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yep, currently windsor to reading isn't super easy by train - but a piece of piss by car as it is directly up the M4. crossrail will alleviate that (same goes for the slightly cheaper Maidenhead)
you'd also be extremely close to swinley @Dammit
Surely the cross rail would help here as it connects to Heathrow, central London and reading. Sure you’ve looked at this but I was speaking to cousin who lives in windsor and had forgotten how good useful it will be (if) it gets built