The funds will help bring the neglected historic buildings back to commercial use and create economic growth in the local areas.
An estimated 230 FTE jobs will also be made by attracting private investment.
Of the five buildings being transformed, is the Merkinch Welfare Hall in Inverness.
It is being awarded a fund of £706,400.
One of only three listed welfare halls in Scotland, Merkinch Welfare Hall was built in 1914 to house a temperance group who sought to attract young men away from the 'dangers' of alcohol.
A Grade C-Listed building, it currently stands vacant and is on the Buildings at Risk register due to serious water ingress and resultant damp. The Hall played a large role in the local community over the past 100 years and now it will return to that tradition when it becomes an amateur boxing club, alongside office space.
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Dame Jenny Abramsky, Chair of HLF, said: "In almost every town and city there is at least one historic building standing empty that at one time was at the heart of the local community. Whilst much-loved, these buildings present huge financial challenges.
"This new scheme works to unlock the potential of these precious old buildings, encouraging private investors and encouraging regeneration. The result is good for us all – substantial economic growth, much-needed new jobs and a wonderful part of our heritage saved from further neglect."
The redevelopment is a partnership between the Merkinch Enterprise - a charitable company set-up to alleviate poverty in Merkinch - City Amateur Boxing club and the Merkinch partnership which is funded by the Highland Council Deprived Area Fund and the Scottish Government.
The vacant buildings receiving this investment, are the first to be awarded funding through HLF's new Heritage Enterprise scheme. The other projects are the Harland and Wolff Drawing Offices (Belfast), the Globe Theatre (Stockton), St Peter and the Old Black Lion Pub (Northampton) and the Northern Counties Club (Londonderry/Derry).
(JP/CD)
