Clutha-Taieri area response manager Senior Sergeant Al Dickie said the two break-ins happened near where resident Nicole Acklin reported hearing footsteps on the roof above her kitchen yesterday morning.
Maddren (25) fled from the nearby Otago Corrections Facility on Tuesday afternoon.
Snr Sgt Dickie attended a 1am break-in where food and milk was taken from a fridge in an unlocked house.
The break-ins were the most solid lead to date in the manhunt and police were looking to "step-up'' their search for Maddren as it was the first "conclusive'' evidence he was still in the area.
Police were conducting forensic work to determine if Maddren was responsible for the break in, but Sgt Dickie believed it was most likely him, saying it would be "odd'' if it was someone else.
"[I am pretty] confident, because there was a dog track, which took us back to the general area he was in.''
It was a "bit disappointing'' the house was not secured and police were keen for people in the area to keep their homes locked.
Sgt Dickie said it was surprising that it appeared Maddren was still in the area close to the prison.
"I just find it strange he is still hanging around the prison, if it is him.''
