Step into this charming and meticulously maintained Cape, nestled in the desirable Cunningham Park neighborhood of Milton. Cherished by a single owner, the home still carries the warmth and character of its era. Serving as a practical entry point, a spacious mudroom with easy interior and exterior access boasts wood paneling and is the perfect space for keeping everyday essentials organized. An inviting, screened-in back porch overlooking a sizable, fenced in back yard with shed is the ideal spot for a quiet retreat. First floor offers cozy and comfortable living while the one-car garage adds convenience. Find three generous sized bedrooms and full bath upstairs. Lower level features a versatile finished basement with fireplace, laundry room, and abundant storage. Bonus workspace includes a built-in workbench, perfect for projects, tools, or crafting. This home combines suburban tranquility with easy access to everything Greater Boston has to offer.
Pretty but make it practical. 256 Robbins Street delivers. Your 5-bedrm, 2.5-bath colonial is well-proportioned, well-lit, and well-dressed—no asterisks required. A renovated kitchen earns every compliment with Wolf, Thermador, Bosch appliances, a generous island, and walk-in pantry. The family room with cathedral, beamed ceiling makes a real impression — a gas fireplace and natural light do the rest. The entry hall welcomes you properly with space for bags, jackets, hugs and kisses. All 2nd-floor bedrooms offer recessed lighting, well-lit closets and flexibility. A stone terrace is already your best feature with room to lounge and be everyone's favorite destination. The upgrades list is recent: windows, siding, electrical, HVAC, appliances, painting, more. This home has been maintained with a level of care that speaks volumes. Commuter rail access puts Boston within easy reach. 256 Robbins Street is the kind of home you stop making excuses to find. It's here. It's ready. So are you.
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.
Looking for a home with historical significance? A home with character, charm, and lots of space? 147 Canton Avenue has arrived. Guests are greeted by a large foyer, 10-foot ceilings, and a sense that lots of love has lived here. The first floor features a front-to-back living room with a fireplace, an office with built-ins, a large dining room, a kitchen with an adjoining family room, a laundry room, a 1/2 bathroom, and a walk-in foyer closet. The second floor has six bedrooms and two bathrooms. The third floor has two additional bedrooms and a bathroom. The basement is partially finished (not heated) and offers a bathroom, gym, and access to the two-car garage. The home is gas-heated and has a 200-amp electrical panel. Outside, there is a hot tub, a patio, and a sprawling 1/2-acre lot. The Milton Hill location is perfect, within walking distance of Milton Academy, Glover School, Turners Pond, the Central Square and Milton Village shopping areas, and the trolley. Come and fall in love
This exceptional Milton home presents a rare opportunity to own a spacious and versatile property in a highly sought-after neighborhood. Previously configured as a two-family residence, it is now thoughtfully presented as a single-family home with a fully equipped in-law apartment—ideal for an extended family or potential rental income. Set on an expansive 11,465 sq ft lot, the home features two kitchens, two full bathrooms, separately metered utilities, and private outdoor spaces for each living area. Hardwood floors run throughout, bringing warmth and timeless character, while the in-law apartment has been freshly painted and boasts beautifully refinished floors, making it move-in ready. The bi-level second unit offers 2–3 bedrooms along with an updated kitchen and bath, providing additional comfort and functionality. Outside offers a detached oversized garage and parking for six+ vehicles. Conveniently located near public transportation, shops, and restaurants. Perfect opportunity
Want to live on a quiet cul-de-sac and still be 6 miles from downtown Boston? Welcome to 13 Cantwell Road in Milton's Columbine neighborhood. This home delivers space, style, and character that's increasingly hard to find. A welcoming entrance and graceful staircase set the stage from the moment you arrive. Hardwood floors and timeless charm carry throughout. The main level offers a living room, den, dining area, and kitchen bathed in natural light through large, elegant windows. Four bedrooms and 2.5 baths offer room for everyone to spread out. The primary suite features soaring ceilings, an en suite bath, dedicated laundry, and multiple closets. A partially finished basement adds flexible space for a home office, gym, or playroom. The Milton Trolley is within walking distance, connecting you to the Red Line and the city with ease. Shields Park, the Neponset River Trail and Turners Pond are all a short walk away. This is Milton living at its finest.
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.
Stunning Modern Farmhouse in one of East Milton's most desirable neighborhoods - Welcome to 100 Gerald Road. This exceptional home was custom redesigned & built by a well known local developer with a perfect blend of refined elegance & comfortable living.. 4 bedrooms with ample closets & 3.5 baths, an open and flexible floorplan that boasts bedrooms with en suite on both main floor & 2nd level. Chef's kitchen with high end fixtures, custom cabinetry & unique millwork throughout. Impressive dining area leads to fireplaced family room with slider to deck & fully fenced 7,584 sq ft yard. Set in the sought after Cunningham Park area, you'll enjoy easy access to parks, trails, schools & more. There's an additional 400+ sq ft in the finished basement. Want to walk through this home in 3D and High Definition? Visit https://tinyurl.com/100GeraldRd or schedule your interior tour today. A true " This is it" home for discerning buyers ready to settle into one of Milton's finest communities.
Set on beautifully manicured grounds, this rarely offered Adams end-unit townhome blends luxury with ease of living. A welcoming front porch opens to soaring 22-foot ceilings and sun filled open spaces. The gourmet kitchen features quartz island and countertops, custom cabinetry, and Jenn Air appliances, flowing seamlessly into the formal dining room with a tray ceiling and an inviting living room with a gas fireplace and private deck access. The first-floor primary suite offers a walk-in closet and spa-inspired marble bathroom. A flexible den/office, first-floor laundry, and mud room add practicality, while an attached two-car garage provides convenience. Upstairs, two spacious bedrooms, a loft, nook, family room and full bath offer versatile living spaces. Meticulously designed, this home combines elegance, function and comfort in a highly desirable location with thoughtful details and an ideal layout for entertaining and everyday family life. Woodmere condominiums are for all ages.
Step back in time with this stunning 12 room Victorian masterpiece-a perfect blend of timeless elegance and modern comfort. This turn-key home features three levels of living with 5 spacious bedrooms and 3 bathrooms, offering room for everyone. From the moment you enter, you'll be captivated by the incredible solid woodwork, ornate architectural details and period charm that define every space. High ceilings, intricate trim and large windows bathe the home in natural light, while modern updates-thoughtfully integrated throughout-ensure effortless living. Whether your're entertaining guests on the stately covered porch or enjoying quiet evenings by the fireplace, this Victorian gem delivers both grandeur and warmth in equal measure. With its meticulous preservation and complete updates, this home is truly a one-of-a-kind treasure ready for you to move right in and enjoy. See attached list of improvements which includes central air, solar panels, hardscaping and boiler.
Set down a meandering, tree-lined drive, this spectacular turn-of-the-century Manor estate in Milton is a truly rare offering. From the moment you step into the welcoming foyer, elegance abounds. Three gracious floors of seamless living provide an exceptional balance of grand scale and warmth, featuring multiple bedroom suites and generous gathering spaces designed to accommodate both everyday living and memorable entertaining. This is a home where families gather, laughter fills the rooms, and life’s most cherished moments are made. A true architectural gem, the residence showcases exquisite period details including thick dentil moldings, rich hardwood floors, and finely preserved craftsmanship throughout. The home has undergone a thoughtful, major renovation that honors its historic character while seamlessly incorporating modern comforts and functionality. Privately sited on an impressive 7.32 acres, the grounds offer serenity, space, and a sense of timeless estate living.
Introducing the newly constructed Icehouse on the Parkway Condominiums! This luxurious building boasts beautiful Quartz countertops, white shaker cabinets with stainless steel appliances. In-unit laundry with a Electrolux washer and dryer included. Generous-sized tiled bathrooms, custom designed closets, Hydro Air AC, and Navian energy-efficient tankless heat/hot water systems in every unit. The building features an elevator, fitness room, and comfortable common areas. Adjacent walking trails lead to the historic Popes Pond. The building pays homage to the once thriving ice harvesting businesses in the area (see attachment for a brief history). All units come with a designated storage space, and underground parking.
Set in a peaceful, leafy neighborhood close to schools and everything Milton has to offer, this home boasts quality construction, thoughtful architectural features, high ceilings and a versatile floor plan with ample space for living, working and hosting plus an in-law/guest suite or 1st fl primary . The great room with dining area and fireplace is bathed in natural light from its oversized windows. The chef's kitchen is warm and inviting with center island and breakfast nook and sitting area. A butler's pantry, laundry, bath, family room + private bedroom suite complete the first floor. The second floor features a loft area perfect for studying, primary suite and two additional bedrooms and 2nd bath. The lower level has an office/gym with full bath and a separate entrance as well as a bonus play room. Outside, you'll enjoy a wrap-around composite deck and brick patio. This property has been meticulously maintained for and is ready for a new owner to add their touches!
Experience unparalleled scale in this reimagined nearly 5,000 sq. ft. Split-Colonial conversion. Fully renovated within the last 5 years, this estate sits on a rare 1-acre corner lot near Wollaston Country Club. The exterior shines with premium Hardie Board siding, a new roof, and high-efficiency windows. Inside, a chef’s kitchen features a 12-foot waterfall quartz island and professional Thermador appliances. The layout seamlessly integrates a split-entry with a massive two-story Colonial addition, offering a sun-drenched Great Room and expansive family room. An entertainer’s dream, the home boasts Sonos in-ceiling speakers throughout, a lower-level wet bar, and a versatile gym space. The backyard is a private resort featuring an in-ground pool, custom paver patio, fire pit, and an architectural 30ft Trex deck with a built in Weber grill. Minutes from Blue Hills and top schools, This home combines massive living space with a pristine outdoor sanctuary. A true turn-key masterpiece.
To those who resist being a foregone conclusion — consider this the on-ramp. The move to the suburbs is often framed as a trade: more space, less edge. At 995 Brush Hill Road, that bargain was never struck. This 6,790-square-foot mid-century residence carries its cool quietly — without announcement, without apology. The kitchen sets the tone with top tier appliances, a resort-scale fireplace, generous pantry and walls of glass dissolving the line between inside and out. Ceilings rise with intention, leaving room for light, art, and good times. Outdoors a generous deck hugs the landscape as though it was always meant to be. And for those whose other collection has horsepower, a new 6-car garage arrives as the final, considered gesture—designed for the discerning, built for the serious. There is room here for collections of every kind. This house doesn't ask what you'll do with the space. It assumes you already know. Mid-century bones. Modern sensibility. Milton, at its most compelling.
Set on a private lane within a five-home enclave, this 10,000+ SF estate is bordered by 7,000 acres of protected land in the Blue Hills Reservation, offering a level of privacy rarely found this close to Boston. Accessed by a stone bridge, the home unfolds across 20 thoughtfully designed rooms with 6 bedrooms and 6 bathrooms. A grand foyer leads to vaulted ceilings, a paneled library with fireplace, multiple living and recreation spaces, a home gym, and a dedicated home theater. The kitchen, equipped with premium appliances, opens seamlessly to a large family room anchored by a floor-to-ceiling stone fireplace. The primary suite features a five-piece bath, steam shower, and multiple walk-in closets. Set on 4+ acres, the grounds include a stone terrace with outdoor kitchen, fireplace, jacuzzi, and mature landscaping. A heated four-car garage, dual driveways, and circular motor court complete the offering. Not just a Milton home; an estate with a Milton address.
Expanded Mission-style ranch in desirable Pope's Pond neighborhood ! This uniquely designed home features hardwood floors, bay windows, and custom woodwork throughout. Bright fireplaced living room opens to an updated kitchen with custom cabinetry, quartz countertops, marble backsplash and stainless steel appliances, oven, stove, hood, microwave and refrigerator. Kitchen overlooks a mid level den with cathedral ceiling and stunning custom stone wall, with view of the private yard and stone patio-perfect for entertaining. Main level offers 3 bedrooms and a full bath. Finished lower level includes bonus room with brick accent wall, wood burning stove and full bath-ideal for home office, guest space or in-law potential. Recent updates include two new mini split A/C systems and upgraded 200 amp electrical. Private backyard with oversized garden shed ready for your finishing touches.
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.
Discover the essence of comfortable living. some updates have been added. This inviting 2,088 sq ft single-family residence, built in 1980, is move-in ready and designed for a seamless transition into your new lifestyle. The kitchen, a central hub for daily life and entertaining, features a practical peninsula, offering both workspace and a casual dining spot. Step into the living room, where the warmth of hardwood flooring creates an inviting atmosphere, perfect for relaxation or gathering with loved ones. One of the well-appointed bathrooms offers a double vanity, providing convenience and ample space for daily routines. This colonial-style home offers five spacious bedrooms, two full bathrooms, and one half bathroom, ensuring comfort and privacy for all. An attached garage provides two spaces for vehicles and additional storage. Enhancing its appeal and efficiency, the property also includes solar panels. HAS A SEPTIC TANK
Exceptional location meets refined luxury in this fully renovated two-level condo in historic Milton! Just 4 mins walk to the Redline Station!! This fantastic 4-bedroom, 3-bath residence features two primary suites and a thoughtfully designed open layout ideal for modern living. The chef’s kitchen impresses with white quartz countertops, a breakfast bar, glass tile backsplash, and premium Bosch appliances. Enjoy hardwood floors, a built-in sound system, and central A/C throughout. The upper-level primary suite offers custom closets and a spa-inspired marble bath with double vanity, soaking tub, and rainfall shower. A second ensuite bedroom on the main level provides flexibility for guests or multigenerational living. Complete with a private deck, garage, driveway parking, and outdoor space. Ideally located near top-rated schools, restaurants, parks, and trails, with easy access to the Red Line for a quick commute to Boston. A perfect blend of space, style, and convenience!
Exceptional location meets refined luxury in this fully renovated two-level home in historic Milton! Just 4 mins walk to the Redline Station!! This fantastic 4-bedroom, 3-bath residence features two primary suites and a thoughtfully designed open layout ideal for modern living. The chef’s kitchen impresses with white quartz countertops, a breakfast bar, glass tile backsplash, and premium Bosch appliances. Enjoy hardwood floors, a built-in sound system, and central A/C throughout. The upper-level primary suite offers custom closets and a spa-inspired marble bath with double vanity, soaking tub, and rainfall shower. A second ensuite bedroom on the main level provides flexibility for guests or multigenerational living. Complete with a private deck, garage, driveway parking, and outdoor space. Ideally located near top-rated schools, restaurants, parks, and trails, with easy access to the Red Line for a quick commute to Boston. This house was listed MLS # 73492718 as a condo
Majestic and truly one of a kind, this exceptionally private equestrian estate is nestled behind gates within the Blue Hills Reservation, offering direct riding access to over 7,000 acres of protected landscape and year-round outdoor pursuits. Set on more than eight tree-lined acres, the grand compound includes a masterfully constructed main residence, carriage house, expansive garage, and beautifully appointed stables. Designed for both refined living and effortless entertaining, the home features a stunning chef’s kitchen, a soaring vaulted great room with an impressive fireplace and hearth, and seamless indoor-outdoor flow to a covered outdoor kitchen and generous fire pit terrace beneath the stars. Located moments from the prestigious Milton Academy and within easy reach of both Boston and Providence, this extraordinary offering delivers rare privacy, scale, and sophistication in a setting that is simply unparalleled.
Set behind a long approach offering the ultimate in wooded privacy and open lawn, 341 Highland is a classic Milton estate defined by land, light, and enduring craftsmanship. Substantial oak doors, rich paneling, French pocket doors between the living and dining rooms, and multiple fireplaces reflect the home's timeless character. The main living spaces balance scale with everyday comfort. A dedicated first floor office with private entrance off the circular drive and a playroom complement rooms suited for both formal entertaining and relaxed living. The primary suite anchors a generous private wing, while two staircases one with its own private entrance offer flexible circulation throughout. The finished third floor provides au pair quarters alongside space for hobbies, music and creative pursuits. Stone walls, patio areas, and an enclosed porch extend living into the landscape perfect for quiet mornings and memorable sunset views near the Blue Hills. Shown by private appointment only.
Introducing the newly constructed Icehouse on the Parkway Condominiums! This luxurious building boasts beautiful Quartz countertops, white shaker cabinets with stainless steel appliances. In-unit laundry with a Electrolux washer and dryer included. Generous-sized tiled bathrooms, custom designed closets, Hydro Air AC, and Navian energy-efficient tankless heat/hot water systems in every unit. The building features an elevator, fitness room, and comfortable common areas. Adjacent walking trails lead to the historic Popes Pond. The building pays homage to the once thriving ice harvesting businesses in the area (see attachment for a brief history). All units come with a designated storage space, and underground parking.
Prominently positioned on Pleasant Street, this custom 1927 home is rich in character and timeless architectural detail while offering wonderful opportunities for personalization. The home blends the charm of yesterday with a thoughtful addition featuring a spacious dining area and family room with a dramatic floor-to-ceiling fieldstone fireplace and striking beamed ceiling—creating a warm and inviting gathering space. Hardwood floors run throughout the home, complemented by classic yesteryear detailing that reflects the craftsmanship of the era. An expansive deck overlooks the beautiful 1.80-acre property, complete with walking trails and natural surroundings ideal for outdoor enjoyment. A barn offers space for one-car parking, storage, or workshop potential. Perfectly located for commuters and convenient to area amenities, this distinctive Milton property presents a rare opportunity to restore, customize, and create your dream home in a sought-after setting.
Milton is located in Massachusetts. Milton, Massachusetts has a population of 28,382. Milton is more family-centric than the surrounding county with 47.49% of the households containing married families with children. The county average for households married with children is 36.79%.
The median household income in Milton, Massachusetts is $153,971. The median household income for the surrounding county is $112,089 compared to the national median of $69,021. The median age of people living in Milton is 39.3 years.
The average high temperature in July is 82.9 degrees, with an average low temperature in January of 18.1 degrees. The average rainfall is approximately 49.6 inches per year, with 45.4 inches of snow per year.
