Work has begun in Coleford, Gloucestershire, to prevent a repeat of the damage caused in 2007 when 57 properties flooded.
Pavements in St John's Street are being reshaped to allow water from heavy storms to reach the drainage system without hitting obstructions.
Road-wide speed humps are being replaced with cushions to prevent water building up and flowing over pavements.
The street will be closed until 12 October while the work is done.
Councillor Terry Hale, county councillor for Coleford, said: "Coleford has suffered for generations yet until the great flood of 2007 we had been a minority.
"Hopefully it will now be possible for further funding to be made available to alleviate the misery first recorded in the late 1700s."
This is Phase 2 of the surface water drainage works in Coleford town centre.
Gloucestershire Highways carried out the first phase in the spring.
The earlier works took in Newland Street, Market Place, High Street and Bowens Hill.
Gloucestershire Highways is carrying out this work following the Coleford Area Drainage Feasibility Study jointly funded by the Forest of Dean District Council, Gloucestershire County Council and the South West Development Agency as part of a major flood alleviation project in Coleford.