The 'Plook on a Plinth', which is awarded each year by Scottish magazine Urban Realm, revealed New Cumnock was the recipient of this year's title.
Reasons for choosing the town ranged from the "haemorrhaging of shops" and "a general absence of maintenance on derelict properties" according to judges.
New Cumnock was last nominated in 2009, but Glenrothes in Fife was awarded the title that year.
Since then, Urban Realm said the town had "taken one step forward and two steps back".
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It added that the "completion of an impressive new primary school" had been "overshadowed by the threatened closure of its town hall", as well as the "sell-off of the Arthur Memorial church - on its 100th anniversary".
The magazine said: "These losses have been compounded by the continued haemorrhaging of shops on the High Street and a general absence of maintenance on derelict properties, raising the very real risk that a tipping point into irreversible decline could be reached soon if action isn't taken now."
John Glenday, Editor of Urban Realm, said: "We have been following New Cumnock and the challenges they face for four years now, giving us a real sense of perspective on the challenges faced.
"There are no quick fixes, however, and I make no pretensions to the contrary. It has taken years for New Cumnock to get to this point and it will take years to put right but the sooner these issues are tackled the sooner they can be resolved."
The 'Plook on a Plinth' award was established in 2000 to create debate about the quality of development in many of Scotland's towns and cities.
(JP/CD)
