Combine first 3 ingredients and 2 tablespoons sugar in a large bowl; cover and chill at least 2 hours.
Beat cream until foamy. Gradually add remaining 2 tablespoons sugar and vanilla, beating until soft peaks form.
Layer 2 tablespoons whipped cream, one half of a crumbled shortcake, and 1/4 cup fruit mixture into each of 8 (12-ounce) parfait glasses. Repeat layers, ending with fruit. Cover and chill 2 to 8 hours. (The longer the parfaits chill, the more the sweet fruit syrup soaks into the crumbled shortcake layers, allowing flavors to blend.)
Top parfaits evenly with remaining whipped cream before serving.
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