Homes in Bewdley and Ironbridge have been evacuated as rising levels in the River Severn topped or compromised flood defences, with more rain forecast and water levels expected to rise.
An emergency evacuation was declared at around midday in the Wharfage area of nearby Ironbridge after flood defences moved overnight.
Explaining the evacuations in a video posted on Twitter, West Mercia Police Chief Superintendent Tom Harding said the flood defences had been "compromised" and were "buckling" in some areas.
He said: "Potentially, we've got water that has started to come underneath the flood barriers and in areas it appears that it is buckling.
"We want to be open and transparent with the public and residents here so they make that informed decision to come with us.
"If you can spread the word and pass that on to any family or friends in the area that we need to make sure that they leave."
Flooding along parts of the river, which remained close to its highest levels in some areas, is likely until at least Sunday, the Environment Agency said.
Police could be seen knocking on doors along the riverside to ensure that residents living on Wharfage had left their homes.
Barriers were also erected in side streets to ensure that people did not approach the river.
Temporary flood defences along Wharfage had been pushed back towards a pub and other businesses, sparking fears that the defences could be fully breached.
Some residents declined to leave their properties, including one occupant who also opted not to move a car parked within yards of the riverside.
War veteran Albert Darlington, a resident of Ironbridge, told ITV News he is not worried about the flooding as it stands as he is "watching the situation" from his home.
He said he's only concerned if the flood barriers break, in which case the water will "come down in a rush and that's a different matter."
Mr Darlington added: "But at the moment it's only slopping over the top and coming underneath, so you only get a dribble down this end."
His home did flood in 2000, when there were no barriers in place, but he said he does not feel in danger.
"Even if the water does come down...you'll have a foot of water on the floor, there's still no need to panic," Mr Darlington said.
"You only panic if you get Niagra Falls and you're underwater and you can't do nothing. It'll take hours to get up to like that, it would have to come under all the doors and you have got an hour or so to get out."
Two severe flood warnings remained in place in Ironbridge and Shrewsbury, meaning there is an immediate risk to life.
Severe flooding is expected to hit low-lying areas along the River Severn on Wednesday amid record-breaking river levels, including in Bewdley, where it is expected to come close to its highest recorded level, which was 5.56m in November 2000.
The Environment Agency forecasts the river level in the town, which has risen more than two metres in the past 72 hours, from 3.36m to 5.45m, will peak at 5.48m on Wednesday.
Homes in the Worcestershire town were also evacuated after the river spilled over barriers at Beales Corner.
Marc Lidderth, environment manager for the Environment Agency, said: "Over the next 24 hours, we will see the river levels remain elevated at Ironbridge and further upstream at Shrewsbury.
"Further downstream into Bridgnorth and Bewdley, the peak is making its way down the system.
"We will be seeing the peak at Bewdley happening round about later this afternoon.
"Unfortunately we have already seen some of our barriers over-topped there in the early hours, where properties have flooded.
"Obviously our thoughts go out to everyone that's been affected by that."
Rupert Evelyn reports from Bewdley where the River Severn has breached flood defences
Geoff Baker is one of those whose home in Bewdley was flooded after water breached the flood defences.
The 88-year-old said he was "upset" that he had not had "enough warning" to move items out of the way of the flood water.
Shrewsbury Railway Station remained closed on Wednesday morning after flood waters hit the Severn Viaduct - the main route in for the majority of lines.
Network Rail described the flooding as a "once in a generation event".
Forecasters have warned of more rain over the coming days - hampering recovery efforts in areas of the UK most affected by the severe weather.
In the wake of Storms Ciara and Dennis and the ongoing flooding, Prime Minister Boris Johnson has come under fire for not visiting flood-hit areas.
During Prime Minister's Questions, Labour leader Jeremy Corbyn - who has visited flood-hit communities - attacked the "part-time" Prime Minister for being "AWOL" and only being prepared "to pose for cameras when there's an election on".
He also highlighted the difficulties of homeowners who live in areas prone to flooding to get insurance.
Mr Corbyn quoted Calder Valley and Tory MP Craig Whittaker who said the PM's lack of appearance was "not good enough".
In response, Mr Johnson said the Government had "not only been investing massively in flood defences and compensating those hit by flooding" but it had also bee busy working on numerous matters, such as "stopping the early release of terrorists".
Earlier on Wednesday, Environment Secretary George Eustice was also forced to defend the Prime Minister.
When questioned by ITV News Political Correspondent Daniel Hewitt about Mr Johnson's absence, Mr Eustice said it would not have made "any difference" if the PM had visited and that people are more focused on sorting out their flood-hit homes than being visited by politicians.
He continued that Mr Johnson had made visits to flood-hit communities during the election period as rules surrounding it made it difficult for individual ministers to go.
Both Mr Eustice and flooding minister Rebecca Pow have both made visits to areas hit by flooding.
According to the Environment Agency, England has already seen more than 200% its average February rainfall but forecasters are warning more is on the way.
The Met Office has predicted further showers across the UK on Wednesday, followed by even more rainfall on Thursday and Friday.
Forecaster John Griffiths said between 5mm to 10mm could fall on the River Severn's source, the Welsh hills, throughout Wednesday, with other parts of the UK seeing up to 2mm.
A further 5mm to 10mm of rain is forecast for most areas on Thursday.
Predictions increase to 10mm to 20mm of rain in a 24-hour period between Friday and Saturday morning.
Downpours are expected to hit areas already deluged including areas in Wales, Cumbria and Yorkshire.
The Environment Agency has warned flooding is possible on the rivers Wye, Ouse and Trent, with other areas at risk from localised flooding caused by heavy rainfall .
Alongside the 103 flood warnings, a further 147 flood alerts are in place - meaning flooding is possible in the affected areas.