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Hillside Street Homes for Sale

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  • /28

    $1,425,000

    Open Sat 11AM - 1PM $74K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 3,074 Sq Ft

    37 Sassamon Ave, Milton, MA 02186

    Set in one of Milton's most desirable neighborhoods, this thoughtfully designed home offers exceptional space, flexibility, and upscale finishes throughout. At its heart is a high-end chef's kitchen featuring premium appliances, custom cabinetry, and generous gathering space for everyday living and entertaining. A rare first-floor primary suite provides ideal accommodations for guests,

    Robin Shea Principal Real Estate Partners

    37 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
  • /39

    $1,699,900

    • 6 Beds
    • 4.5 Baths
    • 5,077 Sq Ft

    52 Ridgewood Rd, Milton, MA 02186

    One of Milton's most desirable neighborhoods. Extensively updated in 2023, this property underwent a comprehensive gut renovation, including all-new plumbing, electrical systems, heating system, roof and numerous high-quality improvements throughout, offering the perfect blend of modern efficiency and timeless charm.The spacious kitchen and living areas provide excellent functionality for both

    Rebecca Huang William Raveis R.E. & Home Services

    52 Ridgewood 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.

Hillside Street Home Prices vs. Nearby Milton, MA Neighborhoods

Hillside Street Milton Hill North Main Carlisle
Median Home Price
$1,499,000
$1,159,500
$1,269,900
$1,399,000
Median Sale Price
$1,200,000
-21% YoY
$1,117,500
+10% YoY
$1,280,000
-12% YoY
$1,384,000
+2% YoY
Median Single Family Price
$1,425,000
$1,155,000
$1,290,000
$1,375,000
Median Condo Price
--
$837,500
$1,138,500
$1,198,000
Total Active Listings
3
4
7
19
Market Conditions
3 Months of Supply
Seller's Market
1 Months of Supply
Seller's Market
5 Months of Supply
Balanced Market
3 Months of Supply
Seller's Market

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 bikeable with minimal 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 14% of residents renting and 86% 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 $1,499,000. If you put a 20% down payment of $299,800 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $7,570 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $324K 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 4.9.
  • Milton Academy has an A+ Niche grade, a student teacher ratio of 7:1 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, North Randolph, Hyde Park and Milton Hill.
Are home prices dropping in Hillside Street?
Yes, home prices in Hillside Street are down 7% in the last 12 months.
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