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Hillside Street Homes for Sale

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  • /31

    $1,490,000

    • 5 Beds
    • 3.5 Baths
    • 4,048 Sq Ft

    161 Sassamon Ave, Milton, MA 02186

    With over 4,000 sq. ft. of living space set on an 11, 286 sq. ft. lot this 5 bed, 3.5 bath historic home offers unmatched size and value. While Milton's average sale is at $512.00 per sq. ft. this home at $372.00 per square foot is priced to sell. Enjoy multiple 1st floor living areas, a kitchen with custom cabinets, a separate office area and expansive decks. The private primary suite features

    Agent Photo

    Thomas O'Neill

    The Firm

    (617) 741-9174

    161 Sassamon Ave, Milton, MA 02186
  • /41

    $14,500,000

    • 5 Beds
    • 8 Baths
    • 11,315 Sq Ft

    610 Harland St, Milton, MA 02186

    Introducing the Alexander Forbes Mansion, a magnificent estate set on 6 beautiful acres in the historic and highly desirable Scott’s Woods district of Milton. This exceptional home showcases every modern amenity and has been meticulously renovated inside and out to the highest standards. The main level features a grand foyer, striking staircase, dramatic floor-to-ceiling windows and doors, formal

    Tracy Campion Campion & Company Fine Homes Real Estate

    610 Harland St, Milton, MA 02186
  • /42

    $1,799,900

    • 5 Beds
    • 4.5 Baths
    • 4,788 Sq Ft

    6 Brewster Rd, Milton, MA 02186

    Set on a prominent corner lot in Milton, this turnkey residence blends classic Garrison architecture with elevated modern design. Renovated in 2020, it features Hardie Board siding, a new roof, underground electrical service, updated plumbing, and a Navien on-demand water heater. The kitchen is crafted for both everyday living and entertaining, offering quartz countertops, a gas cooktop, double

    Kevin Struzziero Lamacchia Realty, Inc.

    6 Brewster Rd, Milton, MA 02186

Why Live in Hillside Street

Hillside Street in Milton features homes with Cape Cod, Colonial Revival, and New Englander designs, dating from the early 1800s to mid-1900s. Many properties have backyards that open to forests and trails. The neighborhood is near Blue Hills Reservation, offering extensive hiking trails, mountain biking, and views of the Boston skyline. Kelly Field provides a playground and sports fields, while the Wollaston Golf Club offers an 18-hole course and social events. Dining options include Newcomb Farms Restaurant, known for all-day breakfast, and Steel & Rye, popular for brunch and craft cocktails. Grocery shopping is convenient with Star Market in Dorchester and America's Food Basket in Mattapan. Annual events like the Milton Music Fest in June and Milton Porchfest in September bring the community together. Commuters have access to Interstate 93, Blue Hill Avenue, and multiple Massachusetts Bay Transit Authority stations. The Beth Israel Deaconess Hospital’s Milton branch is less than 2 miles away, and Boston Logan International Airport is about 13 miles away. Schools in the area are highly rated, with students attending Tucker Elementary School, Charles S. Pierce Middle School, and Milton High School, which is noted for its French immersion program. For higher education, Curry College is nearby.

Frequently Asked Questions

Is Hillside Street a good place to live?
Hillside Street is a good place to live. Hillside Street is considered very car-dependent and somewhat bikeable with some transit options. Hillside Street is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. It has a median age of 43. The average household income is $180,182 which is above the national average. College graduates make up 70.2% of residents. A majority of residents in Hillside Street are home owners, with 13.7% of residents renting and 86.3% of residents owning their home. A local real estate agent serving Hillside Street can help you decide if this neighborhood is the right one for you. Learn more on our Hillside Street neighborhood guide.
Is Hillside Street, MA a safe neighborhood?
Hillside Street, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Hillside Street?
The median home price in Hillside Street is $1,299,999. If you put a 20% down payment of $260,000 and had a 30-year fixed mortgage with an interest rate of 6.01%, your estimated principal and interest payment would be $6,240 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $267K a year to afford the median home price in Hillside Street. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Hillside Street is $180K.
What are the best public schools in Hillside Street?
The best public schools that serve Hillside Street are:
  • Milton High School has an A Niche grade, a student teacher ratio of 13:1 and an average review score of 4.0.
What are the best private schools in Hillside Street?
The best private schools that serve Hillside Street are:
  • Delphi Academy has an A+ Niche grade, a student teacher ratio of 7:1 and an average review score of 4.7.
  • Milton Academy has an A+ Niche grade, a student teacher ratio of 6:1 and an average review score of 4.3.
  • Fontbonne Academy has an A Niche grade, a student teacher ratio of 11:1 and an average review score of 4.2.
What are the most popular zip codes in Hillside Street, Milton, MA?
The most popular zip codes in Hillside Street, Milton, MA include 02186, 02368, 02136, 02169 and 02021.
What are the most popular neighborhoods near Hillside Street, Milton, MA?
The most popular neighborhoods near Hillside Street, Milton, MA are Milton Center, Brush Hill, Milton Hill, North Randolph and Hyde Park.

Home Trends in Hillside Street, MA

Housing Trends

Median Sale Price
$1,065,000
Median Single Family Sale Price
$1,100,000
Average Price Per Sq Ft
$518
Number of Homes for Sale
3
Last 12 months Home Sales
12
Months of Supply
3.00
Median List Price
$1,299,999
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
-28%
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