Linpan settlements (abbreviated as Linpan) form an essential elementary unit of the villages scattered throughout the Chengdu Plain, Southwest China, where is the typical low radiation and calm wind area. Linpan is known for its multiple agroforestry ecosystem services. Building a comfortable microclimate in rural areas is one of its services. To identify the microclimatic effects of Linpan on the surrounding area, the microclimate conditions around 36 traditional Linpan, located in Sandaoyan town, Chengdu Plain, were measured during extreme seasons (i.e., summer and winter) of 2017 and 2018. Results indicate that Linpan exerted a cooling effect in summer and a warming effect in winter on the surrounding area. The mean cooling intensity (1.21 ± 0.49 °C) exceeded the mean warming intensity (0.76 ± 0.81 °C). It also provided decrease humidity (dehumidification), shading, and windbreak effects on the surrounding area. The largest influence distance (LID) of microclimatic variables are different, followed by the order of dehumidification distance (15 m) > cooling/warming distance (10 m) > windbreak distance (5 m in summer and 10 m in winter) > shading distance (5 m). Moreover, the intensities of shading and windbreak were also higher in summer than in winter. Tree canopy cover (TCC) of Linpan exerted a significant influence on the cooling effect in summer and the shading effect in winter. These findings are valuable for the understanding of rural heat stress in the low radiation and calm wind region. Several renewal strategies for Linpan were proposed to adjust the surrounding microclimate to improve the well-being of local inhabitants.