Tax and IRS matters in Chesapeake — audits, back taxes, liens and levies, unfiled returns, offers in compromise, or a U.S. Tax Court dispute — move on the government’s timeline, not yours. A tax attorney brings attorney-client privilege and the standing to represent you before the IRS, the Virginia Department of Taxation, and the federal courts. The lawyer you choose can change both the outcome and the cost.
Updated June 14, 202613 min readEditorially independent
Chesapeake sits at the heart of Hampton Roads, and its residents share a regional market for specialized legal talent with Virginia Beach, Norfolk, Portsmouth, and Suffolk. The tax attorneys and firms below serve Chesapeake and the broader Hampton Roads metro. Each appears consistently across at least two independent professional directories — including Super Lawyers, Best Lawyers in America, Avvo, Justia, Martindale-Hubbell, FindLaw, and Virginia Lawyers Weekly — and each carries verifiable credentials in tax controversy or IRS representation. For a matter that starts as a letter and can end in Tax Court, credentials matter more than advertising.
How we picked these 8 firms: We reviewed peer rankings (Best Lawyers in America, Super Lawyers, Virginia Lawyers Weekly, Avvo, Martindale-Hubbell), bar records, verifiable credentials including LL.M. degrees, CPA licensure, and U.S. Tax Court admission, and cross-referenced each firm across two or more independent directories. Firms that appeared in only a single source or lacked verifiable tax-controversy focus did not make the list. We do not accept payment for placement and we do not publish sponsored reviews. More on our methodology →
1
McDowell Law Group — Gilbert L. Carey, Jr., JD, CPA
Virginia Beach (Hampton Roads)Boutique
Practice focus: IRS audits, tax controversy and resolution, offers in compromise, U.S. Tax Court representation, Virginia Department of Taxation disputes, estate planning
Gilbert L. Carey, Jr. holds a JD and is also a Certified Public Accountant, giving him the dual fluency to handle both the legal and financial dimensions of an IRS dispute. He has been recognized in the 2026 edition of Best Lawyers in America for tax law in Virginia, carries an Avvo rating of 10 (Superb), and has been repeatedly named one of the Top Lawyers of Coastal Virginia by Coastal Virginia Magazine. He is admitted to practice before the U.S. Tax Court and the U.S. District Courts for both the Eastern and Western Districts of Virginia. With 24 years of experience, he regularly represents individuals, business owners, and closely held companies in disputes with the IRS and state taxing authorities at every level.
Practice focus: IRS and Virginia state tax representation, audit defense, tax debt resolution, installment agreements, non-filer compliance, business tax disputes
Poole Brooke Plumlee PC opened its first office in Virginia Beach in 1987 and expanded to Chesapeake in 2009, making it one of the few firms in this area with a physical Chesapeake presence. Their tax team is led by attorney Todd D. Rothlisberger alongside IRS Enrolled Agent Amber Boyd, who together bring more than 20 years of combined experience navigating IRS and Virginia Department of Taxation procedures. The firm assists non-compliant taxpayers in returning to good standing, negotiates installment agreements and currently-not-collectible arrangements, and defends clients through audit and appeals. Its longevity and multi-office footprint in Hampton Roads make it a natural first call for Chesapeake residents who want local in-person service.
Virginia Beach (Hampton Roads)Boutique / Multi-disciplinary
Practice focus: IRS representation, offers in compromise, installment payment plans, tax appeals, tax audits, U.S. Tax Court, Virginia Department of Taxation representation
Harry W. Jernigan III has been representing taxpayers before the IRS and other tax authorities since 1964 — one of the longest track records in Hampton Roads. He holds both a JD and a CPA license, and the firm he founded in its current form in 1994 combines a law practice with an accounting practice under one roof. The team includes attorneys, certified public accountants, IRS enrolled agents, and paralegals, enabling the firm to handle matters ranging from a correspondence audit to a full U.S. Tax Court proceeding. The firm is listed on Justia, FindLaw, Martindale-Hubbell, and lawyers.com. Harry Jernigan CPA Attorney, PC is a genuinely dual-licensed practice in a market where that combination is uncommon.
Brent L. Rowlands earned his Juris Doctor from Regent University School of Law in 1990 and then completed an LL.M. in Taxation from William & Mary’s Marshall-Wythe School of Law in 1992 — one of the most respected tax law master’s programs in the region. He has been advising individuals and businesses on taxation matters for more than 25 years and has been an active member of the Virginia State Bar since 1990. He is listed on Justia and Avvo, where he carries a strong rating. His LL.M. credential and dedicated tax focus distinguish him from general-practice attorneys who take tax cases occasionally.
Virginia Beach (Hampton Roads)Full-service regional firm
Practice focus: Estate and gift taxation, tax planning, IRS notices and responses, Virginia Department of Taxation matters, trust and estate administration, fiduciary litigation
Founded in 1895, Wolcott Rivers Gates is one of the oldest and most established firms serving the Hampton Roads area and maintains offices in both Virginia Beach and Chesapeake. M. Powell Peters joined the firm in 1995 and has built a practice centered on estate and gift taxation, tax-advantaged wealth transfer, and complex trust administration. He brings a background as a former Senior Tax Consultant at Ernst & Young and holds both a JD and an MBA. He has been recognized as a Super Lawyer (2021–2024), a Best Lawyer (Best Lawyers Peer Review, 2024), and has appeared in Virginia Business Magazine’s “Legal Elite” multiple times. The firm as a whole is listed on Super Lawyers in both Virginia Beach and Chesapeake. For clients dealing with estate tax disputes, gift tax audits, or IRS notices tied to trust and estate matters, Wolcott Rivers Gates is a natural fit.
Fee structure
Flat fee / hourly
Consultation
Confidential consultation available
Credentials
JD, MBA; Super Lawyers 2021–2024; Best Lawyers 2024
Firm founded
1895
Office
200 Bendix Rd, Virginia Beach, VA 23452; Chesapeake office
Practice focus: Federal and Virginia tax controversy, IRS dispute resolution, tax planning, estate tax, corporate tax, tax-exempt organizations, real estate tax
Neil L. Rose is a former IRS and U.S. Treasury Special Honors Attorney who joined Willcox & Savage after government service and has spent more than 25 years in private tax practice. In 2025, he was named one of Virginia Lawyers Weekly’s “Go To Lawyers” for Tax Law — a peer-evaluated honor. His lecturing credits include the Tax Section of the American Bar Association, the Virginia State Bar, the ODU Tax Conference, the Virginia Society of CPAs, and Virginia CLE. He practices within Willcox & Savage, a Norfolk firm with approximately 65 attorneys that has been serving Hampton Roads clients for over a century. For complex IRS controversies, corporate tax disputes, or matters requiring both federal and Virginia expertise, Rose’s government background gives him insight into how tax authorities think and negotiate.
Fee structure
Flat fee / hourly
Consultation
Available
Credentials
Former IRS/Treasury Special Honors Attorney; VLW Go To Lawyer 2025
Practice focus: Tax debt resolution, IRS and Virginia Department of Revenue disputes, business tax, U.S. Tax Court representation, business law, business litigation
James S. McNider III has been admitted to the U.S. Tax Court since 1981 and has been selected to Super Lawyers every year from 2006 through 2025 — a remarkable streak that reflects sustained peer recognition. He holds a B.S. in Accounting from Washington and Lee University and a JD from Washington and Lee University School of Law. His accounting foundation and nearly four decades of tax and business practice give him the ability to analyze both the financial and legal dimensions of a tax problem. His firm serves clients throughout Hampton Roads from its Hampton office. He is listed on Super Lawyers, Justia, and FindLaw, and is admitted to the U.S. District Court for the Eastern District of Virginia, the U.S. Supreme Court, and the U.S. Tax Court.
Practice focus: Tax matters, estate planning, trusts, business and corporate law, civil and commercial litigation, family law
Ralph E. Nichols, Jr. has practiced in Chesapeake for more than 36 years, operating from an office at 1117 Eden Way North in the heart of the city. He is listed on Martindale-Hubbell, FindLaw, and Avvo, and his long-standing Chesapeake presence means genuine local familiarity with the community and the courts. His practice spans tax matters alongside estate planning, trusts, and business law, making him a practical option for Chesapeake residents who need tax guidance woven together with estate or business considerations. For clients who prefer to work with an attorney who has deep roots in Chesapeake itself, rather than traveling to Virginia Beach or Norfolk, Nichols provides accessible local counsel.
Match the lawyer to the problem. A first-time correspondence audit, an installment agreement, or an unfiled-return situation is different work from a trust-fund recovery penalty, a criminal tax investigation, or a contested U.S. Tax Court case. Ask directly how many matters like yours the attorney has handled in the last two to three years, and whether they appear before the IRS and the Tax Court regularly — not just occasionally.
Beware national “tax relief” mills that advertise heavily and outsource the actual work. A licensed Virginia tax attorney gives you attorney-client privilege, personal accountability, and someone who will stand between you and the IRS. Confirm you are hiring a licensed attorney, not a “tax resolution specialist” who is neither a lawyer nor an enrolled agent.
The Hampton Roads market has a relatively small number of attorneys with genuine tax-controversy credentials. That makes the eight firms on this list a meaningful shortlist. Meeting two or three before signing is well worth the time when the stakes are back taxes, a lien on your home, or a potential levy on your paycheck.
For a deeper look at what drives attorney selection in tax matters, see our guide at Tax & IRS — full guide.
What to look for in a tax & IRS lawyer
The firms above are a starting point, not a verdict. The right lawyer for you depends on your facts, your budget, and how you communicate. Use these five signals to compare any tax attorney you speak with in Chesapeake or the broader Hampton Roads area.
Genuine tax focus. Tax is a specialty, not a side practice. You want a lawyer who concentrates on tax controversy and IRS resolution — ideally with an LL.M. in taxation, a CPA background, or verifiable IRS-facing experience — not a generalist who takes tax cases because a client asked. Check credentials, not just the firm website.
Straight talk about your exposure. A good tax lawyer tells you at the first meeting what is realistic: whether an offer in compromise is plausible, what penalties may be abated, and where the real risk lies. If everything sounds easy and the debt sounds erasable in the first five minutes, be skeptical.
Attorney-client privilege. Only an attorney gives you this protection, which matters if your case has any criminal dimension or if you want to speak freely about what happened. Enrolled agents and CPAs cannot provide it. Ask how the firm protects sensitive information and whether the matter could escalate.
Fees in writing, in plain English. Tax representation can be flat-fee for defined work such as an installment agreement or offer in compromise, or hourly for litigation. You should leave the initial meeting knowing exactly what you will pay, what it covers, and what could trigger additional charges. Vague pricing is a warning sign, not a courtesy.
Credentials you can verify. Look for U.S. Tax Court admission, an LL.M. in taxation, a CPA license, and peer recognition such as Best Lawyers or Super Lawyers. These are concrete and easily verified. Cross-check what the attorney says against the relevant directory listings.
What a tax & IRS case looks like in Chesapeake
Most Chesapeake tax matters begin with a notice — an audit letter, a balance due, a CP2000 underreporter notice, a lien filing recorded with the Chesapeake Circuit Court, or a levy warning threatening your wages or bank account. The first job of a tax attorney is to stop the clock where possible, communicate with the IRS on your behalf, and establish what the real numbers behind the notice are.
IRS audits. Correspondence audits are handled by mail and are usually narrow. Office and field audits are broader, and a Chesapeake tax attorney controls what information flows to the examiner, keeps the audit within its proper scope, and negotiates any proposed deficiency. If the audit result is disputed, IRS Appeals is the next step before Tax Court.
IRS appeals. The IRS Independent Office of Appeals handles most pre-litigation disputes. Many cases settle here. An attorney who has appeared before Appeals repeatedly knows what arguments move the needle and what documentation the Appeals Officer will require. This stage is where preparation from the audit pays off.
Liens and levies. A federal tax lien attaches to all of your property once it is filed and is public record in Chesapeake. A levy is the actual seizure — of wages, bank accounts, or other assets. Both can be challenged or resolved through a Collection Due Process hearing or by arranging a payment resolution. A tax attorney can often stop a levy that is in process.
Offers in compromise. An offer in compromise lets a qualifying taxpayer settle a tax debt for less than the full balance. Acceptance requires documenting income, expenses, and asset equity to the IRS’s satisfaction. Not every taxpayer qualifies, and the paperwork is exacting. An attorney advises you candidly on whether an OIC is realistic in your situation before you invest the time and fee.
Installment agreements. For taxpayers who owe more than they can pay in full but do not qualify for an OIC, an installment agreement structures monthly payments that stop enforced collection. A tax attorney negotiates the terms and ensures the agreement keeps you in compliance going forward.
Virginia Department of Taxation. Virginia Tax runs on a separate track from the IRS. It has its own audit procedures, appeals process, and collection mechanisms. A Chesapeake tax attorney handles both federal and Virginia matters simultaneously, which matters when the same income discrepancy triggers notices from both agencies. Virginia also has its own offer-in-compromise program, and local experience with Virginia Tax procedures is valuable.
What does a tax & IRS lawyer in Chesapeake cost?
In the Hampton Roads market, straightforward tax work is often flat-fee. An installment agreement with the IRS may cost a few hundred to a couple of thousand dollars in attorney fees. An offer in compromise or audit defense commonly runs approximately $2,500 to $7,500, depending on the complexity of the return, the number of years involved, and how far the matter has progressed. More complex audits or multi-year OIC packages can run higher.
Hourly rates for tax litigation and criminal tax defense in the Hampton Roads area generally run approximately $250 to $450 per hour, with retainers required up front for contested matters. Firms with former IRS or Treasury attorneys, LL.M. credentials, or extensive Tax Court experience tend toward the higher end of that range.
The arithmetic usually favors acting early. IRS penalties and interest compound: a failure-to-pay penalty runs 0.5 percent per month and caps at 25 percent of the unpaid tax, and interest compounds daily at the federal short-term rate plus three percentage points. A levy on wages or a bank account disrupts your life and credit far more than a timely resolution. A good Chesapeake tax attorney tells you at the first meeting whether the fee is proportionate to what is at stake.
Guaranteed outcomes. No ethical attorney can promise a specific result before reviewing your file. If a firm guarantees it can settle your debt for “pennies on the dollar” or promises to make the IRS “go away” in the first phone call, that is a sales pitch, not legal advice.
The disappearing senior lawyer. You meet a named partner at intake and then never speak with that person again while a junior associate or a non-attorney runs your file. Ask in writing who your day-to-day representative will be and what their credentials are.
No verifiable track record. “We have helped thousands of clients” is marketing. Real evidence is verifiable peer recognition such as Super Lawyers or Best Lawyers, named credentials such as an LL.M. or U.S. Tax Court admission, and a clean bar record. All of that is publicly searchable.
Pressure to sign immediately. A reputable firm gives you the engagement letter in writing and time to read it. High-pressure intake — “this offer expires today” — is a sign of a volume operation, not a careful practice.
Vague fee terms. “Don’t worry about the cost right now” is a red flag. Every legitimate firm puts the fee, what it covers, and what could trigger additional charges in writing before any money changes hands.
10 questions to ask in your free consultation
Most firms on this list offer a free or low-cost initial consultation. Use it well: take notes, ask the same questions at each firm, and compare the answers before you sign anything.
Who, specifically, will handle my matter day to day? Get a name and an email address, not just a firm brand.
How many matters like mine have you personally handled in the last three years? You want a number and a description, not a brochure.
Are you admitted to the U.S. Tax Court? If there is any chance this escalates, you want someone who can take it all the way.
What is your fee, and exactly what does it cover? Get the answer in writing before signing anything.
What costs am I responsible for beyond the attorney fee, and when are they due? Out-of-pocket expenses — filing fees, transcripts, expert witnesses — surprise people. Ask up front.
What is the realistic range of outcomes here? A good lawyer gives you a range with assumptions. A weak one promises the best-case result.
Am I a realistic candidate for an offer in compromise? If the answer is yes, ask why. If no, ask what the alternative looks like.
How long will this take, and what are the assumptions behind that estimate? IRS timelines can be long; you should understand why.
What is the worst-case outcome if we do nothing? A lawyer who will not discuss the downside is selling you something.
What happens to my file and my retainer if I want to change lawyers mid-case? Understand your exit rights before you commit.
Talk to a Chesapeake tax attorney — free, no obligation
Tell us what is going on. We’ll match you with vetted Chesapeake-area firms from the list above. Most respond within one business day.
Frequently asked questions
Do I need a tax attorney or will a CPA do?
A CPA is excellent for preparing returns and bookkeeping, but only a tax attorney gives you attorney-client privilege, which matters when a matter becomes contentious or has any criminal dimension. A tax attorney can also represent you before the IRS, file appeals, and take your case to the U.S. Tax Court. Some Chesapeake-area practitioners hold both a JD and a CPA, giving you both skill sets.
Can a lawyer really settle my IRS debt for less than I owe?
Sometimes. The IRS Offer in Compromise program allows qualifying taxpayers to settle for less than the full balance owed, but acceptance depends on documented income, assets, and ability to pay. A reputable Chesapeake tax attorney evaluates your eligibility honestly rather than promising a result before reviewing your file.
What does a tax attorney in Chesapeake cost?
Defined work is often flat-fee: an installment agreement may cost a few hundred to a couple of thousand dollars, while audit defense or an offer in compromise typically runs $2,500 to $7,500 depending on complexity. Litigation and criminal tax defense are billed hourly, generally around $250 to $450 per hour in the Hampton Roads market, with retainers to match. Ask for the fee structure in writing before you sign.
What should I do if I have not filed Virginia or federal returns in several years?
File before the IRS or Virginia Department of Taxation files for you. A tax attorney can help you get current with both agencies, limit penalties through first-time abatement or reasonable-cause arguments, and negotiate a payment arrangement for any balance. Coming forward voluntarily almost always produces a better outcome than waiting for enforcement.
Can the IRS take my wages or bank account?
Yes, through a levy, but only after specific notices and deadlines have passed. A tax attorney can often stop or release a levy by arranging a resolution such as an installment agreement, currently-not-collectible status, or an offer in compromise. Responding promptly to IRS notices is the most effective way to avoid enforced collection.
What is the difference between a civil audit and a criminal tax investigation?
A civil audit examines whether your return is accurate and results in a tax adjustment at most. A criminal investigation involves potential tax fraud or evasion and can lead to prosecution. If you receive any indication that your matter has crossed from civil to criminal, retain an attorney immediately so that attorney-client privilege protects your communications.
How long does the IRS have to collect a tax debt?
Generally ten years from the date of assessment, though certain events such as filing for bankruptcy, signing a collection agreement, or requesting an appeal can pause that clock. The rules are technical and fact-specific. A tax attorney can tell you exactly where your debt stands and whether the collection statute period affects your options.
What is the Virginia Department of Taxation, and does it work like the IRS?
The Virginia Department of Taxation (Virginia Tax) administers state income, sales, and other taxes on a separate track from the IRS. It has its own audit, appeals, and collection procedures, including state tax liens, levies, and a state offer-in-compromise program. A local Chesapeake tax attorney familiar with both agencies handles federal and Virginia matters simultaneously.
Can I handle an IRS audit myself?
You can, but for anything beyond a simple correspondence audit it carries real risk. An attorney controls what information the IRS receives, keeps the exam within its proper scope, and protects you from inadvertently expanding your exposure to additional years or issues. For field audits, trust fund recovery penalties, or any matter with criminal overtones, having representation is essential.
How do I choose between two Chesapeake-area tax firms?
Compare genuine tax-controversy focus, relevant credentials such as an LL.M. in taxation, a CPA license, or U.S. Tax Court admission, candor about your realistic outcome, and written fee terms. Meet with at least two firms before signing an engagement letter, and choose the attorney who is specific about your situation rather than one who promises a guaranteed result.
One last thing. Choosing a tax attorney is personal. Read the listings, verify the credentials on public directories, check the state bar record, and speak with at least two firms before you sign. Ask each attorney how many matters exactly like yours they have handled in the Hampton Roads area in the last three years, and ask for the fee in writing. Those two questions tell you most of what you need to know. — The LawFirmSquare team
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