Charles D. “Chip” MacLeod, Business Attorney in Chestertown, Maryland
Over 28 years of legal practice · focused on Business, Contracts, and Government
MemberatMacLeod Law Group LLC
Chestertown, MD
Practicing business in Chestertown since 1998.
- 28+
- Years practicing
- 1
- Bar admission
Practices in
Are you Charles D. “Chip” MacLeod?
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Quick answer
Charles D. “Chip” MacLeod is a member based in Chestertown, MD. The practice focuses on Business, Contracts, and Government. Charles has over 28 years of legal experience. Currently practicing at MacLeod Law Group LLC.
- Based in
- Chestertown, MD
- Experience
- over 28 years
- Known for
- Business · Contracts · Government
- Handles Business, Contracts, and Government matters from Chestertown, MD.
- Over 28 years of practice as a licensed attorney.
About Charles D. “Chip” MacLeod: Charles D. “Chip” MacLeod is a member based in Chestertown, MD. The practice focuses on Business, Contracts, and Government. Charles has over 28 years of legal experience. Currently practicing at MacLeod Law Group LLC.
Areas of practice
Practice areas handled by Charles D. “Chip” MacLeod
Charles concentrates on business, contracts, government, and real estate. Each area below outlines the kind of case Charles handles, typical outcomes to expect, and how the intake process starts.
Business
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Contracts
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Government
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Real Estate
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Business cases in Chestertown, Maryland
Charles takes business matters in Chestertown, Maryland. Typical engagements include intake calls to scope the issue, review of any records or filings you already have, and a written strategy memo before Charles agrees to represent you.
Contracts cases in Chestertown, Maryland
Charles takes contracts matters in Chestertown, Maryland. Typical engagements include intake calls to scope the issue, review of any records or filings you already have, and a written strategy memo before Charles agrees to represent you.
Government cases in Chestertown, Maryland
Charles takes government matters in Chestertown, Maryland. Typical engagements include intake calls to scope the issue, review of any records or filings you already have, and a written strategy memo before Charles agrees to represent you.
Real Estate cases in Chestertown, Maryland
Charles takes real estate matters in Chestertown, Maryland. Typical engagements include intake calls to scope the issue, review of any records or filings you already have, and a written strategy memo before Charles agrees to represent you.
Biography
About Charles D. “Chip” MacLeod — Over 28 years of Maryland business experience
Charles D. “Chip” MacLeod is a member based in Chestertown, MD. The practice focuses on Business, Contracts, and Government. Charles has over 28 years of legal experience. Currently practicing at MacLeod Law Group LLC.
Mr. MacLeod founded MacLeod Law Group, LLC in 2017 and is head of the firm's Local Government Practice Group. Mr. MacLeod also concentrates in real estate, business and contract law and serves as general counsel to various non-profit organizations and trade associations. As a registered lobbyist, Mr. MacLeod advocates for clients before the Maryland General Assembly and Executive branch agencies.
Prior to founding MacLeod Law Group, LLC, Mr. MacLeod was a member of Funk & Bolton, P.A. in the firm's Chestertown, Maryland office from 1998 to January of 2017. Mr. MacLeod was the head of the firm's Local Government and Real Estate Practice Groups, while serving as special counsel to various non-profit organizations and public entities on a broad spectrum of legal matters.
From 1991 through 1998, Mr. MacLeod served as the County Administrator of Kent County, Maryland. While serving as Kent County Administrator, Mr. MacLeod was elected to the Board of Trustees of the Local Government Insurance Trust (LGIT) and chaired LGIT's Health Benefits Committee.
From 1988 to 1991, Mr. MacLeod served as the Associate Director of the Maryland Association of Counties.
Mr. MacLeod is a 1986 cum laude graduate of Washington College (B.A.,Philosophy and Political Science) and a 1997 graduate of the University of Maryland School of Law (J.D.).
Associations and Memberships:
• Member and Past President, Kent County Bar Association
• Member, Maryland State Bar Association, State & Local Government Section Council
• Member and Past President, Maryland Municipal Attorneys Association
• Member, International Municipal Lawyers Association; Maryland Chair
• Former Member and Chair, Chester River Health System, Inc. Board of Trustees
• Past Member, Local Government Insurance Trust, Board of Trustees
• Member and Past President, Maryland Association of County Administrative Officers
• Shore Leadership - 1998 Class
• Past Chair, Kent County Community Center Authority
Charles's approach to business cases
Mr. MacLeod founded MacLeod Law Group, LLC in 2017 and is head of the firm's Local Government Practice Group. Mr. MacLeod also concentrates in real estate, business and contract law and serves as general counsel to various non-profit organizations and trade associations. As a registered lobbyist, Mr. MacLeod advocates for clients before the Maryland General Assembly and Executive branch agencies.…
Clients Charles works with
Charles reviews new inquiries case-by-case for business, contracts, and government matters in Chestertown and the surrounding Maryland area.
Credentials
Charles D. “Chip” MacLeod's legal education and bar admissions
University of Maryland School of Law
J.D. · 1997
Washington College
B.A. Philosophy · 1986
Jurisdictions
Charles's state bar admissions
Maryland
1998 · ACTIVE
Charles studied at J.D. in University of Maryland School of Law and B.A. Philosophy in Washington College.
Law school and academic background
Charles completed J.D. in University of Maryland School of Law and B.A. Philosophy in Washington College. Formal legal training is one signal of substantive knowledge — the day-to-day practice Charles runs in Maryland is where that training gets applied to real client questions.
Affiliations
Charles's professional memberships and bar associations
Kent County Bar Association Maryland State Bar Association Maryland Municipal Attorneys Association International Municipal Lawyers Association
membership
Locations
Charles D. “Chip” MacLeod's office in Chestertown
Charles's primary office is at 110 North Cross Street, Chestertown, MD, 21620. In-person meetings are by appointment; a phone intake usually comes first.
Client feedback
Client reviews of Charles D. “Chip” MacLeod
Charles has not yet collected verified client reviews on LawyersListed. Reviews here are all from confirmed clients; anonymous ratings are moderated out.
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Schedule your consultationHiring guide
How to hire Charles D. “Chip” MacLeod — what to expect in your first consultation
Working with a new business attorney should feel structured. Here's how the first two conversations with Charles usually go, from the moment you request a consult to the day representation begins.
Consultation formats and pricing
Charles charges for the initial consult. That fee is credited toward representation if you retain Charles'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; Charles will tell you what matters and what doesn't.
Questions to ask a business attorney in Chestertown, Maryland
A short list to run through before you commit: How many business 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 Charles
Charles discusses fees during intake so the arrangement fits the matter. Contingency, hourly, and flat-fee options are all common in business practice — ask which fits.
Hourly rates, contingency fees, and flat-fee options
Every business 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. Charles confirms the model in the engagement letter before any work starts.
Payment methods and payment plans
Charles's office accepts standard payment methods. Ask about payment plans if the retainer is a stretch — many business practices work with clients on structured schedules.
Frequently asked
Frequently asked questions about Charles D. “Chip” MacLeod
How much does it cost to hire Charles for a business case?
Cost depends on the type of matter, the fee model (contingency, flat, hourly), and how contested the case becomes. Charles walks through the likely range during the consult so there are no surprises.
Does Charles offer a free consultation?
Charles charges for the initial consult; that fee is credited toward representation if you retain Charles's office. Some business attorneys offer free consults — check Charles's current terms during booking.
How long do business cases in Maryland typically take?
Simple business 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. Charles gives a realistic estimate for your facts at the consult — vague answers here are a red flag.
Can Charles take my case if I'm outside Chestertown?
Charles is licensed in Maryland. Matters governed by Maryland law are the natural fit. Out-of-state matters are handled case-by-case, sometimes with local co-counsel. Ask during intake — Charles 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 Charles?
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. Charles will filter what matters — over-preparing at intake is always cheaper than needing a second meeting.
Is Charles accepting new business clients right now?
Charles's intake status shifts week to week. Submit the form; the office will confirm availability or refer the matter out.
Areas served
Business attorneys serving Chestertown, Baltimore and Annapolis in Maryland
Charles handles business matters throughout Maryland. Each city below is a direct link into the search page for verified business attorneys in that community.
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