Valuable Things to Steal?

[Rennsellaer]

What are some of the more valuable items to steal in Skyrim? Preferably in Windhelm.

[Brandybuck]

Is this because you have a quest to steel 500 worth of items? Easy peasy. Steal valuable ingredients from apothecary, pickpocket for gems, stuff inside locked cabinets in Jorvaskr, etc. There won't be a lot of good stuff just laying around though, but still enough to get your 500 septim worth.

[Rennsellaer]

Originally posted by Brandybuck:

Is this because you have a quest to steel 500 worth of items?

I sort of already did that. I'm looking to take items worth 1,000 Septims or more, but because you usually only get good items through linear quests, those are hard to come by easily.

[Clever Monkey]

When I need a thievery fix I usually go for the weight to gold ratio items. magical being better.
jewelry of all kinds
silver plates and stuff
ingots and ores
potions can be good as well as some ingredients
I leave the big heavy stuff because the ratio is usaully 3,4,5 to1 if I'm lucky unless it's magical
this way I can go for longer and usually wipe out the whole city of items like that.

[Brandybuck]

The best stuff will need to be pickpocketed.

[MReq]

As Smile N Fire suggested, jewlery and potions are usually great as they're concidered valuable + they're lightweight.

EDIT: Scrolls are also pretty valuable.