"I'd like to get him signed," Shanahan told the Sun. "He's the type of player I like, the type of player we need.
"This is a guy we want to have back. Dave (Leafs GM Nonis) knows I want him back. But any time you are a UFA, there are other factors involved.
"He's got to want to play for us, as well."
Bolland is set to become an unrestricted free agent July 1. As much as the Leafs want him back, the belief is that he is looking for a long-term deal, in the six-to-eight year range, worth more than $5 million per season, which might be too high for Toronto's liking.
Bolland's agent Anton Thun reiterated his client's desire to stay in Toronto, but also told the Sun other elements will come into play.
"There are other considerations involved here," Thun said, "things such as market value along with other factors."
With just over $48.7 million committed to 12 players for next season, according to CapGeek.com, the Leafs will have around $19.3 million to $22.3 million in available cap space to play with, depending on what the final cap number for the 2014-15 season ends up being.
The Leafs plan on tinkering with their roster quite a bit this off-season, which could create more cap space or less, depending on what route Shanahan and Nonis take.
Goalie James Reimer is among those expected to be traded, while pending free agents Nikolai Kulemin and Paul Ranger aren't likely to be re-signed.