5 boats and yachts for sale in Pittsfield, Massachusetts, priced $19,995 to $116,500, including aluminum fishing boats, bass boats, powerboats. 2 of the 5 are listed by their owners; the rest are dealer or broker listings, each badged so you know who you are dealing with. Every listing badged FSBO, Broker or Dealer — contact each seller directly. Newest added 2026-11-08.