
Estate planning works best when you understand it. Browse free guides, checklists, and articles written for families, not for lawyers.
Guide
The Family Estate Planning Primer
A clear overview of wills, trusts, and the decisions every family should make.
Read ArticleChecklist
Long-Term Care Planning Checklist
What to gather, who to talk to, and what to ask before a crisis ever arrives.
Read ArticleGuide
Probate, Step by Step
What probate actually involves, and how thoughtful planning can avoid most of it.
Read Article
Financial clarity · Trusted guidance · Compassionate support
Elder Law Collaborative, LLC
Elder Law Collaborative provides hands-on support so nothing falls through the cracks: client bill pay assistance, trustee accounting and trust administration, and elder care coordination and advocacy. Families receive organized support and compassionate guidance through the responsibilities that come with elder care and financial oversight. Education is part of that work, too.
Common questions families ask
The questions on every family’s mind.
A simple next step
You don’t have to figure this out alone.
Whenever you’re ready, Sheri is here to listen and to build a customized plan tailored to your family’s needs. No pressure, no obligation. Just a conversation.
Honest conversation. No obligation. No pressure.