Wood flour (WF)/polypropylene (PP) composites have been made by extrusion and hot press compression molding. The composite water uptake and flexural properties were investigated. The composite fracture surfaces were studied by SEM. WF esterified with octanoyl chloride was used in WF/PP composites to improve the composites' water resistance. Maleated polypropylene (MAPP) was also studied and compared with esterification by acid chlorides. Esterification by octanoyl chloride reduced the composite water uptake. However, the C-8 chain is still not long enough to form effective entanglements with the PP matrix. So, despite enhancements in hydrophobic interactions, flexural strengths and flexural moduli decreased. MAPP (MW = 47000) polymer chains can entangle with the matrix polypropylene molecules. Therefore, when MAPP's maleic anhydride functions esterify WF surface hydroxyls, improved water resistance and composite flexural properties were achieved. The modifier chain length is of critical importance and more important than the surface density of hydrophobic groups for improving WF-PP interfacial adhesion and composite mechanical performance.