Covenants and restrictions (C&Rs) have increased in popularity in recent decades, being commonly applied in new residential developments. Despite the fact that developers are more commonly writing C&Rs for their developments, little research has investigated how well C&Rs actually fit the preferences of residents. Recognizing this gap in the literature, this paper examines the fit of neighborhood C&Rs with resident preferences in Porter County, Indiana, a growing suburban/exurban place in the Chicago Metropolitan Statistical Area. The researcher conducted in-depth interviews with 51 residents to ascertain how well C&Rs fit resident preferences. The majority of interviewees stated that C&Rs match resident preferences because they believed that C&Rs promoted subdivision tidiness and worked to support property values. The minority view was that C&Rs do not fit because they are too strict and residents do not obey C&Rs. Interviewees who perceived a fit were more likely to have a lower level of engagement with C&Rs and were more likely to live in developments with no C&R enforcement attempts by the homeowners’ association (HOA). The results suggest the particular content of C&Rs does not seem to fit resident preference; rather the fact that C&Rs are not enforced fits resident preference. Seemingly, residents are content being unaware of the C&Rs, then they do not know if someone is breaking the rules or not. This may imply that residents would not want to have C&Rs in the first place.