Tucked away on a remote slope of the Othrys mountain, Anavra had no paved roads, and its farming and agricultural methods had hardly changed in centuries.
The nearest school was in the Greek city of Lamia - a six hour mule ride away - forcing all children above a certain age to leave their hometown.
Things are very different now.
Anavra is famous for being one of the most prosperous farming villages in all of southern Europe, with an average household income of â‚¬70,000.
In stark contrast to the rest of Greece, no-one in the village is unemployed.
"Most of the villagers will be voting 'yes' on Sunday," Dimitris tells me over lunch in Anavra's cosy taverna - and it's not hard to see why.
Walk around Anavra today, and you will encounter a modern school, a library, a gym, football and basketball pitches, a handful of cafes, a resplendent church, and even a museum.
The roads are paved, and most Anavrans drive pick-up trucks, not donkeys.
Residents also enjoy satellite TV and high-speed internet, and as Dimitris is keen to emphasise, "young people stay here".
Much of this is a direct result of Greece's EU membership - alongside Dimitris' astonishing enterprise.
In the early '90s, after 35 years of working at an electrical firm in Athens, Dimitris returned to Anavra, intent on reforming its ailing and rustic economy.
After successfully running for mayor, his first move was to travel to Brussels, where he met with every EU official who would talk to him, and gathered information on all the available subsidies for rural communities.
Upon his return to Anavra, Dimitris bypassed the local bureaucracy and applied for funding from the European schemes he'd learnt of through the relevant ministries in Athens. This, he admits, was "not very Greek".
He quickly realised that many EU development programmes were environmentally focused, and in order to qualify, he encouraged Anavra's farmers to go organic, and to embrace clean energy sources.
An EU-subsidised wind farm followed, as well as EU-subsidised roads, stables, telephone lines and even an environmental park.
Anavra's 30,000 cows, goats and pigs used to roam freely in the village, causing hygiene and health problems, but once modern farming techniques were introduced, the quality of the village's livestock and produce quickly improved, as did the price their wares were able to fetch.
Teachers came to live in Anavra, and a doctor arrived soon after.
"If we weren't in the EU, this could not have happened," Dimitris says, gesturing towards the small, but well-built, village square.
"The European project has been a blessing for us."
But while Europe was the driving force of Anavra's extraordinary ascent, Greece's much lambasted bureaucracy threatens to bring it down to earth.
In 2011, reforms pushed through as part of former prime minister George Papandreou's 'Kallikratis Plan' condensed the number of municipalities in Greece from over 1,000 to just 325.
Anavra, which had been self-governing, suddenly found itself under the care of the relatively vast Almyros municipality.
Its headquarters are an hour's drive away. The new municipality of 43 villages has a population of 21,000 spread over 900 square kilometres.
"They are down by the seafront," Dimitris laments.
"They know nothing of life in the mountains."
Consequently, the "Anavra miracle", as the village's success is colloquially known, has stalled in recent years.
Further funding for a planned hydroelectric project has failed to arrive, and a power plant that was to be fed by manure and wood chippings has suffered a similar fate.
"When Dimitris was mayor, the winter snow was cleared every day, and business would continue," Machi, an Albanian immigrant who runs one of Anavra's cafes tells me.
"Now, it's left until it melts".
Perhaps surprisingly, Dimitris himself will be voting 'no', but only because, having read the EU's proposals, he fears they are misguided.
"If there is no debt write-off, Greeks will suffer for two or three generations," he says, fingering a set of komboloi, or worry beads, nervously.
Asked if he is concerned that a "no" vote would mean an exit from the Eurozone - as the European Commission president Jean-Claude Juncker has warned, Dimitris shakes his head.
That would be a different matter.
"I would never vote to leave Europe".
In the 1960s, when Dimitris Tsoukalas was a teenager, mules were the only form of transport available in his village.