Maintaining permanent forest canopy cover and eventually harvesting timber by predetermined target diameter are often considered as a prototype for future management of the oak natural forest. However, target diameters and harvest age based on average forest growth rates from wide geographical areas often hamper improved management of oak forests. In this study, based on the sampling of 129 target trees from 51 oak natural secondary forest plots in Hunan Province, China, an individual-tree DBH (diameter at breast height) growth model of oak target trees was developed, and the site type (41 levels) was related to the model as random effects by a nonlinear mixed-effects approach. Moreover, the 41 site types were clustered into four site type groups (STG1, STG2, STG3, and STG4) by the K-means clustering algorithm to improve the model performance and practicality. With the help of the model, the five target diameters (including 24, 30, 40, 50, and 60 cm) were simulated in each of the four STGs, and the minimum target diameter was determined for each STG based on the theory of quantitative maturity. In the four STGs, the harvest age of the 24 cm diameter target ranged from 30 to 51 years; the harvest age of the 60 cm target diameter ranged from 131 to 220 years, with the oaks failing to reach 60 cm in the lowest-quality STG4; the minimum target diameter ranged from 21 cm to 29 cm. Results showed that lower-quality sites exclude higher target diameters from optimal harvesting strategies, in contrast to the higher target diameter as a more reasonable strategy in higher quality sites, and that the minimum target diameter is significantly influenced by site conditions. Therefore, it is necessary to develop a diverse target-diameter-harvesting strategy adapted for the complex site conditions of oak forests in Hunan Province towards site-specific timber management to improve the sustainability of timber production in oak forests.