Estate Planning With Sheri

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Providence, RI
Estate Planning With Sheri

My mission is to empower my clients to protect their legacy by making planned decisions through Estate Planning and Elder Law.

Sheri concentrates her practice in the areas of estate and tax planning, asset protection planning, business succession planning, corporate, elder law, probate, guardianship, trust and estate administration, special needs planning and Medicaid planning. She has over 18 years of experience providing counsel to business owners, individuals and families. Sheri owns and manages her own practice, Estat

e Planning With Sheri Montecalvo located in Providence, RI. Sheri takes pride in serving as a trusted advisor to her long-standing clients and their future family generations. She will see her clients through the entire process from document creation, re-titling of assets and complete estate/trust administration.

05/13/2026

Loved being part of the Women & Wealth brunch hosted by Washington Trust at Ocean House. There’s something really special about connecting with women and having thoughtful conversations about planning for the future, protecting their families, and building lives they feel proud of. Grateful to be part of such a wonderful gathering.

05/08/2026

We’re honored to introduce Elder Law Collaborative, LLC an extension of Estate Planning with Sheri L. Montecalvo, LLC, focused on providing practical, ongoing support for individuals and families navigating the complexities that can come with aging, care needs, and financial management.

Elder Law Collaborative, LLC was created to provide structure, clarity, and support when ongoing financial responsibilities, care coordination, and decision-making require more hands-on involvement.

Estate Planning with Sheri focuses on creating and establishing your plan. Elder Law Collaborative provides ongoing support to help carry out and manage those plans when life requires continued attention and coordination.

We assist in three core areas:

• Bill Pay & Financial Oversight�Comprehensive management and tracking of ongoing financial responsibilities, including utilities, mortgages, insurance, medical expenses, and long-term care costs. We help ensure everything is organized, monitored, and accounted for with care and consistency.

• Trustee Accounting & Administration�Clear and accurate trust accounting that tracks income, expenses, and distributions. This provides transparency and organization, helping ensure records are always current and ready for tax preparation or review.

• Elder Care Coordination & Advocacy�Support in navigating care options based on individual needs and circumstances. This includes assistance with nursing home and assisted living placement, in-home care coordination, and connection to available programs and resources.

At its core, this work is about helping families feel more supported during periods that can feel overwhelming or complex.

If you are caring for a loved one, managing their affairs, or finding that the responsibility has become more than you expected to carry alone, we are here to help.

We invite you to reach out to learn more about Elder Law Collaborative and how we can support your family’s specific situation. Together, we will talk through your needs and determine what level of support aligns for you.

05/05/2026

We had a wonderful time at the Rhode Island Assisted Living Conference where a community of professionals came together, all working toward the same goal - to support individuals and families with care and intention.

It was a great day of connection, collaboration, and meaningful conversation. An important reminder that the best outcomes come from working together, and we’re grateful to be part of a community that values that approach.

Thank you to everyone who stopped by to connect with us!

04/27/2026

The One Conversation Every Mom Needs to Have (But Most Avoid)

There’s a moment most moms know well and it’s usually not during the big milestones.

It’s in the quiet, in-between. Folding laundry. Sitting in the car after drop-off. Packing lunches for the next day.

And the thought sneaks in:

If something happened to me … would everything actually be okay for my kids?

Not just emotionally, but legally.

It’s an uncomfortable thought, so it gets pushed aside. Life is full, schedules are packed, and it’s easy to assume it’s something you’ll get to “later.”

When you’re a parent, this kind of planning becomes less about assets and more about decisions:

-Who steps in to raise your children?
-Who makes decisions in an emergency?
-How is money handled for their care and future?
-How do you keep your family out of court during an already difficult time?

Without a plan, those answers may be left up to a judge - someone who’s never met your family.

Even a simple plan can put the right people in place, create structure for your kids’ future, and remove unnecessary stress for your family.

If this is something that’s been sitting in the back of your mind, you’re not alone.

If you’re ready to move from “I should probably do this” to something actually in place, as an estate planner and mom myself, I’m here to help guide you through it.

04/17/2026

One of the most productive meetings we had this week wasn’t just with a client, it was with two generations planning together.

A mother and daughter came into our office with a shared goal: to be proactive and thoughtful about what comes next.

Together, they’re planning for probate avoidance, estate tax efficiency, and Medicaid planning, but more importantly, they wanted to make sure their decisions worked together.

The mother is thinking about protecting what she’s built and planning for long-term care. The daughter is focused on preserving those assets and minimizing future tax exposure.

When families are willing to have these conversations early, planning becomes a lot more intentional. It gives us the ability to structure a plan in a way that supports care, preserves wealth, and avoids unnecessary complications down the road.

There’s something powerful about sitting down together and building a plan that reflects not just individual goals, but shared ones.

Those conversations don’t always feel easy to start, but they’re often the ones that create the most clarity, the most alignment, and ultimately, the most peace of mind.

03/30/2026

As a physician, you’re often the calm in someone else’s emergency. You make critical decisions quickly, guide families through uncertainty and prepare for outcomes most people hope they never face.

That perspective is something most people don’t have, and it naturally shapes how many physicians think about planning.

You understand, better than anyone, how quickly circumstances can change. And while your focus is on your patients, your own planning is often the thing that gets pushed to the side.

If that emergency were yours, would everything outside the practice be just as prepared?

With a demanding career, growing assets, and increased exposure to liability, physicians benefit from having a plan that accounts for those realities. A plan that clearly outlines who can step in to make medical and financial decisions if needed, how income and obligations are handled during a period of incapacity, and how what you’ve built is protected.

And for physicians who own or operate their own practice, there’s an added layer to consider. Patient care doesn’t simply pause. Having clear direction around practice continuity, patient record custody, HIPAA compliance, and how care is transitioned or the practice is wound down or transferred is just as important as personal planning.

Taking the time to put a plan in place means those decisions aren’t left to chance. The people you trust are empowered to step in, your patients are accounted for, and your family isn’t left to navigate uncertainty without guidance.

If planning has been on your to-do list for a while, or if it’s been years since you’ve reviewed it, this is a good time to revisit.

Wishing you a Happy Doctor’s Day! Thank you for the care and dedication you bring to your patients and our community every day!

03/26/2026

Handling the loss of a loved one is hard enough. But if your family has assets in more than one country, the process can feel even more overwhelming.

We’re currently guiding a family through probate in Germany, along with an ancillary probate here in Connecticut.

Many families assume that having a will in place means everything can be handled in one process. In reality, when assets are held in different countries (or even different states) each jurisdiction requires its own probate proceeding to transfer those assets.

Each process has its own rules, timelines, and documentation requirements. Coordinating between them can often add stress during an already emotional time.

That’s where we come in, we’re currently guiding this family through both proceedings, keeping everything aligned and helping them focus on honoring their loved one rather than navigating legal complexities.

These situations are becoming more common as families relocate, inherit property abroad, or maintain homes in multiple countries. With careful planning, it’s often possible to simplify probate or even reduce the need for multiple probate proceedings.

If your family owns property here and abroad, taking proactive steps now can make a meaningful difference for your loved ones later. Does your estate plan account for that? If not, I’m happy to guide you.

03/11/2026

Estate Planning with Sheri is proud to welcome Kaylee Proulx as an Associate Attorney. Kaylee joins the firm during an exciting period of growth, bringing a distinguished academic record and a multidisciplinary legal background that complements our commitment to providing thoughtful and comprehensive estate planning for the individuals and families we serve.

Kaylee earned her Juris Doctor, Cum Laude, from Roger Williams University School of Law, graduating in the top 25% of her class. During law school, she received prestigious academic awards in Federal Income Tax, Patent Law, and Law Firm Management, reflecting her commitment to the practice of law.

Her legal experience spans real estate, family law, and business law, allowing her to approach estate planning with a multidimensional perspective. This background enables Kaylee to identify and address the various legal considerations that often intersect in a client’s estate plan.

Kaylee approaches estate planning as both a legal discipline and a meaningful service to families. As she describes it, “Estate planning is a final act of love and stewardship. I am driven by the opportunity to help clients communicate their deepest values through their legal documents, ensuring their life’s work becomes a lasting gift rather than a legal burden for the next generation.”

Kaylee is a member of the Rhode Island Bar Association, where she participates in the Probate and Trust Committee. She is also a member of the National Academy of Elder Law Attorneys, including the Rhode Island Chapter.

We are proud to welcome Kaylee to the firm and look forward to the knowledge, dedication, and compassion she brings to the clients we serve.

03/05/2026

I built my practice around helping people protect what matters most.

If we haven’t met yet, I wanted to take a moment to reintroduce myself and share a little about why this area of the law matters so much to me.

I’m Sheri, founder of Estate Planning with Sheri L. Montecalvo, LLC. For more than 20 years, I’ve helped individuals and families across Rhode Island, Massachusetts, and Connecticut put the right protections in place, before life demands it of them.

I was drawn to estate planning because it allows me to make a meaningful difference in people’s lives during both the calm and the uncertain moments. What I love most about this practice area is that it’s entirely centered on people - their families, their wishes, and their peace of mind.

Becoming an estate planning attorney wasn’t just a professional decision for me-it was deeply personal.

Through both my work and my own life, I’ve walked alongside the realities that so many families face: caring for aging parents, planning for life’s transitions, and experiencing the loss of loved ones. These moments are emotional, complex, and often overwhelming. They shape how we think about the future and the people we love most.

Because of these experiences, I don’t see estate planning as just documents and legal strategies. I see people, families, and stories. I understand that every situation is unique and often sensitive. That perspective allows me to meet my clients with genuine compassion and to create plans that are truly customized to their goals, values, and concerns.

My mission is simple: to help families feel prepared, protected, and at peace - not just legally, but emotionally as well.

Every plan tells a story about what someone has built and who they love, and it’s a privilege to help protect that.

If you’re thinking about planning for the future, know that you don’t have to navigate it alone.

Outside of my practice, I’m a mom to three awesome children and three loving dogs who keep life busy and my heart full. When I’m not chauffeuring or cheering from the sport sidelines, you’ll usually find me spending time with family and friends, traveling or enjoying a rare quiet moment reading when time permits.

These parts of my life aren’t separate from my work; they’re the reason I deeply understand why planning matters.

If you’ve read this far, thank you for being here. And if we haven’t had the chance to connect, I look forward to it.

02/24/2026

Most people are aware that they should discuss estate planning with their parents.

But very few actually do.

Not because they don't care, but because they don't know always know where to begin. The topic feels heavy. Awkward. Overwhelming. So it gets pushed to the back burner, year after year, until life forces the conversation at the worst possible moment.

Here's the truth: avoiding this conversation doesn't protect your family - it just leaves them unprepared. When a parent passes without an estate plan, the result is often confusion, conflict, and costly legal proceedings during an already painful time.

A conversation today can prevent all of that.

Here are some ideas how to start it:

Use a real-life event as a bridge. A friend's parent who recently passed, a news story, or even your own planning process can open the door naturally. "It got me thinking about our family. Have you ever put anything in writing?"

Lead with their legacy. Most parents want to know that everything they've built will be taken care of. Approach it from that angle: "You've worked hard your whole life, I just want to make sure we have a plan that protects all of it."

Start with curiosity: "I've been thinking, do you have a will? Is there someone you've designated to handle things if you ever need help?

The goal of the first conversation is simply to start one. Everything else can follow from there.

- Do they have a will, trust, or powers of attorney in place?
- Are their beneficiary designations up to date?
- Where are their important documents kept?
- Who do they want making medical and financial decisions if they're unable to?
- Have they communicated their wishes around end-of-life care?

These conversations aren't easy, but they are one of the greatest gifts you can give your parents. Starting the dialogue is the first step toward honoring their wishes and protecting everything they've worked so hard to build.

If you're not sure where to go from here, I am more than happy to sit down with you and your parents to put everything in place.

Address

272 West Exchange Street, Suite 001
Providence, RI
02903

Website

http://www.estateplanningwithsherimontecalvo.com/

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Michael C. Judge, Attorney At Law
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