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I've been told that in Bexhill, there was a similar situation, (not necessarily involving an empty Woolworth's). This shop's area has been turned around by using the general public's need of somewhere to sell their unwanted household goods and chattels. There are car-boot sales, I know, and they're okay for the Summer season, but during the Winter months, a table can be hired or rented on this shop's floorspace for a few pounds.
Alternatively, what about letting it out for a restaurant-cum-sandwich bar-cum-fish and chip eaterie, with a decent sized area for both visitors and locals. There would be plenty of room in this building, so enabling customers to bring inside the buggie or invalid chair, or even the whole family?
Most cafeterias and eating-places are too cramped to move around in freely and if a young mother should want to bring her buggie/pushchair inside, there'd be no need for anyone to shift about or move their shopping and personal belongings. Young Mothers tend to shop, with their young children, in groups these days and they certainly would welcome it. Sounds a bit haphazard, doesn't it, yet some clever planner might make it work. When the Ideal Home Show comes to London, there are always so many different food outlets and eateries to choose from. They're all clumped together on one floor, but it works, somehow. So much space, no crowding and everyone's enjoying the experience and mostly, it's inexpensive.

Is there a back entrance/exit to this building?

The 'clampers' would have to be 'sorted' if Iceland did take this shop over, surely. Any volunteers?
We have an Iceland here, but not in the town-centre, it's about as far away from the centre as perhaps Dedworth is to Windsor....but, trade has increased since the downturn and perhaps it might be a good time for an Iceland or something similar to open in Peascod Street. Empty shops look so mournful and it doesn't look good to visitors either.

We had two Woolworth stores in Eastbourne, one large, one small. We also had a branch in Hailsham. The Eastbourne two were sold many moons ago, leaving us with the small, but popular, Hailsham branch.....Christmastime in Woolies in Hailsham, was always a favourite time - not any more. I don't even know what's in that lovely old Woolies space, because we don't visit the village now.....a village or town can suffer if just one popular and familiar shop closes down.
I hope Windsor can find a suitable replacement, not only for the locals but for the visitors as well. A town needs a magnet. Something to draw the shoppers in....I know, there's the castle, and that will always attract tourists, but women especially love to shop and browse for hours on end, and without reasonably sized shops, it's difficult flitting from one small shop to another. It kind of breaks the rhythm. Add to that the usually bad weather in Autumn and Winter, and the bigger department stores win hands down. I can't even imagine coming to Windsor again and not seeing Caleys, Woolworth's and maybe now, Daniels.....The old bus and railway station does have ample coffee shops and boutiques, but, they're no substitute, in my humble opinion, for the larger, familiar, well-stocked department stores. Let's hope a wise and popular decision is forthcoming, whatever the choice of company may be.