Stephen Wicks, Country & Met's chief executive, said he hoped to meet Bill Cran, chairman of Headway. "At the moment this is trade investment but we are looking to talk to the company," he said.
"If anything happens with Headway we would do it as a joint venture with Allied Commercial [Fleet's parent company], as it has got a lot more resources available."
The joint-venture team is attracted by five brownfield sites belonging to Headway in the north of England and the Cotswolds, which they believe have the potential to produce high levels of rental income.
Allied Commercial is run by property tycoon "Black Jack" Dellal. The firm holds a stake in Country & Met.
Country & Met has long considered Headway a takeover target because its assets would be a good fit with some of Country & Met's developments.
Wicks admitted that Country & Metropolitan's stake-building in Headway had lost some momentum because of the acquisition of NorthCountry Homes for £10.2m in cash and 225,000 shares in July last year.
Wicks said: "We have had shares in Headway for a long time but the Northcountry acquisition put it on the backburner. We still see some value in the company."
Leslie Kent, an analyst at stockbroker JM Finn, said: "Quite clearly, Country & Metropolitan is a residential and commercial property developer that has spent money – not a little money – in Headway, whose assets per share exceed its share price."
Headway's interim results for the six months to 31 December showed that the figure for net assets per share was 102p. On Monday the share price closed at 87p.