Pill Hill

A prestigious historic enclave offering grand Victorian architecture and leafy serenity steps from the Medical Area.

Average Home Price

$2,639,167

Average Condo Price

$950,428

Avg. Price / SF

$749

Avg. Days on Market

41

Walk Score

93

Location & Transit

Please Note: Commute times are estimates based on typical conditions. Actual times may vary based on traffic, weather, and MBTA service.

Pill Hill Schools

William H. Lincoln, Brookline High School

Lincoln School (K-8): Often serves this neighborhood due to its proximity on Kennard Road. Pierce School (K-8): Serves portions of the hill near Brookline Village. Brookline High School (9-12): Located nearby at Greenough Street.

Pill Hill Real Estate


Pill Hill (a.k.a High Street Hill) is one of the most architecturally cohesive neighborhoods in New England. Often called "Pill Hill" for the high concentration of doctors who have lived here since the 19th century, the housing stock is comprised almost exclusively of grand Victorian-era estates. You will find impeccable examples of Queen Anne, Shingle Style, and Second Empire manses, many designed by renowned architects like Peabody & Stearns. There are very few condos or multi-family conversions here compared to other parts of Brookline; it is primarily a neighborhood of single-family forever homes.

Pill Hill Neighborhood Charachter

Stepping into Pill Hill (a.k.a High Street Hill) feels like entering a time capsule. The neighborhood is defined by its steep, winding topography, gas-style streetlamps, and lack of cut-through traffic, which preserves a quiet, village-like atmosphere. It is an "Olmsted neighborhood" in the truest sense, bordering the Emerald Necklace and featuring pockets of green space like Philbrick Square. While it has no commercial district of its own, it sits perched directly above the bustling shops of Brookline Village, offering the perfect "best of both worlds" lifestyle.

Pill Hill Market Insight

Pill Hill (a.k.a High Street Hill) is a “Legacy Market.” Properties here are tightly held, often staying in the same families for decades. When homes do hit the market, they command a significant premium due to the neighborhood’s pedigree and its nickname as a haven for the medical elite. It is widely considered “commute-proof” for those working in the Longwood Medical Area. Buyers should expect competitive bidding for any well-preserved Victorian, but must also be prepared for the maintenance that comes with historic preservation.