Sean B. Leonard is a transactional attorney in Holland & Knight's Boston office, and a member of the firm's Tax Credit Transactions Practice. Mr. Leonard focuses his practice on the representation of major institutional investors and various other participants in tax-advantaged investing, community development and affordable housing. He has extensive experience as lead transaction counsel on a wide range of New Markets Tax Credit (NMTC) and Low Income Housing Tax Credit (LIHTC) transactions.

New Markets Tax Credits: Mr. Leonard represents investors, community development entities, developers and lenders in connection with NMTC transactions. His experience includes assisting clients in the structuring, negotiation and closing of a variety of NMTC transaction structures, including transactions involving federal and state historic tax credit financing, investments involving multiple sources of equity and debt, and investments involving multiple investors and community development entities. He has represented clients in a wide array of NMTC projects, including the development and redevelopment of charter schools, various types of community facilities, transit systems, hotels, college and university facilities, telecommunication systems, solar facilities, supermarkets, and manufacturing and production facilities.

Low Income Housing Tax Credits: Investors, syndicators and developers call on Mr. Leonard for guidance in highly complex LIHTC transactions. He counsels clients in the structuring, negotiation and closing of direct and portfolio LIHTC investments (including proprietary and multi-investor funds) and secondary market transactions (on both the buy and sell sides).

Distressed Tax Credit Investments and Portfolio Asset Management: Mr. Leonard works with clients in all aspects of tax-advantaged investment portfolio management, with an emphasis on troubled assets, advising them on matters of dispute resolution, contract interpretation and pre-litigation enforcement, management company and general partner removals, negotiations with lenders and governmental agencies in connection with foreclosure actions, refinancings and loan workout agreements, and the sale or other disposition of aged assets.

Previously, Mr. Leonard served as an executive at a leading tax credit syndicator, where he focused on the preservation of the value of investor equity, including the oversight of a portfolio of underperforming assets, as well as the development and implementation of workout strategies for troubled properties. This practical, hands-on business experience provides him with an in-depth perspective when advising clients on all facets of tax-advantage investments.

In addition, Mr. Leonard has broad experience in a wide range of traditional corporate transactions, including mergers and acquisitions, venture capital transactions, public offerings of securities, commercial loan facilities and private placements of securities.

Mr. Leonard is also a frequent speaker at NMTC and LIHTC conferences and seminars, and has authored numerous articles on a variety of tax credits and other legal topics.


  • Suffolk University Law School, J.D., cum laude
  • Springfield College, B.S.
Bar Admissions/Licenses
  • Massachusetts
Court Admissions
  • All State Courts in Massachusetts
  • U.S. District Court for the District of Massachusetts
  • American Bar Association, Forum on Affordable Housing and Community Development
  • Massachusetts Bar Association
  • Boston Bar Association
  • Volunteer Lawyers for the Arts of Massachusetts
  • Zoning Board of Appeals, City of Newburyport, Massachusetts, former Member
  • Conservation Commission, Town of Wakefield, Massachusetts, former Member


Speaking Engagements