Thanks to the railroad, streetcar, and parkway, commuters flocked to new single-family houses, two-family dwellings, and three-deckers that lined the neighborhood by the early 20th century. By this time, Boston's Emerald Necklace park system included Olmsted Park, Jamaica Pond, the Arnold Arboretum, and Franklin Park.

Wealthy Bostonians were also attracted to Jamaica Plain as a location for their summer estates. Of these, only the Loring-Greenough House of 1760 at 12 South Street remains. With its adjoining carriage house and gardens, this grand structure retains some of the feeling of a country estate. The house was built for British Royal Navy officer Joshua Loring, who fled to British-occupied Boston during the Revolutionary War. American General Nathanael Greene set up temporary headquarters here, and the house was also used as all military hospital.

This history of Jamaica Plain was provided by the Boston Landmark Commissions.