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$835,000
3 Beds ⋅ 2 Baths ⋅ 73540243 MLS
Welcome to this classic center-entrance Colonial where charm meets comfortable modern living. This nicely maintained home features a spacious over-sized living room with a cozy gas fireplace and attached reading nook, the perfect spot to relax. The kitchen includes stainless steel appliances, granite counters and opens seamlessly to the dining room with a charming built-in hutch. A convenient 1/2 bath completes the first floor. Upstairs, you’ll find three spacious bedrooms plus a versatile bonus space ideal for a nursery, home office or creative retreat. The walk-up attic presents additional finished space along with room to expand. The lower level extends the living area with a finished room perfect for a playroom or office, a washer/dryer and plenty of storage. With classic details and flexible spaces, this Colonial offers timeless appeal and room to grow. A wonderful home filled with warmth and character. 10 minutes walk to trolley into Boston! Come see this gem!

7 St. Mary's Rd., Milton

Listing courtesy of Listing Agent: MonaLisa Team from Listing Office: Compass.
$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.
$999,000
3 Beds ⋅ 2 Baths ⋅ 73537767 MLS
Beautiful Colonial situated on a large corner lot, blending timeless character with modern updates. This charming home features 3 bedrooms and 1.5 baths plus an office, a renovated kitchen with custom cabinets and granite counters , gleaming hardwood floors, high ceilings, and exquisite period details throughout. Central air and heat and gas fireplace. Enjoy relaxing on the inviting wraparound porch or entertaining on the spacious rear deck overlooking the yard. Ample off-street parking accommodates up to 5 vehicles. A perfect combination of classic elegance, space, and convenience—this is a home you won't want to miss.

567 Canton Ave, Milton

Listing courtesy of Listing Agent: Anne Galvin from Listing Office: Coldwell Banker Realty - Dorchester.
$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.
$849,000
3 Beds ⋅ 1 Baths ⋅ 73533488 MLS
Pretty as a picture, this warm and inviting 3-bedroom, 1-bath home with attached garage is set on a charming tree-lined street. The bright and cheerful living room is anchored by a wood-burning fireplace with an updated stone surround and rustic wood mantle, and the formal dining room flows into a timeless white/granite/ss open-plan kitchen, perfect for everyday living and entertaining. Upstairs you'll find 3 bedrooms, 2 with oversized closets, and a tastefully updated full bath. The yard is a private and peaceful oasis complimented by mature plantings, an irrigation system, and a new deck that extends the living space outdoors. Thoughtful updates and tasteful touches show throughout, with an attention to detail that will be appreciated for years to come. Ideally located near Blue Hills recreation, public transportation and major highways. This is a home you'll love coming back to.

17 Landon Road, Milton

Listing courtesy of Listing Agent: Kim Powers from Listing Office: Coldwell Banker Realty - Milton.
$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.
$699,000
4 Beds ⋅ 2 Baths ⋅ 73531370 MLS
Nothing to do but move right into this beautiful home featuring 4 spacious bedrooms and 1.5 baths. Gleaming hardwood floors run throughout the house, complemented by a gorgeous kitchen with stainless steel appliances, granite countertops, and a generously sized island. The open floor plan seamlessly connects the kitchen, dining room, and living room, creating the perfect space for entertaining and everyday living. All bedrooms are located on the second floor along with a full bathroom. The finished basement offers a large family room, plenty of storage closets for additional living space. The property also includes a one-car garage and a driveway that accommodates two cars. Conveniently located within walking distance to the elementary, middle, and high school.

45 Decker St, Milton

Listing courtesy of Listing Agent: Dee Rodrigues from Listing Office: Model Living RE.
$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.
$739,000
1 Beds ⋅ 2 Baths ⋅ 73518950 MLS ⋅ ['The Residences At Milton Landing'] BLDG.
Welcome to this sun-filled top-floor 1-bedroom, 2-bath residence at sought-after Milton Landing with garage parking. An updated kitchen opens to bright living spaces with beautiful hardwood floors, ideal for everyday living and entertaining. The spacious primary en suite offers a comfortable retreat, complemented by in-unit laundry for added convenience. Residents enjoy a concierge-hotel lifestyle with a fitness center, library, and on-site restaurant. Step outside to peaceful nature walks, bird watching, and miles of scenic biking trails, or water activities along the Neponset River, with hiking and equestrian recreation in the nearby Blue Hills. The trolley provides easy access to downtown Boston in minutes, connecting you to renowned universities, hospitals, world-class museums, dining, and theater. This is elevated living at its finest, offering the perfect blend of easy living, with nature and accessibility to city life just outside your door.

88 Wharf Street Unit 607, 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.
$740,000
3 Beds ⋅ 2 Baths ⋅ 73515348 MLS ⋅ ['Ice House'] BLDG.
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

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: South Shore Sotheby's International Realty.
$875,000
3 Beds ⋅ 2 Baths ⋅ 73513200 MLS
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

Listing courtesy of Listing Agent: Tom Wehr from Listing Office: Compass.
$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.
$3,895,000
5 Beds ⋅ 7 Baths ⋅ 73508385 MLS
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

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.
$4,495,000
6 Beds ⋅ 8 Baths ⋅ 73506861 MLS
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

Listing courtesy of Listing Agent: Matthew Freeman from Listing Office: Coldwell Banker Realty - Milton.
$725,000
2 Beds ⋅ 2 Baths ⋅ 73506801 MLS ⋅ ['Ice House'] BLDG.
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

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: South Shore Sotheby's International Realty.
$1,990,000
4 Beds ⋅ 3 Baths ⋅ 73500894 MLS
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

Listing courtesy of Listing Agent: Kimberly Ruiz from Listing Office: eXp Realty LLC.
$3,049,000
4 Beds ⋅ 4 Baths ⋅ 73504839 MLS
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

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

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