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It depends when the town last reassessed. Call the Tax Office in the towns you are looking at and ask. If the sale prices seem far off from the tax assessment, then they probably haven't reassessed for a while and they might be reassessing soon in the future.
Keep in mind, reassessment doesn't mean your tax bill will go up (or down). It depends on what happens in the rest of the town.
Example, if you're in an older house that is assessed below market value in a town that has had a ton of new construction that is assessed at its value when it was built, then your taxes might go up.
But if the whole town is the same age, even if they reassess your taxes may not change all that much. Your taxes are (value of your house/value of whole town)*Town's budget.
When you buy an existing house (unlike new construction), they don't just up your reassessment to the purchase price that you pay, they have to do the whole town together.
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Market Value versus Assessed Value
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