I show and sell properties in both towns, and both are VERY desirable towns. The better choice is of course subjective... which property "feels" right to YOU. But, there are practical issues to consider for re-sale. Properties on busy roads tend to take longer to sell. Privacy is scarce and desirable for re-sale. You almost can't go wrong in this market... a $500,000 property in either town is likely to be very attractive and only go up in value. A good buyer's agent can provide more advice on the subject of investment potential/re-sale.
Good luck in your decision!
Associate Broker, Massachusetts, New York, and Connecticut
Berkshire Property Agents
12 Railroad Street
Great Barrington, Massachusetts 01230