The left-back has spent the past campaign on loan at Brighton & Hove Albion after falling out of favour under former boss Paul Lambert.
Signed from Middlesbrough in August 2012 for £2.75 million, Bennett was a regular starter during his first season at Villa but made just seven appearances last term after losing his place to newcomer Antonio Luna and then loanee Ryan Bertrand.
With the since-departed Paul Lambert going on to add both Aly Cissokho and Kieran Richardson in the summer, the former England Under-21 international was shipped out to Brighton & Hove Albion on a season-long loan, where he earned solid reviews from 41 Championship starts.
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A permanent move either back to the Amex Stadium or to newly-promoted Watford has since been mooted, per the Argus, but the arrival of Sherwood at Villa also looks to have given him a chance of reviving his claret and blue career.
Left-back remains a problem area for the club, despite Richardson putting in some improved performances of late with Cissokho out injured, and the new boss has suggested that Bennett could be in contention for the job while speaking of him in glowing terms.
"I also like Joe. I'm going to assess him,” Sherwood said of the 25-year-old. "There's no reason why he can't come into that as well as he's a similar mould.
"He likes to get forward and has good quality in the final third.
"There's a real chance that he could be part of it next season as well."