Atty. Stephen J. Olsen

Atty. Stephen J. Olsen

Stephen J. Olsen is a member of Gawthrop Greenwood’s Trusts & Estates Department, practicing in the areas of Estate, Trust Administration, Estate Planning Taxation, and Business Transactions.

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Profile Summary

About Stephen J. Olsen at a glance

Stephen J. Olsen is a trusts and tax attorney based in West Chester, Pennsylvania, practicing at Gawthrop Greenwood PC. Admitted to practice in District of Columbia, The District of Columbia Bar and Pennsylvania, Pennsylvania Bar Association. Educated at Villanova University (Taxation and J.D., 2007) and Lycoming College (B.A.). Recognitions include Best Lawyers in America — Trusts and Estates (2026), Best Lawyers in America — Tax Law (2026), and Best Lawyers in America — Additional Areas of Practice: (2026). Serands clients in West Chester, PA and the surrounding metropolitan area.

Verified attorney profile · Updated June 2026

About

Stephen J. Olsen is a member of Gawthrop Greenwood’s Trusts & Estates Department, practicing in the areas of Estate, Trust Administration, Estate Planning Taxation, and Business Transactions. He is also one of the few Pennsylvania attorneys in private practice with a wide breadth of experience supporting the legal needs of medical marijuana operators.

Recently Stephen’s Cannabis Law practice has expanded to provide support to medical marijuana permittees in operation after Pennsylvania issued 25 grower and 50 dispensary permits across the Commonwealth. What began as legal services for medical marijuana operators and executives in compliance and transactional matters has now grown to due diligence services for potential investors, as well as support in employment law, workplace issues, advising fiduciaries on investing in marijuana companies and advising nonprofits in accepting donations from marijuana companies. He has also assisted processors, distributors and retailers of hemp-derived CBD products in a wide array of transactional and compliance issues.

Stephen received his law degree, cum laude, and his Master of Laws in Taxation (3.97 GPA) from Villanova University School of Law.

During law school, he served in the Federal Tax Clinic representing low-income taxpayers before the IRS and Tax Court and participated in the VITA tax preparation program for low-income taxpayers. He received his undergraduate degree in economics, with honors, from Lycoming College, where he was a member of the scholars program.

In addition to working at Gawthrop Greenwood, Stephen is currently assisting in the preparation of supplements and the new edition of the seminal tax procedure treatise, IRS Practice and Procedure (Rev. 2d ed.) (WG&L 2002), written by Michael Saltzman and Leslie Book. He is also a past Chester County Coordinator for the Wills for Heroes program, serves as the co-chair of the steering committee of the Chester County Community Foundation’s (CCF) Imprints program, is a board member of The Hickman, and is a past board member for Aid then Trade.

Stephen is admitted to practice in Pennsylvania, Washington, DC and before the tax court. He is a member of the Chester County, Pennsylvania, Washington, DC, and American Bar Associations. He is also a member of the committees on taxation of the Pennsylvania and the American Bar Associations, and a member of the Chester County Estate Planning Council.

Stephen is a creator of and frequent poster on the popular blog Procedurally Taxing. He has also written many other articles over the years, including:

  • Chuck vs. Goliath: Basis of Stock Received in Demutualization of Mutual Insurance Companies (HBTLJ, 2009)
  • Temporary Repeal of the Federal Estate Tax
  • Pennsylvania Tax Amnesty Program 2010
  • Changes Abounded in 200 to Federal Tax Law
  • Recovery Act Tax Changes for Individuals
  • Recovery Act Tax Changes for Business Owners

Stephen also speaks at a variety of seminars on topics related to tax controversy, tax planning, marijuana law, charitable planning, estate planning, and estate and trust administration. He has been interviewed multiple times on Fox 29 News, speaking about tax issues and his work with the Wills For Heroes program.

Practice Areas Explained

Stephen J. Olsen's Areas of Practice

Each practice area below reflects the types of cases Stephen J. Olsen handles, with a brief overview of what that area of law covers.

Trusts

Stephen J. Olsen is one of 104,172 trusts attorneys indexed nationally. Browse trusts attorneys in Pennsylvania →

Tax Law

Tax attorneys handle IRS audits, tax debt, international tax, estate planning, and tax court litigation.

Stephen J. Olsen is one of 85,302 tax attorneys indexed nationally. Browse tax attorneys in Pennsylvania →

Jurisdictional Context

Why local counsel matters in Pennsylvania

Practicing law in Pennsylvania. Legal matters in Pennsylvania are governed by state-specific rules of civil and criminal procedure, statutes of limitations, and substantive law. Cases originating in West Chester are typically filed in the local municipal court or the appropriate Pennsylvania state district court, depending on subject matter and amount in controversy. An attorney licensed in Pennsylvania brings working knowledge of local procedural deadlines, judicial practices in this andnue, and the substantive law that applies to cases brought here. Out-of-state attorneys generally cannot represent clients in Pennsylvania courts without local counsel or pro hac vice admission.

Looking for additional Pennsylvania attorneys? Browse all attorneys in West Chester or all attorneys in Pennsylvania.

Frequently Asked

Common questions about Stephen J. Olsen

Where is Stephen J. Olsen's law office located?
Stephen J. Olsen's law practice is located in West Chester, Pennsylvania. The firm is Gawthrop Greenwood PC. You can contact the office directly through this profile page.
What practice areas does Stephen J. Olsen handle?
Stephen J. Olsen focuses on trusts, tax. Each practice area listed reflects experience handling cases of that type in Pennsylvania.
Where did Stephen J. Olsen go to law school?
Stephen J. Olsen earned their education at (Taxation and J.D., 2007); (B.A.).
How can I contact Stephen J. Olsen for a consultation?
You can contact Stephen J. Olsen directly through this profile page. Click "Ask the Attorney" to submit a question, or "Schedule a Consultation" to book a meeting. Most claimed-profile attorneys respond within one business day.
What awards or recognition has Stephen J. Olsen received?
Stephen J. Olsen's notable recognition includes: Best Lawyers in America — Trusts and Estates; Best Lawyers in America — Tax Law; Best Lawyers in America — Additional Areas of Practice:; Best Lawyers in America — Real Estate Law; Best Lawyers in America — Cannabis Law.

Practice Areas

Education

Taxation and J.D.
Villanova University
- 2007
B.A.
Lycoming College
- In Progress

Awards

Best Lawyers in America — Trusts and Estates
- 2026
Best Lawyers in America — Tax Law
- 2026
Best Lawyers in America — Additional Areas of Practice:
- 2026
Best Lawyers in America — Real Estate Law
- 2026
Best Lawyers in America — Cannabis Law
- 2026
Best Lawyers in America — Awards:
- 2026
Best Lawyers in America — Main Line Today
- 2026
Best Lawyers in America — Top Lawyers 2014 - 2023
- 2026
Best Lawyers in America — Daily Local News
- 2026
Best Lawyers in America — Top Lawyers 2021 - 2022
- 2026
Best Lawyers in America — Super Lawyers
- 2026
Best Lawyers in America — Rising Star Pennsylvania 2010, 2013 - 2021
- 2026
Best Lawyers in America — The Legal Intelligencer
- 2026
Best Lawyers in America — Lawyers on the Fast Track 2016
- 2026
Best Lawyers in America — Chester County Community Foundation Door Opener Award, 2013
- 2026

Bar Admissions

District of Columbia, The District of Columbia Bar
Pennsylvania, Pennsylvania Bar Association

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