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$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

$1,285,000
3 Beds 3 Baths SOLD Status 73379010 MLS 2,064 SqFt.
This one covers all the bases! Upstairs offers the privacy of two bedrooms, one with its own office, and the full bath of the original Cape-style home, while the main level has been architecturally reimagined and rebuilt with all new systems, windows, and an open floor plan. Living is easy with the dreamy, center island kitchen, the gas fireplace in the dining-living room, first-floor laundry and primary bedroom with ensuite bath and walk-in closet. Effortlessly slide between work and home with the convenient office off the kitchen. Then let the good times roll in the sensational family room addition, out onto the composite deck and into the enviable quarter-acre yard, just in time for summer barbeques, games, or gardening with a charming shed. Bonus points: storage abounds, and the basement has potential! This one is a home run, on a quiet, cul-de-sac next to conservation and walking trails, near Milton Academy and schools in the sought- after Cuningham area and all things Milton!

35 Orchard Road, Milton

$1,100,000
4 Beds 3 Baths SOLD Status 73378952 MLS 2,370 SqFt.
We are excited to present this beautiful colonial, with four bedrooms , three baths and 2 fireplaces , one of which is located in the master suite. It has a two car garage with tons of storage. It has an amazing deck space off the back of the house and the large eat in kitchen. This home sits on a spectacularly quaint dead end street and located at the end of a long private driveway. The outside of the home and the grounds have been meticulously kept and create amazing privacy and curb appeal . There is a large unfinished basement with plenty of height and room to expand . The first level of this home, flows beautifully with an office, a living room, dining room, and a large mudroom off the spacious kitchen . The second level has 4 bedrooms and 2 full baths. This beauty is ripe for its next owner and being sold as is. Open House Sunday 25th, from 12-1:30

1262 Randolph Ave, Milton

$875,000
3 Beds 2 Baths SOLD Status 73378730 MLS 1,596 SqFt.
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 chance to break into the East Milton market at an affordable price point. The surrounding area is known for its tree-lined streets and strong community feel, making it the ideal spot to invest and build equity. Bring your ideas, your contractor, and your imagination — and transform this diamond in the rough into the home of your dreams. This is more than a project — it’s an opportunity. Don’t miss it!

39 Otis Street, Milton

$3,100,000
7 Beds 5 Baths SOLD Status 73374837 MLS 7,312 SqFt.
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 & modern comfort. Original architectural details have been meticulously preserved, reflecting the home's rich heritage, complete w/hand painted frescos, original inlaid hardwood floors, rare pentagonal bay window in the family room, 7 fireplaces & a very special barn + greenhouse w/possibilities. Nestled directly across from the scenic Governor Hutchinson's Field, residents can enjoy breathtaking views of the Neponset River marshes, the city of Boston skyline & Harbor. This private & exceptional estate offers a unique opportunity to own a piece of Massachusetts history.

203 Adams St, Milton

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