437

Hillside Street Homes

Section Image
  • 55 Parkwood Dr, Milton, MA 02186
    55 Parkwood Dr, Milton, MA 02186
    55 Parkwood Dr, Milton, MA 02186
    /41

    $6,999,900

    • 7 Beds
    • 10 Baths
    • 9,320 Sq Ft

    55 Parkwood Dr, Milton, MA 02186

    One of Milton's finest estates. This 1915 mansion sits on nearly three acres of land in a private setting at the foot of the Blue Hills Reservation. The estate consists of a 9,000+ square foot home, an in-ground swimming pool with a pool house, and a two-story, 5-bay garage with an attached greenhouse. The residence features 7 bedrooms, 7 full bathrooms, 3 half bathrooms, and 9 fireplaces. The

    Kevin Keating Keating Brokerage

    55 Parkwood Dr, Milton, MA 02186
  • 65 Sassamon Ave, Milton, MA 02186
    65 Sassamon Ave, Milton, MA 02186
    65 Sassamon Ave, Milton, MA 02186
    /21

    $3,650 per month

    • 2 Beds
    • 2 Baths
    • 1,124 Sq Ft
    • House for Rent

    65 Sassamon Ave, Milton, MA 02186

    Chic & Move-In Ready Single-Family Home in Prime Milton Location! Don’t miss this beautifully updated 2-bedroom, 2-bath ranch tucked into one of Milton’s most charming and quiet neighborhoods—just off Randolph Ave with easy access to I-93, public transportation and the Blue Hills for year-round outdoor adventure. Step inside to find refinished hardwood floors throughout, a sleek remodeled kitchen

    MacKinnon & Co. Compass

    65 Sassamon Ave, Milton, MA 02186
  • 287 Hillside St, Milton, MA 02186
    287 Hillside St, Milton, MA 02186
    287 Hillside 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
    • 60 Ridgewood Rd, Milton, MA 02186
      60 Ridgewood Rd, Milton, MA 02186
      60 Ridgewood Rd, Milton, MA 02186
      /30

      Est $1,080,274 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,516 Sq Ft

      60 Ridgewood Rd, Milton, MA 02186

      60 Ridgewood Rd, Milton, MA 02186
  • 540 Harland St, Milton, MA 02186
    540 Harland St, Milton, MA 02186
    540 Harland St, Milton, MA 02186
    /28

    $11,900,000

    • 5 Beds
    • 7 Baths
    • 9,300 Sq Ft

    540 Harland St, Milton, MA 02186

    Majestic and utterly one-of-a-kind, this ultra-private equestrian estate redefines luxury living. Welcome to your gated sanctuary tucked within the pristine Blue Hills Reservation, featuring a private equestrian entrance to over 7,000 acres of unspoiled natural beauty and year-round outdoor pursuits. Gracefully sited on more than 8 acres of lush, wooded grounds, the Grand Estate encompasses a

    Stephen Kraunelis Gibson Sotheby's International Realty

    540 Harland St, Milton, MA 02186
  • 5 Harbor View Park, Milton, MA 02186
    5 Harbor View Park, Milton, MA 02186
    5 Harbor View Park, Milton, MA 02186
    /24

    $4,500 per month

    • 3 Beds
    • 2.5 Baths
    • 2,764 Sq Ft
    • House for Rent

    5 Harbor View Park, Milton, MA 02186

    Perfect home for your family - large lot, ample space, open floor plan, central A/C, and lots more. New interior painting planned, as well as updates to bathrooms. Be the first to see this gorgeous Milton single located in a child friendly neighborhood, with great highway access, and close to all that Milton and greater Boston has to offer. All showings by appointment. You do not want to miss

    Charles Maneikis The Maneikis Companies, Inc.

    5 Harbor View Park, Milton, MA 02186
  • 84 Sassamon Ave, Milton, MA 02186
    84 Sassamon Ave, Milton, MA 02186
    84 Sassamon Ave, 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
    • 177 Harbor View Rd, Milton, MA 02186
      177 Harbor View Rd, Milton, MA 02186
      177 Harbor View Rd, Milton, MA 02186
      /31

      Est $1,006,600 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,955 Sq Ft

      177 Harbor View Rd, Milton, MA 02186

      177 Harbor View Rd, Milton, MA 02186
  • 44 Ridgewood Rd, Milton, MA 02186
    44 Ridgewood Rd, Milton, MA 02186
    44 Ridgewood Rd, Milton, MA 02186
    /14

    $926,000 Open Sun 1PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft

    44 Ridgewood Rd, Milton, MA 02186

    Welcome to your dream home in one of Milton’s most coveted neighborhoods! Located just steps from the impressive Wollaston Golf Club, this 3-bedroom, 2-bath residence offers the perfect blend of charm, comfort, and convenience. Formal living room with a cozy fireplace — perfect for relaxing or entertaining, inviting den ideal for a home office or quiet retreat, bright porch to enjoy your morning

    Elaine Gilmore Advisors Living - Canton

    44 Ridgewood Rd, Milton, MA 02186
  • 1051 Randolph Ave, Milton, MA 02186
    1051 Randolph Ave, Milton, MA 02186
    1051 Randolph 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
    • 1274 Randolph Ave, Milton, MA 02186
      1274 Randolph Ave, Milton, MA 02186
      1274 Randolph Ave, Milton, MA 02186
      /25

      Est $1,376,213 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,283 Sq Ft

      1274 Randolph Ave, Milton, MA 02186

      1274 Randolph Ave, Milton, MA 02186
  • 4 Mark Ln, Milton, MA 02186
    4 Mark Ln, Milton, MA 02186
    4 Mark Ln, Milton, MA 02186
    /9

    $1,800,000

    • 3 Beds
    • 3.5 Baths
    • 3,997 Sq Ft

    4 Mark Ln, Milton, MA 02186

    Welcome to 4 Mark Lane, a rare gem nestled in one of Greater Boston’s most desirable suburbs—Milton, Massachusetts. This beautifully maintained home blends timeless elegance with modern comfort, featuring spacious living areas, gleaming hardwood floors, a chef’s kitchen with granite countertops and high-end appliances, and a finished lower level perfect for a home office, gym, or guest suite. The

    Peter Mlaguzi M&A Real Estate

    4 Mark Ln, Milton, MA 02186
  • 427 Hillside St, Milton, MA 02186
    427 Hillside St, Milton, MA 02186
    427 Hillside St, 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
    • 176 Hilltop St, Milton, MA 02186
      176 Hilltop St, Milton, MA 02186
      176 Hilltop St, Milton, MA 02186
      /29

      Est $1,276,759 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,015 Sq Ft

      176 Hilltop St, Milton, MA 02186

      176 Hilltop St, Milton, MA 02186
  • 80 Brierbrook St, Milton, MA 02186
    80 Brierbrook St, Milton, MA 02186
    80 Brierbrook St, Milton, MA 02186
    /20

    $2,999,999

    • 5 Beds
    • 3.5 Baths
    • 4,644 Sq Ft

    80 Brierbrook St, Milton, MA 02186

    Quintessential New England Home in one of the most desirable neighborhoods in Milton. This 5 bedroom, 3 full bath and 1 half bathroom is an entertainers dream with a beautifully appointed chef's kitchen with Wolf and Sub-Zero appliances, . This beautifully appointed home has abundant natural light, soaring ceilings with multiple entertainment areas throughout the home. This idyllic home is set on

    Stephen Kraunelis Gibson Sotheby's International Realty

    80 Brierbrook St, Milton, MA 02186
  • 36 Nahanton Ave, Milton, MA 02186
    36 Nahanton Ave, Milton, MA 02186
    36 Nahanton Ave, 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
    • 160 Hilltop St, Milton, MA 02186
      160 Hilltop St, Milton, MA 02186
      160 Hilltop St, Milton, MA 02186
      /31

      Est $1,504,609 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 4,340 Sq Ft

      160 Hilltop St, Milton, MA 02186

      160 Hilltop St, Milton, MA 02186
  • 1262 Randolph Ave, Milton, MA 02186
    1262 Randolph Ave, Milton, MA 02186
    1262 Randolph Ave, Milton, MA 02186
    /42

    $1,189,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,370 Sq Ft

    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
  • 147 Sassamon Ave, Milton, MA 02186
    147 Sassamon Ave, Milton, MA 02186
    147 Sassamon 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
    • 52 Hilltop St, Milton, MA 02186
      52 Hilltop St, Milton, MA 02186
      52 Hilltop St, Milton, MA 02186
      /28

      Est $1,730,820 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,003 Sq Ft

      52 Hilltop St, Milton, MA 02186

      52 Hilltop St, Milton, MA 02186
  • 88 Hilltop St, Milton, MA 02186
    88 Hilltop St, Milton, MA 02186
    88 Hilltop St, Milton, MA 02186
    /29

    $1,049,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,306 Sq Ft

    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
  • 97 Brierbrook St, Milton, MA 02186
    97 Brierbrook St, Milton, MA 02186
    97 Brierbrook St, 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
    • 21 Harbor View Park, Milton, MA 02186
      21 Harbor View Park, Milton, MA 02186
      21 Harbor View Park, Milton, MA 02186
      /29

      Est $919,067 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,980 Sq Ft

      21 Harbor View Park, Milton, MA 02186

      21 Harbor View Park, Milton, MA 02186
  • 0 Sassamon Ave, Milton, MA 02186
    0 Sassamon Ave, Milton, MA 02186
    0 Sassamon Ave, Milton, MA 02186
    /7

    $879,000 Pending

    • Land
    • 0.25 Acre
    • $3,516,000 per Acre

    0 Sassamon Ave, Milton, MA 02186

    This buildable lot is set on the corner of Harborview and Sassamon Ave. This is an amazing opportunity to build your dream home in a fabulous neighborhood.

    Janice Bosworth Coldwell Banker Realty - Milton

    0 Sassamon Ave, Milton, MA 02186
  • 109 Harbor View Rd, Milton, MA 02186
    109 Harbor View Rd, Milton, MA 02186
    109 Harbor View Rd, 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
    • 43 Ridgewood Rd, Milton, MA 02186
      43 Ridgewood Rd, Milton, MA 02186
      43 Ridgewood Rd, Milton, MA 02186
      /32

      Est $1,051,318 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,042 Sq Ft

      43 Ridgewood Rd, Milton, MA 02186

      43 Ridgewood Rd, Milton, MA 02186
    • 10 Nahanton Ave, Milton, MA 02186
      10 Nahanton Ave, Milton, MA 02186
      10 Nahanton Ave, Milton, MA 02186
      /26

      Est $862,092 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,450 Sq Ft

      10 Nahanton Ave, Milton, MA 02186

      10 Nahanton Ave, Milton, MA 02186
    • 8 Nahanton Ave, Milton, MA 02186
      8 Nahanton Ave, Milton, MA 02186
      8 Nahanton Ave, Milton, MA 02186
      /28

      Est $975,100 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,844 Sq Ft

      8 Nahanton Ave, Milton, MA 02186

      8 Nahanton Ave, Milton, MA 02186
    • 440 Harland St, Milton, MA 02186
      440 Harland St, Milton, MA 02186
      440 Harland St, Milton, MA 02186
      /32

      Est $1,929,837 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,184 Sq Ft

      440 Harland St, Milton, MA 02186

      440 Harland St, Milton, MA 02186
    • 24 Brierbrook St, Milton, MA 02186
      24 Brierbrook St, Milton, MA 02186
      24 Brierbrook St, Milton, MA 02186
      /40

      Est $1,995,799 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 4,473 Sq Ft

      24 Brierbrook St, Milton, MA 02186

      24 Brierbrook St, Milton, MA 02186
    • 22 Parkwood Dr, Milton, MA 02186
      22 Parkwood Dr, Milton, MA 02186
      22 Parkwood Dr, Milton, MA 02186
      /42

      Est $3,831,007 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 7,628 Sq Ft

      22 Parkwood Dr, Milton, MA 02186

      22 Parkwood Dr, Milton, MA 02186
    • 63 Sears Rd, Milton, MA 02186
      63 Sears Rd, Milton, MA 02186
      63 Sears Rd, Milton, MA 02186
      /41

      Est $1,393,877 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 4,232 Sq Ft

      63 Sears Rd, Milton, MA 02186

      63 Sears Rd, Milton, MA 02186
    • 25 Nahanton Ave, Milton, MA 02186
      25 Nahanton Ave, Milton, MA 02186
      25 Nahanton Ave, Milton, MA 02186
      /26

      Est $1,010,361 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,971 Sq Ft

      25 Nahanton Ave, Milton, MA 02186

      25 Nahanton Ave, Milton, MA 02186
    • 1006 Randolph Ave, Milton, MA 02186
      1006 Randolph Ave, Milton, MA 02186
      1006 Randolph Ave, Milton, MA 02186
      /31

      Est $995,116 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 3,214 Sq Ft

      1006 Randolph Ave, Milton, MA 02186

      1006 Randolph Ave, Milton, MA 02186
    • 47 Hillside St, Milton, MA 02186
      47 Hillside St, Milton, MA 02186
      47 Hillside St, Milton, MA 02186
      /33

      Est $1,476,740 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 3,300 Sq Ft

      47 Hillside St, Milton, MA 02186

      47 Hillside St, Milton, MA 02186
    • 7 Heather Dr, Milton, MA 02186
      7 Heather Dr, Milton, MA 02186
      7 Heather Dr, Milton, MA 02186
      /37

      Est $1,760,261 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,668 Sq Ft

      7 Heather Dr, Milton, MA 02186

      7 Heather Dr, Milton, MA 02186
    • 52 Ford Ranch Rd, Milton, MA 02186
      52 Ford Ranch Rd, Milton, MA 02186
      52 Ford Ranch Rd, Milton, MA 02186
      /33

      Est $1,862,746 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 6,212 Sq Ft

      52 Ford Ranch Rd, Milton, MA 02186

      52 Ford Ranch Rd, Milton, MA 02186
    • 1210 Randolph Ave, Milton, MA 02186
      1210 Randolph Ave, Milton, MA 02186
      1210 Randolph Ave, Milton, MA 02186
      /39

      Est $1,010,392 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,103 Sq Ft

      1210 Randolph Ave, Milton, MA 02186

      1210 Randolph Ave, Milton, MA 02186
    • 104 Hilltop St, Milton, MA 02186
      104 Hilltop St, Milton, MA 02186
      104 Hilltop St, Milton, MA 02186
      /29

      Est $1,624,471 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,112 Sq Ft

      104 Hilltop St, Milton, MA 02186

      104 Hilltop St, Milton, MA 02186
    • 168 Hilltop St, Milton, MA 02186
      168 Hilltop St, Milton, MA 02186
      168 Hilltop St, Milton, MA 02186
      /27

      Est $1,228,255 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,405 Sq Ft

      168 Hilltop St, Milton, MA 02186

      168 Hilltop St, Milton, MA 02186

Showing Results 1 - 40, Page 1 of 11

Massachusetts Milton Hillside Street

Real Estate & Homes

Learn more about living in Hillside Street

Home Trends in Hillside Street, MA

On average, homes in Hillside Street, Milton sell after 40 days on the market compared to the national average of 51 days. The median sale price for homes in Hillside Street, Milton over the last 12 months is $1,512,500, up 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,512,500
Median Single Family Sale Price
$1,560,000
Average Price Per Sq Ft
$589
Number of Homes for Sale
5
Last 12 months Home Sales
8
Months of Supply
7.50
Median List Price
$1,695,000
Median Change From 1st List Price
10%
Median Home Sale Price YoY Change
10%
How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group