Cushing & Dolan, P.C.
Waltham, MA Courts in Massachusetts
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| Address | Automatically | Confirmed | 2026-07-28 |
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About Cushing & Dolan, P.C.
Cushing & Dolan, P.C. is a law firm established in 1984 in Boston by Leo J. Cushing. The firm concentrates on estate planning and tax matters, and it also handles elder law, real estate, and business law.
Its attorneys are licensed in Massachusetts, New Hampshire, Connecticut, Florida, North Carolina, and Pennsylvania, and the firm serves clients across New England and beyond. The main office is in Waltham, Massachusetts. The firm's estate planning work covers wills, trusts, durable powers of attorney, and advanced planning such as irrevocable trusts and gift and estate tax analysis.
Its elder law practice includes Medicaid planning, long-term care planning, guardianships, and conservatorships. The firm also manages probate and estate administration, trust administration, prenuptial agreements, residential and commercial real estate transactions, business formation and succession, and tax controversies that include IRS and state audits, appeals, and Tax Court representation. The firm reports more than 275 years of combined experience among its attorneys and meets clients at eight locations in the Greater Boston area.
Editor's Review
VerifiedLawFirms editorialOrigins and regional reach
Leo J. Cushing established Cushing & Dolan, P.C. in Boston in 1984. The firm now identifies Waltham as its main office. It also meets clients at eight locations in the Greater Boston area. The firm states that its attorneys assist clients across New England and beyond.
The attorneys hold licenses in Massachusetts, New Hampshire, Connecticut, Florida, North Carolina, and Pennsylvania. The website also reports more than 275 years of combined attorney experience. In my opinion, the 1984 founding date and stated experience provide useful context for a firm that handles tax, estate, property, and business matters.
Estate planning and tax work
The estate planning services cover wills, trusts, durable powers of attorney, and gift and estate tax analysis. The attorneys also work with irrevocable trusts and other advanced planning tools. This gives the firm a defined role in both basic planning documents and plans that address tax or asset concerns.
Catherine E. Aloisi focuses on estate tax planning and long-term care planning. She earned her law degree from Suffolk University Law School while working as a paralegal at the firm, then joined as an associate. Her listed work includes Intentionally Defective Grantor Trusts, Irrevocable Life Insurance Trusts, and generation-skipping transfer trusts.
Tax planning and disputes
The firm's tax work covers income, gift, and estate tax issues. Its controversy work includes IRS audits, state audits, administrative appeals, and representation in Tax Court. These services place planning and dispute work within the same stated practice area.
Leo J. Cushing brings several forms of tax experience to this work. His background includes work as a Big Eight tax attorney, a forensic accountant, and a criminal tax prosecutor with the Massachusetts Attorney General's office. He founded the firm with an initial concentration on income tax and estate tax matters.
Elder law, probate and court matters
Medicaid eligibility and long-term care planning are central parts of the elder law work described on the site. The attorneys also handle guardianships and conservatorships. These matters often involve legal authority, care planning, and the management of another person's financial affairs.
Probate work includes estate administration and trust administration. Caitlin E. Conry focuses on estate planning and probate, as does Daniel R. Foster. Thomas J. McKinnon works on elder law, estate planning, probate, and constitutional matters. He graduated from New England Law Boston in 2014.
Litigation responsibility
Ann M. Cushing is the firm's managing litigation attorney. She handles every phase of litigation, including intake and trial. Her listed areas include probate law, family law, guardianships, conservatorships, and marital agreements.
Ann M. Cushing earned a bachelor's degree from Framingham State College and a law degree from New England School of Law. Her stated role gives clients a named attorney responsible for the firm's contested matters. Guardianship and probate disputes also connect her litigation work with several of the firm's planning and administration services.
Real estate and business services
The firm handles residential and commercial real estate transactions. It also lists conveyancing and land use law among its services. The website reports that Leo J. Cushing and his associates have handled more than 80,000 residential closings.
Kevin N. Dolan focuses on real estate, conveyancing, and land use law. He earned a bachelor's degree in economics from Merrimack College in 1981 and a law degree from Suffolk University Law School in 1985. He was a firm partner between 1989 and January 2004, after which he became a consultant and marketing agent for the firm.
The business law work covers business formation and succession. Those services can connect with ownership transfers, estate plans, and tax analysis. The site's practice descriptions place these business matters beside the firm's planning and real estate work.
How the attorney team is presented
The website names 18 attorneys and supplies detailed background for several of them. The named roster includes Leo J. Cushing, Kevin N. Dolan, Catherine E. Aloisi, Caitlin E. Conry, Ann M. Cushing, Robert J. DuCharme, Daniel R. Foster, Teresa A. Hedley, Zachary William Lichter, Allison Luke, Todd E. Lutsky, and Thomas J. McKinnon. The site reports more names on its attorney profile page.
The available profiles show different concentrations within the firm. Some attorneys focus on estate planning and probate, while others handle litigation, elder law, tax, or real estate. Leo J. Cushing holds CPA and LLM credentials in addition to his law degree. Daniel R. Foster and Zachary William Lichter also carry LLM credentials in the listed names.
The team structure supports matters that touch several legal subjects. An estate plan may involve tax analysis, a trust, business succession, or property. Probate work may also lead to trust administration, guardianship proceedings, or litigation. The firm's stated practice areas account for each of those services.
Public legal education
Todd E. Lutsky has discussed estate and tax subjects through radio and podcast programs. He co-hosted the nationally syndicated call-in show "Money Matters." He answered questions about asset protection planning, Medicaid eligibility, probate avoidance, and income and gift tax issues.
Lutsky also hosted the weekend program "The Legal Exchange with Todd Lutsky." That program covered estate planning and asset protection planning. The firm also identifies him as a podcast host.
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Allison Luke, Esq.
Ann M. Cushing, Esq.
Ann M. Cushing is the managing litigation attorney at Cushing & Dolan, P.C. in Waltham, Massachusetts. She earned a B.S. from Framingham State College and a J.D. from New England School of Law. She is responsible for all phases of litigation at the firm, from intake through trial, handling matters involving probate law, family law, guardianships and conservatorships, prenuptial and postnuptial agreements, breach of contract, and personal injury. She also lectures on topics including family law, estate planning, and guardianship and conservatorship.
Caitlin E. Conry, Esq.
Caitlin E. Conry is an attorney at Cushing & Dolan, P.C. in Waltham, Massachusetts. Her practice focuses on estate planning and probate matters.
Catherine E. Aloisi, Esq.
Catherine E. Aloisi earned her J.D. from Suffolk University Law School while working as a paralegal at Cushing & Dolan, P.C., and joined the firm as an associate after law school. Her practice focuses on estate tax planning and long-term care planning, and she works with techniques such as Intentionally Defective Grantor Trusts, Irrevocable Life Insurance Trusts, GST Trusts, and Medicaid Irrevocable Trusts. She previously worked at Mendel & Associates, where she gained experience in estate and trust administration and the preparation of estate and gift tax returns, before returning to Cushing & Dolan.
Daniel R. Foster, Esq., LLM
Daniel Foster is an attorney at Cushing & Dolan, P.C. in Waltham, Massachusetts. His practice focuses on estate planning and probate.
Glen F. Sutherland, Esq.
Glen F. Sutherland is a business lawyer at Cushing & Dolan, P.C. in Waltham, Massachusetts. He earned a B.A. from Syracuse University in 1983 and a J.D. from Suffolk University Law School in 1991. His practice focuses on business, estate planning, and real estate matters.
Jenna R. Wolinetz, Esq.
Jenna R. Wolinetz is an attorney at Cushing & Dolan, P.C. in Waltham, Massachusetts. She studied at Suffolk University Law School and graduated in 2011. Her practice covers General Litigation, Estate and Trust Litigation, Business Litigation, Business and Corporate matters, and business Real Estate.
Kevin F. Osorio, Esq.
Kevin Osorio is an attorney at Cushing & Dolan, P.C. in Waltham, Massachusetts. He handles matters involving real estate, business and corporate law, and estate planning and probate. He studied at Suffolk University Law School and graduated in 2019. He speaks English and Spanish.
Kevin N. Dolan, Esq.
Kevin N. Dolan earned a B.A. in Economics from Merrimack College in 1981 and a J.D. from Suffolk University Law School in 1985. He practices at Cushing & Dolan, P.C. in Waltham, Massachusetts, where he was a partner from 1989 to January 2004 before becoming a consultant and marketing agent for the firm. His practice focuses on real estate, conveyancing, and land use law, and he represents clients before state and local boards and commissions in matters such as real estate subdivisions, special permits, and zoning variances. He also represents lenders as a conveyancing attorney and provides zoning opinions regarding proposed or existing uses of property.
Leo J. Cushing, Esq., CPA, LLM Founder
Leo J. Cushing established Cushing & Dolan, P.C. in 1984 in Boston, focusing on income tax and estate tax matters. His background includes work as a Big Eight tax attorney, a forensic accountant, and a criminal tax prosecutor with the Massachusetts Attorney General's office. He and his associates have handled more than 80,000 residential closings.
Pamela R. Tankle, Esq., LLM
Pamela R. Tankle is an Associate at Cushing & Dolan, P.C. in Waltham, Massachusetts, where her practice focuses on tax law, corporate law, and estate planning. She earned a Bachelor of Arts in Sociology and Psychology from Boston University, a J.D. from New England School of Law, and an LL.M. in Taxation from Boston University School of Law. During law school she interned with the Clerk's Office of the Supreme Judicial Court for Suffolk County, the City Solicitor's Office in Taunton, and the Plymouth County Probate and Family Court, handling appellate, land use, and family law matters.
Richard H. Woodwell, Esq., LLM
Robert J. DuCharme, Esq.
Ryan Platt, Esq.
Teresa A. Hedley, Esq.
Thomas J. McKinnon, Esq.
Thomas McKinnon is an attorney with Cushing & Dolan, P.C. in Waltham, Massachusetts. He helps clients with Elder Law, Estate Planning, and Probate matters, and also handles Constitutional matters. He received his legal training from New England Law | Boston and graduated from law school in 2014.
Todd E. Lutsky, Esq., LLM
Todd E. Lutsky co-hosted a nationally syndicated call-in radio show called Money Matters, answering questions on asset protection planning, Medicaid eligibility, avoiding probate, and income and gift tax issues. He also hosted his own weekend radio show, The Legal Exchange with Todd Lutsky, covering estate and asset protection planning. He has a podcast.
Zachary William Lichter, Esq., LLM
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Map of 400 Fifth Avenue, Waltham, MA (see the address above for a text alternative).