DHS received a grant in 2011 to improve and further implement landscape plans at the historical society properties on Boston St in Dorchester.

The group received a grant through the Boston Grants Initiative in 2007 to improve the condition of its grounds on Boston Street in order to facilitate their use, to better reflect the historic importance of the site and to improve the public perception of the DHS and its value to the community. In 2009 DHS received a BGI grant to improve the landscape at the Dorchester Historical Society headquarters, to create a greater awareness within a traditionally underserved urban population of the benefits of locally-grown food, and to create an opportunity to emphasize Dorchester's agricultural heritage.