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The empty Nasons department store could be transformed into a shopping thoroughfare akin to the popular Brighton Lanes development, KentOnline can reveal.
It is understood plans are being drawn up for the site, as well the huge Debenhams store opposite, which was last week listed among branches set to close next year.
Official applications to redevelop the sites could even be submitted to council planners within the next three months.
Such a move would bring to an end speculation about the future of the former Nasons store, which closed last August after 90 years of trading.
The demise of the city's Debenhams branch was only confirmed on Thursday, but it is likely to remain open until 2020.
Given their size and location, both sites are considered key parts of the high street landscape.
Nasons has been boarded up since it shut last summer, and traders fear Debenhams faces a similar fate when it closes, creating two prominent city centre eyesores.
But sources have told KentOnline plans are already afoot for both, with work on proposals for Debenhams starting long before its fate was confirmed.
It is understood to involve a conversion of the vast building into a predominantly residential development, while its smaller store fronting Guildhall Street would retain shops on the ground floor.
Plans for Nasons, however, are said to be far more ambitious, with one under consideration a Brighton Lanes-style shopping thoroughfare.
It would lead from the High Street through to the former cafe entrance in St Margaret's Street, with retail units on the ground floor and flats above.
Another idea on the table is understood to be a boutique hotel fronting the High Street, although any scheme would have to take into account planning limitations.
The old building entrance in the High Street is listed and cannot be significantly changed, while the adjacent Yeomanry Memorial Garden also limits design options.
Canterbury Business Improvement District boss Lisa Carlson has already admitted there could be fewer shops in the city centre in the future because of changes in shopping habits.
But she is urging planners to ensure that retail units remain at ground floor level in any future changes.
"We accept that residential will probably be part of the mix," she said.
"But I think the overarching point is that we have people interested in the city centre and I don't think these properties are going to remain boarded up.
"We are discussing options with the city council and would also like to meet developers and architects to generally discuss what it is we want in Canterbury.
"But we must protect ground floor for retail and food and beverage, but would love to see more accommodation above.
"Canterbury will always be a retail city and tourist destination but it's all about the experience. I would also love to know what people think about how it is shaped in the future.
"It is an exciting opportunity for the city and the other units that are currently vacant will not remain so because there is stuff happening."