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Recently Sold Hillside Street Homes

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  • /42

    $1,100,000 Sold Aug 29, 2025

    • 2,370 Sq Ft
    • $464/SF
    • 62 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1987

    1262 Randolph Ave, Milton, MA 02186

    We are excited to present this beautiful colonial, with four bedrooms , three baths and 2 fireplaces , one of which is located in the master suite. It has a two car garage with tons of storage. It has an amazing deck space off the back of the house and the large eat in kitchen. This home sits on a spectacularly quaint dead end street and located at the end of a long private driveway. The

    Joseph McEachern Paramount Properties

    1262 Randolph Ave, Milton, MA 02186
  • /29

    $1,030,000 Sold Aug 22, 2025

    • 2,306 Sq Ft
    • $447/SF
    • 56 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1958

    88 Hilltop St, Milton, MA 02186

    NEW PRICE! $1,049,000. BRAND NEW GAS HEATER TOO! IF YOU'RE LOOKING FOR LAND THIS IS YOUR HOME! 20,199 SQ FT LOT! If you’re looking for a home in a fabulous neighborhood on a beautiful lot & a Two Car Garage you have found it. This home is perfectly sited on a fenced in 0.46-acre yard. This prime location is minutes to Wollaston Golf Club, Milton Academy, Blue Hills, Route 93 and much more.

    Francine Jeffers Kelley & Rege Properties, Inc.

    88 Hilltop St, Milton, MA 02186
  • /42

    $3,200,000 Sold Jul 18, 2025

    • 6,950 Sq Ft
    • $460/SF
    • 40 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 1912

    287 Hillside St, Milton, MA 02186

    Experience the grandeur of this elegant 1912 Colonial sited along a private treelined drive. Beautifully designed for the President of Baker Chocolate, this estate is the perfect blend of exquisite period detail & modern amenities. Its magnificence is apparent upon entering, with high ceilings, front to back expansive foyer, a wood paneled family room and signature staircase leading to 5 beds

    Meredith Hall Coldwell Banker Realty - Milton

    287 Hillside St, Milton, MA 02186
  • /36

    $940,000 Sold Jul 16, 2025

    • 2,600 Sq Ft
    • $362/SF
    • 83 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1922

    84 Sassamon Ave, Milton, MA 02186

    Welcome to this beautifully maintained home nestled in a sought-after Milton neighborhood where the community feels like family and nature surrounds you. Step inside to discover the homes generous space with three well-proportioned bedrooms and 2.5 baths. The large primary suite is a peaceful sanctuary offering partial views of the Boston Skyline. The home's heart is the spacious kitchen that

    Janice Bosworth Coldwell Banker Realty - Milton

    84 Sassamon Ave, Milton, MA 02186
  • /39

    $1,550,000 Sold Jul 15, 2025

    • 2,522 Sq Ft
    • $615/SF
    • 5 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1985

    1051 Randolph Ave, Milton, MA 02186

    At the foot of the Blue Hills tucked behind a stand of trees and just past Wollaston Country Club you'll find 1051 Randolph Avenue. This expansive classic has been tastefully and meticulously renovated throughout and the result is serene, inviting and comfortable. There are so many places to gather and so many options to spread out whether it's the formal living and dining room or eat-in-kitchen

    Kathy McLaughlin William Raveis R.E. & Home Services

    1051 Randolph Ave, Milton, MA 02186
  • /42

    $3,500,000 Sold Jun 10, 2025

    • 8,032 Sq Ft
    • $436/SF
    • 27 Days On Market
    • 6 Beds
    • 7 Baths
    • Built 2006

    427 Hillside St, Milton, MA 02186

    Sometimes all it takes is good instinct, better vision and superb execution. Such is the fortune found at 427 Hillside Street. Set against a backdrop of serene woodlands with a distinctive approach, this 8,000sf 6-bedroom residence offers an extraordinary level of privacy and tranquility. High ceilings with rich coffered detail create a sense of openness and underscore quality, while large

    Julianne Bridgeman Ceres Real Estate

    427 Hillside St, Milton, MA 02186
  • /30

    $670,000 Sold Mar 18, 2025

    • 960 Sq Ft
    • $698/SF
    • 5 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1956

    36 Nahanton Ave, Milton, MA 02186

    Endless Possibilities await in a prime Milton location! Situated on a peaceful dead-end street, this 2-bedroom, 1-bathroom home offers a rare chance to craft the home of your dreams in one of Milton's most coveted neighborhoods. While this property is in need of some TLC, its unbeatable location and incredible potential make it a true gem. Picture the transformation as you add your personal touch

    Mary Anne Rull William Raveis R.E. & Home Services

    36 Nahanton Ave, Milton, MA 02186
  • /30

    $1,062,500 Sold Nov 08, 2024

    • 2,551 Sq Ft
    • $417/SF
    • 82 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1954

    147 Sassamon Ave, Milton, MA 02186

    Welcome to 147 Sassamon Ave., Milton! This beautiful home combines modern convenience with classic charm. The property has undergone numerous updates, making it completely move-in ready for the next fortunate owner. One of the standout features of this home is the private backyard oasis, featuring an inground pool with a brand new liner. This serene space is perfect for summer entertainment and

    Matthew Langlois Keller Williams Realty Signature Properties

    147 Sassamon Ave, Milton, MA 02186

Frequently Asked Questions

What is the average time to sell a house in Hillside Street, MA?
The houses for sale in Hillside Street, MA spend an average of 47 days on the market.
What is the number of active homes for sale in Hillside Street, MA?
There are 9 active homes for sale in Hillside Street, MA.

Home Trends in Hillside Street, MA

Housing Trends

Median Sale Price
$1,062,500
Median Single Family Sale Price
$1,603,450
Average Price Per Sq Ft
$577
Number of Homes for Sale
9
Last 12 months Home Sales
9
Months of Supply
12.00
Median List Price
$1,562,500
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
-26%
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