Gloag has owned Beaufort Castle near Inverness since 1995, and Kinfauns Castle, near Perth since 2004. She has attempted to block off private access at Kinfauns in a high-profile case. On 12 June 2007 she was successful in gaining a court ruling that she was legally entitled to bar the public from a swath of woodland in the grounds of Kinfauns Castle.
Her ex-husband, Robin Gloag, father of her late son, Jonathan, was killed in a car crash on 6 December 2007. Their son, Jonathan, hanged himself in 1999, aged 28. In 1990, Ann Gloag married David McCleary, a widower and a successful owner of multiple businesses, who was previously an organist and minister at the local Church of the Nazarene.