Hillside Street
Neighborhood in Milton, Massachusetts
Norfolk County 02186
Historic plaques on Colonials and New Englanders
Home styles in the Hillside Street community include Cape Cod, Colonial Revival and New Englander designs that were commonly constructed between the early 1800s and mid-1900s. “It's really nice to drive around and see all of the signs on houses that show just how old they are,” Truog says. Lot sizes can vary heavily, but many open up in the backyard to forests and trails. Homes commonly range between $800,000 and $1.8 million.Local trails and Milton sports fields
Hillside Street residents are close to the Blue Hills Reservation, an expansive park with miles of hiking trails, mountain bike tracks and views of the Boston skyline in the distance. Kelly Field has a playground and a number of sports fields for softball, tennis and even floor hockey games. The community is also just south of the Wollaston Golf Club, a private club with an 18-hole course, a pool and regular social events.Milton Public Schools and Curry College
Students in Hillside Street can start off their education at Tucker Elementary School before continuing to Charles S. Pierce Middle School. Both schools earn an overall A-minus rating on Niche. Milton High School scores an A. “The school is very well known for its French immersion program, only one other school in the state has it,” Truog says. The neighborhood is also close to Curry College, known for its numerous degree options and small class sizes.Local band concerts in yards and parks
The Milton Music Fest is held each year in June in Hutchinson Park. Here, the town comes together for a day full of local bands, vendors and a fireworks show over the water. “We don’t do big Fourth of July because the festival happens only a few weeks beforehand,” Truog says. In September, residents can attend Milton Porchfest, where bands play from porches, driveways and front lawns.Multiple routes from Milton to Boston
Commuters can take Interstate 93 or Blue Hill Avenue via Randolph Avenue to head to Boston. The area also offers access to multiple Massachusetts Bay Transit Authority stations for the Red Line, commuter rail and bus stops. The Beth Israel Deaconess Hospital’s Milton branch is less than 2 miles away, and Boston Logan International Airport is about 13 miles away.Local diners and nearby brunch spots
Newcomb Farms Restaurant, part of the community for over 40 years, is a diner-style eatery that serves all-day breakfast and lunch specials. Steel & Rye is a newer spot, also known for its brunch and custom craft cocktails. “I typically tend to dine outside of Milton, but when I’m in town, these are my go-to spots,” Truog says. Nearby grocery stores include Star Market in Dorchester and the America's Food Basket in Mattapan.

Agents Specializing in this Area
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Vanessa Foster
Coldwell Banker Realty - Milton
(857) 816-8446
73 Total Sales
3 in Hillside Street
$1.5M - $1.7M Price Range
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Kevin Lewis
Responds QuicklyColdwell Banker Realty - Hingham
(339) 217-3520
290 Total Sales
1 in Hillside Street
$1,400,000 Price
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Deb Piazza
Responds QuicklyColdwell Banker Realty - Sharon
(774) 273-9005
192 Total Sales
1 in Hillside Street
$1,560,000 Price
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The Goodrich Team
Responds QuicklyCompass
(781) 512-7472
461 Total Sales
1 in Hillside Street
$1,335,000 Price
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Brian Caluori
Responds QuicklyGibson Sotheby's International Realty
(781) 488-7488
83 Total Sales
1 in Hillside Street
$674,778 Price
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Mary Anne Rull
William Raveis R.E. & Home Services
(339) 210-1242
65 Total Sales
4 in Hillside Street
$670K - $1.4M Price Range
Schools
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Hillside Street Demographics and Home Trends
On average, homes in Hillside Street, Milton sell after 32 days on the market compared to the national average of 49 days. The median sale price for homes in Hillside Street, Milton over the last 12 months is $1,427,500, down 1% from the median home sale price over the previous 12 months.
Housing Trends
Neighborhood Facts
Open Houses
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Saturday, Jun 1412 - 1pm
Distribution of Home Values
Homes for Sale
Homes for Rent
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Property Mix - Square Feet
This Neighborhood Has More Owners
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Education and Workforce
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Area Factors
Somewhat Bikeable
Bike Score®
Car-Dependent
Walk Score®
Some Transit
Transit Score®
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