5 Bedroom homes for sale & real estate in Milton, MA

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676-a Brush Hill Rd, Milton, MA 02186

ABOUT THIS HOME
5 Bedroom Homes for Sale in Milton, MA
Welcome to 676-a Brush Hill Road, Milton, MA, where elegance meets modern living in this newly constructed custom home. Nestled amid scenic landscapes, this exquisite residence offers breathtaking views of the iconic Blue Hills. Impeccably designed, the home boasts a harmonious blend of contemporary architecture and luxurious finishes. The expansive interiors feature a thoughtfully designed layout, ideal for entertaining and everyday living. The gourmet kitchen is a chef's delight, equipped with state-of-the-art appliances and sleek countertops. Retreat to the serene primary suite, complete with a spa-inspired bathroom and generous closet space. Enjoy the tranquility of your private outdoor

$3,295,000

5 beds4.5 baths5,500 sq ft

676-a Brush Hill Rd, Milton, MA 02186

1.88 acre lot • 2 garage spots • Car-dependent

2 Fletcher Steele Way, Milton, MA 02186

ABOUT THIS HOME
5 Bedroom Homes for Sale in Milton, MA
Step into this stunning New England Contemporary, set on a sprawling 43,998 sq ft lot. This 5129 sq ft residence offers 10 rooms, including 5 bedrooms and 6.5 baths across 3 floors, plus a 3-car garage. Designed by William Lee Architect & Associates, its open floor plan connects the living room, dining room, and chef’s kitchen featuring a Quartz Island and Thermador appliances. The first floor includes a family room and primary suite with a soaking tub, double sinks, walk-in closet, and deck access. The second floor has three en-suite bedrooms. The lower level is ideal for a media room, gym, or more, complete with a full bath. With oversized windows, natural light, and custom mi

$3,599,000

5 beds6.5 baths5,129 sq ft

2 Fletcher Steele Way, Milton, MA 02186

1.01 acre lot • 3 garage spots • Car-dependent

50 Brush Hill Ln, Milton, MA 02186

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Milton, MA
Sellers are MOTIVATED! Now is your opportunity to discover, or re-discover, 50 Brush Hill Lane. This estate-property perched high on a 1.82 acre lot exudes grandeur. Its exterior is a blend of cedar shingles & stone accents with a sweeping driveway & gracious receiving court. This home was reimagined by renowned architectural firm Goody & Clancy, whose mid-century modern addition extends from the original 1940's classic colonial. The heart of the home is the state-of-the-art chef's kitchen. A full catering kitchen further elevates the culinary experience. Laundry zones can be found in both the scullery kitchen and on the bedroom level. The expansive great room overlooks a

$3,595,000

5 beds6.5 baths8,600 sq ft

50 Brush Hill Ln, Milton, MA 02186

1.82 acre lot • 2 garage spots • Car-dependent

1362 Canton Ave, Milton, MA 02186

ABOUT THIS HOME
5 Bedroom Homes for Sale in Milton, MA
If privacy and serenity are your aim, then 1362 Canton Ave hits the mark. While thoughtfully sited on 2.7 acres of woodland and lawn, 7000+ acres of trails and green space are happily adjacent in the Blue Hills Reservation and Eustis Estate. Current owners were instantly smitten by the surrounding natural beauty and big sky feel. With that in mind they set to work expertly renovating but always with a nod and glimpse of nature as art. Custom chef’s kitchen with Sub-Zero, Wolf appliances features sylvan views and morning light. First-floor guest suite comfortably accommodates friends or family. The family room with large fireplace is the warm focal point for gatherings. The new owners&

$2,600,000

5 beds4 baths5,208 sq ft

1362 Canton Ave, Milton, MA 02186

2.71 acre lot • 5 garage spots • Pool

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15 Rugdale Rd, Boston, MA 02124

NEW 1 HR AGO

ABOUT THIS HOME
5 Bedroom Homes for Sale in Milton, MA
Nestled in Dorchester's historic and picturesque Lower Mills, this 12-room Colonial offers an unrivaled blend of space, and convenience. With an expansive 4,000 square feet of living space and freshly refinished white oak flooring, this residence has been owned and loved by the same family for generations. The versatile first floor offers a sun-drenched eat-in kitchen, a formal dining room, and a charming living room. For added flexibility, a large rec room with a full bath can easily be used as a primary suite or guest retreat. Upstairs, you'll find five generously sized bedrooms and two full baths, ensuring comfort and privacy for all. The garden level is perfect for multigenerational liv

$1,200,000

5 beds4.5 baths3,797 sq ft

15 Rugdale Rd, Boston, MA 02124

7,269 sq ft lot • Garage • Very walkable

188 Woodrow Ave, Boston, MA 02124

ABOUT THIS HOME
5 Bedroom Homes for Sale in Milton, MA
Welcome to this exceptional two-family home in the heart of Dorchester! Originally a seven-bedroom property, this residence has been thoughtfully reconfigured to maximize space and comfort, now offering a total of five bedrooms and three full bathrooms. The first unit features a generous layout with two bedrooms and one full bath, perfect for rental income or multi-generational living. The second unit spans two floors, showcasing three spacious bedrooms and two bathrooms—ideal for an owner’s unit or a growing family. This reimagined layout enhances living space while preserving ample room for work-from-home setups, guest accommodations, or personal retreats. Both units boast hig

$879,900

5 beds3 baths2,072 sq ft

188 Woodrow Ave, Boston, MA 02124

4,000 sq ft lot • Community pool • Very walkable

9 Hall Pl, Quincy, MA 02169

ABOUT THIS HOME
5 Bedroom Homes for Sale in Milton, MA
So much space! This house offers much more than your average home. The 1st floor features an oversized primary bedroom boasting extra storage and French doors leading to a deck with a covered pergola, a living room with a gas fireplace, and a versatile room that can serve as a home office/bedroom/gym, plus two full baths. Upstairs you’ll find an additional family room, another full bath, second primary bedroom and a convenient 2nd floor laundry. Each bedroom has generously sized closets. The home includes front and rear staircases and beautiful hardwood floors throughout. It is equipped with gas heating and newer mechanicals, plus rooftop solar panels to help save on your electricity

$990,000

5 beds3 baths2,907 sq ft

9 Hall Pl, Quincy, MA 02169

8,289 sq ft lot • Somewhat walkable

97-99 Wellsmere Rd, Boston, MA 02131

ABOUT THIS HOME
5 Bedroom Homes for Sale in Milton, MA
Discover this charming two-family home with great potential! Perfect for first-time homebuyers and investors alike, this property offers a blend of modern updates and classic appeal. The main level includes 2 spacious bedrooms, while the second floor boasts 3 bedrooms—ideal for maximizing rental income or extended family living. New first-floor windows, newer heating systems, separate utilities for convenience, and a full walk-up attic just waiting to be expanded. A one-car garage and private driveway add practicality and value. Situated a mere half mile from vibrant Roslindale Village, you’ll have quick access to local shops, cafes, and public transportation. Don’t miss t

$999,974

5 beds2 baths2,588 sq ft

97-99 Wellsmere Rd, Boston, MA 02131

4,730 sq ft lot • Garage • Somewhat walkable

99 Pierce St, Boston, MA 02136

ABOUT THIS HOME
5 Bedroom Homes for Sale in Milton, MA
99 Pierce St offers the perfect opportunity to attain a part in wonderful Hyde Park!! An absolute spot perked within the epicenter to everything, restaurants, shopping, nature trails, public transportation, sports facilities, swimming, golf, and more. The home is over 2,000 sq. ft. with flexibility to accommodate 4 or 5 bedrooms, plus a flex room make a great home office or other best determined functionality. Built in 1984, makes it free of lead paint concerns. Corner lot and no through traffic, dead-end street.

$800,000

5 beds2 baths2,105 sq ft

99 Pierce St, Boston, MA 02136

7,514 sq ft lot • Community pool • Very walkable

30 Massasoit St, Boston, MA 02136

ABOUT THIS HOME
5 Bedroom Homes for Sale in Milton, MA
Welcome to this beautifully maintained colonial home, blending timeless character with modern upgrades located on a peaceful dead-end street. The property boasts a brand-new roof, new windows with updated exterior trims, and beautifully refinished floors. Inside, you'll find a fully equipped kitchen with top-of-the-line Samsung appliances, new cabinets Quartz countertop, and a stylish new kitchen floor. The first floor offers a spacious sunroom, perfect for soaking in natural light, while the large backyard and ample parking make outdoor living a breeze. Home offers five generously sized bedrooms, two fully updated bathrooms, and a sprawling third-floor loft-a perfect retreat with boundless

$875,000

5 beds2 baths2,500 sq ft

30 Massasoit St, Boston, MA 02136

5,000 sq ft lot • Somewhat walkable

5 Bedroom Homes for Sale in Milton

There are currently 4 5 bedroom homes in Milton. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Milton stay on the market for 34 days and receive 1 offers. Popular neighborhoods include Hyde Park, Lower East Mills-Cedar Grove, East Milton, West Quincy, Roslindale, Cedar Grove / East Lower Mills, North Randolph, Mattapan, Readville, and South Dorchester. This map is refreshed with the newest listings in Milton every 15 minutes.

In the past month, 27 homes have been sold in Milton. In addition to houses in Milton, there were also 5 condos, 5 townhouses, and 4 multi-family units for sale in Milton last month. Milton is a minimally walkable city in Norfolk County with a Walk Score of 37. Milton is home to approximately 27,365 people. Find your dream home in Milton using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Milton are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Milton. Our Milton real estate stats and trends will give you more information about home buying and selling trends in Milton. If you're looking to sell your home in the Milton area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Milton with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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