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Stephen J. Olsen, Tax Attorney in West Chester, Pennsylvania

focused on Tax and Trusts

Gawthrop Greenwood PC

West Chester, PA

Trusted tax attorney serving West Chester.

2
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Stephen J. Olsen is an attorney based in West Chester, PENNSYLVANIA. The practice focuses on Tax and Trusts. Currently practicing at Gawthrop Greenwood PC.

Based in
West Chester, PENNSYLVANIA
Experience
attorney
Known for
Tax · Trusts
  • Handles Tax and Trusts matters from West Chester, PENNSYLVANIA.
  • Recognized with Best Lawyers in America — Trusts and Estates (2026).

About Stephen J. Olsen: Stephen J. Olsen is an attorney based in West Chester, PENNSYLVANIA. The practice focuses on Tax and Trusts. Currently practicing at Gawthrop Greenwood PC.

Areas of practice

Stephen's practice areas in West Chester

Stephen concentrates on tax and trusts. Each area below outlines the kind of case Stephen handles, typical outcomes to expect, and how the intake process starts.

Tax cases in West Chester, Pennsylvania

Stephen takes tax matters in West Chester, Pennsylvania. Typical engagements include intake calls to scope the issue, review of any records or filings you already have, and a written strategy memo before Stephen agrees to represent you.

Trusts cases in West Chester, Pennsylvania

Stephen takes trusts matters in West Chester, Pennsylvania. Typical engagements include intake calls to scope the issue, review of any records or filings you already have, and a written strategy memo before Stephen agrees to represent you.

Biography

Stephen J. Olsen, tax attorney serving West Chester

Stephen J. Olsen is an attorney based in West Chester, PENNSYLVANIA. The practice focuses on Tax and Trusts. Currently practicing at Gawthrop Greenwood PC. Stephen works from West Chester, Pennsylvania and takes on tax matters across the region.

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.

How Stephen handles tax matters

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…

Who Stephen represents

Stephen reviews new inquiries case-by-case for tax and trusts matters in West Chester and the surrounding Pennsylvania area.

Credentials

Credentials — where Stephen studied and practices

  • Villanova University

    Taxation and J.D. · 2007

  • Lycoming College

    B.A.

Jurisdictions

Stephen's state bar admissions

  • Pennsylvania, Pennsy

    ACTIVE

  • District of Columbia

    ACTIVE

Stephen studied at Taxation and J.D. in Villanova University and B.A. in Lycoming College.

Law school and academic background

Stephen completed Taxation and J.D. in Villanova University and B.A. in Lycoming College. Formal legal training is one signal of substantive knowledge — the day-to-day practice Stephen runs in Pennsylvania is where that training gets applied to real client questions.

Recognition

Stephen's legal honors and published work

Stephen has received 15 formal recognitions from bar associations, industry bodies, and peer-review services.

  • 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

Legal awards and honors

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).

Locations

Stephen J. Olsen's office in West Chester

Stephen's primary office is at 17 East Gay Street, West Chester, Pennsylvania, 19381. In-person meetings are by appointment; a phone intake usually comes first.

Main office

Gawthrop Greenwood PC

17 East Gay Street

West Chester, Pennsylvania 19381

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Client feedback

Client reviews of Stephen J. Olsen

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Hiring guide

How to hire Stephen J. Olsen — what to expect in your first consultation

Working with a new tax attorney should feel structured. Here's how the first two conversations with Stephen usually go, from the moment you request a consult to the day representation begins.

Consultation formats and pricing

Stephen charges for the initial consult. That fee is credited toward representation if you retain Stephen's office.

What to bring to your first meeting

Bring any documents you already have — police reports, medical records, filed pleadings, correspondence from an insurer, a copy of the contract at issue. If you're not sure, err on the side of bringing everything; Stephen will tell you what matters and what doesn't.

Questions to ask a tax attorney in West Chester, Pennsylvania

A short list to run through before you commit: How many tax matters have you handled in the last year? What's your fee structure? Who else in the office will work on this? What's your realistic estimate of timeline and range of outcomes? How do I reach you between meetings?

Fees & payment

Fees, payment methods, and consultation options for Stephen

Stephen discusses fees during intake so the arrangement fits the matter. Contingency, hourly, and flat-fee options are all common in tax practice — ask which fits.

Hourly rates, contingency fees, and flat-fee options

Every tax matter is priced differently. Simple document review might be a flat fee. Injury litigation is often contingency. Complex commercial disputes usually run hourly with a retainer. Stephen confirms the model in the engagement letter before any work starts.

Payment methods and payment plans

Stephen's office accepts standard payment methods. Ask about payment plans if the retainer is a stretch — many tax practices work with clients on structured schedules.

Frequently asked

Frequently asked questions about Stephen J. Olsen

  • How much does it cost to hire Stephen for a tax case?

    Cost depends on the type of matter, the fee model (contingency, flat, hourly), and how contested the case becomes. Stephen walks through the likely range during the consult so there are no surprises.

  • Does Stephen offer a free consultation?

    Stephen charges for the initial consult; that fee is credited toward representation if you retain Stephen's office. Some tax attorneys offer free consults — check Stephen's current terms during booking.

  • How long do tax cases in Pennsylvania typically take?

    Simple tax matters can wrap in a few weeks; disputed cases can run 6–18 months from intake to resolution, longer if the matter goes to trial. Stephen gives a realistic estimate for your facts at the consult — vague answers here are a red flag.

  • Can Stephen take my case if I'm outside West Chester?

    Stephen is licensed in Pennsylvania. Matters governed by Pennsylvania law are the natural fit. Out-of-state matters are handled case-by-case, sometimes with local co-counsel. Ask during intake — Stephen will tell you if the case is a fit or refer you to someone closer to your court.

  • What should I bring to my first meeting with Stephen?

    Bring every document that touches the dispute: contracts, correspondence, police or medical reports, filed pleadings, invoices, photographs, insurance letters. Also bring a written timeline of what happened, in your own words. Stephen will filter what matters — over-preparing at intake is always cheaper than needing a second meeting.

  • Is Stephen accepting new tax clients right now?

    Stephen's intake status shifts week to week. Submit the form; the office will confirm availability or refer the matter out.

Areas served

Tax attorneys serving West Chester, Philadelphia and Pittsburgh in Pennsylvania

Stephen handles tax matters throughout Pennsylvania. Each city below is a direct link into the search page for verified tax attorneys in that community.

More counsel

If Stephen's intake is full or the fit isn't right, these tax attorneys in West Chester handle similar matters. Every profile below is verified and open to consultations.