The Crown Office has formally restrained four homes and a bar valued at around £1 million under a joint Proceeds of Crime operation with Spanish authorities.
Their action, part of a much bigger investigation, means the owners of the property, believed to the friends and family of suspected underworld figures, cannot sell up without the permission of Scottish courts.
The Herald understands that prosecutors believe all five properties are "tainted gifts" - assets that criminals give, or sell at an undervalued price, to third parties such as wives or girlfriends.
Lesley Thomson, QC, Scotland's solicitor general, said the action was part of a widening reach of Scottish prosecutors across the world as the nation effectively internationalises its efforts to track the ill-gotten gains of criminals.
Ms Thomson said: "We have experienced prosecutors in relation to the Spanish system and a good working relationship with Spain."
One senior prosecutor has just returned from a lengthy secondment as liaison magistrate in Spain. It is believed she was instrumental in the astonishingly complex procedure of imposing restraints on the cul-de-sac.
Another Scottish fiscal is now heading to Dubai - another jurisdiction frequently used by Scottish organised criminals - on secondment as Britain's liaison magistrate there.
Scotland, which was among the first jurisdictions to ramp up use of legislation such as the Proceeds of Crime Act (Poca) as an opportunity to disrupt organised crime, is playing an increasingly major international role in the field.
It is Scottish fiscals, for example, who are drawing up an international Poca handbook on behalf of the 112 states represented in the International Association of Prosecutors (IAP).
Ms Thomson - who has specialised in Poca for nearly 20 years - said: "One of the things we have been looking at is whether we are maximising our contacts across the globe. We are half way through the handbook and will present it to the next IAP conference in November.
"When that exercise is complete that will give us more than just contacts. If there is anything a country is doing better than we are then we will look at that for legislative opportunities."
Ms Thomson was speaking as she revealed as the latest Crown Office figures on income raised through Poca, some £8m in 2013-14 that will now be passed on the Scottish Government.
That number, down from a £12m in 2012-13, included £3.6m recovered from convicted criminals such as Kwai Fun Li, who was forced to hand over £723,000 at Glasgow Sheriff Court last September.
Ms Li had earlier been fined just £6000, for employing six illegal immigrants at her Kings Lodge Buffet restaurants in Glasgow and Bishopbriggs. Ms Thomson said she believed this was the most "significant" case of the year.
The Crown Office during the year also secured a confiscation order against Charles Swan after he was convicted of running an illegal puppy farm.
Civil recovery - actions against those who have not been convicted of a crime in 2013-14 accounted for more than half of the total raised, some £4.4m.
They included £57,000 in cash first seized from Glasgow businessman Russell Stirton in 2007 after a suspected drugs courier was seen to hand him a carrier bag. Mr Stirton also spent years fighting one of Scotland's biggest civil recovery actions, for £1m.