In 1974, with MurraySilverstein, he founded the JS partnership, an architectural firm providing comprehensive design and project management services.
Silverstein was a co-founder of the Center for Environmental Structure with Christopher Alexander and Sara Ishikawa, and between 1967-73, worked on numerous CES projects and buildings.
Silverstein's publications include Dorms at Berkeley: An Environmental Analysis, with Sim Van der Ryn, A Pattern Language and The Oregon Experiment, with his associates at the Center for Environmental Structure.
He has contributed to the legal community as St. Petersburg Bar president 1977-1978; Executive Committee, Board of Governors 1983-1985; convention chairman, The Florida Bar Annual Meeting 1984; candidate for president of The Florida Bar; chair of the Real Property, Probate and Trust Law Section, 1992-1993 and president of The Florida Bar Foundation 1990-1991.
Silverstein is currently president of the Community Law Program, Inc., an organization providing pro bono legal services, and is on the executive committee of the All Childrens Hospital Development Council.
Silverstein has served on the editorial board of the Florida Bar Journal, and is a member of several sections of The Florida Bar, including the Pro Bono Service Awards Committee, Board of Governors and Business Law Section.