Hello everybody.

I recently took a few month break from this game and I am going to create a pure stealth character for the first time in 14 months. The reason why I quit on my previous stealth character is that most of the houses in Skyrim did not have any good loot to steal from. I did not really feel like a thief. Outside of Jarl's palaces and shops, I only found around 40 coins worth of things in regular homes. Are there any houses in the game that actually have gems, jewels and similar stuff?

Nowhere really with massive valued items, but you can make a nice profit off of fine clothes.

The best way to make sure there is loot in the house is to get a Radiant TG quest that sends you there.

However, as you discovered, poor is the thief who limits themselves to residential targets.

Endon's house comes to mind. I don't usually do Thieves Guild but I remember it always used to be my first stop for Bedlam jobs in Markarth.

This. I loved every second of robbing his home after hearing that he was a silver smith.

Other than that I really can't think. But just imagine what treasures Understone Keep is hiding. I implore you to find out!

The homes in Solitude don't have anything worth stealing? I would imagine the upper class at least has a few gems or some gold lying around.

You think there's no loot in skyrim!? You should try playing Oblivion then!

Remember - thieves aren't rich. If they were then everyone would be thieves . 100 Septims a house is more than enough profit

Are you playing by any rules? I remember last time I played a pure thief, I used to use the self-enforced rule that if I was caught sneaking in, I would leave straight away and if a guard caught me I would go to jail. That way it's risky carrying around your stolen loot - I also gave myself the Fence perk, because it's unrealistic that merchants will know that a piece of generic clothing is stolen.

The money will get big once you're on high enough level. You are bound to get richer and richer as both the weapon/apparel quality and amount of gold in chests and drawers go up. So, level up, then continue stealing. Suddenly, a lot of gold everywhere... You'll get too wealthy at some point. My Argonian, Hides-Swift-Strikes, a DB/TG guy, is level 46 and he has about 100,000g now, and nothing to spend it on.

Also remember - if you are playing a Pacifist style thief - the TES-Lore styled Thief, then you can go into dungeons. Use a bow/arrow to distract the guards/bandits/monsters and sneak your way in Throw in some illusion to cause your foes to Frenzy and you'll be laughing

OP-If you are on PC then the mod Immersive Loot would be good for you. It adds tons of unique items to NPC's and containers throughout Skyrim.

Nothing but the Black-Briar Lodge and Pinewatch come to mind. But then again I don't usually play stealth oriented characters.

Pinewatch is a dungeon though.. but I get the jist of what you're saying.

Check this place out if you can OP!

All stores have a strongbox in them. They carry around 200 septims, a leveled ingot, and a gem (from my experience). Most stores double as a home, so be careful.