Coming Soon... Hopefully!
Will be in ASCII Art, then transformed into Paint.

Here's what I have so far (I hope it works)
________________________________________Free Country, USA________________________________________
|                                                                                                |
|                                                                                                |
|                                                                                                |
|                                                                                                |
|                                                                                                |
|                                                                                                |
|                                            __________                                          |
|                                           |Marzipan's|                                         |
|               _____________               |___House__|                                         |
|               |           |                                                                    |
|               | The Field |                                                                    |
|               |___________|                                                                    |
|                                                         __________                             |
|                * * * *                                 |          |                            |
|                I I I I                                 | The KoT's|                            |
|               The Forest                               |  Castle  |                            |
|                   __                                   |__________|                            |
|                 _|__|__                                                                        |
|                 |Bubs'|                    Homestar's                                          |
|                 |Stand|                       _                                                |
|                                              / \                                               |
|                                              \_/                                               |
|                                             House                                              |
|                                                                                                |
|                                                                                                |
|                   |                                                                            |
|                   |                                                                            |
|              The Stick                                                                         |
|                                                                                                |
|                                                                                                |
|                                                                                                |
|                                                                 The Dumpster                   |
|                                                                   ___                          |
|                                           ________               |   |                         |
|                                          |  The   |          ____|___|__                       |
|                                          | Strongs|         |Strongbadia|                      |
|                                          |__House_|         |___________|                      |
|                                                                                                |
|                                                                                                |
|                                                                                                |
|                                                                                                |
|                                                                                                |
|                                                                                                |
|                                                                                                |
|________________________________________________________________________________________________|

It does!


Comments
I have to add the forest 'cause if you've seen the Strong Bad is in Jail Cartoon, you find there's a forest behind it. -MG_Racoon

Heated Debate

Isn't Strongbadia referred to as a piece of land behind the dumpster when someone emails him "if you rule so much why dont you rule a country, or at least some kind of field?" Wheres the dumpster?-SephirothBadReligion

Strong Bad said he lived next to the King of Town
I think you should add a dungeon for Thy Dungeon Man, I know he is never explicitly said to live in Free Country USA, I think he needs some love too. Quasi
Strong Bad also says the KOT lives in a apartment
Thy Dungeonman is a Video Game, not real life.
most of the Strong Bad emails seem to be a fantasy
What about that marshmallow place homestar likes to hang out at?