The MassHealth lookback period is not the same thing as the MassHealth disqualification period. The MassHealth lookback period is a flat five (5) year period. When a MassHealth application is filed, the state MassHealth agency looks back at financial transactions for the five (5) years preceding the application date. Based on whatever the state MassHealth agency finds in the lookback period, a disqualification period can be imposed by the agency.
The MassHealth disqualification period is not five (5) years, but rather is calculated by the state MassHealth agency based on the facts of the application. The disqualification period is based on how much was given away during the lookback period, and is also based on how much the average Massachusetts nursing home costs at the time of the MassHealth application.
When a MassHealth application is filed, the lookback period is created. In some cases, there is a lengthy MassHealth disqualification period that could be avoided if the filing of the MassHealth application were delayed. Thus, a thorough understanding of the interaction between the MassHealth lookback and disqualification periods is needed before deciding when to file a MassHealth application.
MassHealth: Medicaid in Massachusetts 
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[…] 14. Ineligibility or Disqualification Period. Any gifts or below market sales during the five-year lookback period can be penalized by a period of MassHealth ineligibility. Unfortunately, that period does not begin until you are left with only $2,000 in countable assets. (See What Is the Difference Between the MassHealth Lookback and Disqualification Periods?) […]