After his playing career ended in 1978, he worked on radio broadcasts for the Yankees until 1981. In 1979, he added the Yankees' cable television broadcasts on SportsChannel (which became Fox Sports Net New York) to the resume, staying with the cable crew until the end of the 1983 season. Healy worked on Mets telecasts from 1984 to 2005, also working as the host of Mets Inside Pitch and Halls of Fame, a series that profiled careers of famous athletes (and originally taking its name from the cough drop company that shared the name). He is one of three sportscasters who was a regular announcer for both the Yankees and the Mets; the others are Tom Seaver and Tim McCarver.
When Keith Hernandez was added to Mets telecasts, Healy and Hernandez's game-calling often became humorous, pointing to a sometimes-contentious relationship between the two. Healy was not signed to be part of the Mets' new cable channel, SportsNet New York, for 2006. Healy is the current host of "The Game 365" on MSG Network, in New York. The show profiles many athletes and coaches in sports.