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$1,100,000
7 Beds ⋅ 3 Baths ⋅ 73564495 MLS
*****RARE OPPORTUNITY TO OWN A TWO FAMILY IN MILTON***** [Unit 1]: New kitchen, new bath, gleaming hardwood floors, recessed lighting [Unit 2]: New kitchen, 2 new baths, loft space, hardwood floors, recessed lighting This home is centrally located in Milton on the Boston line. Easy access to public transportation and major roadways. Close proximity to Neponset River Reservation, Blue Hills, and nearby parks/trails. Lower Mills, Milton Village offer access to amenities such as restaurants, shops, and cafes.

168 Brook, Milton

Listing courtesy of Listing Agent: Team Galvin from Listing Office: The Galvin Group, LLC.
$2,995,000
5 Beds ⋅ 6 Baths ⋅ 73560323 MLS
Welcome to your brand new construction home in the beautiful town of Milton. Thoughtfully designed with over 5,300 square feet of refined living space, this custom built residence offers 5 bedrooms, 4 full baths, 2 half baths & an attached 2 car garage w/ extra storage. Entering through the arched front doorway you are greeted by an extensive open layout w/ high ceilings, natural light, a spacious dining room, and an oversized chef's kitchen featuring: taj mahal quartz counters, Thermador panelized appliances, a custom built venetian plaster vent hood, Mouser custom cabinetry & a massive pantry w/ a custom built door for easy loading direct from the garage. The 1st floor continues w/ a large living room area including a venetian plaster electric fireplace, custom built-ins, an extra office space or 1st floor bedroom flex space. The second level features a stunning primary suite bedroom w/ a parquet ipe private deck & a spa-inspired en-suite bath w/ a large wet-room shower and tub. Three guest bedrooms all include walk in closets and hardwood flooring. A dedicated laundry room and two more full baths complete the 2nd floor. The finished lower level offers flexible space for a media room, playroom, home gym area, wellness center, and/or an extra bedroom w/ a full bath. The exterior includes a fully landscaped yard, composite privacy fence, a massive Ipe deck, and irrigation. A 1 year builder warranty is included as well. Come see this custom designed home built by one of the best custom home builders in the area!

33 Harbor View Park, Milton

Listing courtesy of Listing Agent: The Quirk Group from Listing Office: Coldwell Banker Realty - Boston.
$3,295,000
5 Beds ⋅ 5 Baths ⋅ 73553103 MLS
Welcome to 16 Longmeadow Road, a custom-built masterpiece showcasing exceptional architectural detail at every turn. A dramatic two-story foyer with grand staircase and soaring ceilings sets the tone for this five-bedroom, four-and-a-half-bath residence in the highly sought-after Indian Cliffs Estates. The luxurious primary suite spans 500 square feet and features a spa-inspired ensuite with whirlpool tub, steam shower, and dual walk-in closets. The gourmet eat-in kitchen is a chef's dream, with a center island featuring a gas stove, dual sinks, and French doors flooded with natural light—flowing seamlessly into the formal dining room and sophisticated lounge complete with fireplace and wet bar, creating an entertainer's paradise. An additional living room with 11-foot tray ceiling, fireplace, and custom media cabinetry offers the perfect retreat. The home features a guest suite with separate entrance—ideal for an au pair, multi-generational living, or a private office sanctuary. Throughout, five walk-in closets, multiple linen closets, and a cedar closet provide unparalleled storage. The three-car garage and expansive rear patio with private well irrigation complete this exceptional property. Situated on nearly one acre and just 300 yards from Wollaston Golf Club, this residence offers both privacy and prestige.

16 Longmeadow Rd, Milton

Listing courtesy of Listing Agent: Emily Edwards from Listing Office: Gibson Sotheby's International Realty.
$1,100,000
4 Beds ⋅ 2 Baths ⋅ 73552983 MLS
Welcome to this inviting Colonial, ideally located in one of East Milton’s most desirable neighborhoods. With hardwood floors throughout the main and second floor staircase and hall, it awaits your personal touch. Enjoy the convenience of being just moments from local schools, directly across from Cunningham Park, and close to major highways, making commuting a breeze. You’ll also appreciate the nearby restaurants, shops, and amenities that make East Milton such a sought-after place.

106 Edge Hill Rd, Milton

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: South Shore Sotheby's International Realty.
$4,500,000
7 Beds ⋅ 8 Baths ⋅ 73552866 MLS
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

Listing courtesy of Listing Agent: Sarah Glovsky from Listing Office: The Charles Realty.
$1,499,900
4 Beds ⋅ 4 Baths ⋅ 73552355 MLS
Nestled in the heart of Milton's coveted Columbines neighborhood, 187 Hinckley Rd. offers the perfect blend of timeless charm, generous living space, and an unbeatable location. This 4-bedroom, 3.5-bath home features a warm, functional floor plan, spacious living areas, a partially finished lower level, and an unfinished walk-up attic offering exceptional expansion potential. Step outside to a private backyard ideal for entertaining, relaxing, and making lifelong memories. Just moments away, enjoy the convenience of walking to Glover Elementary, Pierce Middle School, Turner's Pond, Steel & Rye, and the trolley for easy access to Boston. The Columbines is celebrated for its tree-lined streets, welcoming neighbors, children playing outside, and traditions that make this one of Milton's most beloved communities. A rare opportunity to put down roots in a neighborhood you'll be proud to call home.

187 Hinckley Rd, Milton

Listing courtesy of Listing Agent: Brian Gagnon from Listing Office: Coldwell Banker Realty - Boston.
$4,995,000
5 Beds ⋅ 5 Baths ⋅ 73551180 MLS
Set off a lovely cul-de-sac, this restored Greek Revival sits on 4+ acres of open field, rare this close to Boston, stretching out rather than closing in. The expansive field: open, level, and bordering the 7,000 acre Blue Hills Reservation, accessible and yours to explore. A buildable lot: room to expand, a family compound, simply hold as open space, you decide. Fine millwork and French doors speak to fine craftsmanship. The kitchen is anchored by top appliances and built for serious cooking. A well-appointed mudroom keeps the everyday beautifully managed. A glass-walled garden room with fireplace, woodland views and stillness. Modern systems (geothermal heating/cooling, solar array, EV charger) reflect a commitment to sustainability. Privacy and peace without sacrificing reach: commuter rail, Rts 128/95, and Logan Airport all close. Access to Milton's public and the area's prestigious independent schools. This is where sophistication, sanctuary, and the wide-open sky meet.

1632 Canton Ave, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.
$1,185,000
4 Beds ⋅ 3 Baths ⋅ 73550414 MLS
Nestled on one of Milton’s most picturesque streets, this classic center-entrance Colonial offers the perfect blend of timeless charm, exceptional space, and an unbeatable location. Just a short stroll to Glover Elementary School, the Milton Public Library, and all the amenities that make Milton such a special place to consider home, this property delivers both convenience and community. Lovingly maintained by its original owner, this four-bedroom home reflects pride of ownership throughout. Generous living spaces include a rarely available first-floor family room, providing the flexibility and comfort today’s buyers seek. The well-designed floor plan offers plenty of room for everyday living and entertaining, while the two-car garage adds valuable convenience. A wonderful opportunity to own a cherished home in one of Milton’s most sought-after neighborhoods, where classic Colonial architecture, an outstanding location, and years of meticulous care come together beautifully.

40 Cape Cod Ln, Milton

Listing courtesy of Listing Agent: Matthew Freeman from Listing Office: Coldwell Banker Realty - Milton.
$1,249,000
5 Beds ⋅ 3 Baths ⋅ 73550347 MLS
Peacefully tucked away at the end of a quiet dead end street in East Milton, this 5 bedroom home offers a rare combination of privacy and space. With both a living room and a family room on the first floor, there is plenty of space for everyday living or room to entertain. The eat in kitchen overlooks the backyard and flows seamlessly to the dining room. Upstairs, the expansive primary suite is a true retreat, featuring a gas fireplace, cozy sitting area, his and her closets and a private ensuite bath. Step out to the attached deck - an ideal spot to enjoy the tranquill surroundings. Four additional bedrooms provide ample space for family and guests. Each bedroom has generous sized closets and can easily fit queen size beds. The spacious heated basement presents an excellent opportunity for future finishing, perhaps a rec room or home gym! The attached 2 car garage is large enough to accommodate 2 SUV's + storage. Walking trail at the end of street leads to golf course.

44 Quarry Lane, Milton

Listing courtesy of Listing Agent: Kathy McDevitt from Listing Office: Kelley & Rege Properties, Inc..
$1,195,000
4 Beds ⋅ 2 Baths ⋅ 73546064 MLS
Offering exceptional curb appeal in Milton's Hospital Hill neighborhood, this colonial blends timeless charm with comfortable living space. Gleaming hardwood floors flow throughout the home. The first floor offers a front-to-back living room with fireplace, a bright sunroom, a formal dining room with a built-in china cabinet, an eat-in kitchen & a half bath. Upstairs, you'll find four corner bedrooms, a full bath and a walk-up attic for storage/expansion options. The partially finished basement provides additional living space, ideal for a playroom, home office or gym. The backyard is perfect for entertaining family & friends, featuring a patio and play structure. Well maintained & updated, the current owners have replaced the roof (2018), water heater (2023) and gas furnace (2024). Ideally located minutes from Milton Academy, Milton Hospital, Turner's Pond & Milton's highly regarded public schools and a convenient location for commuting to Boston. Don't miss out on this great home!

8 Clifton Road, Milton

Listing courtesy of Listing Agent: Robinson / Rull Team from Listing Office: William Raveis R.E. & Home Services.
$1,299,000
5 Beds ⋅ 3 Baths ⋅ 73539896 MLS
Welcome home to this exceptional 5-bedroom, 3-bath residence that seamlessly blends timeless 1925 character with modern luxury of a 2015 substantial addition. Offering just under 3,000 square feet of living space, the home features a stunning kitchen with quartz countertops and new appliances. Beautifully done baths, radiant heat, air conditioning throughout, a spacious mudroom, versatile sunroom/home office, and convenient second-floor laundry enhance everyday living. House is now empty and move in ready. Bonus room in basement offers additional flexible living space. A substantial addition completed in 2014 creates the perfect balance of old-world charm and contemporary convenience. Ideally located within walking distance of East Milton Square's popular restaurants, cafés, and shops, near Andrews Park, and just minutes from Quincy Center Commuter Rai

24 Victory Avenue, Milton

Listing courtesy of Listing Agent: Jennifer Fortin from Listing Office: Frakes Realty.
$1,595,000
4 Beds ⋅ 4 Baths ⋅ 73540395 MLS
A true architectural statement, this custom contemporary blends iconic Mid-Century Modern design with refined European sensibility. Perfectly situated on a private acre, it’s a masterclass in light, volume, and timeless style. Dramatic angled beam ceilings and expansive walls of glass frame the sky and landscape, creating a seamless connection between indoors and out. Thoughtful renovations honor the home's original architectural integrity while introducing a fresh, sophisticated aesthetic. A chef's kitchen opens to dining room, designed for everyday living and elegant entertaining. The primary suite is a private sanctuary featuring custom Italian wardrobe systems and a spa-inspired bath. A media room, beautifully renovated baths, four to six flexible bedrooms provide versatility & potential for an au pair or guest suite. A covered patio overlooks terraced yard. Direct proximity to Longwood Medical area, Milton Academy, Fairmont commuter T station. It's a property that stands alone.

285 Brush Hill Rd, Milton

Listing courtesy of Listing Agent: Sandra Keller from Listing Office: Coldwell Banker Realty - Milton.
$1,895,000
4 Beds ⋅ 5 Baths ⋅ 73538357 MLS
Tucked away in Milton’s coveted Emerson Woods neighborhood, this beautifully maintained contemporary home offers exceptional space, flexibility & timeless design. Soaring ceilings, oversized windows, crown molding & a wood-burning fireplace create a bright, welcoming great room ideal for everyday living & entertaining. The chef’s kitchen features stone countertops, shaker cabinetry, a large center island, double ovens, a breakfast nook & dining area. A versatile first-floor suite with private entrance & full bath is perfect for guests, an au pair, or a primary bedroom option. Upstairs, the skylit primary suite is joined by two additional bedrooms, a loft & another full bath. The finished lower level offers flexibility for a gym, office, guest suite, or 5th bedroom. Enjoy outdoor living on the wraparound composite deck & brick patio, all in a peaceful setting close to top schools, local amenities, the Blue Hills Reservation & Milton Academy. Extensively renovated between 2012-2014.

375 Atherton Street, Milton

Listing courtesy of Listing Agent: David Green from Listing Office: Coldwell Banker Realty - Boston.
$1,199,999
4 Beds ⋅ 2 Baths ⋅ 73538210 MLS
Blending timeless character with modern versatility, this charming Milton home showcases beautiful original dark woodwork and a classic fireplace mantel. The spacious eat-in kitchen offers abundant cabinetry and a large butler’s pantry for exceptional storage and prep space. A first-floor den provides the option of a fifth bedroom, ideal for guests, a home office, or multigenerational living. The expansive third floor offers endless possibilities as a family room or office, featuring four skylights, exposed beams, ceiling fans, wall-to-wall carpeting, and built-in bookcases, with space to create two rooms if desired. Outside, the fully fenced backyard provides a private setting for entertaining, pets, and outdoor enjoyment. Set on a quiet dead-end street with convenient access to public transportation, downtown Boston, dining, bike trails, and recreational amenities.

14 Brookside Park, Milton

Listing courtesy of Listing Agent: Richard Fish from Listing Office: Conway - Hingham.
$1,199,000
4 Beds ⋅ 3 Baths ⋅ 73537540 MLS
Welcome to this conveniently situated property in East Milton Square. This neighborhood offers the perfect blend of suburban charm and urban accessibility; this home is located just steps away from local shops, restaurants, cafes, grocery stores, and other everyday conveniences.The property features a spacious and private backyard, providing open space for outdoor entertaining. There is also ample parking in the rear of the property.This 4 bedroom, 2 full and one half bath, and a finished basement is found in the heart of East Milton. This home is ready to be your next chapter - schedule a viewing today!

635 Adams St, Milton

Listing courtesy of Listing Agent: Connor Withington from Listing Office: Kelly Group Properties.
$1,195,000
3 Beds ⋅ 3 Baths ⋅ 73536896 MLS
Some homes ask you to choose. This one doesn't. Set on a private half-acre corner lot, this three-bedroom, three-bath Milton home is move-in ready and freshly painted throughout. Hardwood floors run the length of the main level. The living and dining areas open to one another, anchored by a sunroom and a bright kitchen with granite counters and stainless steel appliances. A finished lower level with a full bath offers room to spread out. Guests. A place to gather. A home office that stays separate when it needs to. Separation without distance. Two fireplaces. An oversized two-car garage. Central air-conditioning. The everyday details are handled. A fully fenced yard with a stone patio, pond, and retractable awning. Quiet when you want it. Ready when you don't. Minutes from Milton Academy, the Blue Hills, Wollaston Golf Club, Houghton's Pond, and Route 93. Space, comfort, and room to grow are yours for the taking.

79 Hilltop St, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.
$1,425,000
5 Beds ⋅ 5 Baths ⋅ 73533982 MLS
Set in one of Milton's most desirable neighborhoods, this thoughtfully designed home offers exceptional space, flexibility, and upscale finishes throughout. At its heart is a high-end chef's kitchen featuring premium appliances, custom cabinetry, and generous gathering space for everyday living and entertaining. A rare first-floor primary suite provides ideal accommodations for guests, multigenerational living, or single-level convenience, while the second floor features four additional bedrooms including a luxurious primary suite. The finished lower level with half bath adds approximately 500 square feet of versatile living space perfect for a media room, playroom, gym, or home office. Enjoy private outdoor space ideal for relaxing or entertaining, along with convenient access to the scenic walking and hiking trails of the Blue Hills Reservation. Meticulously maintained and built just 10 years ago, this home combines comfort, functionality, and timeless appeal.

37 Sassamon Ave, Milton

Listing courtesy of Listing Agent: Robin Shea from Listing Office: Principal Real Estate Partners.
$1,995,000
4 Beds ⋅ 4 Baths ⋅ 73532795 MLS
Designed to grow with you, this beautifully maintained, young home offers nearly 4,000 square feet of flexible living space on a spectacular 1.6-acre lot. The thoughtfully designed floor plan includes a first-floor primary suite, an additional first-floor bedroom, and two spacious bedrooms upstairs—ideal for a variety of lifestyles and living arrangements. At the heart of the home is a stunning custom kitchen by Faneuil Kitchens, opening to inviting spaces perfect for everyday living and entertaining. A bright living room with a dramatic two-sided fireplace creates a warm and welcoming gathering place, while oversized windows frame views of the beautifully landscaped grounds.Whether you're hosting holidays, working from home, accommodating guests, or simply looking for a home that will serve you for years to come, this exceptional property offers the space, flexibility, and setting to make it all possible!

282 Highland St, Milton

Listing courtesy of Listing Agent: Beth Rooney from Listing Office: eXp Realty LLC - Corporate Office.
$1,240,000
6 Beds ⋅ 3 Baths ⋅ 73532297 MLS
Great location! This classic Garrison Colonial sits on a desirable corner lot and features a cozy fireplace living room, hardwood floors, and an eat-in kitchen. The main level also offers a deck, formal dining room, and a flexible first-floor bedroom or home office. Upstairs you will find four generously sized bedrooms and a tiled full bath. Additional highlights include a partially finished basement, updated windows, central A/C, and a fenced, private yard. An attached two-car garage is topped by a full in-law apartment with its own kitchen/living room, hardwood floors, two bedrooms, and a full bath. All this just a short walk to Andrews Park and conveniently close to East Milton Square, restaurants, and highway access.

73 Washington Street, Milton

Listing courtesy of Listing Agent: Robert Mcauliffe from Listing Office: Duhallow Real Estate.
$1,395,000
4 Beds ⋅ 4 Baths ⋅ 73531855 MLS
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

Listing courtesy of Listing Agent: Scott Farrell & Partners from Listing Office: Compass.
$1,699,900
6 Beds ⋅ 5 Baths ⋅ 73529479 MLS
One of Milton's most desirable neighborhoods. Extensively updated in 2023, this property underwent a comprehensive gut renovation, including all-new plumbing, electrical systems, heating system, roof and numerous high-quality improvements throughout, offering the perfect blend of modern efficiency and timeless charm.The spacious kitchen and living areas provide excellent functionality for both everyday living and entertaining. The walk-out basement, offering tremendous potential for a future Accessory Dwelling Unit (ADU), in-law suite, guest quarters, home office, or additional income-producing space, subject to local approvals. The direct exterior access creates endless possibilities for multi-generational living or investment opportunities. Located near top-rated schools, parks, shopping, restaurants, and major commuter routes.

52 Ridgewood Rd, Milton

Listing courtesy of Listing Agent: Rebecca Huang from Listing Office: William Raveis R.E. & Home Services.
$14,500,000
5 Beds ⋅ 8 Baths ⋅ 73527740 MLS
Introducing the Alexander Forbes Mansion, a magnificent estate set on 6 beautiful acres in the historic and highly desirable Scott’s Woods district of Milton. This exceptional home showcases every modern amenity and has been meticulously renovated inside and out to the highest standards. The main level features a grand foyer, striking staircase, dramatic floor-to-ceiling windows and doors, formal living and dining rooms, an open kitchen and family room, solarium, home office, and a mudroom with access to the 3-car garage. On the 2nd floor, 5 bedroom suites include the luxurious primary suite with a spa-like bath and separate dressing rooms. The impeccably landscaped grounds offer a private utopia, featuring a heated in-ground pool, multiple patios and seating areas, garden area, grill, fire pit, tennis court, and a carriage house. Located at the foot of the Blue Hills, this outstanding home is minutes from top schools including Milton Academy and just eight miles from downtown Boston.

610 Harland Street, Milton

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.
$2,590,000
4 Beds ⋅ 4 Baths ⋅ 73525151 MLS
Recently reimagined by Design Construction Plus of Wellesley, this exceptional 4-bedroom, 3.5-bath home blends classic New England charm with sophisticated modern design across three finished levels beneath a timeless gambrel roofline. Sunlight fills the home through oversized windows, highlighting soaring ceilings, designer lighting, and curated finishes throughout. The open-concept living area features a dramatic stone fireplace and flows seamlessly into a chef’s kitchen with a quartz waterfall island, custom cabinetry, and premium Wolf, Thermador, and Liebherr appliances. Spa-inspired baths, a private en suite office, six heating zones, three zones of central air, updated systems, integrated sound, and exterior lighting add comfort and convenience. Ideally located near Glover Elementary, parks, shopping, dining, and commuter access, this turnkey Milton home offers timeless architecture, luxury finishes, and modern living.

196 Canton Ave, Milton

Listing courtesy of Listing Agent: Scott Farrell & Partners from Listing Office: Compass.
$3,299,000
5 Beds ⋅ 4 Baths ⋅ 73524569 MLS
Beautifully renovated and appointed 5-bedroom, 3.5-bath home in coveted Indian Cliffs Estates set on just under an acre of impeccably manicured grounds. This exceptional home features a spectacular 784 sq ft great room with 14-ft vaulted coffered ceilings, a dramatic 14-ft fieldstone fireplace, and custom mouldings, finishes and lighting throughout. The chef’s kitchen showcases a 9 foot island, custom Scandia cabinetry, Sub-Zero refrigerator, and a 48” Wolf dual-fuel 6-burner range with griddle and double ovens. Spacious, sun-filled interiors include a luxurious primary suite, finished basement, finished attic, ample storage, and flexible living space throughout. The private backyard retreat offers a resort-style salt water pool, spa, expansive patio, and lush landscaping perfect for entertaining. Ideally located less than one mile from Wollaston Golf Club, Milton Academy, Milton High, and Blue Hills Reservation. A rare turnkey opportunity in one of Milton’s premier neighborhoods.

85 Old Farm Rd, Milton

Listing courtesy of Listing Agent: Jay Rooney from Listing Office: Jay Rooney.
$1,895,000
3 Beds ⋅ 3 Baths ⋅ 73523755 MLS
Set on over 1.4 acres in one of Milton’s most picturesque settings, 268 Highland Street is a timeless brick-front Colonial where elegance, warmth, and unforgettable gatherings have defined this home for decades. From the slate roof and copper downspouts to the sweeping green lawns and mature landscape, every detail reflects classic New England charm. Inside, beautifully updated kitchens and baths blend seamlessly with gracious living spaces designed for entertaining and everyday comfort. A stunning home office overlooks the patio and expansive backyard, creating an inspiring work-from-home retreat. Beyond the main residence sits an extraordinary three-story barn—offering endless possibilities for creative space, storage, hobby use, or potential future ADU opportunities. Rarely does a property offer this combination of character, land, flexibility, and legacy just minutes from Boston.

268 Highland St, Milton

Listing courtesy of Listing Agent: Beth Rooney from Listing Office: eXp Realty LLC - Corporate Office.
$1,200,000
4 Beds ⋅ 2 Baths ⋅ 73519606 MLS
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

Listing courtesy of Listing Agent: Bridget Conroy from Listing Office: Coldwell Banker Realty - Milton.
$2,725,000
4 Beds ⋅ 3 Baths ⋅ 73519240 MLS
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

Listing courtesy of Listing Agent: Kim Powers from Listing Office: Coldwell Banker Realty - Milton.
$1,495,000
2 Beds ⋅ 2 Baths ⋅ 73517093 MLS ⋅ ['Milton Landing'] BLDG.
Perched at the pinnacle of luxury, this exceptional 2-bedroom, 2-bath penthouse offers an elevated lifestyle with two garage parking spaces and a truly rare private rooftop terrace showcasing sweeping views of the Neponset River Estuary and ever-changing, painted sky vistas. Inside, light-filled living spaces invite effortless entertaining and quiet relaxation, while the sprawling primary en-suite provides a serene retreat with generous proportions and comfort. A concierge building enhances daily living with a fitness center, library, and on-site restaurant, offering everyday convenience with a boutique-hotel feel. Outside your door, miles of walking and bike trails await, with the Milton Yacht Club nearby for weekends on the water. Just minutes to the Trolley and easy access to downtown Boston, with Milton Village and Milton Academy just outside your door. This is more than a home, it’s your elevated escape. Truly Milton living at it's finest.

88 Wharf Street Unit 604, Milton

Listing courtesy of Listing Agent: Kim Powers from Listing Office: Coldwell Banker Realty - Milton.
$3,400,000
5 Beds ⋅ 5 Baths ⋅ 73511555 MLS
Set off a lovely cul-de-sac, surrounded by woodland and sky, this restored Greek Revival offers grace, modern sustainability, and space for you and yours. Fine millwork and French doors speak to fine craftsmanship. The kitchen is anchored by top appliances and built for serious cooking. A well-appointed mudroom keeps the everyday beautifully managed: a quiet workhorse. A glass-walled garden room with fireplace and woodland views offers needed stillness. A bluestone terrace flows to the private trailhead into the Blue Hills Reservation: 7,000 acres for hiking or exploration. Modern systems — geothermal heating/cooling, solar array, and EV charger — reflect a commitment to sustainability. On 2+ acres of natural beauty, find privacy and peace without sacrifice: the commuter rail, Rts 128/95, Logan Airport within easy reach. Access to Milton's public and the area’s prestigious independent schools makes the address practical and inspiring. This is where sophistication and sanctuary meet.

1632 Canton Ave, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.
$1,995,000
8 Beds ⋅ 5 Baths ⋅ 73509983 MLS
Welcome to 147 Canton Avenue, a home where historical significance, rich character, and grand proportions come together. From the moment you step into the expansive foyer with its soaring 10-foot ceilings, you can feel the warmth and history of a home that has been deeply loved. Designed for effortless living and entertaining, the main level boasts a stately front-to-back living room with a cozy fireplace, a dedicated office with custom built-ins, a generous formal dining room, and a kitchen that flows seamlessly into an adjoining family room. A practical laundry room, a half bath, and a deep walk-in foyer closet complete this floor. With eight bedrooms and three finished baths spread across the upper levels, there is no shortage of space: Situated on a sprawling, half-acre level lot, the outdoor oasis features a private patio and a relaxing hot tub. The home is equipped with efficient gas heating and an updated 200-amp electrical panel. The Milton Hill location is unbeatable!

147 Canton Avenue, Milton

Listing courtesy of Listing Agent: Kevin G. Keating from Listing Office: Keating Brokerage.

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