Replacing flat roof with pitched roof on timber framed extension above garage

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Hello, new poster here.

Recently purchased my first house. It's a bit of a renovation project, a 1960's 3 bed detached that had as some point in the early 90's had an additional room added above the garage. The house was bought from probate from an 101 year old man. Much of house has never been touched including the 1960s kitchen and bathroom etc, but there have been some alternations such as the room above the garage (which I'm currently using as a bedroom).

The room is actually fine, its insulated and water tight and sound but it does have a (fairly recently replaced) flat roof.

Just wondering what my options are here, the flat roof is both a bit of an eyesore these days (all surrounding properties have pitched extensions - albeit on proper brick walls), and the flat roof also obviously is fairly noisy / has less insulated properties.

The garage below is single skin with piers, the extension appears to have been build early 90's. If things weren't so financially untenable atm I would be considering tearing down the garage and construction a proper brick double storey extension (which is what the neighbours with the identical houses around have done) but as it stands prices are through the roof for that kind of construction and house prices are going down so I don't think that's a very clever move.

Ultimately just want to know if it's possible to at least make it look like a normal extension (and have the added piece of mind of removing one flat roof failure point), not sure if the garage below would be able to support if you know what I mean.
 
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Hello, new poster here.

Recently purchased my first house. It's a bit of a renovation project, a 1960's 3 bed detached that had as some point in the early 90's had an additional room added above the garage. The house was bought from probate from an 101 year old man. Much of house has never been touched including the 1960s kitchen and bathroom etc, but there have been some alternations such as the room above the garage (which I'm currently using as a bedroom).

The room is actually fine, its insulated and water tight and sound but it does have a (fairly recently replaced) flat roof.

Just wondering what my options are here, the flat roof is both a bit of an eyesore these days (all surrounding properties have pitched extensions - albeit on proper brick walls), and the flat roof also obviously is fairly noisy / has less insulated properties.

The garage below is single skin with piers, the extension appears to have been build early 90's. If things weren't so financially untenable atm I would be considering tearing down the garage and construction a proper brick double storey extension (which is what the neighbours with the identical houses around have done) but as it stands prices are through the roof for that kind of construction and house prices are going down so I don't think that's a very clever move.

Ultimately just want to know if it's possible to at least make it look like a normal extension (and have the added piece of mind of removing one flat roof failure point), not sure if the garage below would be able to support if you know what I mean.
The first question an SE or building control will ask is, what are the existing foundations like (depth width thickness etc)?
Was there any paperwork accompanying the existing roof room? Is it safe, legal? Is there a staircase or escape route?

You need to consider what would be the most economical route, via say a designer, in order to establish the best way forward. We have in the past, dug down internally, laid new internal foundations and built a compliant insulated structure, from within. I.e. adding a load bearing skin from the inside. From there you could potentially build the rest how you wish, as long as the exiting brickwork foundations are adequate.
 

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