High Street Hill Real Estate

High Street Hill is a residential neighborhood in the southeast section of Brookline, also known as “Pill Hill” for its close proximity to the Longwood Medical Center. Because of its easy commute, High Street Hill is home to many doctors, researchers, and other medical employees. In addition to its convenient location, Leaverett Pond is another of the area’s attractions, providing residents with outdoor space complete with gardens, playground and paths for biking and running. Frederick Law Olmsted, the “father of landscape architecture” was actively involved in designing many of Brookline’s neighborhoods and inspired the landscaping surrounding several historic homes in the area, including the Philbrick Estate. The majority of the homes on High Street Hill were built between 1870 and 1930 on winding roads and set back from the street. Many homes were specifically constructed to take in views of the area’s green spaces as well as the city. The streets are lined with period examples of Victorian, Greek Revival, English Cottage, and Mansard architecture. Many homes have been renovated inside to offer the latest conveniences while preserving the exteriors and period finishes inside.   Read more about High Street Hill real estate.

High Street Hill Homes & Condos For Sale

High Street Hill Homes & Condos For Sale September 27, 2023
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Welcome to Walnut Crossing, Brookline village's latest ground up development! This corner 2 BD 2 BA unit with southeast exposures features open concept living with tremendous light through oversized...

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High Street Hill Location

High Street Hill is centered along High Street but also encompasses Allerton and Cumberland Streets; Glen, Hawthorn, and Edgehill Roads, and Pond Avenue. The neighborhood borders the neighborhood of Brookline Village to the north;”The Point” neighborhood to the south, and the Emerald Necklace, the meticulously designed chain of parks linked by parkways and waterways in Boston and Brookline, to its east. Located just over five miles from Downtown Boston and close to Route 9, High Street Hill is a short walk to the Brookline Village MBTA stop on the Green Line.

High Street Hill History

 High Street Hill is the older, more formal name for the neighborhood which became part of Brookline when it was annexed from Boston in 1844. The neighborhood claims a number of historically significant buildings as well as homes. Noted abolitionist, Samuel Philbrick, lived in Brookline at 182 Walnut street during the mid-1860s. His home served as a stop for the Underground Railroad during the Civil War. The National Register of Historic Places lists the neighborhood as a Historic District as well as designating several landmarks as historically significant.

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