The last sighting of Wayne Fleming, known as Bagsy, was in the Cadham area in February/March this year.
He is described as being white, about 5ft 3in tall, of stocky build. He has blue eyes, black shaved hair and a tattoo of a mushroom on his arm.
Police have urged anyone who may have seen him to contact them.
Insp Derek Paxton, of Police Scotland, said: "We are issuing leaflets in the Cadham area showing two significantly different photos of Wayne in the hope that this will jog people's memory.
"We have information that he was seen in this area around February/March 2015 and I would urge anyone who thinks they may have seen him to come forward.
"We are also asking residents to check their outbuildings and gardens and we will be deploying specialist search units in the area."
Police are carrying out door-to-door inquiries and searches in the Cadham area of Glenrothes following the disappearance of a Fife man.