Place washed raspberries in a blender and blend until there are no more chunks except for the seeds. Strain mixture through a fine mesh colander. Set aside. (If you don't mind the seeds running through the cheesecakes, skip the straining step.)
Place cream cheese in a bowl. Using a hand mixer, whip cream cheese until smooth about 1 minute. Add in the vanilla and sweetened condensed milk, mix together on low until combined. Add in the raspberry puree and carefully on low speed mix in, scraping the bowl if needed. Add in the whipped topping and with a spatula carefully fold it into the mixture until combined. Set aside.
Place Oreos in a food processor and pulse until they turn into crumbs. Add in the butter and pulse until everything is coated in butter. Set aside.
Using silicone cupcake liners, pour the raspberry mixture into the bottom of 18 molds about 3/4 of the way up. Top with cookie crust, evenly distributing the crumbs. Pat down the crust with the back of a spatula so the crust will have an even surface. Place in fridge for at least 4 hours or until set.
Take cheesecakes out of mold carefully by placing the bottoms into warm water, the molds should slide right off when place crust side down onto serving dish. Serve with optional whipped topping and fresh raspberries, enjoy!