Combine flour, paprika, salt, and black pepper in a large bowl and coat each beef chunk thoroughly.
Heat one tablespoon of olive oil in a large pot or Dutch oven and brown the beef in batches, about 5 minutes per side, adding oil before each batch. Set browned beef aside.
After searing all meat, add remaining olive oil to the pot, then cook onions, green peppers, and celery over medium heat until softened, about 5 minutes.
Stir in garlic and tomato paste and cook another minute, ensuring even mixing.
Pour in red wine, beef stock, and Worcestershire sauce, scraping the pot bottom to loosen browned bits.
Return the seared beef and any juices back into the pot, along with Italian seasoning and bay leaves.
Bring mixture to a boil, then reduce heat, cover, and simmer gently for 2 hours.
Remove the lid and add potatoes and carrots to the pot, continuing to simmer uncovered for 1 hour or until vegetables are tender and beef is fork soft.
Take the stew off the heat and serve immediately or refrigerate for a day to enhance the flavors before reheating and enjoying.
