With the aim to separate and purify procyanidins from chestnut-shells (CSPCs) by macroporous resin, twelve macroporous resins were tested for their static adsorption/desorption performance towards CSPCs. Based on the static adsorption experiments, the suitable macroporous resin was screened to carry out dynamic adsorption experiment, the content and the relative molecular weight of CSPCs were analyzed. The results showed that AB-8 was the optimal macroporous resin for separating and purifying CSPCs, the optimum separating condition was as follows: the mass concentration and the sampling rate were 1.864 mg/mL and 2 mL/min, respectively. The total recovery of CSPCs reached 94.2% eluted with 50% ethanol of 4 BV at a flow velocity of 1 mL/min, and the content of the total CSPCs in the obtained fine product was 89.8%. Analysis of CSPCs by ESI-MS demonstrated the molecular weight ranged from 289.4 to 1154.9 (M+H) within 4 of average polymeric degree.