South Brookline Real Estate

Tucked away between Chestnut Hill Village and the Buttonwood neighborhood, South Brookline is characterized by rolling hills, winding roadways, and large estates. Originally a farming community in the 18th century, the area still retains the mossy stonewalls and large open spaces that were common then. Conservation laws have helped preserve many of the larger estates as single-family residences. Early residents in the area built simple, wood homes which were replaced in the 1880s by larger homes of granite and brick as the wealthy Bostonians who designed them became exposed to European style in their travel overseas. With access to Brookline’s top-notch schools and close proximity to Boston, South Brookline attracts executives, medical professionals, and young families.   Read more about South Brookline real estate.

South Brookline Homes For Sale

South Brookline Homes For Sale November 29, 2022
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Lovely Fairgreen Place townhouse with spectacular views of The Country Club's 5th Fairway. 3 bedroom, 3 bath condominium. A past renovation by the current owners created an open floorplan and extra...

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South Brookline Location

South Brookline borders Newton Street to the north, northwest and northeast; Allendale Street to the northeast; and the VFW Parkway to the south. The area is served by MBTA bus lines and is eight miles from Downtown Boston.

South Brookline History

In the late 18th century, South Brookline served as a summer destination for Boston’s elite, who built seasonal estates among the rolling hills. By the mid-19th century the homes had expanded in size and were known for their luxurious details and lush gardens. Ignatius Sargent purchased the "Holm Lea" estate in 1845, creating a world-class collection of rhododendrons fringed with majestic trees and a pond. The Anderson estate “Weld” was known for its eclectic style and regal Italian garden. Upon the Anderson family’s death, the estate was deeded to the town, becoming a premier park. South Brookline is a mecca for landscaping artistry, claiming a couple of the nation’s most influential designers and architects as residents — Frederick Law Olmsted and H.H. Richardson. Today, select estates from the era have been successfully repurposed for institutional use, including using the historic buildings and grounds as schools.

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