Paul Donovan is a tax attorney and Certified Public Accountant whose tax-first practice, focused on real estate, serves clients nationwide. For thirty years he has advised real estate developers, investors, funds, and the high-net-worth families behind them on the federal income tax issues that drive the economics of their structures including passive activity rules under § 469, depreciation and cost segregation under § 168, partnership and tenancy-in-common structures under § 761, and the net investment income tax under § 1411. The practice covers tax planning, transactional structuring, and tax controversy representation.

Mr. Donovan began his career in the New York and Chicago offices of PwC, where he advised Wall Street venture capital firms and real estate investment funds on structured transactions, sponsor and limited-partner tax planning, and fund-level entity selection. While at the firm, he performed tax due diligence on three real estate investment trust initial public offerings, work that required detailed examination of activity-grouping, REIT income and asset testing, and operator-level passive activity considerations. He went on to practice law in Massachusetts, building a transactional real estate, tax, business, and litigation practice, before relocating to Delray Beach in 2019. His tax practice serves clients nationwide, with particular experience advising Northeast investors and families establishing Florida residency and Florida real estate holdings.

His real estate work spans the full life cycle of an investment including entity formation and capitalization, partnership and LLC structuring, acquisition and disposition planning, like-kind exchanges, debt and equity financings across the capital stack, FIRPTA and cross-border real estate matters, and exit planning. Representative engagements include the acquisition, financing, development, and sale of multifamily housing projects throughout the Southeastern United States; formation of domestic private equity real estate funds for the acquisition of residential properties; and partnership tax counsel during a hotel investment company’s IPO as a real estate investment trust.

Mr. Donovan’s practice extends to cross-border tax structuring in both directions, originating in his international tax work at PwC. On the inbound side, the firm advises foreign individuals, families, corporations, and funds on the acquisition, holding, and disposition of U.S. real estate and U.S. business interests, including FIRPTA, U.S. estate tax planning for non-resident aliens, treaty positions, and choice of entity for tax-efficient ownership. On the outbound side, the firm advises U.S. individuals, families, investors, funds, sponsors, and operating businesses on the acquisition and operation of foreign real estate and foreign business interests, including the application of the U.S. anti-deferral regimes (Subpart F, GILTI, PFIC), foreign tax credit planning, and the international information return reporting that follows. Geographic focus is primarily on European Union countries, with additional work in Latin America and the Caribbean.

Tax controversy is a substantial part of the practice. Mr. Donovan represents businesses and high-net-worth individuals in audits, examinations, appeals, and disputes involving the Internal Revenue Service and state taxing authorities. His controversy work has included multiple multi-million-dollar federal and state matters across the country, addressing income tax, partnership tax, and sales-and-use tax issues, with particular depth in partnership and real estate positions. The combination of CPA and JD credentials allows the firm to coordinate transactional planning, return preparation, and examination defense without the handoffs that introduce gaps between advisors. In December 2025, Mr. Donovan prevailed at the United States Court of Appeals for the First Circuit in Donovan v. Massachusetts Parole Board, No. 23-1810 (1st Cir. Dec. 23, 2025), reversing the District Court on a constitutional question of federal habeas procedure with implications for federal review of juvenile sentencing under Miller v. Alabama and its progeny.

Beyond his tax practice, Mr. Donovan brings perspective most tax counsel cannot offer. He has personally developed luxury townhouses in Boston and single-family homes on Martha’s Vineyard, holds a professional certificate in construction management, and is a licensed Massachusetts real estate broker. Cost segregation, building component and FF&E classification, and operational economics get a different read from a practitioner who has actually built and operated real estate than from one who has only advised on it from the outside. His non-tax real estate work including eminent domain, permitting and zoning, transaction structuring, and negotiation of acquisition, construction, and permanent financing informs how he reads deal structures and integrates tax planning with the upstream commercial terms.

Mr. Donovan practices on a focused, accountable basis. He reads the underlying documents himself, performs the analysis himself, signs the opinions and pleadings himself, and remains available to defend the work product if a position is later examined.

ADMITTED TO PRACTICE

• Florida
• Massachusetts
• United States Supreme Court
• United States Court of Appeals, First Circuit
• United States District Court, District of Massachusetts

PROFESSIONAL CREDENTIALS

• Certified Public Accountant – Massachusetts
• Licensed Real Estate Broker – Massachusetts
• Certified Construction Manager

EDUCATION

• Suffolk University Law School, J.D., cum laude – Boston
• Northeastern University, Certificate in Construction Management – Boston
• Northeastern University, B.S., cum laude – Boston

PROFESSIONAL AFFILIATIONS

• American Bar Association – Section of Taxation; Section of Real Property, Trust and Estate Law
• Florida Bar – Tax Section; Real Property, Probate and Trust Law Section
• Massachusetts Bar Association
• American Institute of Certified Public Accountants
• Massachusetts Society of Certified Public Accountants

PUBLICATIONS & PRESS

• Featured in Authority Magazine, “Top Lawyers: Paul Donovan On The 5 Things You Need To Become A Top Lawyer,” October 2021.
• Author of various tax articles addressing the formation and tax structuring of limited liability companies for small businesses.

LANGUAGES

• English
• Spanish (conversant)

OTHER

• Dual citizen, United States and Ireland

DIRECT CONTACT

• Email: paul@donovan.law
• Mobile: (781) 575-0055
• Office: (561) 666-6022
• Fax: (833) 829-9993
• Address: Donovan Legal PLLC, 301 W. Atlantic Avenue, Suite 5, Delray Beach, FL 33444