In many ways this is one of the most important drawings that I have ever submitted to this particular site, mostly because I have been asked numerous times over the last few years, either in comments sections or through private "notes," how do I do this, how do I draw perspective, how do I come up with these designs, etc. Make no mistake, it takes years and years of practice to get good at this essentially obsolete and esoteric art form. Hopefully, this rather large file will help illustrate the madness of hand-drawn perspective illustration drawn using my typical methods.
Admittedly, it's missing a bit of information on two-point perspective and it's principles. You can simply look that up on the internet. For example, I left out the horizon line, something you might see on Google Sketchup. The idea is to build up a simple geometric shape which represents the "massing" and outlines of the house, based on main exterior walls, floor planes, and fairly complicated roof structure arrangements. It's important for the first outlines to be reasonably accurate or the house will have incorrect or skewed perspective lines. Sometimes later I "tweak" perspective lines a bit to achieve better accuracy.
Once you have the basic shape of the home sketched in, you can start to add details and "wings" to the house like the garage addition and the master suite to the right. All the while, you should have either a rough idea or an actual floor plan in mind as you lay this out. You can start to design a house like this, with no plan at all, and call it a concept sketch, OR, this can be a final rendering of a set of complete floor plans and elevations. I do both!
Getting a feel for perspective angles is very mysterious and difficult for many artists. To understand it, it's a good idea to sketch houses from life (sit on the curb and draw an old house!), draw AND trace from photos of houses, and draw rough perspective sketches of your own designs into a sketchbook. Practice, practice, practice!
Final details look correct when you actually know how a house goes together. For example, it helps to have a clear understanding of porch framing to draw clearly the porch piers, the beams they support, and the corner brackets. Yes, I DO build this stuff, all the time.
Finally, don't neglect landscaping plants. I also personally do gardening and installation of landscape plants on my own property, so I have a working knowledge of basic landscaping plants, trees, flowers, and how to draw them. Usually, on these types of illustrations, a simple tree line behind the house is enough to suggest how the home will actually look on a particular property.
Technical: The six drawings above are pencil drawings executed in sheets of 8 and a half by 11 inch paper, mostly HB, H, and 2H pencils, scanned, assembled, and labeled with software.
Anybody may use this as they please, except for commercial purposes. I may see a lively discussion on this piece in the comments. Feel free to speak your mind, ask more questions, critique, or whatever. You can send me a private "note" too.