Barry grew up near Philadelphia, graduating from Springfield High School in Montgomery County. At Princeton, he majored in economics. He served as treasurer of Cannon Club and roomed at the club senior year with Des Barry, Dan Webb, and Bob Casey. He played freshman and JV baseball and was a member of Orange Key, Pre-Law Society, Whig-Clio, the Grinder Agency, and ROTC.
Following graduation Barry went to business school at Wharton, where he met and married Gail Agerton. They had two daughters: Gretchen, born in 1972 and Stefanie, born in 1974. After his MBA in 1969 he began a career in the Philadelphia area in finance and real estate, first as president of Ebert Associates and then as executive vice president of Dominion Holdings, a real-estate development corporation. He also served six years in the Army Reserve near Philadelphia.
In 1992, Barry moved to Melbourne. Working through his company Optima Realty, he specialized in business brokerage, commercial properties, and small-business consulting and became a respected business broker in Melbourne before retiring in 2018.
After moving to Florida, Barry married Susan Boulware Ebert, gaining three stepsons, Drew Smith, Schuyler Boulware, and Jonathan Boulware — in addition to the daughters from his first marriage. All survived him, along with four grandchildren.