Underwood Legal guides Wisconsin families through estate planning with plain-language advice, thoughtful attention to detail, and genuine care for what matters most to you.
Why Families Choose Us
Wisconsin families consistently rate their experience with Underwood Legal at the highest level — a reflection of the care and quality we bring to every client relationship.
Your questions deserve real answers, promptly. Our clients regularly cite Matthew's responsiveness and attention to detail as what sets us apart.
We believe you should fully understand every document you sign. We explain everything clearly — using visuals when it helps — before you make any decision.
Meet in person at our Madison office, by phone, or virtually. We make it easy for Wisconsin families to get the legal guidance they need.
No templates, no one-size-fits-all approaches. Every plan we create is tailored to your specific family, circumstances, and long-term goals — because your legacy deserves nothing less.
What We Do
Wills · Trusts · Powers of Attorney
Wills, trusts, and powers of attorney crafted to protect your wishes and give your family clarity and peace of mind when it matters most. Every document is tailored to your specific family situation and long-term goals.
Learn MoreAdministration · Representation · Guidance
Compassionate guidance for personal representatives and families navigating probate and administering a loved one's estate in Wisconsin. We help you fulfill your responsibilities efficiently during a difficult time.
Learn MoreTransfers · Transactions · Ownership
Legal assistance with property transfers, real estate transactions, and ownership matters — often integrated as part of a broader estate plan to ensure your property passes exactly as you intend.
Learn MoreFormation · Structuring · Protection
Formation of LLCs and thoughtful structuring of business ownership integrated into a comprehensive plan that protects both your family and your business interests for generations to come.
Learn MoreHow We Work
We translate complex legal concepts into clear, straightforward terms — so you make confident decisions without confusion or overwhelm.
Every estate plan begins with listening. We learn your family's unique situation before recommending a single strategy.
We use visuals and clear explanations to connect the dots, making estate planning approachable for first-timers and experienced planners alike.
Meet in person, by phone, or virtually — we work around your schedule to make the entire experience smooth and stress-free.
Our reputation is built on real client experiences. Families across Wisconsin consistently praise our care, thoroughness, and responsiveness.
From estate plans and probate to real estate transactions and business formation, we handle the legal matters that shape your family's future.
Client Stories
"If you are thinking of creating an estate plan but fear it will be too intimidating, I strongly recommend you give Matthew Underwood a call. From the first meeting, Matthew put my parents at ease, respectfully listening to their specific needs, clearly explaining complex legal structures... He made us feel as though we were his highest priority. Matthew is an intelligent lawyer and a genuinely kind person."
Rachael S.
Estate Planning Client
"We recently worked with Matt completing our family's estate plan. Matt took the time to really listen to our needs and objectives. We felt he truly understood us and what is important to our family... Matt does a great job explaining complex concepts in simple, easy to understand language. We sleep well at night now after going through Matt's process."
Jason K.
Estate & Business Planning Client
"I needed to update my estate plan, and Matthew was recommended to me by a respected pre-planning funeral advisor. Matthew is kind, personable, and professional. I was comfortable working with him, and he and his team made the entire process smooth from start to finish. I am impressed by his attention to detail and his degree of thoroughness."
Norm D.
Estate Planning Client
"My husband and I recently completed estate planning with Matt & can't say enough good things about the entire process! Matt kept us on track, thoroughly explaining every option until we completely understood... He was also very flexible with scheduling each meeting and made the whole experience feel so easy! As a business owner myself, I'd HIGHLY recommend Underwood Legal."
Cassie S.
Estate & Business Planning Client
Book a phone, virtual, or in-person meeting at a time that works for you. It's a no-pressure conversation to get started.
We listen first. Tell us about your family, your assets, and what you want your plan to accomplish — every detail matters to us.
We draft a tailored estate plan — wills, trusts, powers of attorney — designed specifically around your situation and goals.
We walk through every document in plain language, answer all your questions, and revise until everything aligns perfectly with your vision.
Finalize your properly executed documents and move forward with lasting peace of mind for you and your family.
Common Questions
Every adult benefits from having basic estate planning documents in place. A will, healthcare directive, and power of attorney ensure your wishes are honored and protect your loved ones from difficult decisions — regardless of your age or the size of your estate.
A will directs how your assets are distributed after you pass and goes through probate. A trust allows assets to pass to beneficiaries without probate, offering greater privacy and efficiency. We'll help you determine which approach — or combination — best fits your goals.
We discuss your family situation, assets, and goals in detail so we can recommend the right planning approach. It's a collaborative conversation focused on understanding what matters most to you.
Most estate plans are completed within a few weeks of the initial consultation. The timeline depends on the complexity of your situation and how quickly we can finalize details through the review process — we move at your pace.
Yes. We provide compassionate, practical guidance for personal representatives and families navigating probate and estate administration in Wisconsin, helping you fulfill your responsibilities efficiently during a difficult time.
Absolutely. We assist with LLC formation and business ownership structuring, often as an integrated part of a broader estate plan that protects both your family's future and your business interests.
Yes. We offer phone, virtual, and in-person consultations to fit your schedule and preferences. Clients from throughout Wisconsin are welcome to work with our office.
The first step is scheduling a consultation. Reach out by phone, email, or our online contact form and we'll find a time that works for you. Most clients find the first conversation puts them completely at ease.
Take the First Step
Most clients tell us the first conversation puts them completely at ease. Schedule a consultation and discover how simple — and empowering — estate planning can be.
Virtual & phone consultations available