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Motorists are bracing themselves for a month of diversions as Southern Water prepares to replace an underground valve.
The firm has applied for the A250 Sheerness High Street to be closed at the canal where it meets the Halfway Road on Sheppey from Monday to February 25.
Residents say there has been a leak at that location since 2017.
Swale councillor Cameron Beart (Con, Queenborough and Halfway) said: "It is incredibly frustrating that a major route is having to be closed again for utilities works. There has been a persistent leak there for several years.
"It is about time that responsibility was taken for it and the cause of the leak found and repaired for good."
Cllr Beart, who is also a Kent County Council councillor for the Island, added: "The water main at this location is the main supply for some 5,500 homes. Residents have been reporting this leak since a new main was fitted in 2017.
"I dread to think how much it has cost in wasted water during all that time."
It is understood a trench will have to dug across the full width of the road, forcing motorists from Halfway to take six-mile diversions.
They will either have to go through Minster and along Marine Parade in Sheerness or go via Queenborough Corner, Brielle Way and Blue Town putting extra pressure on the small roundabout by Tesco in Bridge Road.
The road in front of the town's railway station is often gridlocked when extra traffic is funnelled into it caused by roadworks elsewhere on the Island.
Bus operators have been notified of the diversions.
Cllr Beart added: "The new works will include a full closure of the road from January 24 and will potentially last until February 25 although the road will be reopened as soon as the work is complete."
A specialist emergency valve had to be installed by a team from Derby back in October 2017.
Southern Water had planned to close the road in January 2019 for three weeks but called off the work at the last minute saying it was "no longer needed."
Sheppey has suffered a string of serious water leaks in recent years.
In January 2016, the Island was cut off after its principal main burst beneath the A249 at Sittingbourne.
A spokesman for Southern Water said: "We are renewing a pressure relief valve which has come to the end of its life, capping off a six-inch and 10-inch main which are now redundant and repairing a nearby leak."
He stressed it was not related to the previous repair and added: "We will get this completed as quickly as possible. We apologise to everyone in advance for any inconvenience this may cause."