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75 Canton Ave, Milton
$4,375,000
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.
103 Canton Ave, Milton
$3,500,000
6 Beds ⋅ 5 Baths ⋅ 73508697 MLS
There is a particular feeling that comes with finding the right home — recognition. And so it is with 103 Canton Ave, the feeling you’ve always known it. Set on a rare 2.65 acres, this residence carries a quiet confidence. The entry hall signals something significant ahead with each gathering space unfolding like a revelation. 6+ bedrooms, 4.5 renovated baths, and a floor plan that accommodates the full arc of life. The kitchen — custom cabinetry, Wolf and Sub-Zero — is the heart, as it always is. Floor-to-ceiling windows in the living room frame a bluestone terrace and expansive lawn. Light moves through this room in a way that reminds you why people fall in love with established addresses. Beneath its good bones: updated HVAC, electrical, roof, plumbing. The investment is sound; the comfort is modern. An oversized 2-car garage and mudroom complete the picture. Easy access to Milton Academy, Glover School, the trolley. This is the kind of home you explore once and already miss.

103 Canton Ave, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.
203 Adams St, Milton
$3,100,000
7 Beds ⋅ 5 Baths ⋅ 73374837 MLS
Once in a lifetime opportunity to own this home w/expert craftsmanship, discover the timeless elegance of the historic Dr. Amos Holbrook House. Built around1800, this distinguished Federal-style residence offers over 7,300 square feet of living space, featuring seven spacious bedrooms & four & a half bathrooms. Set on a generous 2.56-acre lot, the property boasts a blend of historical charm & modern comfort. Original architectural details have been meticulously preserved, reflecting the home's rich heritage, complete w/hand painted frescos, original inlaid hardwood floors, rare pentagonal bay window in the family room, 7 fireplaces & a very special barn + greenhouse w/possibilities. Nestled directly across from the scenic Governor Hutchinson's Field, residents can enjoy breathtaking views of the Neponset River marshes, the city of Boston skyline & Harbor. This private & exceptional estate offers a unique opportunity to own a piece of Massachusetts history.

203 Adams St, Milton

Listing courtesy of Listing Agent: Jackie O Real Estate Team from Listing Office: Keller Williams Realty Boston-Metro | Back Bay.
263 Adams St, Milton
$2,900,000
4 Beds ⋅ 6 Baths ⋅ 73534896 MLS
Perched atop prestigious Milton Hill and set on nearly an acre of beautifully landscaped grounds, this extraordinary estate offers over 7,500 square feet of refined living space. A dramatic atrium foyer welcomes guests into elegant interiors featuring rich hardwood floors, soaring ceilings, and exceptional craftsmanship throughout. Designed for both grand entertaining and everyday living, the home includes a chef’s kitchen, wood-paneled library, media room, and temperature-controlled wine cellar. The luxurious primary suite serves as a private retreat with natural light and a spa-inspired bath, while four additional bedrooms provide ample space for family and guests. Outdoors, a resort-style setting awaits with a sparkling pool, cabana, expansive patios, and manicured grounds ideal for entertaining or relaxation. Complete with a three-car garage and offering the perfect balance of privacy and convenience, this residence is just minutes from Boston, renowned schools, and amenities.

263 Adams St, Milton

Listing courtesy of Listing Agent: Michael Carucci from Listing Office: Serhant.
191 Adams St, Milton
$2,650,000
4 Beds ⋅ 3 Baths ⋅ 73550784 MLS
Welcome to 191 Adams Street, a fully reimagined sprawling Ranch offering effortless first-floor living, stylish updates, and spaces made for entertaining. Every room has been thoughtfully redone, creating a bright, open floor plan that feels inviting from the moment you walk in. The stunning kitchen features new appliances, a generous workspace, and a seamless connection to the living and dining rooms, where scenic views of Hutchinson Field and the Boston skyline steal the show. The finished lower level adds incredible flexibility with a bedroom, full bath, office, and multiple living areas ideal for guests, extended family, a gym, or media room. Step outside to an expansive patio and huge backyard perfect for cookouts, yard games, and summer nights. An attached garage, easy highway access, nearby restaurants, shopping, and the bike path complete this move-in-ready gem! PRIVATE SHOWINGS ONLY!

191 Adams St, Milton

Listing courtesy of Listing Agent: Kim Powers from Listing Office: Coldwell Banker Realty - Milton.
20 Herrick Dr, Milton
$2,575,000
5 Beds ⋅ 4 Baths ⋅ 73458908 MLS
Leave your worries at the door and follow your bliss—20 Herrick Drive is that rare home where every day feels lighter and brighter. Set on one of Milton’s premier cul-de-sacs and embraced by conservation land, the acre lot offers privacy that is increasingly hard to find. Lofty spaces elevate the experience while generous windows and glass doors draw in the sun’s warmth and light. A home office supports modern requirements. The expansive family room is designed to gather comfortably. Flexible options for a guest suite or live-in arrangement. A renovated primary bath offers everyday comfort. The inground pool and bluestone terrace promise long summer afternoons with plenty of lawn for play, gardening, or peace. An oversized garage, newer windows and modern HVAC are all here. With the trolley, restaurants, Glover School, Milton Academy and Turner’s Pond close at hand, convenience becomes part of the lifestyle. If you’ve been waiting for a home that simply feels right—this is your moment.

20 Herrick Dr, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.
196 Canton Ave, Milton
$2,515,000
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.
213 School St, Milton
$2,100,000
5 Beds ⋅ 4 Baths ⋅ 73497233 MLS
There are homes that welcome you, and then there are homes that claim you. From the moment you step inside, this Milton Hill original announces itself—high ceilings, sweeping wall spaces, hefty moldings, an irresistible personality. Set on a lush acre, this residence has only grown more compelling with each refinement. Grand wall spaces beg for the art you've been waiting to hang, while a sense of graciousness moves through every room like a long exhale. A renovated eat-in kitchen is beautiful and deeply livable—mornings full of promise, evenings that stretch long. Every thoughtful update (windows, electrical, roof) honors what the house has always known about itself. Interior life unfolds over 4,300sf, 5+ bedrooms and 3.5 baths. And just beyond your door: Milton Academy, Glover School, Steel & Rye, the trolley. This is a home for someone who understands that where you live shapes how you live — a backdrop for the art, the dinners, the mornings in the garden, a life available here.

213 School St, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.
7 Russell St, Milton
$1,552,500
4 Beds ⋅ 3 Baths ⋅ 73497661 MLS
Welcome to 7 Russell Street, a home rooted in history. Long before modern Milton took shape, this home was built on the site of the former Governor Hutchinson estate and was originally the gardener James Morrissey’s house. Only two families have ever owned this home, and that kind of stewardship shows. Thoughtfully curated gardens surround the home, designed for year-round beauty and lovingly maintained. Inside, original hardwood floors, multiple fireplaces, and a 4-bedroom, 2.5-bath layout blend historic charm with modern updates. Located on Milton Hill, you’re minutes to Lower Mills’ dining & river paths, a short stroll to Turner’s Pond or Glover Elementary, and steps to the trolley into Boston. Homes with this kind of story are rare. 7 Russell St truly is where history feels like home.

7 Russell St, Milton

Listing courtesy of Listing Agent: Foster/ Harrington Team from Listing Office: Coldwell Banker Realty - Milton.
10 Brookside Park, Milton
$1,280,000
4 Beds ⋅ 3 Baths ⋅ 73487920 MLS
Some homes are simply built to stay, firmly grounded, beautifully proportioned, and designed to serve their owners for years to come. 10 Brookside Park welcomes its next steward, someone ready to settle into this vibrant Milton Hill neighborhood. The inviting front porch is perfect for morning coffee and evening conversations. Inside, high ceilings and abundant natural light create a sense of warmth and ease. The spacious kitchen anchored by a generous picture window is a favorite gathering place, offering lush views and ready for the furry companion in your entourage. A dedicated home office and 4 bedrooms provide flexibility. The 3rd floor primary suite offers a walk-in closet, full bath, and privacy. Updated HVAC, wiring, windows, car charger. Can’t wait for 400 tulip bulbs to pop this spring! Ideally situated near the trolley, Steel & Rye, Glover School, and the bike trail, this location supports a lifestyle defined by convenience and community. Built to stay. Built to be loved.

10 Brookside Park, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.

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