Oral diseases are a common health concern within the United States, and have been associated with increased risk of certain chronic disease and reduced overall quality of life. A unique starch-based confection containing freeze-dried strawberries was developed for sustained, targeted phytochemical release to the oral mucosa for use in future chemoprevention trials. Sensory evaluation was used to optimize the confectionery formulation for this investigation. Physicochemical properties, scanning electron microscopy and dissolution studies revealed the effects of 14-day storage on phytochemical release from the amorphous semisolid matrix. Upon storage, moisture content decreased 4% and water was more tightly bound. Rheological testing revealed Newtonian-like response to shear below 10 s−1 and pseudoplastic behavior at higher shear. Changes in the food structure were observed with scanning electron microscopy. Total phenolics released in phosphate buffer (47.2 ± 2.7 mg GAE/L) or simulated saliva (66.7 ± 1.2 mg GAE/L) after 10 h from fresh confections was significantly (p = 0.001) greater compared to stored confections in phosphate buffer (39.0 ± 2.9 mg GAE/L) and simulated saliva (56.4 ± 1.0 mg GAE/L). Strawberry confections may be a novel strategy for localized delivery and sustained release of strawberry bioactive compounds.