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Hillside Street Homes for Sale

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  • /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
  • /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
  • /14

    $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
  • /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
  • /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
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