Shopping for a home? The list price isn't the only consideration when looking at affordability. What is the annual tax bill? Did the real estate agent provide the most current year's assessment and tax amount? What is the monthly cost? My taxes are $5,000 which adds $420 per month to my mortgage payment. That's a car payment for a lot of folks. Here's are the cities and towns with the biggest property tax bills in Massachusetts. Use this tool to search your town or the town you are considering moving to.