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BOSTON POST ROAD: Weston
Now among the wealthiest towns in Massachusetts, Weston began in the 1600s as a farming community that sprang up along the Boston Post Road, an important Colonial mail route first pounded out of forest by the feet of Indians. Stretching to the Connecticut River Valley, the roads best-preserved 3.5 miles is in Weston, with a well-maintained mix of architectural styles spanning the centuries. At the moment, the houses on the market range from a 1,200-square-foot 1852 Colonial -- asking price just $499,900 -- to a seven-bedroom Federal style five times the size and going for nearly $3 million.