Amanda B. Chesterfield

Amanda B. Chesterfield, Esq. joined Gleason, Dunn, Walsh & O’Shea in January 2026, bringing with her more than a decade of experience in estate planning, elder law, trusts and estates, and guardianships.

Amanda is admitted to practice law in New York State. She earned her Juris Doctor from Albany Law School of Union University in 2016 and holds a Bachelor of Science degree in accounting from The College at Brockport (SUNY). Her academic background in accounting, combined with her legal training, allows her to provide clients with thoughtful, comprehensive guidance in both planning and administration matters.

Prior to joining the firm, Amanda practiced at an elder law firm serving clients throughout New York City and Long Island, and most recently, at a prominent trusts & estates and elder law firm here in the Capital Region. By working while attending law school, she developed strong practical skills early in her career, and she continues to draw upon that experience in her practice today.

Amanda is known for her compassionate, client-centered approach and her ability to guide individuals and families through complex and often sensitive legal issues. She assists clients with the administration of trusts and estates following the loss of a loved one, helps families evaluate long-term care options, and develops customized estate plans designed to meet each client’s personal objectives during life and upon death.

Amanda has been named a Super Lawyers Rising Star from 2022 through 2025. She is a member of the New York State Bar Association’s Elder Law and Special Needs Law Section, Trusts and Estates Law Section, and Young Lawyers Section, as well as the Albany County Bar Association, and Estate Planning Council of Eastern New York.