Real Estate Law
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Does the lease state that the tenant has to exercise that option within a certain period of time?
Do they have to exercise it before the current lease expires?
Ok, then this is pretty clear to me.. If they didn't exercise the option as required under the lease contract, or they can't prove that they did, then that option lapsed and when the lease expired, if the parties continued on with the tenancy, then it converts to a month to month by default with either party being able to terminate with a 30 day written notice. See Mass. Gen. Laws Ann. ch. 186 § 12.
So no, he can't do a 14 day, as the tenant is a month to month tenant if they pay monthly and that requires a 30 day written notice.
As an aside, in addition to being an attorney, I have also been a landlord for over 26 years...
Yes, landlording is lots of fun...no work, we just ride around and collect rent and wave at people....at least that is what the tenants and non landlords think... And yes, I have residential rentals as well... and I do all my own maintenance..
If you didn't give them a written 30 day, then there is nothing that would prevent you from sending a new notice stating you are rescinding the previous one and the tenant now has 30 days to vacate (make sure you count starting the day after delivery) as you are terminating the tenancy under Mass. Gen. Laws Ann. ch. 186 § 12.
Then you just sit back and wait for the 30 days to expire. However, if they get the idea that they don't have to pay rent when due for the next month, you can accelerate that notice to a 14 day notice for to pay or vacate. That doesn't negate the 30, it just might allow you to get them out sooner. For example rent is due on the 15th... you give them a 30 day notice tomorrow, the 11th. It starts counting the 12th. But if they didn't pay rent when due on the 15th, you can then give them a 14 day and cut off about 2 weeks if they didn't pay. If they did pay, the 30 day is still in effect and you just have to wait the roughly 2 weeks extra to file to evict if they don't vacate.
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