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$1,899,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73573617 MLS ⋅ 4,772 SqFt.
Where in Milton can you find a single-family home offering this much space, land, and lifestyle at this price? This exceptional property checks all the boxes. Set alongside the private golf course at Wollaston Country Club, this home offers over 4,000+ sq. ft. of living space, 4+ rooms, and over an acre of land. The open-concept kitchen flows seamlessly into the private backyard, complete with an in-ground pool perfect for entertaining and enjoying the outdoors. Turnkey and move-in ready, all that’s left to do is bring your belongings and make this spacious Milton home your own.

901 Randolph Ave, Milton
$765,000
3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73567467 MLS ⋅ 2,784 SqFt.
Nestled on 5 wooded acres, this distinctive property combines a beautiful 2+ bedroom main home, a newly built two story ADU, and outdoor space designed for making memories! You will find plenty of flexibility for rental income, multigenerational living, or private guest quarters. The new rental-ready ADU reflects impressive quality! An enclosed second floor porch overlooks a stunning heated saltwater pool, while a lower-level patio comes wired for a future hot tub. Inside, you'll find a beautiful kitchen with granite counters, electric fireplace, efficient heating and cooling, and a roomy bedroom with an oversized walk in closet. Buyers looking for extra income will value the turnkey appeal.The main house welcomes you with a large, open eat in kitchen centered on a generous island, with granite counters and rich hardwood floors. New sliders in the primary bedroom open onto an expansive deck ideal for morning coffee or evening sunsets. Freshly renovated tile bathroom.All new exterior doors and new heating and cooling units to add to better heating efficiency. Oversized detached garage built in 2024.Downstairs, the walkout basement includes a 12x12 finished room with its own heat zone, perfect as an office, gym, or guest space, plus plenty of storage or room to expand.Outside, the brand new heated saltwater gunite pool becomes the natural gathering spot, framed by a newly installed concrete paved patio. Surrounded by peaceful woods and jaw dropping sunset views. Deeded access to Northeast Pond sits just down the road, for boating, swimming, kayaking, fishing, etc. Milton Town Beach is minutes away for an easy beach day. With strong earning potential and undeniable appeal, this property is both a smart investment and a private paradise. Come see the possibilities before someone else does!

162 Bolan Road, Milton
$1,225,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73566740 MLS ⋅ 3,182 SqFt.
Situated in Milton’s Brush Hill Estate area, this 9-room, mid-century split-entry home on nearly an acre offers 3182 square feet of living space and a wonderful opportunity to add your personal touches. The property includes a two-car garage and several well-maintained updates over the years, including an addition and a renovated finished lower level, all adding to its appeal. On the main level, the home features a semi-open living room with a fireplace, a well-appointed chef's kitchen, a formal dining room with built-ins, and a sunroom/den with a wall of windows. There’s also a breakfast area with a skylight and sliding doors leading to a small deck for your convenience and easy maintenance. Three bedrooms, each with ample closet space, including a primary en-suite bedroom and a main hallway bathroom, complete the main level. The finished lower level features a spacious family room with a second fireplace, a separate office with custom cabinetry, a laundry room, a mud room/pantry with an extra refrigerator and upright freezer, and direct access to the garage. The utility/mechanical room houses all the home's systems, including five heating zones and central air conditioning for year-round comfort. The expansive grounds include a patio area, an in-ground swimming pool that needs some repairs, and three sheds providing extra storage for gardening tools and outdoor furniture. Move in now and make your desired alterations over time. Do not miss this unique opportunity. Enjoy easy access to the commuter rail, downtown Boston, Longwood Medical Area, the Neponset Bike Path, Blue Hills, Milton Academy, and more.

355 Brush Hill Road, Milton
$1,099,000
4 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73565687 MLS ⋅ 2,100 SqFt.
Only the second owners have ever called this house home, and that kind of stewardship is impossible to fake. It shows in every room. Warm floors, generous light, and rich original woodwork greet you at the door and carry through the main level. The kitchen was updated a decade ago with choices that were timeless then and still feel current now, the mark of an owner who renovated for the long haul rather than the trend. Out front, a welcoming porch looks across the street to the park, the kind of spot where mornings slow down and neighbors stop to talk. Out back, a patio sits level with both the house and the yard, an easy flow from kitchen to grill to pool. The pool itself was renovated three years ago, with a dedicated changing room right off the deck. Four well proportioned bedrooms anchor the sleeping level, while the finished attic adds flexible space above and two dedicated offices mean working from home never means working from the dining table.

45 Wendell Park, Milton
$2,195,000
6 Beds ⋅ 5 Baths ⋅ UNDER AGREEMENT Status ⋅ 73565411 MLS ⋅ 4,227 SqFt.
This is the Milton Hill home you have been waiting for! Character abounds and the gardens are stunning. The layout flexes with whatever stage of life walks through it. The first floor is anchored by fireplaces. There is a gas fireplace in each of the living spaces and a wood burning fireplace in the dining room, so the main level has four different places to gather and each one has a reason to sit down. Ceilings are high, windows are tall, and the original detail is still here. The kitchen is ready for its next chapter, and the footprint is the gift. There is genuine room to work with, enough for the island, the second sink, and the double ovens without borrowing an inch from anywhere else. Six bedrooms and four baths across three levels give every generation a floor of its own, whether that means a guest suite, a home office with a door that closes, a playroom, or all three. Wood floors run under the second floor carpeting. The primary has its own bath. The rest of the baths are all in working order and ready to take whatever finishes you have in mind. The systems have been handled. The home has been converted to gas, and mini splits run throughout, so every level stays comfortable through a July afternoon and a January night without a single window unit. Then there is the yard, and it is the moment. Water spills over a waterfall into the pool, the flower gardens frame it, and the stone tower of St. Michael's Church rises just beyond the property line. It reads like a courtyard in Europe and it sits on one of Milton's most recognizable streets. The equipment behind it is all new, with a new filter system, a new heater, and new pumps, so the season starts when you say it does and runs as long as you want it to. The gardens have been planted and tended for years, the kind of maturity you cannot buy new. They climb the stone terraces behind the pool with steps winding up through the beds. A deck off the back steps down to the terrace and the pool patio, and a walkout below sits a few steps from the water with a full fifth bathroom right there, so nobody tracks through the house in a wet suit. Pines and cedars close the property in on all sides. Outdoor living here is not a patio and a grill. It is a destination. Minutes to Milton Village, the Trolley to the Red Line, Milton Academy, Cunningham Park, the Blue Hills, and downtown Boston.

105 Randolph Ave, Milton
$4,500,000
7 Beds ⋅ 8 Baths ⋅ UNDER AGREEMENT Status ⋅ 73552866 MLS ⋅ 6,404 SqFt.
A rare opportunity to own one of Milton Hill's most distinguished homes. Set on nearly an acre just moments from Milton Village, this beautifully updated residence offers the space & versatility desired by the buyers of today. Designed to evolve with every stage of family life, the property features a 6 BR main home plus a newly completed 1 BR ADU, offering exceptional flexibility for extended family, guests, an au pair, private office or multigenerational living. Inside, generous gathering spaces, a chef's kitchen w/La Cornue range, formal & casual living areas, home office options & a finished 3rd floor provide room for families to grow, gather & entertain. Outside, enjoy a heated pool, pergola, wraparound deck & expansive fenced grounds designed for everything from childhood adventures to summer celebrations. Rich architectural detail blends seamlessly w/thoughtfully modern, yet classic updates. Minutes to Milton Academy, Milton Village, parks, restaurants & an easy commute.

75 Canton Ave, Milton
$1,395,000
4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73531855 MLS ⋅ 2,575 SqFt.
Welcome to 45 Foster Lane, a beautifully maintained four-bedroom home at the end of a coveted cul-de-sac in one of Milton's most desirable neighborhoods, just moments from East Milton Square. The bright and inviting floor plan features granite countertops, stainless steel appliances, gas cooking, hardwood floors, central air, and abundant natural light. The home offers four spacious bedrooms and three full baths, including a private primary suite with walk-in closet and en-suite bath. Outside, enjoy a resort-style backyard highlighted by a PermaCrete saltwater vinyl liner pool built by Easton Pool & Spa in 2020 and first enjoyed in 2021. Complete with an electric heater and expansive stamped concrete patio, the space is ideal for entertaining. A detached cabana with finished living space and a full bath adds exceptional flexibility for guests and poolside gatherings, creating a true private retreat.

45 Foster Lane, Milton
$987,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73519606 MLS ⋅ 2,232 SqFt.
This spacious 9-room home on Hillside Street offers 4 bedrooms in one of Milton's most coveted settings, nestled at the edge of the Blue Hills Reservation. With miles of trails, open space, and stunning natural scenery right outside your door, the location is truly special. The generous layout gives buyers real flexibility to update and personalize, with good bones and a highly desirable address to build from. The property includes a pool currently in need of repair, presenting a great opportunity to create a standout outdoor space on your own terms. Milton is known for its excellent schools, beautiful neighborhoods, and easy access to Boston, and Hillside Road delivers all of it. For a buyer with vision and an eye for value, this is a rare chance to put your stamp on a property where nature and neighborhood come together beautifully.

1066 Hillside St, Milton
$2,725,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73519240 MLS ⋅ 3,149 SqFt.
A rare and private Blue Hills retreat set on 2.6 wooded acres abutting conservation land, approached by a winding drive. Designed for those who value privacy and refined living, this exceptional property offers a peaceful escape just minutes from Boston and major routes. The beautifully renovated residence features 4 bedrooms and 2.5 baths, including a luxurious first-floor primary suite with a spa-style bath, custom cabinetry/closets and attached sunroom, perfect for quiet mornings and serene evenings. Elevated finishes and craftsmanship are showcased throughout, highlighted by a chef’s kitchen with Wolf double oven, built-in Miele coffee machine and striking marble and custom concrete countertops. Three bedrooms upstairs offer flexibility. The estate includes a detached 3-car barn-style garage with game room, plus a newly built garage connected by a slate-accented portico. A heated in-ground pool and cabana complete this private, resort-like setting. A truly exceptional offering.

135 Milton Street, Milton
$3,845,000
5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 73508385 MLS ⋅ 9,435 SqFt.
This fully renovated Georgian Colonial offers exceptional living and entertaining in one of Milton’s most desirable neighborhoods. Privately set at the end of a cul-de-sac in Indian Cliff Estates, the home sits on 1.88 acres with a three-car attached garage. The main level features an eat-in kitchen, formal dining room, and a gracious living room that flows into a sitting area. A dramatic family room with cathedral ceilings and a floor-to-ceiling stone fireplace anchors the home, complemented by a wet bar and direct access to the indoor heated pool and hot tub. An elegant foyer with a curved staircase leads to five well-appointed bedrooms. The expansive lower level offers multiple flex spaces, including a home gym, recreation rooms, and a private theater. Designed for both everyday living and memorable entertaining, this home delivers a rare blend of space, privacy, and resort-style amenities.

90 Countryside Ln, Milton

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