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Heat oven to 400 F, Cut an "X" into the flat side of each chestnut shell. Place chestnuts in a single layer on a sheet pan with a lip. Roast until shells begin to peel back, about 15 to 20 minutes, stirring after 10 minutes. Remove from oven and let stand 5 minutes to cool. Peel shells and let chestnuts cool completely. In a medium saucepan, bring roasted and peeled chestnuts, sugar, and water to a boil. Reduce heat and simmer 25 to 35 minutes until most of the liquid has evaporated. Remove from heat and stir in vanilla. Strain the chestnuts, reserving the liquid. Blend chestnuts in a food processor until smooth. While the food processor is running, slowly add as much reserved syrup as necessary through the food chute to achieve the desired consistency. Let cool completely before refrigerating.
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