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2 days late, but I actually have a couple book that do exactly this with fictional settlements in different parts of the world. Lebek, Barmi, Umm El Madayan, and San Rafael. They have incredible illustrations and thorough details about what developments have happened since the last snapshot and why. They're wonderful books. Great for inspiration when developing your own cities.

I see this sentiment in r/papertowns a lot. I think it's a bit misguided. The Romans had an impressive, sprawling empire. But in many ways they were anti-technology.

For instance, Vespasian paid off inventors to keep quiet because he was worried industrial technology would cause mass unemployment. Dark age and early-medieval Europeans were much more interested in labor-saving technologies and constructed tons of mills. We think the empire had a few major grain mills to serve Rome itself that would have been quite large, but otherwise weren't that interested in mechanization of agriculture or crafts.

The sort of "rise and fall" narrative of Rome is incredibly compelling, but the distinction between Rome and its successors gets overdrawn. Great (but somewhat dated) book on this if you're interested, explores technological advances in the early medieval ages.

Beautiful.

The story of the Siege of Szigetvar is astounding. Would make a great movie, or the basis for the climax of a season of something like Game of Thrones. I see OP has already posted the Wikipedia link.

For more on the Siege, I recommend Andrew Wheatcroft's ridiculously entertaining "The Enemy at the Gate," a history of the Siege of Vienna and of the general conflict between Hapsburgs and Ottomans in the late medieval-early modern period.

Before the final assault, the defenders prepared to kill their own families to prevent them falling into the hands of the Turks. The day before the assault, the Sultan died, though his death was kept secret. Then (this is from Wikipedia, but read Wheatcroft's account for a more thrilling telling):

>The final battle began on 7 September, the day after Suleiman's demise. By this time, the fortress walls had been reduced to rubble by mining with explosives and wood fueled fires at the corners of the walls. In the morning an all-out attack began[4] with fusillades from small arms, "Greek fire", and a concentrated cannonade.[Note 7] Soon the castle, the last stronghold within Szigetvár, was set ablaze and cinders fell into the apartments of the count.[4]
The Ottoman army swarmed through the city, drumming and yelling. Zrinski prepared for a last charge addressing his troops:

>>“...Let us go out from this burning place into the open and stand up to our enemies. Who dies – he will be with God. Who dies not – his name will be honoured. I will go first, and what I do, you do. And God is my witness – I will never leave you, my brothers and knights!...

And then there was a final, explosive twist at the very end. And it's all true.

It's very cool to see the fortress reconstructed like this.

Great catch! The Conservatory building is tucked away behind the much taller East Village building in most of the shots, so I definitely missed that one! Here's a good shot from a reverse angle which shows some of the same details on the roof of the Conservatory building, such as the chimney, which can be seen in the old map. Here's an old timey postcard depicting the Conservatory Building.

It looks like Building 2, a block up Huntington Avenue, is the Symphony Hall, built a couple of years before the map was drawn, and is still standing today. Building 3 is Horticulture Hall, built just a year before the map was drawn, and survives today as the William Morris Hunt Library.

Amazon Prime has a documentary on this place that I thought was pretty good. It details the rise and fall of the city over three or four centuries.

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Link here.

Hey mate, John Riley Smith is probably the most respected academic on the topic, I've read 2 of his books -- this was the better one:
https://www.amazon.com/First-Crusade-Idea-Crusading-Middle/dp/0812220765

In Nick Offerman's book Gumption (at least I think that was the book) he talks about the story behind Central Park, the people who championed it, how it was built. It's a really interesting piece of history.

This is from Barmi: A Mediterranean City Through The Ages. I know because I memorized every square inch of this book this as a kid. I highly recommend this book and others like it (San Rafael, Lebek, Umm El Madayan).

I have literally just bought this one as a gift to myself (dont judge), as well as this, they are both so beautiful.

For another way to have a paper town... I received this book as a gift many years back. In the end, I didn't have the time/skill to finish it - As the reviews say, assembly is a significant project. But it was gorgeous...

I highly, highly recommend this book about the history of the Dutch colony of New Amsterdam and its lasting influence on modern American culture and politics.

https://www.amazon.com/Island-at-Center-World-ebook/dp/B000FCK2Z6/ref=sr_1_1?ie=UTF8&qid=1503297955&sr=8-1&keywords=island+at+the+center+of+the+world

New York and Brooklyn (and New Jersey).

Some neat things about NJ in this:

• Morris Canal entrance on the bottom right, which went through the entire state out to the Delaware River. Map
  
• The railyards in the bottom center were still around through the 1960s. Here's a photo from 1961. Nowadays that area is office towers and expensive condos. The Delaware & Lackawanna Western Railroad/Ferry Terminal is still there though, in Hoboken.

There's a short mini-series on the London fire that is the best depiction I've seen in the medium on large scale city fires from the general era.

This looks like it comes from the Mannahatta project and its associated book.

Here is an interactive map of precolonial Manhattan.

Here is a TED talk about the mapping project.

There is also a scientific paper about this mapping project.

The developers would need to find a book like this one only for the Roman Empire.

Sarmant, Thierry, Histoire de Paris: Politique, urbanisme, civilisation 2012

I found it by the way.

yes

https://www.amazon.com/Assemble-Crusader-Castle-Full-Color/dp/0486252000/ref=sr_1_1?s=books&ie=UTF8&qid=1536258941&sr=1-1&keywords=cut+and+assemble+crusader+castle&dpID=51WBH21HQ2L&preST=_SX218_BO1,204,203,200_QL40_&dpSrc=srch