Land for sale in Massachusetts's Berkshire County recently totaled nearly $495 million and almost 100,000 acres. Berkshire County ranks second in the Colony State based on the combined acreage of land for sale of all the counties in the Bay State. Among cities in Berkshire County with farms and rural real estate for sale, Pittsfield had the most land for sale. Based on its natural assets, Berkshire County's economy is dependent on tourism and recreation. Berkshire County is one of the ten largest counties in Massachusetts (946 square miles). It's located in the Western Massachusetts region of Massachusetts.