Based on a Joyce Maynard novel, the film will tell the story of a 13-year-old boy and his reclusive mother who take in an escaped convict over Labor Day weekend.
Collider reports that Up in the Air director Jason Reitman is helming the project, which he held back for a year so that both Winslet and Brolin could be free to star.
Reitman also wrote the adapted screenplay for the drama, which is now shooting in New England.
Labor Day is expected for a 2013 release date.
Josh Brolin currently stars in Men in Black 3, in which he plays a younger version of Tommy Lee Jones's character.
Watch Josh Brolin discuss Men in Black 3 with Digital Spy below: