Ipswich's Great White Horse Hotel and Stoke By Nayland Parish Church are two of Suffolk's best-known buildings and are strongly associated with Charles Dickens and John Constable.
But now both are on Historic England's "Heritage at Risk" register - although there are hopes that neither will stay there long.
The Great White Horse dates from the 16th or 17th century - although took on its current appearance during Georgian times.
It was historically Ipswich's leading hotel and coaching inn used by carriages travelling between London and the East Anglian coast.
Charles Dickens visited it twice - although he may only have stayed there on one occasion - and it featured strongly in part of one of his early works, The Pickwick Papers.
The Great White Horse continues to operate as a hotel, but Historic England has identified problems with the roof and detected dry rot in one room that is not currently open to guests.
The drainpipes and guttering is in a poor condition and parts of the exterior joinery needs attention.
Historic England says it is working with the owners of the building and Ipswich council to ensure the work is undertaken.
A spokeswoman for Historic England said: "We have had discussions with the local authority and the owner and we are offering what support we can to get the work completed."
She said the fact that the building was on the Heritage at Risk register meant it was easier for the owners to get advice and help with its restoration.
Carole Jones, Ipswich Borough Council portfolio holder for museums said: “The Great White Horse Hotel is historically important to Ipswich and we fully support Historic England’s decision to add it to their Heritage At Risk Register.
"We are working closely with the owners of the building to achieve updated condition surveys for the Grade II listed building, which has also been added to our own Buildings at Risk Register.”
Dickens was no fan of the Great White Horse - in The Pickwick Papers he poked fun at its small rooms and winding corridors.
That didn't go down well with the owners at the time - but by the 20th century the Dickensian connection became a key selling point for the hotel which boasted the Pickwick Grill which was a favourite place for a quick meal for many local people.
St Mary's Church in Stoke By Nayland was put on the Heritage at Risk register at the end of last year as work started to repair damage that caused part of a wall to collapse in 2020.
The first sign that something was wrong came when a window fell out of its frame and had to be repaired - that has now been completed as part of the overall work.
The church and its spire are a landmark in the Dedham Vale - and it features in many pictures by local artist John Constable.
Historic England's spokeswoman said the church was added to the Heritage at Risk Register as they were facing the prospect of having to complete very urgent repair work to the chancel to make the roof watertight.
Since then the Parochial Church Council had undertaken amazing fundraising efforts to achieve the repairs.
She said Historic England has awarded a repair grant of £135,507. The repairs are due to be completed by the end of this year.
Once the work has been completed it will need to be checked by Historic England - and if the problems have been addressed it is likely to be taken off next year's Heritage at Risk register.
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