The aim of this paper is to investigate native and non-native linguistic intuitions, by focusing on one of the most controversial topics in second language (L2) literature, i.e. the acquisition of word order and the role of the native language (L1) during different developmental stages. Data are elicited with the use of a Magnitude Estimation task. The target language is Greek, a language with a flexible word order. L2 learners come from two L1 backgrounds, namely Albanian (+ flexible word order) and English (- flexible word order), and are divided into two groups: elementary (N: 34) and advanced (N: 50). Their judgments are compared to those of a control group of native speakers (N: 27). Preliminary results indicate that L1 structure and level of proficiency in the L2 may have an effect on learners' judgements; additionally, processing and conceptual accessibility are found to affect word order preferences in different ways for each group of speakers.