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$1,495,000
2 Beds 2 Baths UNDER AGREEMENT Status 73517093 MLS 1,911 SqFt.
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

$740,000
3 Beds 2 Baths ACTIVE Status 73515348 MLS 1,333 SqFt.
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.

485 Blue Hills Parkway Unit 39, Milton

$549,000
3 Beds 2 Baths UNDER AGREEMENT Status 73513641 MLS 1,209 SqFt.
Prime Milton value-add opportunity with rare upside & a potential additional bonus home in the rear. Attached single-family, townhouse-style property ready for a straightforward cosmetic renovation ideal for investors, contractors, and savvy buyers looking to create immediate equity. Strong bones and layout allow for efficient repositioning and multiple exit strategies: fix-and-flip, long-term rental, or end-user renovation in one of Greater Boston’s most desirable suburbs. Milton offers top-tier schools, close proximity to Boston, and access to outdoor trails and amenities. There is a bonus fully constructed rear structure offering additional potential value. Buyer to perform all due diligence regarding zoning and allowable use of rear building. Proper permitting will be required to get the 2nd house in the rear approved. Opportunities like this in Milton are limited. CONTACT NOW FOR DETAILS AND SHOWINGS!

70 Brush Hill Rd, Milton

$875,000
3 Beds 2 Baths CONTINGENT Status 73513200 MLS 1,718 SqFt.
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.

15 Rose St, Milton

$3,400,000
5 Beds 5 Baths ACTIVE Status 73511555 MLS 4,310 SqFt.
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

$1,550,000
6 Beds 8 Baths UNDER AGREEMENT Status 73510632 MLS 3,216 SqFt.
Milton — Rare Opportunity! This beautifully renovated (2016) duplex offers 10 rooms, 6 bedrooms, 4full baths & 2 half baths. The main level features a spacious kitchen with stainless steel appliances, granite countertops, and an open-concept living and dining area, along with convenient first-floor laundry. The second floor includes two bedrooms and two full baths, while the third-floor bedroom offers a private retreat complete with a walk-in closet. Enjoy a generous yard perfect for outdoor entertaining. The unfinished basement provides ample storage and potential for future expansion. Ideally located with easy highway access and close proximity to Milton Academy and local public schools. Set in the heart of Milton, this home is just moments from Blue Hills Reservation scenic trails, Cunningham Park ballfields and pool, and the shops and dining of East Milton Square, including Abby Park, Novara, The Fruit Center Marketplace, The Cue & Nutshell.

403-405 Reedsdale Rd, Milton

$1,995,000
8 Beds 5 Baths ACTIVE Status 73509983 MLS 4,500 SqFt.
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

$3,200,000
6 Beds 5 Baths UNDER AGREEMENT Status 73508697 MLS 6,072 SqFt.
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

$3,895,000
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

$1,950,000
5 Beds 3 Baths UNDER AGREEMENT Status 73508119 MLS 5,458 SqFt.
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.

30 Magnolia Rd, Milton

$4,495,000
6 Beds 8 Baths ACTIVE Status 73506861 MLS 8,764 SqFt.
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.

650 Canton Ave, Milton

$725,000
2 Beds 2 Baths UNDER AGREEMENT Status 73506801 MLS 1,193 SqFt.
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.

485 Blue Hills Parkway Unit 21, Milton

$1,990,000
4 Beds 3 Baths PRICE CHANGED Status 73500894 MLS 4,772 SqFt.
Welcome to 901 Randolph Avenue, a beautifully renovated estate set on over an acre overlooking Wollaston Country Club. Offering nearly 5,000 square feet of thoughtfully designed living space, this 4-bedroom, 3-bath home blends luxury, comfort, and functionality. The chef's kitchen features premium Thermador appliances, custom cabinetry, quartz countertops, and a stunning 12-foot island. Multiple living areas, three fireplaces, a dedicated office, gym space, and flexible bonus rooms provide room for every lifestyle. Step outside to your private backyard retreat featuring a in-ground pool, expansive Trex deck, outdoor grilling area, fire pit, and professional hardscaping. Recent updates include new windows, doors, HVAC, roof, flooring, Hardie Board siding, and designer finishes throughout. A rare opportunity to enjoy luxury living in one of Milton's most desirable locations.

901 Randolph Ave, Milton

$3,049,000
4 Beds 4 Baths UNDER AGREEMENT Status 73504839 MLS 6,790 SqFt.
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.

995 Brush Hill Rd, Milton

$5,995,000
6 Beds 6 Baths ACTIVE Status 73499732 MLS 10,524 SqFt.
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.

3 Stone Bridge Lane, Milton

$859,000
3 Beds 2 Baths UNDER AGREEMENT Status 73498044 MLS 1,801 SqFt.
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.

15 Norman St, Milton

$2,250,000
5 Beds 4 Baths CONTINGENT Status 73497233 MLS 4,314 SqFt.
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

$1,100,000
7 Beds 3 Baths ACTIVE Status 73493874 MLS 3,500 SqFt.
Welcome to this spacious and beautifully updated two-family home offering comfort, style, and versatility. Unit 1 features 2 bedrooms and 1 updated bathroom, while Unit 2 offers an expansive layout with 5 bedrooms and 2 updated bathrooms, providing plenty of space for larger households or multi-generational living.Inside, you'll find brand-new kitchen cabinets, recessed LED lighting, beautiful hardwood floors, and a bright, inviting atmosphere throughout. Both units also include convenient washer/dryer hookups.Step outside to enjoy the spacious deck, perfect for entertaining guests, relaxing with family or friends, or enjoying your morning coffee. With its thoughtful updates, generous living space, and prime Milton location, this move-in-ready two-family home is one you won't want to miss. Come view this property now!

168 Brook Road, Milton

$3,500,000
6 Beds 4 Baths ACTIVE Status 73488165 MLS 7,169 SqFt.
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.

341 Highland St, Milton

$725,000
3 Beds 2 Baths UNDER AGREEMENT Status 73486879 MLS 1,333 SqFt.
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.

485 Blue Hills Parkway Unit 23, Milton

$1,725,000
4 Beds 2 Baths UNDER AGREEMENT Status 73484306 MLS 2,930 SqFt.
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.

207 Pleasant Street, Milton

$1,725,000
UNDER AGREEMENT Status 73484307 MLS
Rare opportunity to create your dream estate on this expansive 1.80-acre parcel prominently positioned on Pleasant Street in Milton. The beautiful property offers mature landscape, natural walking trails, and a picturesque setting ideal for a private residence or future estate. Currently improved with a charming 1927 custom home and barn, the land provides endless possibilities for renovation, expansion, or new construction. Whether restoring the existing home, designing a custom residence, or creating a private retreat, this property offers exceptional potential. The barn provides additional space for storage, workshop, or garage use. Ideally located for commuters and convenient to local amenities, schools, and area attractions, this distinctive property presents a rare opportunity to build or create something truly special in a sought-after Milton location.

207 Pleasant Street, Milton

$600,000
2 Beds 2 Baths ACTIVE Status 73474203 MLS 1,062 SqFt.
Last remaining two bedroom unit in this size and pricepoint! 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.

485 Blue Hills Parkway Unit 2, Milton

$715,000
2 Beds 2 Baths ACTIVE Status 73474181 MLS 1,220 SqFt.
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. This unit has a larger bedroom with double custom closets and room for home office 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.

485 Blue Hills Parkway Unit 12, Milton

$699,999
2 Beds 2 Baths ACTIVE Status 73473427 MLS 1,159 SqFt.
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.

485 Blue Hills Parkway Unit 13, Milton

$4,500,000
UNDER AGREEMENT Status 73058876 MLS
Developer's Dream! Incredible generational opportunity to purchase newly cleared land in gorgeous ultra desirable Milton with direct frontage and views over the river. Accessed via an easement over conservation land and under the tracks, wide open site which years ago went through a bylaw process to allow residential use of not more than 90 units (at the time, basic drawings were done for two buildings totaling 89 units). Approx 1/2 mile to MBTA Fairmount Commuter Rail in Boston! Referenced in the Milton housing plan of 2020 discussing the bylaw for up to 90 units with 10% affordable housing. No approvals or permits have been applied for and no representations made, buyer to perform their own due diligence. Priced for immediate sale and an exceptional development or land-use opportunity.

Truman Parkway, Milton

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