Milton, MA Homes

• 

  

  

  /7

  $739,900

  Open Sun 1PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,124 Sq Ft

  15 Churchill St, Milton, MA 02186

  Some houses announce themselves at the curb. This one waits until you are inside. A mudroom entry opens to a wide first floor where dark stained beams cross the ceiling and hardwood runs unbroken beneath a bay of windows. The kitchen carries navy shaker cabinetry, quartz counters, a farmhouse sink beneath a triple window, gas cooking, and marble tile run the full height of the wall. The full bath

  Tayla Andre Thumbprint Realty, LLC

  15 Churchill St, Milton, MA 02186
• 

  

  

  /12

  $3,500 Per Month

  • 2 Beds
  • 1.5 Baths
  • 3,565 Sq Ft
  • Apartment for Rent

  18 Fairfax Rd Unit 1, Milton, MA 02186

  Welcoome to this maintained rental home in one of the Milton residential neighborhoods 18 Fairfax Road offers the blend of comfort, convenience and suburb charm. This unit features generous living are and office space filled with natural light, well-proportioned bedrooms, and functional layout.

  Karolina Brotschi Kelly Group Properties

  18 Fairfax Rd Unit 1, Milton, MA 02186
• 

  

  

  /30

  $658,000

  Sold Feb 10, 2026

  60 Meagher Ave, Milton, MA 02186

  • 2 Beds
  • 1.5 Baths
  • 1,306 Sq Ft
  • Built 1925

  Last Sold Summary

  • 1% Below List Price
  • $504/SF
  • 19 Days On Market

  Current Estimated Value $691,949

  Last Listing Agent Matthew Freeman Coldwell Banker Realty - Milton

  60 Meagher Ave, Milton, MA 02186
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  /42

  Est $3,727,535

  Not Listed For Sale

  427 Hillside St, Milton, MA 02186

  • 6 Beds
  • 7 Baths
  • 8,032 Sq Ft
  • Built 2006

  427 Hillside St, Milton, MA 02186

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Julianne Bridgeman Ceres Real Estate
• 

  

  

  /35

  $699,000

  Pending

  • 4 Beds
  • 1.5 Baths
  • 1,945 Sq Ft

  82 Dyer Ave, Milton, MA 02186

  Idyllically set in a neighborhood where people move in and never leave and that's exactly what you'll find on Dyer Ave. Generations have called this address home and now it's time for its next chapter. The space is here, three levels ready for your vision. This one needs work so if you're only after turn-key, keep scrolling. But for those who want to build equity and make it their own, don't miss

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

  82 Dyer Ave, Milton, MA 02186
• 

  

  /8

  $2,000 Per Month

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Apartment for Rent

  26 Houston Ave Unit 3, Milton, MA 02186

  Welcome to 26 Houston Avenue in Milton! All Utilities included! This charming 1-bedroom rental offers a comfortable and efficient layout, perfect for those seeking a cozy place to call home. The apartment features a bright living area, a well-appointed galley kitchen with ample cabinet space, and a bedroom with generous closet storage. Conveniently located near local shops, public transportation,

  Connor Withington Kelly Group Properties

  26 Houston Ave Unit 3, Milton, MA 02186
• 

  

  /36

  $2,375,000

  Sold Sep 26, 2025

  76 Cliff Rd, Milton, MA 02186

  • 5 Beds
  • 4.5 Baths
  • 4,244 Sq Ft
  • Built 1930

  Last Sold Summary

  • 20% Above List Price
  • $560/SF
  • 6 Days On Market

  Current Estimated Value $2,188,358

  Last Listing Agent Matthew Freeman Coldwell Banker Realty - Milton

  76 Cliff Rd, Milton, MA 02186
• 

  

  /29

  Est $1,826,741

  Not Listed For Sale

  97 Brierbrook St, Milton, MA 02186

  • 3 Beds
  • 3.5 Baths
  • 3,180 Sq Ft
  • Built 1987

  97 Brierbrook St, Milton, MA 02186

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Vanessa Foster Coldwell Banker Realty - Milton
• 

  

  /17

  $745,000

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

  485 Blue Hills Pkwy Unit 44, 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 44, Milton, MA 02186
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  /14

  $2,000 Per Month

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Apartment for Rent

  4 Mechanic St Unit 1, Milton, MA 02186

  Live in the heart of vibrant East Milton Square! Head to Starbucks for your morning coffee. Drop in to Stella's for lunch. Grab provisions for dinner at the Fruit Center Marketplace a few minutes away! You can't ask for more convenience! This 1BR has a large kitchen with gas stove and breakfast bar plus room for a small table. The living room with coat closet has plenty of space for furniture

  Kerry Elinskas Coldwell Banker Realty - Hingham

  4 Mechanic St Unit 1, Milton, MA 02186
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  /26

  $825,000

  Sold Nov 18, 2025

  60 Concord Ave, Milton, MA 02186

  • 4 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1930

  Last Sold Summary

  • 3% Above List Price
  • $550/SF
  • 5 Days On Market

  Current Estimated Value $843,289

  Last Listing Agent Vanessa Foster Coldwell Banker Realty - Milton

  60 Concord Ave, Milton, MA 02186
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  /40

  Est $2,116,700

  Not Listed For Sale

  24 Brierbrook St, Milton, MA 02186

  • 5 Beds
  • 4.5 Baths
  • 4,473 Sq Ft
  • Built 1973

  24 Brierbrook St, Milton, MA 02186

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Jim Fitzgerald RE/MAX Realty Plus
• 

  

  /41

  $3,295,000

  $205K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 5,700 Sq Ft

  16 Longmeadow Rd, Milton, MA 02186

  Welcome to 16 Longmeadow Road, a custom-built masterpiece showcasing exceptional architectural detail at every turn. A dramatic two-story foyer with grand staircase and soaring ceilings sets the tone for this five-bedroom, four-and-a-half-bath residence in the highly sought-after Indian Cliffs Estates. The luxurious primary suite spans 500 square feet and features a spa-inspired ensuite with

  Emily Edwards Gibson Sotheby's International Realty

  16 Longmeadow Rd, Milton, MA 02186
• 

  

  /19

  $715,000

  Sold Jan 21, 2026

  70 Warren Ave, Milton, MA 02186

  • 4 Beds
  • 2 Baths
  • 1,395 Sq Ft
  • Built 1915

  Last Sold Summary

  • 5% Below List Price
  • $513/SF
  • 22 Days On Market

  Current Estimated Value $748,251

  Last Listing Agent Karen Fallon John J. Canney

  70 Warren Ave, Milton, MA 02186
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  /36

  Est $1,034,141

  Not Listed For Sale

  84 Sassamon Ave, Milton, MA 02186

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 1922

  84 Sassamon Ave, Milton, MA 02186

  Last Sold Summary

  • 83 Days On Market

  Last Listing Agent Janice Bosworth Coldwell Banker Realty - Milton
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  /30

  $1,595,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,803 Sq Ft

  285 Brush Hill Rd, Milton, MA 02186

  A true architectural statement, this custom contemporary blends iconic Mid-Century Modern design with refined European sensibility. Perfectly situated on a private acre, it’s a masterclass in light, volume, and timeless style. Dramatic angled beam ceilings and expansive walls of glass frame the sky and landscape, creating a seamless connection between indoors and out. Thoughtful renovations honor

  Sandra Keller Coldwell Banker Realty - Milton

  285 Brush Hill Rd, Milton, MA 02186
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  /37

  $860,000

  Sold May 28, 2026

  82 Blue Hill Ave, Milton, MA 02186

  • 4 Beds
  • 2 Baths
  • 1,905 Sq Ft
  • Built 1928

  Last Sold Summary

  • 1% Above List Price
  • $451/SF
  • 3 Days On Market

  Current Estimated Value $863,197

  Last Listing Agent Anne Fitzgerald William Raveis R.E. & Home Services

  82 Blue Hill Ave, Milton, MA 02186
• 

  

  /31

  Est $1,047,938

  Not Listed For Sale

  1006 Randolph Ave, Milton, MA 02186

  • 3 Beds
  • 2 Baths
  • 3,214 Sq Ft
  • Built 1940

  1006 Randolph Ave, Milton, MA 02186

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Nghia Nguyen PRIVI Realty LLC
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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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  /24

  $1,835,000

  Sold Mar 11, 2026

  72 Columbine Rd, Milton, MA 02186

  • 4 Beds
  • 2.5 Baths
  • 2,328 Sq Ft
  • Built 1957

  Last Sold Summary

  • 15% Above List Price
  • $788/SF
  • 6 Days On Market

  Current Estimated Value $1,789,804

  Last Listing Agent Brian Gagnon Coldwell Banker Realty - Boston

  72 Columbine Rd, Milton, MA 02186
• 

  

  /20

  Est $922,872

  Not Listed For Sale

  4 Eileen Rd, Milton, MA 02186

  • 3 Beds
  • 1 Bath
  • 1,516 Sq Ft
  • Built 1948

  4 Eileen Rd, Milton, MA 02186

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Brian Gagnon Coldwell Banker Realty - Boston
• 

  

  /37

  $2,575,000

  Pending

  • 5 Beds
  • 5 Baths
  • 4,217 Sq Ft

  7 Phyllis Ln, Milton, MA 02186

  You've been looking for a while. You can stop now. 7 Phyllis Lane was custom-built by a trusted local builder as a forever home. And it shows. Ten-foot ceilings, custom millwork, built-ins. Hardieplank siding, Harvey windows, hydro air heating...infrastructure chosen for longevity and efficiency, not just aesthetics. The kitchen just works: massive island, Thermador appliances, Cambria quartz,

  Erin Feeney Ceres Real Estate

  7 Phyllis Ln, Milton, MA 02186
• 

  

  /19

  $1,335,000

  Sold Apr 14, 2026

  214 Brook Rd, Milton, MA 02186

  • 7 Beds
  • 3 Baths
  • 3,443 Sq Ft
  • Built 1919

  Last Sold Summary

  • 1% Below List Price
  • $388/SF
  • 118 Days On Market

  Current Estimated Value $1,334,686

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

  214 Brook Rd, Milton, MA 02186
• 

  

  /35

  Est $1,652,780

  Not Listed For Sale

  4 Carisbrooke Rd, Milton, MA 02186

  • 4 Beds
  • 4 Baths
  • 4,486 Sq Ft
  • Built 2002

  4 Carisbrooke Rd, Milton, MA 02186

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Beatrice Murphy Lamacchia Realty, Inc.
• 

  

  /35

  $2,590,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,450 Sq Ft

  196 Canton Ave, Milton, MA 02186

  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

  Scott Farrell & Partners Compass

  196 Canton Ave, Milton, MA 02186
• 

  

  /20

  $645,000

  Sold Nov 21, 2025

  88 Decker St, Milton, MA 02186

  • 3 Beds
  • 1.5 Baths
  • 1,008 Sq Ft
  • Built 1937

  Last Sold Summary

  • 23% Above List Price
  • $640/SF
  • 5 Days On Market

  Current Estimated Value $632,390

  Last Listing Agent Kim Powers Coldwell Banker Realty - Milton

  88 Decker St, Milton, MA 02186
• 

  

  /41

  Est $1,194,762

  Not Listed For Sale

  71 Silver Brook Rd, Milton, MA 02186

  • 4 Beds
  • 3 Baths
  • 3,144 Sq Ft
  • Built 1952

  71 Silver Brook Rd, Milton, MA 02186

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Linda Tucker Coldwell Banker Realty - Easton
• 

  

  /34

  $995,900

  $79K PRICE DROP Pending

  • 3 Beds
  • 1.5 Baths
  • 1,994 Sq Ft

  25 Waldeck Rd, Milton, MA 02186

  7 room, 3 bedroom, 1 & 1/2 bath New England Colonial with a 1 car garage set on a cozy side street location in sought after East Milton. You will feel welcomed as you enter the front foyer and through the french doors to the comfortable fireplaced living room, formal dining room with built-in china cabinet and 1/2 bath. You will love the eat in kitchen with ample room for your table with plenty

  Bob Germaine Germaine Realty LLC

  25 Waldeck Rd, Milton, MA 02186
• 

  

  /33

  $1,570,000

  Sold May 01, 2026

  30 Ridge Rd, Milton, MA 02186

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft
  • Built 1937

  Last Sold Summary

  • 14% Above List Price
  • $617/SF
  • 6 Days On Market

  Current Estimated Value $1,492,457

  Last Listing Agent Julianne Bridgeman Ceres Real Estate

  30 Ridge Rd, Milton, MA 02186
• 

  

  /26

  Est $1,951,399

  Not Listed For Sale

  410 Atherton St, Milton, MA 02186

  • 4 Beds
  • 4 Baths
  • 3,764 Sq Ft
  • Built 1987

  410 Atherton St, Milton, MA 02186

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Barbara Alavi William Raveis R.E. & Home Services
• 

  

  /16

  $600,000

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  485 Blue Hills Pkwy Unit 2, Milton, MA 02186

  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

  Timothy Driscoll South Shore Sotheby's International Realty

  485 Blue Hills Pkwy Unit 2, Milton, MA 02186
• 

  $1,425,000

  Sold Aug 27, 2025

  332 Eliot St, Milton, MA 02186

  • 4 Beds
  • 3 Baths
  • 2,269 Sq Ft
  • Built 1927

  Last Sold Summary

  • 6% Above List Price
  • $628/SF
  • 8 Days On Market

  Current Estimated Value $1,358,634

  Last Listing Agent Humphrey Realty Group Coldwell Banker Realty - Easton

  332 Eliot St, Milton, MA 02186
• 

  

  /42

  Est $2,419,369

  Not Listed For Sale

  59 Crestview Rd, Milton, MA 02186

  • 6 Beds
  • 4.5 Baths
  • 4,705 Sq Ft
  • Built 1999

  59 Crestview Rd, Milton, MA 02186

  Last Sold Summary

  • 105 Days On Market

  Last Listing Agent Rose Hall Blue Ocean Realty, LLC
• 

  

  /25

  $1,499,900

  Pending

  • 4 Beds
  • 3.5 Baths
  • 2,621 Sq Ft

  187 Hinckley Rd, Milton, MA 02186

  Nestled in the heart of Milton's coveted Columbines neighborhood, 187 Hinckley Rd. offers the perfect blend of timeless charm, generous living space, and an unbeatable location. This 4-bedroom, 3.5-bath home features a warm, functional floor plan, spacious living areas, a partially finished lower level, and an unfinished walk-up attic offering exceptional expansion potential. Step outside to a

  Brian Gagnon Coldwell Banker Realty - Boston

  187 Hinckley Rd, Milton, MA 02186
• 

  

  /30

  $1,500,000

  Sold Nov 25, 2025

  48 Patricia Dr, Milton, MA 02186

  • 5 Beds
  • 4 Baths
  • 3,388 Sq Ft
  • Built 1969

  Last Sold Summary

  • 8% Above List Price
  • $443/SF
  • 3 Days On Market

  Current Estimated Value $1,548,802

  Last Listing Agent Kevin Keating Keating Brokerage

  48 Patricia Dr, Milton, MA 02186
• 

  

  /27

  Not Listed For Sale

  1362 Canton Ave, Milton, MA 02186

  • 5 Beds
  • 4 Baths
  • 5,208 Sq Ft
  • Built 1975

  1362 Canton Ave, Milton, MA 02186

  Last Sold Summary

  • 138 Days On Market

  Last Listing Agent Julianne Bridgeman Ceres Real Estate
• 

  

  /35

  $1,240,000

  Pending

  • 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
• 

  

  /24

  $810,000

  Sold Dec 19, 2025

  795 Brook Rd, Milton, MA 02186

  • 3 Beds
  • 1.5 Baths
  • 1,744 Sq Ft
  • Built 1957

  Last Sold Summary

  • 10% Below List Price
  • $464/SF
  • 34 Days On Market

  Current Estimated Value $928,418

  Last Listing Agent Ellen Mak Coldwell Banker Realty - Milton

  795 Brook Rd, Milton, MA 02186
• 

  

  /35

  Est $2,007,225

  Not Listed For Sale

  2 Atherton Ln, Milton, MA 02186

  • 4 Beds
  • 2.5 Baths
  • 4,686 Sq Ft
  • Built 1986

  2 Atherton Ln, Milton, MA 02186

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Matthew Freeman Coldwell Banker Realty - Milton
• 

  

  /38

  $949,900

  • 3 Beds
  • 4 Baths
  • 1,738 Sq Ft

  80 Blue Hills Pkwy, Milton, MA 02186

  Refreshed and Reimagined center-entrance Colonial in desirable Milton, offering three bedrooms, two full baths, and two half baths. This thoughtfully updated home features a spacious primary ensuite and a sun-filled bonus sunroom—ideal for a home office, reading nook, or relaxation space. The refined open-concept kitchen blends beauty and function with quartz countertops, a pot filler, and a

  Shawn Burgess Compass

  80 Blue Hills Pkwy, Milton, MA 02186

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