Stereochemistry of cyclic hemiketal formation
No, the stereochemistry of the methyl group is not dependent on which face the $\ce{-OH}$ attacks from. This is apparent in the products of the cyclization of aldopyranoses; only two isomers (called anomers) are formed, which are classified as either $\alpha$ or $\beta$:



Depending on which position we are considering the stereochemistry of, a wedge in the straight chain could appear as either a wedge or a dash in the cyclic form. For the molecule you are considering:

$\hspace{.7cm}$

To visualize this, convert the skeletal structure into its Fischer projection:

$\hspace{4.5cm}$

$\hspace{2cm}$