Reynolds, Rappaport, Kaplan & Hackney specializes in Real Estate law, Corporate and Business law, Trust and Estate law, Municipal law, and Civil Litigation.

Real Estate Law

Reynolds, Rappaport, Kaplan & Hackney serves clients engaged in a variety of real estate projects with a particular emphasis on the purchase, sale, and financing of both residential and commercial real estate. Our real estate attorneys represent buyers, sellers, and lenders in a wide array of acquisition and loan transactions.

The firm is also more generally involved in the negotiation and drafting of leases, various forms of easement agreements, and protective covenant schemes. Over the years, we have become known for our careful and thorough review of titles to property on the Island and the negotiation of title insurance coverage tailored to our clients’ specific needs.

We have formed and represent a number of homeowner’s associations.

The firm is actively engaged in representing the Martha’s Vineyard Land Bank Commission and other local and national private conservation organizations in the acquisition of open-space properties, as well as various public and private community housing groups committed to establishing affordable housing opportunities for year-round residents of Martha’s Vineyard.

We have expertise in working in close cooperation with purchasers and their estate planners, accountants and other professional advisors to ensure that clients’ purchases of IsIand property are consistent with their financial and planning objectives.

EsTate and trust Law

Estate planning and trust and estate administration are perhaps the most personal areas of the law, and the firm provides full-service legal assistance to Massachusetts residents and those out-of-state clients owning real estate on Martha’s Vineyard. We have the skill and sensitivity required in helping people plan for their loved ones and their assets.

With the Massachusetts estate tax applying to more and more estates, proper planning is crucial in order to avoid or reduce, insofar as possible, estate taxes owed at one’s death. Additionally, clients want to make sure their dispositive provisions (who gets what and when) are achievable and enforceable.

Owning highly appreciated real estate can present complex planning opportunities. While nobody should be without a will, more sophisticated instruments and lifetime gift planning tools have become more commonplace for Island property owners.

When the time comes to settle an estate or administer a trust, our estate planning and trust attorneys provide local, efficient, and knowledgeable service on matters within and outside of the probate court.

Corporate & Business Law

The firm provides a broad range of advice in areas such as business acquisitions and sales; business formation, planning, and organization; ongoing corporate maintenance and filing obligations; agreements among business partners; and succession planning.

The firm also negotiates and drafts a variety of business agreements for our clients, including limited liability company operating agreements, shareholder agreements, commercial leases, construction contracts and commercial finance documents.

Our business lawyers work as part of a team, with our real estate and litigation counsel as necessary, as well as with our clients’ accountants and other professionals, to ensure that our clients’ business needs, including proper consideration of tax planning and liability issues, are met.

Municipal Law

Reynolds, Rappaport, Kaplan & Hackney municipal law attorneys have more than 60 years of combined experience representing Martha’s Vineyard towns in all aspects of the law. On a daily basis, the firm advises its municipal clients on a wide range of substantive areas, including zoning, land use, ethics, governance, finance and real estate. This requires extensive legal and regulatory knowledge, as well as political acumen.

Ron Rappaport serves as Town Counsel to the towns of Aquinnah, Chilmark, Edgartown, Oak Bluffs and West Tisbury and as counsel to the Martha’s Vineyard Land Bank Commission. He has argued numerous landmark cases before all levels of Massachusetts courts in the areas of land use and zoning, including several cases before the Supreme Judicial Court and the Appeals Court (see Notable Cases). Ron has been named as a Super Lawyer in the practice area of State, Local and Municipal Law in the years 2055-2006, and in 2010-2023. Firm Director Michael Goldsmith has been names as a Super Lawyer in the practice area of State, Local and Municipal Law in the years 2013-2023.

The firm provides superior and vigorous advocacy from trial through appeal. We take pride in searching out cost-effective solutions to our towns’ legal problems and assisting them with avoiding expensive legal entanglements.

Civil Litigation

The Civil Litigation attorneys at RRKH draw on over 75 years of combined experience in trial and appellate work to achieve consistently successful results not only in zoning and land use cases on behalf of our municipal clients, but also in a variety of other areas, including private property rights, contracts, construction law, business disputes and probate matters. Our firm handles cases at all stages, and in all Massachusetts and Federal courts, from initial investigation through trial and appeal. Our highly experienced title examiners provide us with outstanding support in analyzing property and zoning issues

Our attorneys have successfully litigated cases in which the opposing side was represented by the largest law firms in Boston and elsewhere. Ron Rappaport, a founding partner, has argued numerous cases before the Supreme Judicial Court, and tried cases in the various Massachusetts courts. Michael Goldsmith has tried numerous cases to verdict in the Massachusetts Appeals Court and in the United States First Circuit Court of Appeals. The firm is comfortable with sophisticated litigation and will provide aggressive representation when necessary, but we always endeavor to maintain a focus on the end goals of our clients.