Hillside Avenue Housing is a 10-unit affordable rental community located in Great Barrington, within walking distance of the town center and one block from public transportation. The project sits on three acres of town-donated land — two of which are permanently preserved as open space — and includes one-, two-, and three-bedroom units (including one ADA-accessible unit) spread across three buildings. All units are Energy Star certified and served by town water and sewer, and the development serves as a model of Smart Growth design for rural towns.

Completed in 2009, Hillside Avenue was the first new construction of affordable rental housing in Great Barrington in more than a decade. The property is managed by Berkshire Property Managers (under co-developer/operating manager Berkshire Housing Development Corporation/Hearthway). In late 2022, the project received a $199,610 ARPA grant from the Town of Great Barrington for facility improvements.