Leena Chandavarkar came into the limelight after finishing as one of the runners-up for the Fresh Face Competition organized across the country by Filmfare. Initially, she worked in advertisements but eventually ventured into films. She made her debut in Man Ka Meet for Sunil Dutt, and it was his wife Nargis who groomed her to be an actress. Between 1969 and 1979, Leena acted in many films. She was cast opposite many of popular heroes of that era. She gave one of her best performances in Mehboob Ki Mehndi with Rajesh Khanna in 1971.
She appeared as a guest judge for the first 2 episodes of "K for Kishore", a new reality TV singing show launched by Sony TV during December 2007. She is now appearing for the reality shows. She also penned some songs for Amit Kumar and Rajesh Bambal for a music album.
She had an arranged marriage to her first husband, Siddharth Bandodkar, who came from a prominent political family. He died from an accidental gunshot wound, a few days into the marriage, leaving Leena a widow at age 25. A few years later, she defied her father by marrying singing legend Kishore Kumar. Her father initially objected because Kumar had been married three times already, and was more than 20 years older than her, but he soon came around and welcomed Kumar into the family. She has a son with Kishore Kumar named Sumit Ganguly. Kishore died in 1987, leaving Leena once again a widow at age 37. She lives with her son Sumit, her step-son Amit, his wife, and with Amit's mother.