Yes and no. You'll never see a $100 bond callable today selling for $105, because nobody would buy it knowing they might instantly lose $5 on the transaction if it were called tomorrow. IF the bond was selling for $105, yes you'd lose it the $5. But it won't (or shouldn't be), so you won't.
Two of the advertised yields on a callable bond are Yield To Maturity (if you hold it until matures) and Yield To Worst (if the bond your paid a premium for is called). Example:
-You buy a $100 bond for $105 with a 10% coupon callable in one year. In a year they call it. On one hand you got your $10 from the interest. On the other, they gave you back $100 so you lost $5 in principle. The Yield to Maturity would likely have been close to 10%, but your Yield to Worst would have been 5%. Both of these rates should be advertised for a bond you're buying and it's important to know both.
If current rates are way lower than the rates at issue, than the issuer may very likely call their bonds asap and the re-issue them at the current lower rate. If the current rates are lower, they're less likely.