In a large pot, bring salted water to a boil. Add the halved baby potatoes and cook until tender, about 15-20 minutes. Drain and let cool slightly.
In a large mixing bowl, combine the cherry tomatoes, cucumber, red onion, Kalamata olives, feta cheese, and parsley.
In a small bowl, whisk together the olive oil, red wine vinegar, dried oregano, salt, and pepper.
Once the potatoes are cool enough to handle, cut them into bite-sized pieces and add them to the mixing bowl with the other vegetables.
Pour the dressing over the salad and gently toss to combine all ingredients. Adjust seasoning with more salt and pepper if needed.
Chill the salad in the refrigerator for at least 30 minutes before serving to allow the flavors to meld.