Pill Hill

Pill Hill Historic District

Pill Hill Historic District

Pill Hill, a.k.a. "High Street Hill," is a historic neighborhood listed on the National Register of Historic Places. Its nickname originated from the large number of doctors who lived there due to its close proximity to the Longwood Medical Area of Boston. The medical area has expanded over the years and today Boston Children’s Hospital and Brigham and Women’s Hospital both occupy space at 1 Brookline Place, which is essentially across the street from the foot of High Street.

Speaking of High Street, Pill Hill is centered along it, and includes beautiful side streets like Allerton, Maple and Irving Streets, Cumberland Avenue, and Hawthorn, Glen, Upland, and Edgehill Roads. It borders Brookline Village to the north and the historically working-class neighborhood once known as Whiskey Point to the south. While some long-time residents may be familiar with “Whiskey Point” that name is rarely heard anymore.

The Pill Hill neighborhood is adjacent to Olmsted Park and Leverett Pond, part of the Emerald Necklace park system, and is off Route 9, a major 2-lane road that runs all the way from Boston to Western Massachusetts.

To the East of Pill Hill is Pond Avenue and the Jamaicaway, each of which borders Olmstead Park. The Jamaicaway is a two-lane road that leads to Jamaica Plain (part of Boston) in one direction, and into the Fenway area in the other.

Pill Hill is predominantly residential, and contains some of the most beautiful Victorian homes in Brookline. Homes in Pill Hill are a mix of luxury homes and historic houses, boasting well-preserved Victorian architecture. The streets are lined with mature trees, and ample green spaces enhance the area's curb appeal.

There are 110 single family homes and 93 condos in Pill Hill. The average single family was assessed at $3,327,333 in fiscal year 2025, while the average condo was assessed for $909,610. Interestingly, in The Point, which is adjacent to Pill Hill and where condos outnumber single family homes 7.5 to 1, the average home was assessed for $826,149 during that same period.

Philbrick Square, a park designed by Frederick Law Olmsted in the 1880s, is located in Pill Hill, and is a pretty green space surrounded by stately mansions.

Pill Hill residents enjoy easy access to Brookline Village (down High Street and right across Route 9) and its diverse set of shops and restaurants. In addition, the area is just a short drive from Central Boston, with attractions in the city center.

Home Values

Corner of Cumberland Ave. and High St.

Corner of Cumberland Ave. and High St.

The average assessed home value in Pill Hill was $2,146,828 for fiscal year 2025.

Below is a sampling of home values by street in the Pill Hill area according to the fiscal year 2025 assessed values:

• Walnut Pl.: $4,289,950
• Maple St.: $3,382,323
Edgehill Rd.: $3,346,915
• Hawthorn Rd.: $2,958,900
Irving St.: $2,558,686
• Upland Rd.: $2,491,713
• High St.: $1,920,514
• Walnut St.: $1,882,712

Notable 2024 Pill Hill Homes Sold

• 35 Hawthorn Rd.: $2,300,000

Public Transportation

Public transportation in Pill Hill includes easy access to the MBTA's Green Line D-train at Brookline Village and the Green Line E-train line in the Mission Hill neighborhood of Boston, notably the Riverway stop. The area is also served by MBTA bus service​​​​ which runs along Route 9 (Boylston Street) and takes passengers to Longwood Medical Area, Kenmore Square, Northeastern University, and downtown Boston.

Schools

Elementary school students living in Pill Hill typically attend the Lincoln School but some that live in a buffer zone opt for Pierce School or one of the nearby private schools like The Park School or Dexter Southfield each of which is a 5-10 minute car ride.

Brookline High School, the town’s lone public high school, is less than a mile from the neighborhood.

Downes Field

Downes Field

Parks

Pill Hill boasts several nearby sports fields including Downs Field and Robinson Park.

Downs is a combination park, turf athletic field, track and grass field for dogs to play off leash. This is a popular place for pickup soccer games, track teams to train at, and Brookline high Field Hockey and Lacrosse teams to play on. In addition, there are a number of youth soccer games played at Downs in the Spring and Fall.

Robinson is a quieter playground along Cypress Street that was redone in 2023-24 and hosts Little League baseball games.

Restaurants

The beauty of Pill Hill is its close to all the restaurants in Brookline Village, Washington Square, and Coolidge Corner but also quite close to the happening restaurant scene in Jamaica Plain.

• La Morra: Cozy restaurant serving homemade pasta & Tuscan-style wood-grilled entrees in a fun atmosphere.
• Punch Bowl: Part of the Hilton Garden Inn along Brookline Avenue, this modern city tavern offers a large patio area on the ground floor as well as a roof deck terrace with phenomenal views of Brookline and its’ historic Muddy River.
• Garrison House: With a happening downstairs music scene, this Brookline Village hot spot is a fun place to grab a drink and some food.
• Mahaniyom: Thai Tapas with a variety of vegetarian options.
• Martin's Coffee Schop: Classic diner serving up breakfast and lunch classics.
• Orinoco: Venezuelan restaurant serving up authentic Latin American flavors in a casual, lively atmosphere.
• Sapporo Ramen: If you enjoy big bowls of Ramen and delish rice bowls this Brookline Village spot is for you.
• Tres Gatos: Cozy Spanish tapas & wine bar with a tiny shop in back selling books & music located in nearby Jamaica Plain.
• Blue Nile: No frills restaurant in Jamaica Plain with a casual vibe serving Ethiopian classics.

Daycares

• Clinton Path Preschool: On the corner of High and Irving Street right in Pill Hill.
• Little Children Schoolhouse: Multiple locations in nearby Brookline Village.
• Rainbow Star Learning Center: Across from the Brookline Village T stop on Station Street, this daycare encourages a multilingual atmosphere in English, Mandarin, and Spanish.

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-standing grocer stocks fresh produce, meat, dairy & gourmet items, plus beer & wine and is located in The Point, less than a mile from most of Pill Hill.
• Stop & Shop: This Coolidge Corner staple is about a mile from Pill Hill.
• Trader Joe's: One of Brookiline’s most popular grocery stores is a straight shot from High Street across Route 9 and into Coolidge Corner.

Paths

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