The title says it all. I am rather impressed by the Vladislav Hall but I wonder how the whole complex looked around 1400-1500.
Found some pictures:
1493
Some year between 1526-1538
Some year between 1509-1541
16th century
Not sure if it’s correct.
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Thanks 
Is it just me or is the castle not yet connected to the town by the river and the old bridge in the first two pictures?
The Charles bridge was already standing by 1493 (The earliest supplied picture). They started to build it in 1357 and by 1406 there are already mentions that the bride was standing and functional.
Also Charles Bridge was not the first stone bridge built over the river in that place. Older one (Judith’s bridge) was standing there for few hundred years and was destroyed by a flood in 1342.
The town was on both sides of the river Mala Strana and Old Tow are both the oldest parts of Prague and New town was already existing at that time. The villages there were included in Prague by Charles IV and lot of new houses were built there as well.
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I’m pretty sure that the oldest representation is the one Shock linked (from 1493). There are of course many reconstructions based on archeological findings, but I haven’t managed to find a nice one from the 1400s as archeologists seem to focus more on the earlier developments (800-1200) of the area.
There is one funny thing about the St. Vitus Cathedral, which is in the central part of the complex. The construction of the cathedral it started in 1344 (replacing a church built in 1060 which was still preceded by a rotunda from 930) and was later interrupted by the Hussite wars.
In 1403 the construction was likely still going strong especially after involvement of new building masters which happened in 1399.
The thing is that the cathedral was finished no earlier than in 1929. My grandfather always liked to point out that he saw the last “bricks” being put in. 
The damn thing took more than half a millenium to complete. 
We were lucky it didn’t end up being destroyed in ww2.
Here is the cathedral in 1836, can be compared nicely with the painting from 1493.
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Jeesh that took a long time.
Did the old castle actually have a keep like many Western European castles do?
Prague Castle is less like a castle and more like city quarter. But yes. It did have a keep or keeps (It was rebuilt several times) few of the keep towers are still standing. You have to be aware that as a castle it is huge (It is in the Guinness Book of Records as largest ancient castle in the world). It does have a moat and walls. It contains several gardens, several palaces, three churches and several chapels. Few large halls and many other buildings.
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(Johannes Wechter, View of the City of Prague 1606 - MET)
(Johannes Wechter, View of the City of Prague 1606 - MET)
(Johannes Wechter, View of the City of Prague 1606 - MET)
Prague, The Crown of Bohemia, 1347–1437 look under “Additional Resources” you find more Pictures in HighRes. up to 4000 × 3940… 
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That’s going to take a lot of time to make.
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Nice pictures again
I suppose we need some fitting music.
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@Dushin Take a look at this ebook… http://books.google.de/books?id=AbZ-rhlSlxsC&printsec=frontcover&redir_esc=y#v=onepage&q&f=false
perhaps you find some answers there…
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That one is neat but I gotta study now.