To satisfy this and Architect, you will need to fully build on all three available plots of land (so get "Land Baron" unlocked first). This will include the three available wing additions to the houses. To most quickly do this, make sure you have a steward at the house (list) and a sizable bank account to purchase materials. You'll want to buy out blacksmiths of their Iron and Corundum ingots, and then order plenty of stone and wood from your steward. Use the anvil to create a large supply of locks, nails, hinges and iron fittings as well.

Once you've got a large supply of materials, use the drafting table near your home to setup the outline. Then step over to the carpenter's workbench to begin building up the structure. Once you have the house built, you can add the main hall in the same fashion and convert the small house into an entryway. Then you'll choose one wing at a time from each section (north, west and east) and build them up in the same fashion as well. Once all three homes have been built up completely with three wings the achievement will unlock.

If at any time you run out of materials, simply order more from your steward or fast travel to a town for more ingots and create the needed materials from the anvil again.