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I haven't done this, but did own a share of freehold until recently. If you own the freehold I'd have thought this should be simple, presumably needing little less than an agreement with the other owners (and it's in all your benefit to do it).
Sounds like a question for a solicitor but they should be able to draft a new lease which just refers back to the current one but with an extended term on it and this should be relatively inexpensive.
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The vendor I just bought my flat from did this. I researched a lot before making my offer as originally the vendor was reluctant to sort it herself. It's a relatively simple process provided the other freeholders want to extend as well. How many freeholders are there? The more there are the more complex it will be.
If you all want to extend then you simply charge yourselves £1 for the lease and get the paperwork written out for a new 999 year lease.
The only issue you could encounter is if any of the other freeholders don't want to renew (because they never plan to sell or some other reason) they are entitled to charge marriage value for your effective uplift.PM if you want the details of the guy who did ours, he was efficient and cheap. Especially compared to some quotes I had.
has anyone ever extended the underlying lease on a share of freehold property? How hard is this, and did you encounter any issues along the way?