Seven fire crews were dispatched to the scene in Kilmux Park, Kennoway, shortly after 5:00pm.
Eyewitnesses said the fire spread from a caravan to two nearby homes as wind fanned the flames.
Fire crews spent several hours at the scene, but it is understood no-one was injured.
Dramatic photos and video footage revealed the full extent of the blaze.
It showed flames taking hold in the roof of one of the homes, causing extensive damage.
The Scottish Fire and Rescue Service confirmed they sent six appliances and a special appliance to the scene.
A spokeswoman said: “We received the first call at 5.12pm. “Two properties and caravan were on fire during the incident.
“Crews were called from the Blackness Fire Station in Dundee and assisted colleagues.”Polic were also in attendance.
A Police Scotland spokesman said: “Inquiries are ongoing into the cause of the fire.”