Karl Duguid has been offered a new two-and-a-half-year contract by Colchester United.
The U's striker has less than six months to run on his current deal and boss Steve Whitton is keen to tie him to a long-term contract before the end of the season.
Duguid, who came through the successful youth system at Layer Road, is thinking over Whitton's offer before committing his future to the club.
It is thought the main stumbling block could be the U's insistence the 21-year-old forward moves from his home near Luton to live in Colchester.
Letchworth-born Duguid, who was part of the U's play-off winning side in 1998, has always commuted to Layer Road for training and matches.
But Whitton wants him to live nearer the club and it's a decision the player is currently discussing with his family.
The U's boss said: "We have offered Karl a new contract and we're hopeful he will be a big part of the future at Layer Road. It is reward for his hard work and sheer endeavour this season and I am delighted with his progress.
"There is no rush for him to sign the deal. We have made him an offer and I am confident he will sign it after he has discussed everything with his family."
Duguid, who began the season as a wing-back under former U's boss Mick Wadsworth, has blossomed under Whitton's guidance.
Restored to his favoured striking position he has scored some vital goals for the U's as they bid to climb away from the Second Division relegation zone.
Meanwhile, the U's are still waiting to hear back from Luton Town whether their bid for central defender Alan White has been successful.
The U's are thought to have offered somewhere in the region of £30,000 for the 23-year-old.
It is understood contract rebel David Greene was offered in exchange for White but Luton boss Lennie Lawrence wants the cash to finance his own rebuilding programme.
Luton want more than £30,000 for White, but know he can leave on a free transfer at the end of the season.
Whitton said: "Alan did well on loan at Colchester earlier in the season and I am hopeful something will happen before the end of the week."
Greene's possible move to Cardiff has been shelved following the departure of manager Frank Burrows earlier today.
Defeat at Reading on Saturday means Whitton has been pipped for the Nationwide manager of the month award for Division Two. The honour goes to Ian Holloway of table-topping Bristol Rovers.
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