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 May 19, 2022
6
Listed
13
Avg. DOM
$556.06
Avg. $ / Sq.Ft.
$1,674,000
Med. List Price
6 Properties
Open 5/21
102 Princeton Rd Brookline, MA 02467
4
Beds
3F11/2
Baths
4,176
Sq.Ft.
1938
Year Built
3
Days on Site
72983044
MLS
Set on a double lot in prestigious Chestnut Hill, this stately single family residence offers a well-designed floor plan for grand entertaining and everyday living. An inviting foyer, with bowed...
5
Beds
3
Baths
3,475
Sq.Ft.
1945
Year Built
10
Days on Site
72979040
MLS
Located on a picturesque tree lined street in Chestnut Hill. This special 5 bed 3 bath home is easy living at its finest. The versatile layout features a gracious entry foyer with cathedral ceiling,...
4
Beds
3
Baths
3,209
Sq.Ft.
1936
Year Built
15
Days on Site
72977204
MLS
NEW PRICE:This classic colonial full of character and charm in the popular Baker School neighborhood is an opportunity that awaits you! Slate roof, 2 car garage, attractive serene yard, and stone...
3
Beds
2F11/2
Baths
2,817
Sq.Ft.
1946
Year Built
10
Days on Site
72978924
MLS
Wonderful 3 bed, 2.5 bath home located in Chestnut Hill. All 3 bedrooms are gracious in size and the primary suite has a beautifully updated bathroom. The other 1.5 baths have been updated as well....
4
Beds
3
Baths
2,240
Sq.Ft.
1966
Year Built
31
Days on Site
72968075
MLS
This amazing South Brookline raised ranch with a wonderful layout and spacious yard, is ready for you just in time for summer. The home features a kitchen and living area with an open floor plan and...
Open 5/22
25 Clearwater Rd Brookline, MA 02467
4
Beds
3
Baths
2,428
Sq.Ft.
1946
Year Built
17
Days on Site
72975714
MLS
This sparkling Brookline home, stands out with its fabulous open spaces and 4 bedrooms, in 2,425 sq ft of above ground living space. The main level features a spacious open floor plan, with a double...

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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