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$945,000
4 Beds 2 Baths SOLD Status 73393239 MLS 1,893 SqFt.
Welcome to this charming Milton gem! This beautifully updated 4-bedroom, 2-bath home offers just under 1,900 square feet of light-filled living space, perfect for comfortable family living and entertaining. The heart of the home is the stunning, freshly renovated kitchen featuring stainless steel appliances, shaker-style cabinetry, and ample prep space. Enjoy spacious dining and living areas complete with a cozy gas fireplace. Step into the gorgeous enclosed porch or out to the private patio and fenced yard—ideal for relaxing or hosting. Recent updates include a new roof, central A/C, fresh interior and exterior paint, and a semi-finished basement offering extra space to work or play. A garage provides convenient parking, and the home's prime location offers easy access to Boston, public transportation, top-rated schools, and all of Milton’s shopping and dining options. Don’t miss this perfect blend of charm, space, and modern convenience—your dream family home awaits!

249 Blue Hills Pkwy, Milton

$1,058,000
6 Beds 3 Baths SOLD Status 73393151 MLS 2,744 SqFt.
Rare opportunity to own a two-family in highly desirable Milton! Perfect for investors or owner-occupants looking to offset the mortgage with rental income. The first-floor unit features 2 bedrooms, a sunroom or office, and a private patio—freshly painted and updated. The second and third floors offer a spacious 4-bedroom plus office, 2-bath layout with a huge deck off the living room—ideal for entertaining. Both units have hardwood floors throughout, and the property features blown-in insulation, a newer roof (2020), full dormer on top floor, and great natural light. Off-street parking (garage) and a private driveway add to the appeal. Located near top-rated schools, shops, parks, restaurants, and public transit. Great rental history and potential make this a smart investment in one of Greater Boston’s most sought-after towns!

88 Brush Hill Road, Milton

$2,850,000
6 Beds 6 Baths SOLD Status 73392907 MLS 6,800 SqFt.
Welcome to your dream home in the much sought after neighborhood of Indian Cliffs, just 20 minutes outside of Boston Proper. This stunning brick home is truly designed for luxury living - inside and out. The main floor offers open concept living with gorgeous hardwood floors,10 foot ceilings, chef’s kitchen, expansive living and dining areas and a private office adorned with sophisticated wood wainscoting. The main floor primary suite is a true retreat, with a large en-suite bathroom, steam shower, soaker tub and an enormous walk in closet. The solarium off the main living area leads to the property’s magnificent backyard with an expansive stone terrace, grilling bar, stunning pool and sports court for extraordinary outdoor living. The finished basement is designed for exceptional entertaining and includes a kitchen, bath, bar and movie theater. The spacious upstairs landing hosts 5 bedrooms, including a primary suite. This is a rare find and must see!

60 Whittier Rd, Milton

$1,185,000
3 Beds 2 Baths SOLD Status 73392855 MLS 2,025 SqFt.
Beautiful 3-bed, 1.5-bath Center Entrance Colonial in Milton’s sought-after Columbine/Cliffs neighborhood. This home blends timeless charm with thoughtful modern updates, featuring an open-concept gourmet kitchen with high-end appliances and custom cabinetry, a spacious front-to-back living room with a cozy fireplace, and a bright sunroom perfect for a home office or retreat. Upstairs offers three generous bedrooms and a renovated full bath. The finished basement adds bonus living space, and there's plenty of storage in the attic and basement. Enjoy a prime location close to parks, the bike path, local restaurants, and public transportation—classic character and modern comfort in an unbeatable location!

56 Allen Cir, Milton

$1,450,000
4 Beds 3 Baths SOLD Status 73392520 MLS 3,226 SqFt.
The hard work is done! The major exterior renovations of the main house and two outbuildings, with new windows, siding, trim, insulation and roofs, makes this property the perfect trifecta! Retained is the comfortable farmhouse feel and the ease which transcends a home that has stood the test of time. Living and dining rooms with high, wood-beamed ceilings and exposed brick accents blend into the renovated kitchen through a sizeable entry foyer that could also be a family room. The upstairs layout boasts a two-room primary suite plus 3 more bedrooms. You are sure to find your muse in the heated studio retreat and the over-sized 3-car garage/workshop. Then relax in the outdoor spaces: a shaded patio for morning coffee, dinner on the deck, and a yard to finish the day with sunset views after a hike in the Blue Hills across the street! Make this your “forever home” knowing you can lay out your future here and let life unfold in the desirable Town of Milton, minutes from downtown Boston!

1395 Canton Avenue, Milton

$770,000
3 Beds 2 Baths SOLD Status 73392307 MLS 1,363 SqFt.
OPEN HOUSE CANCELLED Offer has been accepted. Perfectly situated in a wonderful neighborhood, within walking distance to schools, parks and playgrounds, 12 Lincoln St is an exciting opportunity for anyone looking to live in Milton! This charming home enters into a welcoming foyer that flows into a big living room with fireplace, a formal dining room with french doors that provide access directly to the back deck. Finishing off the first floor is the eat in kitchen with pantry and the half bath! Another back door is conveniently located next to the bath, providing easy access into the home from the driveway or garage. Back through the foyer and up the stairs to the second floor, where you'll find the full bath and all three good sized bedrooms. There is a stairway to the attic through one bedroom, providing additional storage and a cedar closet! The basement offers a wide open, well lit, dry space, currently used as a workshop.

12 Lincoln St, Milton

$1,425,000
4 Beds 3 Baths SOLD Status 73391859 MLS 2,269 SqFt.
***OPEN HOUSES JUNE 21 SAT & 22ND SUN 12-2PM***ALL OFFERS HIGHEST AND BEST DUE TUES. 6/24 AT 5PM Spectacular renovated home in the desirable Columbine Cliff area where you can walk to Shields Park, Trolly/T Access, Turners Pond and local stores and restaurants. The home has a wrap-around porch, circular driveway, new black windows, new roof, Rhino-shield exterior paint, whole house water filtration system, natural gas heat (2 zones) and central air (2 zones), irrigation system, fenced in backyard with custom shed, stunning landscaping. The first floor has dramatic 11'+ ceilings with a beautiful kitchen that has high end appliances, quartz countertops, breakfast bar, pantry and tile backsplash. The dining room has its original rich walnut woodworking/wainscoting. First floor bedroom/guest room and study plus 3 bedrooms on the second floor. Room for expansion in the basement which is currently being used as a gym/playroom and includes a recently updated full bath. Floor plan attache

332 Eliot St, Milton

$945,000
5 Beds 2 Baths SOLD Status 73390339 MLS 2,591 SqFt.
Rarely does a property of this stature come to the market. This Classic Greek Revival 4/5 bedroom home has been in the same family for over 6 decades. Solidly built in 1859 to stand the test of time with superior craftsmanship and materials, impressive architectural details including soaring ceilings, large original windows, exquisite original molding, front curved staircase, rooms made for entertaining including a large eat-in kitchen, an abundance of sunlight, back staircase, and generous storage space. With some TLC, 167 Brook Road offers endless possibilities. Graciously set back on a flat level 1/3 acre. Situated on bike path, near public park, public and private schools, with access to public transportation, all major highways, 9 miles from Boston. This special gem awaits its new steward to write the next chapter. Shown by Appointment Only.

167 Brook Rd, Milton

$830,000
3 Beds 2 Baths SOLD Status 73390146 MLS 1,308 SqFt.
Beautiful East Milton home, nestled on a tree-lined street with a wide array of neighborhood amenities at your finger tips! Easy walking distance within a few blocks of several popular restaurants, coffee shops, fitness options.... and of course - stalwart local "Fruit Center" grocery store. This lovely home features three bedrooms, a terrific layout, a lovely three season front porch, 1 & 1/2 baths, garage parking and amazing curb appeal. Updates include a new roof, updated full bath, newer Gas heating & HW systems, windows - all you have to do is move in and enjoy! Milton is one of the most sought-after communities in the area with top schools, only 8 miles from Boston and is consistently rated one of the best towns in the country! This could be just the opportunity you have been waiting for!

102 Franklin St, Milton

$1,375,000
3 Beds 3 Baths SOLD Status 73389741 MLS 2,612 SqFt.
Discover the potential of 1386 Canton Ave in Milton. Set on an expansive 1.74 acre lot, this prime Milton parcel offers endless opportunities for those looking to build their dream home or update the current single-family home. Ideally positioned adjacent to the historic Eustis Estate and the breathtaking Blue Hills Reservation, renowned for its extensive hiking trails. Imagine designing your dream home with immediate access to nature's wonders, providing the perfect backdrop for outdoor activities and tranquil living. A harmonious blend of privacy and convenience - this picturesque setting provides a rare chance to create something special in one of the most desirable communities, just minutes from Boston. Whether you're a builder, developer or future homeowner, this is your canvas—bring your vision to life at 1386 Canton Ave.

1386 Canton Ave, Milton

$1,260,000
4 Beds 3 Baths SOLD Status 73388776 MLS 2,481 SqFt.
What’s Not to Love? With a reno/expansion completed in 2024, this home takes a classic center-entrance Colonial and reimagines it for today with smart updates, light-filled spaces, and flexible living.The main level features a front-to-back living room with French doors that lead to a patio & fenced yard that feel just right. The open, airy kitchen delivers crisp white finishes, sleek new appliances, and playful pops of color. Upstairs, find three generously sized bedrooms w/ample closets and a renovated full bath. But the true wow comes with the guest suite addition—a stunning space with vaulted ceilings, spa bathroom, bedroom, and a den with wet bar. Whether you want a private retreat or need multigenerational living, this space adapts. The oversized 2-car garage leads to a mudroom/drop zone—keeping everything organized and out of sight. The lower level features a workbench, storage, and lots of potential! . With all new systems, windows, roof, and siding, this one is truly turnkey.

28 Adanac Road, Milton

$871,500
3 Beds 2 Baths SOLD Status 73387444 MLS 2,251 SqFt.
Set on a quiet street in a neighborhood of well-kept homes, this expanded 3-bedroom, 1.5-bath New England Cape is just minutes from downtown Boston. Lovingly maintained, the home features hardwood floors throughout, original glass doorknobs, and ceiling fans in all bedrooms. The layout: a bright living room with fireplace, sunroom, finished basement, and a full walk-up attic with plenty of space and potential for finishing. The fenced backyard includes a custom stone firepit, covered patio, and a newly-landscaped yard. Recent updates include fresh paint inside and out, refinished floors, central air, gas heat, replacement windows, and an upgraded heating system. Less than a mile to East Milton Square and Adams Corner, and close to the Neponset River Reservation’s trails, Martin Hilltop Playground, Pope John Paul II Park, Presidents Golf Course, and Neponset Valley Yacht Club. Easy access to highways, MBTA bus routes, and commuter rail.

65 Courtland Circle, Milton

$1,155,000
3 Beds 2 Baths SOLD Status 73388716 MLS 1,821 SqFt.
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 landscaped backyard with a waterfall koi pond and a covered patio off the kitchen, 7-zone sprinkler system and storage shed. Front-to-back primary bedroom with 3 closets. Updated bathroom with Italian Bardiglio marble. A finished family room in the basement with a separate laundry and workshop. New plumbing and electric wiring. Walking distance to elementary school. restaurants, food market, gym, salons, and shops. Park abuts at end of street with sport fields, town swimming pool, tennis courts, peaceful wooded walking trails, sledding hills, a pond for ice skating and playground. This one will be popu

28 Westvale Road, Milton

$950,000
4 Beds 2 Baths SOLD Status 73386069 MLS 2,653 SqFt.
Unlock the potential of this Milton two-family home! Situated on a corner lot along a stately, center island street, this property offers classic charm and outstanding opportunity. Each unit features six spacious rooms, including two bedrooms, separate living and dining rooms, and heated sunrooms. The walk-up attic offers two additional rooms with windows, closets, and radiators—perfect for expanding the second-floor unit. Additional highlights include a brand-new roof and detached two-car garage. Enjoy the conveniences of city living with easy access to the T, highways, and local amenities—while still savoring the quieter, suburban lifestyle that Milton is known for. Delivered vacant. First open Sunday 6/8 12pm to 2pm. Here’s your chance!

1 Chilton Park, Milton

$850,000
3 Beds 2 Baths SOLD Status 73385792 MLS 1,927 SqFt.
SUNDAY OPEN HOUSE CANCELLED - PROPERTY IS UNDER AGREEMENT - Charming 3BR/1.5BA Corner Lot Home on Meagher Ave! First floor features chef's kitchen, cozy living room with fireplace, elegant dining room with built-in china cabinet, convenient office space, and half bath. Hardwood floors throughout need some TLC but offer great potential. Energy-efficient vinyl windows provide abundant natural light. Second floor offers three bedrooms (one with custom built-in desk) and luxurious full bathroom with radiant heated floors and heated towel rack. The primary bedroom has a huge walk in closet with custom shelving. Partially finished basement includes built-in entertainment area perfect for recreation. Corner lot location with convenient public transportation access. Great bones with thoughtful custom features throughout - wonderful opportunity to restore and personalize in desirable Milton!

37 Meagher Ave, Milton

$1,550,000
4 Beds 4 Baths SOLD Status 73385364 MLS 2,522 SqFt.
At the foot of the Blue Hills tucked behind a stand of trees and just past Wollaston Country Club you'll find 1051 Randolph Avenue. This expansive classic has been tastefully and meticulously renovated throughout and the result is serene, inviting and comfortable. There are so many places to gather and so many options to spread out whether it's the formal living and dining room or eat-in-kitchen with stunning family room. Four bedrooms on the second floor are highlighted by the en suite primary with gleaming new bathroom. The finished lower level rooms are yours to craft as media room, playroom, home office or guest suite with private bath and direct access to the lush grounds and sparkling pool. Oversized two car garage and countless thoughtful improvements. When so much takes place at home these days, 1051 is the perfect setting to work, to play and to reset.

1051 Randolph Ave, Milton

$920,000
4 Beds 2 Baths SOLD Status 73385077 MLS 2,004 SqFt.
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 be reimagined. Recent updates include a brand-new roof and energy-efficient blown-in insulation, giving you a head start on your renovation dreams. The heart of the home is the beautifully renovated sunroom, a bright, inviting space perfect for morning coffee, a home office, or relaxed entertaining. Whether you're looking to move in and make updates over time or embark on a full-scale transformation, 21 Otis Street delivers unmatched potential in a prime Milton location close to top-rated schools, parks, and commuter routes.

21 Otis St, Milton

$735,000
4 Beds 2 Baths SOLD Status 73385021 MLS 1,875 SqFt.
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 seeking one level living without sacrificing space. With 4 bedrooms and 2 full baths spread across 3 levels, there’s plenty of room for guests, a home office, or multi-generational living. Investors take note this property offers excellent flexibility for long-term value with updated roof and windows, gas heating, central air and vinyl siding offering peace of mind with low maintenance ownership. Enjoy being just minutes from Milton Academy, Cunningham Park and East Milton Square, with easy access to shops, dining, and outdoor recreation. This gem might be the cure you've been waiting for!

641 Pleasant St, Milton

$625,000
2 Beds 2 Baths SOLD Status 73384871 MLS 1,048 SqFt.
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 is available for an additional cost.

485 Blue Hills Parkway Unit 7, Milton

$645,000
2 Beds 2 Baths SOLD Status 73384869 MLS 1,047 SqFt.
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 is available for an additional cost.

485 Blue Hills Parkway Unit 36, Milton

$1,375,000
4 Beds 4 Baths SOLD Status 73384179 MLS 2,411 SqFt.
When asked, “Why this house?”, the clear answer was and still is, “location”. Set in Milton’s desirable Columbine neighborhood, 51 Rustlewood offers proximity to Milton schools, Milton Academy, Turner’s Pond, and trolley access. Owners jumped right in, expanding to a rare 4-bedroom, 3.5-bath home with room for all. The coveted primary suite now includes a walk-in closet and sumptuous bath, choices smart and current. Expansion came easily with a complete 3rd floor takeover, including cathedral ceilings, recessed lighting, bedroom, full bathroom, lounge area and generous storage. A flexible first-floor office easily serves as a den or 5th bedroom. The eat-in kitchen with newer stainless-steel appliances opens to a fenced backyard and brick patio, perfect for play and outdoor entertainment. A screened porch off the living room, recessed lighting, newer windows, newer roof, gas heat, wired for EV, lower level recreation space complete the picture. Now the better question is, “Why wait?”!

51 Rustlewood Rd, Milton

$1,975,000
4 Beds 5 Baths SOLD Status 73384044 MLS 3,620 SqFt.
Your dream backyard awaits—complete with a heated saltwater pool, hot tub, patio, playground, and lush green space perfect for entertaining or unwinding in peace. Inside, modern updates complement timeless charm, with a bright kitchen, stainless steel appliances, and a sunlit dining area. The living room features crown molding and a tiled fireplace, while French doors open to a private home office. A skylit family room leads seamlessly to the outdoors. Upstairs, you'll find four generously sized bedrooms, including two with en suite baths and a versatile bonus room. The luxurious primary suite is the perfect retreat, featuring custom California closets and a spa-inspired bathroom with double vanity. A partially finished basement with its own fireplace and bath adds flexible living space. From front porch mornings to backyard nights, this home is built for comfort, beauty, and lasting memories.

290 Lyman Rd, Milton

$3,400,000
5 Beds 7 Baths SOLD Status 73381645 MLS 7,290 SqFt.
Welcome to 81 Countryside Lane, a rare single-level estate in one of Milton’s most desirable neighborhoods. Privately set on a beautifully landscaped acre, this nearly 7,000 sq ft custom home offers 5 spacious bedrooms (4 with en suites), 6.5 luxurious interior baths, plus a separate cabana with 1 bed and 2 full baths by the resort-style pool and outdoor bar. Soaring knotted pine ceilings and two coral fireplaces anchor the elegant, open living areas, perfect for entertaining. Enjoy a chef’s kitchen with Wolf appliances, a massive home gym or yoga studio, and a heated 3-car garage. Every detail reflects quality, from the new cedar shake roof to pristine systems throughout. Designed for indoor-outdoor living and maintained by one meticulous owner, this home offers luxury, comfort, and enduring value—all on one level, ideal for aging in place, creating an in-law wing or a multi-generational home. 81 Countryside Lane isn’t just a home; it’s a lifestyle.

81 Countryside Ln, Milton

$1,375,000
4 Beds 2 Baths SOLD Status 73381570 MLS 2,100 SqFt.
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 stove) which flows seamlessly into both the dining room (w/coffee bar) and sunroom. A fireplace and built-in shelving make the front-to-back living room an ideal place to relax and entertain off-season (the inviting rear deck with hot tub overlooking the back yard is perfect the rest of the year!). New Andersen windows/doors; Sunnova solar panels with EV charger; finished basement; attached garage with plenty of driveway parking. Easy access to E. Milton Sq., 93/95/3 & downtown Boston. Deep double lot may offer expansion possibilities. Seller welcomes offers with requests for buyer concessions.

50 Badger Cir., Milton

$1,705,000
4 Beds 3 Baths SOLD Status 73381197 MLS 2,568 SqFt.
This Classic Stone front Colonial is the look and feel you've been craving! Set on one of Milton's popular tree-lined streets, where friends and lifelong memories are made! Come take a look, as 51 Clifton Road will not disappoint. With entertaining size rooms and elegant features such as high ceilings, hardwood floors and custom built-ins throughout, the versatile layout and three floors of living will sure to impress! And wait until you see the fabulous open and airy Chef's kitchen with an abundance of storage! The expansive deck overlooking the manicured lawn is perfect for summer BBQ's, throwing the ball around or simply relaxing! All set in Premier Hospital Hill neighborhood with close proximity to Milton Academy, Turners Pond and all the great things Milton as to offer!

51 Clifton Rd, Milton

$1,225,000
3 Beds 2 Baths SOLD Status 73380966 MLS 2,311 SqFt.
Set on a picturesque, tree-lined street in one of Milton’s most sought-after neighborhoods The Columbines. This move in ready home offers space for modern living and entertaining. With an ideal layout which includes a kitchen that opens to a sun-filled family room plus a front to back living room. Upstairs you’ll find three generously sized bedrooms, including a primary with a rare walk-in closet. The finished lower level provides flexible living space ideal for a playroom, home office, or guest space. Step outside to a fenced in quarter acre lot ready for summer gatherings, playing fetch with Scout and enjoy crisp fall nights around a fire pit. Just a short stroll to the trolley for easy access to Boston, Shields Playground for recreation, and the beloved Steel & Rye restaurant for dining. Outdoor lovers will enjoy quick access to the Neponset River Green Trail and its scenic views the perfect city escape. With tasteful updates throughout we guarantee it will not disappoint!

1 Columbine Rd, Milton

$1,350,000
4 Beds 3 Baths SOLD Status 73380101 MLS 3,197 SqFt.
Welcome to 118 Dudley Lane, a spacious 4-bed, 2.5-bath Colonial set on a beautifully landscaped 1.01-acre lot on a private lane in one of Milton’s most desirable locations. This sun-filled 10-room home features a welcoming foyer with sitting area and double-sided fireplace, spacious living and dining rooms, and a bright family room with views of the expansive backyard. Upstairs offers a large primary suite with a 22' x 21' bedroom, full bath, and wall of closets, plus three additional bedrooms and full bath. Gleaming hardwood floors throughout. Finished lower level with game room and laundry. Enjoy outdoor living with a deck, patio, and an incredible yard perfect for entertaining or play. Minutes away from Milton Academy, Fontbonne, and East Milton Square. Easy access to Rt. 93—just 8 miles to Downtown Boston. Rare opportunity to own a home on over an acre in a prime Milton neighborhood!

118 Dudley Ln, Milton

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