Tottenham have been monitoring the progress of Grealish for months, with the player himself keen to join Mauricio Pochettino's side.
The 22-year-old, who joined Villa as a trainee in 2011, is destined to leave Villa Park this summer after the club missed out on a return to the Premier League.
Despite being a key part of Steve Bruce's side that made it to the Championship play-off final last season, former Spurs manager Redknapp does not believe moving to the North London club this summer would be the right choice for Grealish.
Speaking at the launch of AIB's The Toughest Series, Redknapp said:
He needs to go somewhere where he can play. If he goes somewhere to be a squad player, his career is going to go down.
He looks to me to be a kid who needs to be told he is great, that "we will build a team around you. You will be our main man. You will make things happen, everything has to go through you Jack, this is how we are going to play".
I think if he goes to a club like that he will keep progressing. If he goes to a club where is only a bit-part player, I don't know where he is going.
He's not going to replace Dele Alli, that's for sure. Or (Christian) Eriksen. You can't have a team of artists. We all want good players, but you also need (Victor) Wanyama's or whoever else you want to play in there.
He is a real good player but Tottenham are a bit overloaded in those areas.