Harold Franklin Shepherd, a player in Hamptons real estate during the boom years of the 1980s and ’90s, died of heart failure on Sunday after a long illness. He was 81 years old.
Mr. Shepherd styled himself a self-made man. He was born on May 6, 1930, in Manhattan, the only child of Simon and Rose Shapiro. They raised him in Washington Heights and the Bronx, where Harold was a rebellious youth, getting kicked out of several high schools and briefly attending Bryant University in Rhode Island. He was exempt from service because his half brother, Jerome, died while serving in World War II.
After some tough years in the garment trade, Mr. Shepherd and his wife, Arlene Friedman, bought a house on Two Holes of Water Road in East Hampton, not long after which he began his real estate work. Mr. Shepherd loved East Hampton and its waters. He referred to the area as “paradise on earth.”
He earned a real estate license and worked for Barry Fleishman Realtors for three years. In 1984, Leonard Ackerman, a lawyer and developer, offered up co-op storefronts for sale on Main Street. Mr. Shepherd pounced on the opportunity, and the investment paid off until he sold it in 2006 to retire.
Described by his loved ones as possessing a glib repartee and a keen intellect, Mr. Shepherd was a regular sight at the Palm restaurant. He was an armchair political pundit and athlete and was certain to comment on the latest crisis or scandal in Washington or on the basketball court.
He is survived by his wife, Arlene Friedman of Manhattan and East Hampton, the former president and publisher of Doubleday Books.
Funeral services will be held on Sunday at 11:30 a.m. at the Frank E. Campbell funeral chapel, 1076 Madison Avenue in New York.