Burlington 802.864.0217       Middlebury 802.388.6356 Payments

Andrew J. Kestner


Andy advises both individuals and businesses, in a variety of transactions and planning matters, and on tax and financial issues. His practice includes traditional estate and business planning, as well as advising business owners on succession planning, and complex matrimonial issues relative to the preservation and protection of family wealth.

Andy has an up-to-date and in-depth knowledge of the provisions of the Tax Act of 2017, including the Act’s impact on the most tax-efficient form of business entity, the newly introduced qualified business income deduction available to pass-through entities, and the revised gift and estate tax exclusion amounts.

Andy’s estate planning practice involves working closely with clients of all levels of wealth to prepare tailored, yet comprehensive, estate plans including revocable and irrevocable trusts, wills, durable powers of attorney, and advanced health care directives. He assists clients in meeting their objectives for the transfer of personal and financial legacies, and also offers strategic planning to mitigate gift and estate tax when appropriate.

Andy has particular expertise in negotiating and preparing prenuptial and postnuptial agreements. His experience and breadth of knowledge in estate planning and complex matrimonial issues make him uniquely able to counsel clients in these sensitive negotiations. Andy’s experience in this regard is invaluable to individuals planning for second marriages or endeavoring to protect family wealth, including business interests and generational wealth.

Andy joined Langrock Sperry & Wool in August 2015. Previously, he was a senior associate at a boutique practice in downtown Boston focused primarily on complex, high-net worth matrimonial and estate matters. Following law school, he served as law clerk to the Chief Justice of the Massachusetts Probate Court. Andy has twice been named a Rising Star by Boston Magazine’s Super Lawyers edition and New England Super Lawyers. Andy has also authored materials published by Massachusetts Continuing Legal Education, relating to tax and asset division matters.

Andy is originally from upstate New York and resides in South Burlington with his wife and son. When he’s not practicing law, you will find him enjoying the mountains on his bike or his skis.


Boston University School of Law, Graduate Tax Program (LL.M. in Taxation); Villanova University School of Law (J.D. 2005) (Moot Court Board); Union College (B.A., with honors, 2002)

Bar Admissions

Admitted to state courts in Vermont and Massachusetts


Vermont Bar Association; Chittenden County Bar Association