Homes for Sale in 02186

• 

  

  

  /39

  $1,280,700

  • 4 Beds
  • 2 Baths
  • 2,548 Sq Ft

  14 Brookside Park, Milton, MA 02186

  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

  Richard Fish Conway - Hingham

  14 Brookside Park, Milton, MA 02186
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  /33

  $1,995,000

  • 4 Beds
  • 4.5 Baths
  • 4,398 Sq Ft

  375 Atherton St, Milton, MA 02186

  Tucked away in Milton’s coveted Brush Hill 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

  David Green Coldwell Banker Realty - Boston

  375 Atherton St, Milton, MA 02186
• 

  

  

  /41

  $949,000

  • 3 Beds
  • 3 Baths
  • 1,570 Sq Ft

  30 School St, Milton, MA 02186

  Lovingly maintained by the same family since 1949, this charming 3-bedroom home offers a rare opportunity to own a piece of Milton history. Set on a beautiful private lot abutting peaceful woodlands, the home blends timeless character with thoughtful updates. The updated kitchen opens seamlessly to the main living areas, while the stunning family room with soaring vaulted ceilings and abundant

  The Jenkins Group Keller Williams Realty

  30 School St, Milton, MA 02186
• 

  

  

  /33

  $1,150,000

  • 4 Beds
  • 1.5 Baths
  • 2,486 Sq Ft

  3 Windsor Rd, Milton, MA 02186

  Curb appeal that stops you in your tracks. This classic 1929 Colonial sits proudly on a corner lot in Milton's coveted Columbines neighborhood, where tree lined streets and lush colorful gardens and flowers greet you before you even reach the front door. Step inside and the light does the talking, sun filled rooms all day long, with gleaming hardwood floors carrying that warmth from room to room.

  Cahill+Co. Team William Raveis R.E. & Home Services

  3 Windsor Rd, Milton, MA 02186
• 

  

  

  /35

  $899,000

  • 3 Beds
  • 1.5 Baths
  • 2,000 Sq Ft

  570 Eliot St, Milton, MA 02186

  Welcome to this beautifully maintained and charming Colonial, where classic character meets modern convenience. Relax on the spacious front porch or entertain on the private back patio surrounded by lush gardens filled with peonies, allium, lilies, and stunning roses.Inside, you'll find a spacious updated chef’s kitchen featuring granite countertops, custom cabinetry, and abundant storage. Just

  Sharon Ryan Coldwell Banker Realty - Milton

  570 Eliot St, Milton, MA 02186
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  /30

  $1,199,000

  • 4 Beds
  • 2.5 Baths
  • 2,042 Sq Ft

  635 Adams St, Milton, MA 02186

  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. This 4 bedroom, 2

  Connor Withington Kelly Group Properties

  635 Adams St, Milton, MA 02186
• 

  

  /25

  $799,000

  • 3 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  71 Capen St, Milton, MA 02186

  Get ready to fall in love with this sweet and stylish Cape bursting with personality! Step inside and you're instantly welcomed by rich hardwood floors and sun-splashed rooms that make every space feel bright, cheerful, and full of life. This home has that perfect mix of cozy charm and open, airy vibes.Location? It doesn't get much better. Set in a popular, convenient neighborhood, this gem abuts

  Matthew Freeman Coldwell Banker Realty - Milton

  71 Capen St, Milton, MA 02186
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  /28

  $849,000

  • 3 Beds
  • 1.5 Baths
  • 1,722 Sq Ft

  35 Craig St, Milton, MA 02186

  The one you've been waiting for! Beautiful and versatile 3-bed, 1.5-bath Colonial on a spacious corner lot offering classic charm and modern updates in one of Milton's most desirable neighborhoods. Gorgeous hardwood floors throughout. The main level features a front-to-back living room with wood-burning fireplace opening to deck and backyard, formal dining room, and an updated kitchen with quartz

  Leslie MacKinnon Compass

  35 Craig St, Milton, MA 02186
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  /32

  $999,000

  • 3 Beds
  • 1.5 Baths
  • 1,806 Sq Ft

  567 Canton Ave, Milton, MA 02186

  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

  

  Anne Galvin

  Coldwell Banker Realty - Dorchester

  (617) 752-8352

  567 Canton Ave, Milton, MA 02186
• 

  

  /34

  $1,500,000

  • 4 Beds
  • 1.5 Baths
  • 2,960 Sq Ft

  17 Duggan Ln, Milton, MA 02186

  Rarely does an opportunity arise on this coveted cul-de-sac one block from East Milton Square. This meticulously maintained Colonial offers exceptional living space with a spacious living room just off the kitchen, featuring cathedral ceiling with an abundance of natural light. Hardwood, marble, and tile flooring add timeless elegance throughout. The finished lower level provides versatile bonus

  Brendan Henry Redfin Corp.

  17 Duggan Ln, Milton, MA 02186
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  /27

  $1,195,000

  • 3 Beds
  • 3 Baths
  • 2,257 Sq Ft

  79 Hilltop St, Milton, MA 02186

  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

  Julianne Bridgeman Ceres Real Estate

  79 Hilltop St, Milton, MA 02186
• 

  

  /28

  $3,095,000

  • 4 Beds
  • 6 Baths
  • 7,506 Sq Ft

  263 Adams St, Milton, MA 02186

  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

  Michael Carucci Serhant

  263 Adams St, Milton, MA 02186
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  /28

  $879,900

  • 3 Beds
  • 1.5 Baths
  • 1,700 Sq Ft

  29 Buckingham Rd, Milton, MA 02186

  Presenting a distinguished single-family in the heart of town at 29 Buckingham Rd. This property spans 1700 square feet of meticulously designed living space, offering an exceptional opportunity for discerning homeowners. Features include three well-proportioned bedrooms, hardwood floors and a fireplace in the living room. The bonus room on the first floor is designed for a variety uses. The

  

  Thomas O'Neill

  The Firm

  (617) 675-9377

  29 Buckingham Rd, Milton, MA 02186
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  /28

  $1,499,000

  • 5 Beds
  • 5 Baths
  • 3,074 Sq Ft

  37 Sassamon Ave, Milton, MA 02186

  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,

  Robin Shea Principal Real Estate Partners

  37 Sassamon Ave, Milton, MA 02186
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  /35

  $1,240,000

  • 6 Beds
  • 2.5 Baths
  • 2,954 Sq Ft

  73 Washington St, Milton, MA 02186

  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

  Robert Mcauliffe Duhallow Real Estate

  73 Washington St, Milton, MA 02186
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  /39

  $7,800,000

  • 5 Beds
  • 5.5 Baths
  • 10,054 Sq Ft

  85 Forbes Rd, Milton, MA 02186

  Set discreetly on Milton Hill, this architecturally significant contemporary is defined by intention, proportion, and light. Clean, modern lines are softened by warm materials, creating a residence that feels both striking and deeply livable. Expansive glass frames elevated views while preserving privacy, allowing the landscape and skyline to become part of the design. Interior spaces unfold with

  Tracy Kok Keith Brokerage, LLC

  85 Forbes Rd, Milton, MA 02186
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  /38

  $2,300,000

  • 4 Beds
  • 3.5 Baths
  • 3,804 Sq Ft

  1375 Brush Hill Rd, Milton, MA 02186

  Welcome to 1375 Brush Hill Road, a spacious 4 bedroom colonial with two primary suites. This elegant colonial will greet you with charm, quality and attention to detail. The newly constructed first floor primary suite provides beautiful views of the private setting from sliders to the back deck. You'll also find an amazing primary bath with two sinks, a soaking tub & an accessible shower. The

  Mary Anne Rull William Raveis R.E. & Home Services

  1375 Brush Hill Rd, Milton, MA 02186
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  /39

  $2,100,000

  • 4 Beds
  • 4 Baths
  • 3,565 Sq Ft

  282 Highland St, Milton, MA 02186

  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

  Beth Rooney eXp Realty LLC - Corporate Office

  282 Highland St, Milton, MA 02186
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  /37

  $1,495,000

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft

  45 Foster Ln, Milton, MA 02186

  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

  Scott Farrell & Partners Compass

  45 Foster Ln, Milton, MA 02186
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  /42

  $1,149,000

  $150K PRICE DROP

  • 8 Beds
  • 5 Baths
  • 2,785 Sq Ft

  112 Brush Hill Rd, Milton, MA 02186

  Discover this beautifully updated 2-family home in one of Milton’s most desirable locations! This spacious three-story property is perfect for both investors and owner-occupants. The first floor has been fully renovated, showcasing a modern kitchen with stainless steel appliances, quartz countertops, and a bright open layout. The second unit extends across two levels, with generous bedrooms,

  Angela Cui Keller Williams Realty

  112 Brush Hill Rd, Milton, MA 02186
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  /12

  $749,000

  • 4 Beds
  • 1.5 Baths
  • 1,392 Sq Ft

  45 Decker St, Milton, MA 02186

  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

  Dee Rodrigues Model Living RE

  45 Decker St, Milton, MA 02186
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  /39

  $1,699,900

  • 6 Beds
  • 4.5 Baths
  • 5,077 Sq Ft

  52 Ridgewood Rd, Milton, MA 02186

  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

  Rebecca Huang William Raveis R.E. & Home Services

  52 Ridgewood Rd, Milton, MA 02186
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  /41

  $14,500,000

  • 5 Beds
  • 8 Baths
  • 11,315 Sq Ft

  610 Harland St, Milton, MA 02186

  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

  Tracy Campion Campion & Company Fine Homes Real Estate

  610 Harland St, Milton, MA 02186
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  /41

  $5,995,000

  • 7 Beds
  • 10 Baths
  • 9,320 Sq Ft

  55 Parkwood Dr, Milton, MA 02186

  Experience the pinnacle of Milton living at this 1915 French Colonial masterpiece. Set on nearly three acres at the foot of the Blue Hills Reservation, this legacy estate offers a rare blend of privacy and prestige. The grounds are an entertainer’s dream, featuring an in-ground pool, pool house, and a two-story, five-bay garage with an attached vintage greenhouse. Spanning 9,000+ sq. ft., the

  Kevin Keating Keating Brokerage

  55 Parkwood Dr, Milton, MA 02186
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  /31

  $739,000

  • 1 Bed
  • 2 Baths
  • 1,297 Sq Ft

  88 Wharf St Unit 607, Milton, MA 02186

  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

  Kim Powers Coldwell Banker Realty - Milton

  88 Wharf St Unit 607, Milton, MA 02186
• 

  

  /40

  $2,725,000

  • 4 Beds
  • 2.5 Baths
  • 3,149 Sq Ft

  135 Milton St, Milton, MA 02186

  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

  Kim Powers Coldwell Banker Realty - Milton

  135 Milton St, Milton, MA 02186
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  /39

  $1,200,000

  Pre-Foreclosure

  • 4 Beds
  • 1.5 Baths
  • 2,232 Sq Ft

  1066 Hillside St, Milton, MA 02186

  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

  Bridget Conroy Coldwell Banker Realty - Milton

  1066 Hillside St, Milton, MA 02186
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  /15

  $740,000

  • 3 Beds
  • 2 Baths
  • 1,333 Sq Ft

  485 Blue Hills Pkwy Unit 39, Milton, MA 02186

  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

  Timothy Driscoll South Shore Sotheby's International Realty

  485 Blue Hills Pkwy Unit 39, Milton, MA 02186
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  /27

  $499,999

  $13K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 802 Sq Ft

  1243 Adams St Unit PM207, Boston, MA 02124

  Welcome to Historic Baker Square Condominium, located in vibrant Dorchester’s Lower Mills.This spacious, renovated unit has it all! Pet friendly, and perfectly situated with a deeded parking space as well as ample guest parking. Within the building are many amenities including security, gym, indoor swimming pool, hot tub, sauna and club room. Across the charming cobblestone street is a beautiful

  Patricia Logan Patricia M. Logan

  1243 Adams St Unit PM207, Boston, MA 02124
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  /26

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,209 Sq Ft

  70 Brush Hill Rd Unit 72, Milton, MA 02186

  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

  Markese Daise Stony Brook & Lennox Realty Advisors

  70 Brush Hill Rd Unit 72, Milton, MA 02186
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  /26

  $3,600,000

  • 5 Beds
  • 5 Baths
  • 4,310 Sq Ft

  1632 Canton Ave, Milton, MA 02186

  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

  Julianne Bridgeman Ceres Real Estate

  1632 Canton Ave, Milton, MA 02186
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  /43

  $1,550,000

  • 10 Beds
  • 8 Baths
  • 2,935 Sq Ft

  403405 Reedsdale Rd, Milton, MA 02186

  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

  Paul Rege Kelley & Rege Properties, Inc.

  403405 Reedsdale Rd, Milton, MA 02186
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  /41

  $1,995,000

  • 8 Beds
  • 4.5 Baths
  • 4,500 Sq Ft

  147 Canton Ave, Milton, MA 02186

  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

  Kevin Keating Keating Brokerage

  147 Canton Ave, Milton, MA 02186
• 

  

  /40

  $3,895,000

  • 5 Beds
  • 6.5 Baths
  • 9,435 Sq Ft

  90 Countryside Ln, Milton, MA 02186

  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

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  90 Countryside Ln, Milton, MA 02186
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  /41

  $4,495,000

  • 6 Beds
  • 7.5 Baths
  • 8,764 Sq Ft

  650 Canton Ave, Milton, MA 02186

  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

  Matthew Freeman Coldwell Banker Realty - Milton

  650 Canton Ave, Milton, MA 02186
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  /28

  $725,000

  • 2 Beds
  • 2 Baths
  • 1,193 Sq Ft

  485 Blue Hills Pkwy Unit 21, Milton, MA 02186

  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

  Timothy Driscoll South Shore Sotheby's International Realty

  485 Blue Hills Pkwy Unit 21, Milton, MA 02186
• 

  

  /37

  $5,995,000

  • 6 Beds
  • 6 Baths
  • 10,524 Sq Ft

  3 Stone Bridge Ln, Milton, MA 02186

  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

  Ricardo Rodriguez Coldwell Banker Realty - Boston

  3 Stone Bridge Ln, Milton, MA 02186
• 

  

  /37

  $2,250,000

  • 5 Beds
  • 3.5 Baths
  • 4,314 Sq Ft

  213 School St, Milton, MA 02186

  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

  Julianne Bridgeman Ceres Real Estate

  213 School St, Milton, MA 02186
• 

  

  /25

  $1,249,000

  $50K PRICE DROP

  • 7 Beds
  • 3 Baths
  • 3,500 Sq Ft

  168 Brook Rd, Milton, MA 02186

  Turnkey renovated two-family home in a prime Milton location! Unit 1 features 2 bedrooms, 1 bath, a living room, dining room, and kitchen—ideal for comfortable living or rental potential. Unit 2 offers 5 bedrooms and 2 updated baths, with a spacious living room, formal dining room, updated kitchen with quartz countertops and stainless steel appliances, plus a second level of living. Both units

  Team Galvin The Galvin Group, LLC

  168 Brook Rd, Milton, MA 02186
• 

  

  /27

  $11,900,000

  • 5 Beds
  • 7 Baths
  • 9,300 Sq Ft

  540 Harland St, Milton, MA 02186

  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

  Stephen Kraunelis Gibson Sotheby's International Realty

  540 Harland St, Milton, MA 02186

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