Bring a large pot of salted water to a boil. Add the asparagus and blanch for 2-3 minutes until bright green and tender-crisp. Immediately transfer the asparagus to a bowl of ice water to stop the cooking process. Drain and pat dry.
In a large bowl, combine the blanched asparagus, cherry tomatoes, cucumber, red onion, Kalamata olives, and feta cheese.
In a small bowl, whisk together the olive oil, red wine vinegar, dried oregano, salt, and pepper until well combined.
Pour the dressing over the salad and toss gently to combine all ingredients.
Garnish with fresh parsley before serving.