Map of The Point

Public Transportation

The Point residents enjoy a couple of public transportation options. The Green Line’s D branch stops at Brookline High School on the opposite side of Route 9 and takes passengers to Brookline Village, Longwood, Fenway and into downtown Boston and Somerville on the inbound side, and western points of Brookline and Newton on the outbound side.

In addition, the MBTA 60 bus turns right onto Cypress Street and picks up passengers at 3 stops before turning onto High Street en route to the Longwood Medical Area and Kenmore Square. The same bus originates at the Chestnut Hill Mall giving residents the ability to get to The Street, a popular shopping area in Chestnut Hill.

Downes Field

Downes Field

Parks

One of the highlights of The Point is Downes Field, a turf athletic field surrounded by a track that is used for soccer, lacrosse, field hockey and some football. There are always a number of people, including both collegiate and high school teams, using the track for practice. There is also a playground for kids at Downes and a good size grass field where dogs are normally roaming off leash.

But Downes is not the only park in The Point. Robinson Field, which was renovated in 2023, is a park for little leaguers along Cypress Street. If that’s not enough, residents of The Point have quick access to the newly built park at Brookline High School just across Route 9, Boylston Playground which is on Route 9 across from the old Lincoln School, and the reservoir along Route 9, which is a great place to walk a dog, run, or just sit on a bench and soak up the scenery (including an unobstructed view of the Boston skyline).

The park at BHS is quite nice and features modern play equipment for children, a basketball court, and soccer field, while Boylston Playground has a grass field, some older play equipment and a basketball court.

In the opposite direction of Route 9 is Jamaica Pond, which is roughly 1.5 miles around and a fantastic place to walk, jog or even rent a boat on a sunny day. About a half mile further along the Arborway is the Arnold Arboretum, a 281-acre preserve in the heart of Boston.

Restaurants

Residents in The Point often venture out of the neighborhood for food. Being so close to Boston, Brookline Village, Washington Square, Chestnut Hill and Jamaica Plain makes it easy to get to a number of excellent restaurants closeby. With that said, there are a few great places in The Point along Cypress Street worth eating at.

• Chiharu: Located along Boylston Street (Route 9), this welcoming spot serves a variety of Japanese favorites including fresh sushi, noodles and more.
• Drive-By Pies: Local bakery with scrumptious dessert and mouth-watering pies.
• Pizza Stop: A neighborhood staple since 1988, the name says it all.
• Rifrullo Café: This neighborhood favorite has some of the finest healthy lunch options and is also a great place to grab a coffee and pastry while you work.

Kurkman’s Market on Cypress Street

Kurkman’s Market on Cypress Street

Supermarkets

Although there are technically no supermarkets in Pill Hill (it’s too residential for supermarkets to inhabit it), there are two located in nearby Coolidge Corner and one in The Point.

• Kurkman’s Market Co.: This long-running grocer is centrally located in the neighborhood along Cypress Street and stocks fresh produce, meat, dairy, gourmet items, and more.
• Stop & Shop: Located in nearby Coolidge Corner, this long-standing market features all your family’s favorite foods.
• Trader Joe's: Popular grocery store along Beacon Street in Coolidge Corner.
• Star Market: Located in nearby Washington Square, this market is a 7-10 minute drive from The Point and offers a variety of fresh and packaged foods.

Daycares

• Clinton Path Preschool: Located in neighboring Pill Hill, this preschool has been around for more than 45 years.
• Friends Childcare: Located on Cypress Street across from the Brookline High School freshman building, Friends Childcare provides an enriching environment for early childhood development with a focus on learning through play.
• Children's Center of Brookline: A play-based predominantly outdoor program that’s been operating since 1970.
• Little Corner SchoolHouse Too: Located on the Corner of Cypress and Washington Street in Brookline Village, Little Corner SchoolHouse Too has four locations in the Brookline Village area.
• Little Children Schoolhouse: With three locations in nearby Brookline Village, the closest to The Point is on Boylston Street.

Paths

• Walnut Path: Links Walnut Street to Boylston Street and is perhaps the oldest path in Brookline.

The Point stands out as a neighborhood of distinct character and charm. The neighborhood's well-maintained parks, top-rated schools, and handful of dining options contribute to its appeal. Excellent public transportation connectivity further enhances its attractiveness for a wide range of residents. Overall, The Point blends modern convenience with a strong sense of community, making it a coveted area to live in.