Scott's Woods Historic District is the area of Hillside, Harland and Forest Streets between Randolph Avenue and the ridge between Hancock and Bugbee Hills, now the MDC Blue Hills Reservation. Originally known as the "Blue Hill Land," a three thousand-acre tract of land sold by the town of Boston in 1711 to four residents of Milton, the area in the southwest part of Milton is thought to have been named for a member of the Scott Family that lived in the area in the early eighteenth century. Hillside Street, named for being literally on the 'side' of Blue Hill, is the major thoroughfare in the district.
The area of Scott's Woods, a 122-acre district, has remained a rural residential enclave separated from Randolph Avenue by a distinctly country-like atmosphere. Among the houses in this area are the Capen House (c.1655) that was moved to Milton in 1909 from Dorchester, Massachusetts. This First Period house, in addition to significant eighteenth through early twentieth Century houses, in addition to their outbuildings, give the best representation of the pre-twentieth century aspect of Milton as a suburban town of Boston. Despite the opposition of the Historical Commission, a new owner of this property had the Capen house disassembled and removed from the Hillside Street site in 2006. The commission has no information regarding any future reconstruction of this important building.
- Capen House - Highland Street (moved from Dorchester 1909) (c.1658)
- John Gibbons House - Highland Street (c.1815)
- Miller House - Hillside Street and Randolph Avenue (1798)
- Samuel Tucker House - Hillside Street (c.1798)
- Daniel French House
- Artemus Kennedy House
- Bezer Thayer House
- Hunt House
- Reed House Highland and Reed Streets (c.1724)