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

New
239 Wolcott Road, Brookline
  • Single Family
  • 5 Beds
  • 3.5 Baths
  • 4,521 SqFt

239 Wolcott Road, Brookline

$2,395,000
86 Woodcliff Road, Brookline
  • Single Family
  • 4 Beds
  • 3 Baths
  • 4,064 SqFt

86 Woodcliff Road, Brookline

$1,879,900 ↓ $20,000
296 Russett Road, Brookline
  • Single Family
  • 3 Beds
  • 3.5 Baths
  • 2,402 SqFt

296 Russett Road, Brookline

$1,388,000

More About South Brookline Real Estate

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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