Milton Hill Homes

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  $3,475,000

  • 6 Beds
  • 4.5 Baths
  • 5,392 Sq Ft

  277 Adams St, Milton, MA 02186

  Simply Stunning! Set on Premier Milton Hill, this 1910's charmer will not disappoint! Elegant and formal yet comfortable and casual. #277 offers you the lifestyle you've been looking for and more! From the classic features of hardwood floors, thick dentil moulding and custom built-ins to the gourmet chef's kitchen, tastefully renovated baths and three floors of living, this one offers room to

  Matthew Freeman Coldwell Banker Realty - Milton

  277 Adams St, Milton, MA 02186
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  /15

  $2,650 per month

  • 2 Beds
  • 1 Bath
  • 1,118 Sq Ft
  • Apartment for Rent

  392 Reedsdale Rd Unit 3, Milton, MA 02186

  Spacious Top-Floor 2-Bedroom in a Three-Family Home – Prime Location!Welcome to your new rental home! Enjoy the privacy and quiet of the top floor, with ample natural light and a roomy layout ideal for relaxing or entertaining.This bright and spacious unit in a three-family home offers the perfect blend of comfort and convenience. Two generously sized bedrooms, bathroom with step-in shower,

  Kerry Elinskas Coldwell Banker Realty - Hingham

  392 Reedsdale Rd Unit 3, Milton, MA 02186
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  /30

  $1,150,000 Sold Jul 28, 2025

  • 2,028 Sq Ft
  • $567/SF
  • 3 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1959

  5 Christopher Dr, Milton, MA 02186

  Location, Location, Location! This East Milton Colonial offers an open kitchen, Fireplaced living room and gleaming hardwood floors throughout. First floor offers an updated bath with shower and a formal dining room. Second floor has 4 bedrooms and full bath. Large playroom in basement with wall-to-wall carpet. Good sized fenced in yard with patio. Expanded 2 car attached garage, a 3-year-old

  Robert Mcauliffe Duhallow Real Estate

  5 Christopher Dr, Milton, MA 02186
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  /40

  Est $1,220,801 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,425 Sq Ft

  1133 Brook Rd, Milton, MA 02186

  1133 Brook Rd, Milton, MA 02186
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  /29

  $3,300,000 Pending

  • 7 Beds
  • 4.5 Baths
  • 7,312 Sq Ft

  203 Adams St, Milton, MA 02186

  Once in a lifetime opportunity to own this home w/expert craftsmanship, discover the timeless elegance of the historic Dr. Amos Holbrook House. Built around1800, this distinguished Federal-style residence offers over 7,300 square feet of living space, featuring seven spacious bedrooms & four & a half bathrooms. Set on a generous 2.56-acre lot, the property boasts a blend of historical charm &

  Jacquelyn O'Connor Keller Williams Realty Boston-Metro | Back Bay

  203 Adams St, Milton, MA 02186
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  /10

  $3,700 per month

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Apartment for Rent

  65 Waldeck Rd Unit 2, Milton, MA 02186

  Beautiful three bedroom apartment with additional room that can be used as an office or storage. Spacious duplex with one and half bedrooms on the first level and two spacious bedrooms on the second floor. Open floor plan dinning and living room. Eat in Kitchen. Three season porch at the rear of the building. Lots of storage and natural light are just a few of the many features this apartment has

  Catherine McDermott The Galvin Group, LLC

  65 Waldeck Rd Unit 2, Milton, MA 02186
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  /26

  $920,000 Sold Jul 25, 2025

  • 2,004 Sq Ft
  • $459/SF
  • 1 Day On Market

  • 4 Beds
  • 2 Baths
  • Built 1927

  21 Otis St, Milton, MA 02186

  OPEN HOUSES CANCELLED -- Nestled on a picturesque half-acre lot in one of Milton’s most sought-after neighborhoods, this classic 4-bedroom, 2-bath Colonial offers the perfect blend of charm, location, and potential. From the moment you arrive, you'll be drawn in by the home’s timeless curb appeal and unbeatable setting. Inside, discover hardwood floors throughout and a traditional layout ready to

  Brendan Malanga William Raveis R.E. & Home Services

  21 Otis St, Milton, MA 02186
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  /31

  Est $1,131,527 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,260 Sq Ft

  30 Governors Rd, Milton, MA 02186

  30 Governors Rd, Milton, MA 02186
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  /17

  $809,000

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft

  36 Pleasant St, Milton, MA 02186

  Welcome Home to Milton! Bursting with sunshine and charm, this single-family A frame colonial style home offers the perfect mix of modern comfort and convenience along with character all hardwood floors. Upstairs, you’ll find three bedroom large master bedroom, while the recently renovated bathroom brings a modern touch to this classic home. Start your mornings on the inviting front porch

  Kevin Dacey Dacey Realty, LLC

  36 Pleasant St, Milton, MA 02186
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  /2

  $4,900 per month

  • 3 Beds
  • 1.5 Baths
  • 2,545 Sq Ft
  • House for Rent

  19 Brae Burn Rd, Milton, MA 02186

  Fabulous family neighborhood, close to everything...walk to schools, Cunningham Park and East Milton Square. Minutes to Southeast Expressway.....extremely accessible to downtown. Charming colonial with an amazing chefs kitchen; Viking stove, three good sized bedrooms, hardwood floors throughout and just refinished, one car garage and private yard.

  Denise Petitti Coldwell Banker Realty - Milton

  19 Brae Burn Rd, Milton, MA 02186
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  /42

  $3,400,000 Sold Jul 24, 2025

  • 5,104 Sq Ft
  • $666/SF
  • 30 Days On Market

  • 5 Beds
  • 6.5 Baths
  • Built 1855

  152 Adams St, Milton, MA 02186

  At 152 Adams Street, the Neponset River is your personal canvas—sunrises, seasons, and sky, all unfolding outside your windows. Perched on a 1.38-acre parcel of gently sloping grounds, this Milton Hill estate is one of the rare properties to offer panoramic vistas. A full-scale renovation in 2017 overhauled the home’s systems—electrical/plumbing/HVAC/building envelope—while preserving its soul

  Erin Feeney Ceres Real Estate

  152 Adams St, Milton, MA 02186
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  /27

  Est $1,034,861 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,590 Sq Ft

  45 Hurlcroft Rd, Milton, MA 02186

  45 Hurlcroft Rd, Milton, MA 02186
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  /37

  $1,275,000

  • 6 Beds
  • 2.5 Baths
  • 2,606 Sq Ft

  15 California Ave, Milton, MA 02186

  East Milton Location! This spacious home consists of 6 bedrooms and 2 and a half baths. Fireplace living room with bow window, hardwood floors throughout. Large open kitchen with granite countertops and an island that fits 4 stools. Dining area flows into family room and out to fenced in yard, patio and 3-season porch. Oversized shed for storage in side yard. First floor laundry room. Primary

  Robert Mcauliffe Duhallow Real Estate

  15 California Ave, Milton, MA 02186
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  /31

  $1,740,000 Sold Jul 23, 2025

  • 2,764 Sq Ft
  • $630/SF
  • 8 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1855

  185 School St, Milton, MA 02186

  Just love a rare Milton Hill Greek Revival, exuding commanding presence and stability, set on nearly 1/2 acre of verdant canvas inviting parties, play, and pups. Architectural details include tall pilasters, soaring ceilings, and pedimented windows pulling light into every room. Move through the library-style entry hall over finely finished hardwoods to a fully renovated chef’s kitchen: oversized

  Julianne Bridgeman Ceres Real Estate

  185 School St, Milton, MA 02186
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  /32

  Est $761,569 Not Listed For Sale

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

  80 Pleasant St Unit 2, Milton, MA 02186

  80 Pleasant St Unit 2, Milton, MA 02186
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  /40

  $8,200,000

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

  85 Forbes Rd, Milton, MA 02186

  85 Forbes Rd, Milton, MA – Modern LuxuryDiscover elegance at 85 Forbes Rd, a 2020-built, 5-bed, 5.5-bath home spanning 9,600 sq ft on a 40,935 sq ft lot with Boston skyline and Neponset River views. Enter via a mudroom with custom cubbies and laundry, near a half-bath and private suite with full bath. Work in a study with custom cabinets, next to a pantry with dishwasher and sink. Host in the

  John Keith Keith Brokerage, LLC

  85 Forbes Rd, Milton, MA 02186
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  /39

  $1,155,000 Sold Jul 14, 2025

  • 1,821 Sq Ft
  • $634/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1941

  28 Westvale Rd, Milton, MA 02186

  Beautiful turn-key Colonial in a sought-after neighborhood with period details and hardwood floors on a lovely side street! Open dining room and kitchen with custom cabinets, quartz countertops, and stainless-steel appliances. Sun-drenched sunroom off the living room. The front-to-back living room with a wood-burning fireplace has a sliding door to the deck and a stunning, professionally

  Kevin Keating Keating Brokerage

  28 Westvale Rd, Milton, MA 02186
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  /23

  Est $1,259,989 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,118 Sq Ft

  1054 Brook Rd, Milton, MA 02186

  1054 Brook Rd, Milton, MA 02186
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  /22

  $1,680,000

  • 6 Beds
  • 8 Baths
  • 3,216 Sq Ft

  403405 Reedsdale Rd, Milton, MA 02186

  Milton—Rare find! This fully renovated 2016 duplex offers 5 rooms, 3 bedrooms, and 2.5 baths. The first floor features a spacious kitchen with stainless steel appliances, granite countertops, an open living/dining area, and first-floor laundry. The second floor boasts 2 bedrooms and 2 full baths, while the third-floor bedroom includes a walk-in closet. A generous yard is ideal for summer

  Paul Rege Kelley & Rege Properties, Inc.

  403405 Reedsdale Rd, Milton, MA 02186
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  /23

  $817,500 Sold Jul 07, 2025

  • 1,457 Sq Ft
  • $561/SF
  • 74 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 2003

  88 Wharf St Unit 409, Milton, MA 02186

  With brilliant natural light and exquisite, panoramic water views from the floor to ceiling windows this unique 5 room condo is located in the beautiful, waterfront residences on the Wharf at Milton Landing. Featuring stainless steel appliances, granite countertops, two full baths and a bonus room that could be used as a 2nd bedroom or home office. The main bedroom has a large walk-in closet and

  Thomas O'Neill The Firm

  88 Wharf St Unit 409, Milton, MA 02186
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  /30

  Est $1,390,700 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,121 Sq Ft

  650 Pleasant St, Milton, MA 02186

  650 Pleasant St, Milton, MA 02186
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  /38

  $849,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,664 Sq Ft

  27 Saint Agatha Rd, Milton, MA 02186

  Welcome to this 4 bedroom East Milton home on hidden gem Saint Agatha Rd! Enter via mudroom w/ ample closet space. Spacious family room features gleaming HW floors, brick fireplace & custom built-ins. Den connects to formal living room – perfect as playroom or office. Eat-in kitchen boasts SS appliances & granite counters. Bonus heated sun porch adds living space & opens to large deck & backyard

  Dynan Team Seaport Realty Group

  27 Saint Agatha Rd, Milton, MA 02186
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  /34

  $600,000 Sold Jun 26, 2025

  • 1,442 Sq Ft
  • $416/SF
  • 6 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  80 Pleasant St Unit 1, Milton, MA 02186

  All offers due Monday, May 19 at 5 PM. MILTON -- Impeccably updated and move-in ready, this gorgeous, low-maintenance 2-bed condo on the first floor of a 2-family home offers comfort, convenience, and quality. Enjoy a beautifully renovated kitchen and bath, gleaming hardwood floors, updated systems, and central air. Set in a peaceful setting with mature landscaping, this home provides easy access

  Esposito Group eXp Realty

  80 Pleasant St Unit 1, Milton, MA 02186
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  /23

  Est $955,699 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,488 Sq Ft

  45 Chesterfield Rd, Milton, MA 02186

  45 Chesterfield Rd, Milton, MA 02186
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  /27

  $750,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,875 Sq Ft

  641 Pleasant St Unit 1, Milton, MA 02186

  Feeling blue about the real estate market? Here’s your rare chance to own a charming Philadelphia-style attached single-family home in one of Milton’s most convenient and quiet pockets, Pleasant Street, nestled between Brook Road and Centre Street. This thoughtfully laid out home offers flexibility for all stages of life. The first floor bedroom, full bath, and cozy den make it perfect for those

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

  641 Pleasant St Unit 1, Milton, MA 02186
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  /24

  $830,000 Sold Jun 23, 2025

  • 1,404 Sq Ft
  • $591/SF
  • 4 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1925

  590 Pleasant St, Milton, MA 02186

  This Cunningham Park/East Milton Colonial is ideally situated within walking distance to the "Square," schools, parks, and playgrounds, and it has easy access to major highways. The home offers an updated kitchen with custom cabinets and granite countertops, a formal living room with a working wood-burning fireplace, a dining room, a first-floor office or den, and a half bathroom. There are

  Kevin Keating Keating Brokerage

  590 Pleasant St, Milton, MA 02186
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  /39

  Est $1,391,576 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,774 Sq Ft

  521 Centre St, Milton, MA 02186

  521 Centre St, Milton, MA 02186
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  /29

  $750,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,875 Sq Ft

  641 Pleasant St, Milton, MA 02186

  Feeling blue about the real estate market? Here’s your rare chance to own a charming Philadelphia-style attached single-family home in one of Milton’s most convenient and quiet pockets, Pleasant Street, nestled between Brook Road and Centre Street. This thoughtfully laid out home offers flexibility for all stages of life. The first floor bedroom, full bath, and cozy den make it perfect for those

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

  641 Pleasant St, Milton, MA 02186
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  /32

  $875,000 Sold Jun 20, 2025

  • 1,596 Sq Ft
  • $548/SF
  • 5 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1890

  39 Otis St, Milton, MA 02186

  Opportunity knocks in one of East Milton’s most sought-after neighborhoods! Set on a generous lot, this property offers the perfect canvas for your vision. While the home is in need of significant renovation, it’s bursting with possibilities — whether you’re looking to restore its original charm, expand, or start fresh. With plenty of room to grow and a location that can’t be beat, this is a rare

  Melanie Berge Lamacchia Realty, Inc.

  39 Otis St, Milton, MA 02186
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  /28

  Est $1,230,077 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,952 Sq Ft

  64 Lodge St, Milton, MA 02186

  64 Lodge St, Milton, MA 02186
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  /31

  $1,250,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 2,100 Sq Ft

  50 Badger Cir, Milton, MA 02186

  Move right in! Well kept 4 bedroom, 1 1/2 bath center entrance Colonial tucked away on a quiet, tree-lined circle in an ideal Milton Center location. Just minutes from Cunningham/Collicott Schools, Cunningham Park and Milton Academy. Picture yourself creating deliciousness in the beautifully renovated chef's kitchen (quartz counters/island/stainless appliances including a Bertazzoni induction

  Jay Balaban Gibson Sotheby's International Realty

  50 Badger Cir, Milton, MA 02186
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  /42

  $1,338,000 Sold Jun 03, 2025

  • 2,640 Sq Ft
  • $507/SF
  • 7 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1930

  29 Governors Rd, Milton, MA 02186

  Welcome to 29 Governors Road – a beautifully expanded Colonial in one of Milton’s most desirable neighborhoods! This thoughtfully updated 3-bedroom, 3-bathroom home offers over 2,600 sqft of living space across three levels, including a partially finished basement. The main level features a spacious living room with a gas fireplace, formal dining room, and a bright kitchen with granite

  J.T. Kelly Keller Williams Realty

  29 Governors Rd, Milton, MA 02186
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  /26

  Est $1,392,231 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,362 Sq Ft

  150 Pleasant St, Milton, MA 02186

  150 Pleasant St, Milton, MA 02186
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  /6

  $4,375,000 Pending

  • 6 Beds
  • 6 Baths
  • 6,900 Sq Ft

  3 Hutchinson St, Milton, MA 02186

  Milton Hill! Escape the ordinary and step into the extraordinary! French architecture meets modern luxury in the latest stunning Dev Group design. With grand features, an oasis-like outdoor area and smart-house system, it’s more than just a home—it’s a lifestyle. Say hello to your own personal sanctuary! Delivery date estimated at August 2025

  Matthew Freeman Coldwell Banker Realty - Milton

  3 Hutchinson St, Milton, MA 02186
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  /37

  $1,800,000 Sold Jun 02, 2025

  • 3,553 Sq Ft
  • $507/SF
  • 5 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1937

  24 Wyndmere Rd, Milton, MA 02186

  OH 4/25 5:15P-6:15P,OH 4/26 Sat 12-2pm & 4/27 OH Sun 12-1:30 Nestled in an amazing neighborhood on a peaceful dead-end street, 24 Wyndmere presents a special opportunity with its prime location just 0.9 mile from East Milton Square and a mere 7 miles from downtown Boston. This spacious three-story residence features 5 large bedrooms, 2 of which have ensuite ,multiple home office options, ample

  Sharon Ryan Coldwell Banker Realty - Milton

  24 Wyndmere Rd, Milton, MA 02186
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  /40

  Est $1,684,400 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 4,008 Sq Ft

  156 Pleasant St, Milton, MA 02186

  156 Pleasant St, Milton, MA 02186
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  /32

  $799,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,487 Sq Ft

  46 Century Ln, Milton, MA 02186

  Coveted Cunningham Park neighborhood, a rare offering! Classic center entrance straight front colonial with an oversized attached 2 car garage. Stunning details such as custom fluted woodworking, hardwood floors throughout, lovely fireplace, picture window looking out to large, open, leveled private backyard with shed. Three generously sized bedrooms, two with dressing rooms. Staircase to large

  Dynan Team Seaport Realty Group

  46 Century Ln, Milton, MA 02186
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  /39

  $1,050,000 Sold May 30, 2025

  • 3,170 Sq Ft
  • $331/SF
  • 71 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  4 Adams St, Hyde Park, MA 02136

  PRICE Improvement ! Best Value on the Market. Spacious New Construction single-family residence combines Energy Efficiency with Modern Design & Peace of Mind Low to No Maintenance. Nestled in a Convenient. Location making Commuting a breeze with major access roads and public transportation nearby.The heart of the home boasts a State of the Art Kitchen with stainless Appliances / Quartz

  Michael Hunt Insight Realty Group, Inc.

  4 Adams St, Hyde Park, MA 02136
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  /28

  Est $1,071,046 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,464 Sq Ft

  185 Gun Hill St, Milton, MA 02186

  185 Gun Hill St, Milton, MA 02186
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  /37

  $1,030,000 Sold May 29, 2025

  • 2,248 Sq Ft
  • $458/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  84 Badger Cir, Milton, MA 02186

  Badger Circle...It's the place to be! Crisp, clean and pride of ownership throughout, #84 Badger Circle will put a smile on your face! With a dramatic, vaulted ceiling living room, the space is great with versatile living spread over two floors. Open and airy with sunsplashed rooms, rarely does a property like this come to market. Our comfortable lower level offers home office, media and

  Matthew Freeman Coldwell Banker Realty - Milton

  84 Badger Cir, Milton, MA 02186

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