How to make Skyrim more challenging at higher character levels?

There are 2 console commands if you are on PC that makes things harder without ruining the experience:

• The first is: player.modav healrate x where x is any value less than the 0.7 vanilla Skyrim grants you. I have mine personally at player.modav healrate 0.2. This allows for me to still regen when out of combat or when resting, but when in combat, the regen does nothing for me.

• The second is: player.advlevel. This will allow you to "level up" your character strictly for the numerical value. You WILL NOT gain any perk points or stat points from this approach. Instead, it will simply put you x amount of levels above your "true" level, thus making enemies scale up to this imaginary level, and therefore making the game as adjustable in difficulty past master as you wish!

The Total Realism - Basic Needs mod adds realism and can make it somewhat harder to survive.

The Deadly Dragons mod makes dragons more powerful as they should be.

I had this same problem. This is what I am trying. YMMV.

You can try this play style. Go without killing anyone for as many levels as possible on Adept or Master difficulty. This was proposed by @Alex as well in the comments to your question.

It is a very challenging play style, for quests where I simply have to kill as part of the quest objective, it gets difficult, but even then with Mayhem/Frenzy/Fear etc it is possible that your quarry gets killed.

For an example of this challenging play style check out Felix The Peaceful Monk

You can start using 2 handed weapons. If your skill is still low and you haven't put points in that skill tree, killing oponents will be harder and more challenging.

Or you can try to only use magic in fights. Destruction to damage your oponents, Restoration to heal yourself (no potions), Conjuration to call for allies, Alteration for defensive spells, ...

If you are a PC gamer: galacticninja gave some nice mods to try out. Another mod that makes Skyrim more challenging in my eyes is Imp's More Complex Needs. If you don't eat, drink or sleep, you die. That's the mod in a nutshell, but it is way more complex than that. It's available on Steam so it's easy to install too.

Start a new game, play normally but never use your perks

You will have weapons that will do 20 (tops) damage and enemies with 150+ hp (some have a lot more)

If you're playing on the PC try a mod called High Level Enemies. It adds something like 400+ higher level Bandits, Draugr, Dragon Priests, Forsworn... (it covers all enemy types) to the game. Really keeps the difficulty up at high levels.

Main Files

• Adds 708 new enemies starting at level 10 to Skyrim, Dawnguard and Dragonborn!
• Now includes an optional version with full level scaling so all enemies (even Vanilla enemies) will scale to your level!
• Each of Skyrim's main enemy types are covered including Bandits, Draugr, Dragon Priests, Falmer, Forsworn, Thalmor, Dwarven Constructs, Vampires, Warlocks, Trolls, Chaurus, Spriggans, Hagravens, Spiders, Skeletons, Witches, Ice Wraiths, Mammoths, Dremora and Wild Animals!
• Each of Dawnguard's main enemy types are covered including Vampires, Vampire Hunters, Falmer, Gargoyles, Armored Trolls, Death Hounds and Chaurus Hunters!
• Dragonborn Cultists, Rieklings, Ash Spawn, and Dragonborn Bandits Included!
• For each enemy type the highest level variant scales with player level so the game doesn't get too easy!
• Countless hours were spent customizing the Stats, Skills, Perks, Spells, Damage Done and Armor Rating of each added creature to ensure that the difficulty stays consistent as the player levels!
• The scaling is non-linear and takes into account that high level players invest in at least 1 crafting skill (Smithing, Enchanting or Alchemy).

Optional Files

• Includes an optional file that increases difficulty at all levels.
• Includes an optional file that increases armor cap to 90% and max magic resist to 90% encouraging high-level play.
• Includes an optional file that scales Illusion, Raise Dead, Summons, Turn Undead Spells and Werewolf Howl so they are still viable in high-level play.

Just change how you play. You seem to mostly be a warrior. Just use skills that you haven't gotten to high. I know that for myself, not using enchanted items other than the ones I have found has kept the game fun.

You're not being penalized for your hard work, in some eyes it's a reward, but it's up to you to make it fun or boring. You're right - the only way is stop using your great items. Maybe you should sell them so you are not tempted to kick too much ass, just enough.

A good way to improve your gaming experience is to play something what I call "Iron Man" challenge - when you die, you just start a new game, there is no reloading. I can assure you you will suddenly start playing much more cautiously and the game will become much more of a challenge :)

I had the same issue! Here's how to make it difficult:

1. No glitch use
2. Leveling up skills using cheap ways is banned (like leveling up restoration by jumping on blacksmith fire and heal)
3. You can only put perks in four trees only (example: one hand + destruction + light armor + archery)
4. (this is most important). You can't pick perks that require skill level 70 or more! Because such perks are overpowered, like dual savegery and elemental protection
5. enchanting can accept only 2 perks, because more will make you overpowered
6. Your character is allowed to use 2 shouts only. You assign them at the begining of the game and don't use other shouts execept for quests

Ideas i thought of is,

• Restrict yourself from certain things like no fast traveling.
• No skill boosting via glitches.
• No trading or training with vendors or followers.
• No followers unless quest involved.
• All materials you need must be foraged from the world. (Eg. Iron can only be obtained by finding. Stealing. Or mining)
• play completely on the hardest difficulty.
• Craft all your own things such as potions and gear.
• Turn the hud completely off.

don't craft items. only use items you find. makes the game much harder when you don't have gear that you got through blacksmithing potions + grindstone

Just reset difficulty to legendary then legendary all your skills. You'll have the same gear and have the same enemies though.

My first character was just a leveling up fiend and the same thing happened to me as to you. I got too powerful and the game lost its appeal. One of the ways I've found useful to play Skyrim is to play using a set character theme in mind. Some examples from my play are; a Barbarian that won't use any magic other than heal and wields a two-handed sword almost exclusively. I have a Paladian that has leveled up his restoration but won't use destruction, conjuration or other spells, except calm and courage. Having a set character theme has helped keep my game interesting and given me a variety of interesting paths through the game and different 'feels' each time.