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Hillside Street Homes for Rent

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  • /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
  • /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

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.

Frequently Asked Questions

What are the most popular neighborhoods for renters near Hillside Street?
The most popular neighborhoods for renters near Hillside Street are Brush Hill, Milton Hill, Milton Center, Hyde Park and North Randolph.
What are the most popular zip codes for renters near Hillside Street?
The most popular zip codes for renters near Hillside Street are 02186, 02136, 02368, 02169 and 02126.
How to Rent a Home