9

Hillside Street Houses for Sale

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  • 161 Sassamon Ave, Milton, MA 02186
    161 Sassamon Ave, Milton, MA 02186
    161 Sassamon Ave, Milton, MA 02186
    /31

    $1,656,900

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

    161 Sassamon Ave, Milton, MA 02186

    Take advantage of the reduced price of this spacious, historic home. Set on an 11,286 sq. ft. lot and containing 4,008 sq. ft. of living space it includes 5 bedrooms and 3.5 baths. The open 1st floor has 2 living areas, a dining area, a sitting room, an office, an original fireplace & a kitchen with custom cabinetry. There is also a private office and the sliding doors provide access to the

    Agent Photo

    Thomas O'Neill

    The Firm

    (617) 545-0113

    161 Sassamon Ave, Milton, MA 02186
  • 6 Brewster Rd, Milton, MA 02186
    6 Brewster Rd, Milton, MA 02186
    6 Brewster Rd, Milton, MA 02186
    /42

    $1,950,000

    • 5 Beds
    • 4.5 Baths
    • 4,472 Sq Ft

    6 Brewster Rd, Milton, MA 02186

    This stunning home nestled on a generous lot presents an attractive single-family home in great condition, a gourmet kitchen Quartz countertop stainless steel appliances gas cooktop and double oven, fireplace living room, first floor office with French doors, family room with bar and full bath, exercise room, primary bedroom has large walk-in closet full bath with separate tile shower and soaking

    Robert Mcauliffe Duhallow Real Estate

    6 Brewster Rd, Milton, MA 02186
  • 610 Harland St, Milton, MA 02186
    610 Harland St, Milton, MA 02186
    610 Harland St, Milton, MA 02186
    /31

    $15,000,000

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

    610 Harland St, Milton, MA 02186

    Set on nearly 6 acres in the prestigious Scott’s Woods, the Alexander Forbes Mansion is a rare stone estate where timeless elegance meets modern sophistication. Reimagined with exceptional attention to detail, this iconic residence features expansive, impeccably designed interiors and luxurious finishes. A grand foyer opens to formal living and dining rooms and a custom-milled chef’s kitchen that

    Maggie Gold Seelig MGS Group Real Estate LTD

    610 Harland St, Milton, MA 02186
  • 63 Sears Rd, Milton, MA 02186
    63 Sears Rd, Milton, MA 02186
    63 Sears Rd, Milton, MA 02186
    /42

    $1,279,999 Open Sat 11AM - 12PM

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

    63 Sears Rd, Milton, MA 02186

    Welcome to 63 Sears Rd — a rare opportunity in one of Milton’s most coveted neighborhoods, close proximity to the Blue Hills Reservation. Perfectly set on a picturesque half-acre lot, this sun-filled custom multi-level home offers 4,232 sq. ft. of versatile living space. The open kitchen/dining area flows seamlessly into a stunning stone fire-placed living room, while a spacious three-season

    Alex Walsh Access

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

    $5,995,000

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

    55 Parkwood Dr, Milton, MA 02186

    Significant price reduction for 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+ s.f. 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

    Kevin Keating Keating Brokerage

    55 Parkwood Dr, 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
  • 44 Ridgewood Rd, Milton, MA 02186
    44 Ridgewood Rd, Milton, MA 02186
    44 Ridgewood Rd, Milton, MA 02186
    /15

    $899,000

    • 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
  • 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
  • 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
Massachusetts Norfolk County Milton Hillside Street

Houses for Sale in Hillside Street, Milton

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.
Learn more about living in Hillside Street

Home Trends in Hillside Street, MA

On average, homes in Hillside Street, Milton sell after 47 days on the market compared to the national average of 52 days. The median sale price for homes in Hillside Street, Milton over the last 12 months is $1,062,500, down 26% from the median home sale price over the previous 12 months.

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%
How to Buy a Home How to Finance a Home How to Sell a Home

In Hillside Street, there are currently 9 houses for sale, offering a variety of options for prospective buyers. With houses ranging from $899,000 to $15,000,000, there's something for every budget. As of September, 2025 the median home price in Hillside Street, Milton is $1,562,500, while the average sale price is $1,564,722, providing insight into local market trends. On average, houses spend 47 days on the market before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options available to suit every lifestyle. Browse properties and houses for sale in Hillside Street, Milton and find the perfect place to call home.

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.

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