Reminds me of a Warhammer40k (more specifically rogue trader) version I saw once.
https://1d4chan.org/images/9/90/Monopoly_RogueTrader.jpg"GO" should be the Castle gates.
The two "Community Chest" should be wall candles
"Free Parking", either a save room from one of the Metroidvanias, or the church from Simon's Quest.
"Won the beauty contest" card could be "Found Meat in the wall".
Go directly to jail could be "fell down a giant hole into the dungeons" or "Petrified by a Medusa Head" with the jail itself being either the dungeon or temporary state of being turned to stone.
I don't remember the other cards, but they could be tied on cards with being hit by enemies for negative effects and finding hearts/weapons/upgrades in candles for positive effects.
"Luxury Tax" could be "Hit by Dracula's Fireball" or "Lost to Dracula"
"Income Tax" could be "Knocked Backwards off a Ledge" or "Lost to Medusa" (or whatever boss you feel like)
Instead of houses and hotels, you could call them ramparts and turrets.
Each of the set of properties could be represented by pictures of the same castle area from different games and time periods. For example Oriental, Vermont and Connecticut Avenues could be 3 versions of the arena. Named either by game like "Symphony of the Night Arena" or by time period "Old Arena" "Mid Arena" "New Arena".
Oh, or the jail could be the continue screen, like you lost your last life and have to start the level all over, and you're just waiting to press continue again.