Benjamin Realty lists 33 homes for sale in Winchendon, MA right now, with a median asking price of $425,000 (from $290,000 to $1,275,000). 3 listings came on the market in the last 7 days. By type: 28 single-family homes and 5 multi-family homes. The median asking price per square foot is $242. Median prices by size: two-bedrooms $311,000, three-bedrooms $461,950 and four or more bedrooms $424,500.