[4] His father Selwyn was a dentist and president of West Harbour RFC, while his mother Ruth was a preschool teacher.

Freelanders family has had a long history with the Labor party with his father being friends with former Prime Minister Ben Chifley.

His paternal grandfather William Freelander arrived in Australia as a cabin boy and became mayor of Katoomba and the City of Blue Mountains.

Freelander studied medicine at the University of Sydney and is a Fellow of the Royal Australasian College of Physicians (FRACP).

In 1984 he moved to the Macarthur region of Sydney and established his own practice, also working at Camden and Campbelltown Hospitals for several decades.