South Brookline

South Brookline is a picturesque neighborhood that offers a blend of suburban charm and urban convenience. Home to some impressive mansions on sizable plots of land, surrounded by lush green landscapes and beautiful trees, residents here enjoy a tranquil environment that's a mere 5-10 minutes from many of Brookline’s restaurants and shops and only a little further to Boston. Despite its close proximity to Boston, South Brookline maintains a sense of seclusion and peace, often feeling more like a quiet retreat than a suburb on the edge of a major city.

The architecture in South Brookline consists mainly of grand, historic homes, but recently some modern singles have been built - and the construction of new homes in the area persists. It’s easy to be awed by homes in South Brookline, which are a huge part of the neighborhood's character. Property values in South Brookline tend to be high, reflecting the area's desirability.

The average 2025 assessed value for homes in South Brookline was approximately $1,615,000. However, if you consider the estates near the Brookline Reservoir and Heath Street areas as part of South Brookline as we do, the average home value was substantially more. The average "estate" home was assessed for about $4.8 Million. So when looking for a home in South Brookline, you will find a wide range of streets with an even wider range of home values. 

The parks in South Brookline, including Larz Anderson Park and the Brookline Reservoir along Route 9, are popular spots for families and outdoor enthusiasts. They provide a scenic backdrop for a range of activities, from jogging and picnicking to ice skating and sledding in the winter. And let’s not forget Skyline Park, home to many Brookline high school and youth soccer games.

When it comes to dining, South Brookline does not disappoint. It boasts an array of restaurants in Chestnut Hill, ranging from coffee shops to upscale dining experiences. These establishments offer a variety of cuisines, catering to diverse palates and dining preferences. As an added bonus, parking is free and easy.

Public transportation in South Brookline is served by the Green Line’s D train, and the 60 and 51 buses, connecting the neighborhood to other parts of Brookline and Boston. The D train is a reliable means of transportation in and out of Boston but its location in Chestnut Hill makes it less accessible for many South Brookline residents. The fact is that most South Brookline residents own and rely on a car to get around.

The Baker School is the main public elementary school serving South Brookline children. However, there are a portion of South Brookline students that attend Hayes School(formerly Heath). In addition, there are five private schools in the area including The Chestnut Hill School, Brimmer and May, Beaver Country Day School, Park School, and Dexter Southfield, making South Brookline a hub of academic excellence.

Living in South Brookline offers a balanced lifestyle with the benefits of both suburban living and urban accessibility. Its parks, schools, and community atmosphere, combined with the convenience of nearby city amenities, make it a highly sought-after place to live. So if you’re looking to live in an area where single family homes outnumber condos by a wide margin, and want more space, with fewer people, South Brookline is an excellent area to consider.

Map of South Brookline

Notable 2024 South Brookline Homes Sold

• 43 Health Hill St.: $9,950,000
• 204-212 Clyde St.: $8,900,000
• 50 Lyman Rd.: $8,600,000
• 64 Dudley St.: $8,600,000
• 70 Lyman Rd.: $8,175,000
• 280 Dudley St.: $8,000,000

Preschools

• Apple Orchard School: Founded in 1971, this preschool is part of Allandale Farm and takes a unique approach to early childhood learning.
• Putterham Extended Learning: Part of the Brookline Early Education Program, this is the most affordable preschool option if you can get in.
• Brookline Schools Staff Children's Center: The BSSCC is an early education CO-op serving toddlers and preschoolers of Jamaica Plain, West Roxbury, and Brookline and is located on Goddard Avenue by Larz Anderson Park.
• Panda Club Academy: A Mandarin Immersion Montessori school located at the intersection of Hammond and Boylston Streets.
• Soule Early Childhood Center: Run by the Town of Brookline, this preschool’s philosophy is The Montessori Method of education.
• Boston College Children's Center: Preschool program for children 2 years 9 months – 5 years old providing early childhood education to preschoolers in Chestnut Hill and South Brookline.
• BeiBei Cub Academy: This bilingual home daycare focuses on Mandarin.

Schools

• Baker School: One of the eight public elementary schools in Brookline, this 3-4 section school serves some 650 children from South Brookline.
• Hayes School: The former Heath School, is another of Brookline’s eight public elementary schools and teaches some 425 children from South Brookline and Chestnut Hill.
• Beaver Country Day School: A private school for 6th-12th graders that is situated on 17 acres in the heart of Chestnut Hill / South Brookline.
• Dexter Southfield: Located in South Brookline, across from Larz Anderson Auto Museum and Park, this private school is home to over 1,000 students from Pre-K through high school.
• Brimmer and May School: This private school on one of Chestnut Hill’s most beautiful streets begins in Pre-K and goes all the way through high school.
• Chestnut Hill School: Private school in the heart of Chestnut Hill for Pre-K through 6th grade.
• Solomon Schechter: Located in Newton, just a short distance from the border of South Brookline, this private school’s mission is to “create a Jewish educational experience in which each student will be known, belong, be engaged, be inspired and be prepared.”

Restaurants

• Bernard's: Traditional Chinese food in a fun atmosphere, this restaurant is a favorite of South Brookliners.
• Cheesecake Factory: Located in The Shops at Chestnut Hill, this popular chain attracts families from all over Brookline and Newton.
• Chef Dave's: A small and hard-to-get-into restaurant that serves some tasty, authentic southern food.
• Davio's: This popular Italian steakhouse serves delicious pasta, meat, fish and more, and is on the second floor next to the Showcase SuperLux.
• Frank Pepe Pizzeria Napoletana: Casual pizzeria serving coal-fired pies, beer & wine in The Shops at Chestnut Hill.
• Legal's Seafood: Classic New England seafood, this two-story fish emporium elevates the 40-year legacy of its original location in Chestnut Hill (a few doors down from where it is now.)
• Seasons 52: Rotating menu of seasonal American dishes alongside international wines in an upscale setting.
• Shake Shack: A popular and fun place for kids where ping pong is offered outside among other games.
• The Capital Grille: High-end steak house serving up fresh cuts of meat, fish and more.
• Mandarin Gourmet: Classic Chinese food in the Shops at Putterham.
• Bertuccis: Wood oven pizza chain with a variety of salads, pastas, sandwiches and more near Hancock Village.
• Misono: Japanese food located in the Hancock Village Shopping Center.

Supermarkets

• Allandale Farm: The only farm in Brookline that grows its own vegetables.
• Putterham Market: Local bodega offers convenience to residents throughout South Brookline.
• Wegmans: Located along Route 9 in Chestnut Hill, this impressive multi-story grocery store attracts people from all over Brookline and Newton.
• Star Market: Longstanding supermarket in the heart of Chestnut Hill at the corner of Hammond and Boylston streets.

Parks

• Soule Playround: The splash pad and turf soccer field are the main attractions of this popular park along Hammond Street.
• Skyline Park: Situated atop a hill on the Brookline-Newton border, Skyline Park doubles as a soccer field and a place for people to enjoy the outdoors.
• Hammond Pond Reservation: Located in back of The Street, this popular spot for dogs features a picturesque pond that’s home to swans and ducks and other wildlife.