Homes for Sale in Pill Hill, Brookline, MA

Pill Hill or High Street Hill is a lovely historic district close to the downtown area of Brookline, MA. Washington Street borders the neighborhood to the north, Leverett Pond and Olmstead Park to the east, and Downes Field to the south. The southwestern edges of the community are roughly bordered by Cypress Street, Franklin Street, and Highland Road. The area was developed in the mid-19th century, with many historic residences being built during that era. The suburb was designed as an upper-middle-class community for professionals that work in the city of Boston. The district actually got its name from the many notable doctors that moved into the area. Pill Hill was added to the National Register of Historic Places in 1977, and this day takes great effort in preserving its rich history and beautiful landmark structures.

Homes for sale in the Pill Hill neighborhood are a mix of beautiful luxury homes and historic houses. Residences in the community boast well-preserved Victorian architecture that reflects exquisite craftsmanship and highly detailed furnishings. Streets are lined with mature trees, and ample green spaces add to the area’s overall curb appeal. Properties here are priced around $1 million to $2.5 million and typically feature builds with two to five bedrooms and one to six baths. Many of these residences were built in the initial development of the area, which was around the mid-1800s. Some of the community’s larger estate-style residences do come with a higher price tag, with one property currently listed at $9.2 million. If you’re interested in an entry-level home, there are modest townhouses in some sections, but these require some repairs and renovation to bring them up to date.

Market Overview

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What's To Love

Pill Hill is a convenient neighborhood that enjoys easy access to the central portion of Brookline, MA. The neighborhood is also a short drive away from Central Boston. Residents can enjoy the many attractions in the city center. If schools are an important consideration for your buying decision, there are well-ranked schools available to families living in the neighborhood. Lovely outdoor amenities are readily available to residents with several ballparks, a sports field, Leverett Pond, vast wooded green spaces, and so much more.

What's Not To Love

Homes are a bit dated in the area, with some properties requiring some upgrades. Renovations can also be a challenge as there are several restrictions in this community. But if you're interested in a historically rich and vibrant neighborhood with tremendous curb appeal, you'll surely love what the Pill Hill community has to offer. As a luxury suburb, property prices in PIll Hill are slightly higher than the median average in Brookline.

Is it for me?

Who is this neighborhood for

Families in Pill Hill enjoy the serenity and privacy that comes with living in the neighborhood while still having the luxury of going to establishments that proudly show how amazing the city is. The perfect combination of relaxed and modernity could be found in the town of Pill Hill. Are you interested in purchasing your future home in Brookline? Give us a call, and we will gladly assist you as you get your dream home!

Find Your Home

Latest homes for sale in Pill Hill



69 Walnut 4

Brookline, MA, 02445


69 Walnut 5

Brookline, MA, 02445


69 Walnut Street 10A

Brookline, MA, 02445
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Meet the locals

Who Lives in Brookline?



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Things to do in Pill Hill

Olmsted Park

A vast urban park featuring well-preserved green space, a large lake, sports facilities, and other outdoor amenities.

Margaret E Robinson Playground

A lovely neighborhood park complete with baseball field, basketball court, dog park, walkways, and more.

Brother's Roast Beef & Pizza

Casual eatery serving your favorite comfort food.

Harry Downes Field

Large sports field perfect for football, soccer, and track.

Schools near Pill Hill

School Name
Brookline High School
9 – 12
Maimonides School
K – 12
Pierce Elementary School
K – 8

Pill Hill Map

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