I am assuming this is a property in England or Wales. If not, this may not be helpful at all...
If you know the person entitled to enforce the covenant is likely to try to do so you may have a problem. It is possible to go through a procedure to get the Lands Tribunal to decide that the covenant is no longer needed. This procedure is likely to be quite expensive so is only worth doing when the benefits obtained make the application worthwhile.
If the covenant is quite an old one and you do not know of anyone actually enforcing it - (local solicitors may well be able to tell you, because normally they AREN'T enforced and the covenant holders who do enforce or who are still active are generally quite notorious in their area!) - then you can often obtain restrictive covnenant indemnity insurance. This is more expensive if you get it before you commit the breach. If you think the risk is small, then you could break the covenant and wait a year and then seek insurance. The rates are generally cheaper then, as it is most likely that if a claim is going to be made it will happen in the first year.
It goes without saying that you mustn't approach anyone entitled to enforce the covenant at any stage, nor broadcast to the world and his wife the fact that you have the insurance (obviously serious buyers of the property are allowed to know).
Hope this helps.
As a conveyancing solicitor I believe the information given in the post to be useful but I accept no liability except to fee-paying clients.
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