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Recently Sold Hillside Street Homes

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  • /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
  • /29

    $1,475,000 Sold Sep 04, 2024

    • 3,180 Sq Ft
    • $464/SF
    • 41 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 1987

    97 Brierbrook St, Milton, MA 02186

    Nestled at the end of a tranquil cul-de-sac, 97 Brierbrook St combines privacy, comfort, and a prime location, making it a truly rare find. Featuring three spacious bedrooms, each with an ensuite bath, plus an additional half bath, this 3180 sqft ranch-style home is perfect for single-level living. The open floor plan, illuminated by oversized windows, provides a bright, airy atmosphere. The

    Vanessa Foster Coldwell Banker Realty - Milton

    97 Brierbrook St, Milton, MA 02186
  • /42

    $1,560,000 Sold Aug 08, 2024

    • 3,041 Sq Ft
    • $513/SF
    • 5 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1960

    109 Harbor View Rd, Milton, MA 02186

    This modern beauty underwent a complete redesign and reconstruction just 12 years ago.The meticulous design presents an attractive exterior and a spacious open floor plan.As you approach, you're welcomed by a covered front porch adorned with elegant columns and a stone facade. Inside, the living room boasts built-in cabinetry surrounding a gas fireplace. The gorgeous center island kitchen

    Amy March The Firm

    109 Harbor View Rd, Milton, MA 02186
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