Homes and businesses were left under water in Bewdley after the River Severn breached the flood barriers at Beales Corner on Friday night.
The river level is now reducing again after peaking at 5.43 metres (17ft 10in) on Saturday afternoon but some areas are still under water and the river level is expected to stay high for several days.
Many residents were evacuated late on Friday as the river became dangerously high and firefighters have been busy helping residents across Bewdley and nearby Stourport.
Some home and business owners had only just recovered from the damage caused by flooding last February - with this year's water level falling just short of the height reached last year - and it is the third year of flooding in the town in a row.
The highest river level ever recorded in the town was 5.56m (18ft 3in) in November 2000.
Lindsay Wilson, 59, who has lived in Bewdley all her life, lets a property on Beales Corner and is also flood volunteer.
She said: "It has taken me 10 months to get the house back into a habitable state. I had just got a tenant in who has paid one month's rent and now she is homeless.
"I had done as much damage limitation as possible, even had flood defence doors fitted, but it was a deluge, the water came up through the floor and walls. There was nothing anyone could do.
"My tenant was asked to evacuate at 10.30pm last night and is safe staying with friends.
"After last year's floods, the insurance renewal wanted £5,000 excess to cover the house.
"We are getting permanent flood barriers, but due to funding, it is estimated these won't be installed for two to three years.
"The whole town suffers when it floods, and this has a real knock on effect, particularly in normal circumstances when people are travelling to work and school."
Sara Hemmings, who lives with husband Giles and their four children, used to live in Beales Corner and witnessed the floods first-hand last year.
The family has now moved to nearby Westbourne Street and escaped the floods this time round.
Sara said: "In the last floods we lived on Beales Corner and the water stopped just before our house although our cellar flooded to shoulder height and we lost items that we did not have time to move out.
"The floods this morning have reached exactly the same point they did last February.
"The same houses have flooded in the same way with the barriers being breached.
"Some people have not even moved back home from last time while others have just finished re-fitting their homes, only to be flooded again.
"The essential shops that are able to open will now be unreachable for some and for those now shielding or trying to stay local or self isolating, suffering with Covid-19, this is just another huge blow at such a difficult time.
"I just hope a full support package can be quickly put in place for people especially those who are maybe now struggling to get home insurance."
During a visit in March 2020, Boris Johnson was heckled by residents and branded a “traitor” for failing to meet badly-affected communities during the height of the flooding.
Mr Johnson claimed he would “get Bewdley done”, but more permanent defences are yet to be put in place.
Temporary flood defences were erected in the town in both 2019 and 2020 as the National Audit Office warned that the share of funding for flood defences going to deprived areas had “reduced substantially” in recent years.
Last year, Bewdley was among the worst-hit areas in England.
During his 2020 visit, Mr Johnson received a mixed reception, as while many locals greeted him warmly, one person told him to “do your f****** job” as he posed with teenagers for a selfie on a bridge in the town.
Over in Stourport, Severn Caravan Park has been evacuated and is completely under water, as is the nearby fun fair.
Hereford and Worcester Fire Service rescued two people from a flooded caravan on Friday.
Richard Clarke, 59, who has lived in Stourport for more than 20 years said he was 'gobsmacked' by the damage caused by the floods.
He said: "I'm a fisherman, so at least once a week I walk down to the river and when I went along today I thought it was really high.
"We had floods about a month ago, but this time it is much worse, I was gobsmacked.
"The funfair has been flooded and is completely under water, and it has taken out all of the recreation area by the river."
One business that is offering to support residents in need is Greatfield Small Animal Rescue, from nearby Kidderminster.
Lindsey Hill, who works at the Sanctuary is keen for anyone who has been affected by the floods and needs support looking after their small animals to get in touch.
She can be reached by calling 07807117359.