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$755,000
4 Beds 3 Baths SOLD Status 73427764 MLS 1,684 SqFt.
NEW roof, NEW siding, NEW windows and gutters, NEW hot water tank plus a NEW walkway and front stairs leaving you free to design your DREAM kitchen or simply enjoy the mid century modern look. This charming gem offers 3 levels of versatile living space, giving you the flexibility and privacy for two home offices, overnight guests, and more. The welcoming foyer provides breathing room when guests arrive, while the graceful double French doors, wood burning fireplace, gleaming hardwood floors, and inviting screened in porch add timeless character. If you’re considering leaving the cityscape, you’ll find comfort in the lush master gardens and serene greenery. For buyers who value quality and consistency, this home is a must-see. All this, just 8 miles south of Boston, close to public transportation, top-rated schools and the scenic Neponset River paths. Curious about Milton? Stop by and discover why it has been recognized by Money Magazine as one of the "Best Places To Live."

55 Concord Ave, Milton

$2,550,000
5 Beds 4 Baths SOLD Status 73426168 MLS 4,522 SqFt.
Stunning 2014 shingle-style contemporary filled with light, thoughtful design, and quality amenities. With more than 4,500 sq. ft. of living space, the open-concept first floor features a chef’s kitchen with Jenn-Air appliances, quartz countertops, a generous island with gas range, and pantry. The dining room opens to a sleek IPE deck, while the living room with fireplace offers a warm gathering space. There is a home study/office, first floor laundry, a half bath, and a luxurious first-floor suite with dual walk-ins, steam shower, and soaking tub that completes the first level. Upstairs are three spacious bedrooms with a shared double-sink bath. A private suite above the garage with walk-in and full bath offers flexible use—au pair, in-law, or guest retreat. Quality shines through with Marvin Integrity windows, Rinnai hot water, three HVAC systems (five zones), white oak floors and Emtek hardware. Very close to Milton Academy, this home blends modern convenience with timeless style.

141 Gun Hill St, Milton

$1,120,000
3 Beds 2 Baths SOLD Status 73425852 MLS 2,077 SqFt.
Welcome to 1111 Brook Road in Milton! This updated home features a bright fireplaced living room, custom mudroom, and dining room that flows into a modern kitchen with white cabinetry, center island, upgraded appliances, vented hood, and new hardware. Upstairs offers a vaulted primary with exposed brick, two additional bedrooms, renovated bath, and laundry. The finished lower level with new vinyl flooring and surround sound adds flexible space for work, play, or fitness, with walkout access to a private backyard, patio, and refreshed landscaping. Recent upgrades include a new water heater and thoughtful improvements throughout. All in a walkable location near Milton Village, schools, parks, public transit, and easy access to Route 93.

1111 Brook Rd, Milton

$785,000
3 Beds 1 Baths SOLD Status 73425119 MLS 1,004 SqFt.
Welcome to 36 Pleasant Street, a 3-bedroom, 1-bath home that feels ready for new memories the moment you arrive. The bright kitchen is the heart of the house with a walk-in pantry, a peninsula for casual dining, and direct access to the back deck for summer barbecues or quiet evenings under the stars. An open floor plan flows easily from room to room, filled with natural light that makes the home feel bright and welcoming. Out back, the fenced yard is designed for both play and relaxation with space for gardening, a fireplace for cozy nights, and sunsets from the deck. Living in Milton means you don’t have to choose between convenience and community—you’re just minutes from Boston while still enjoying vibrant local restaurants, tree-lined streets, and the small-town charm that makes this community so special.

36 Pleasant Street, Milton

$2,200,000
5 Beds 5 Baths SOLD Status 73424735 MLS 5,250 SqFt.
Get ready to say YES to 48 Cypress Rd! YES to brand new construction. YES to the open floor plan that includes 5 bedrooms, 5 full baths, a spacious living room, a dedicated dining room, a 2nd floor laundry room AND a fully finished lower level with 9 ft ceilings. YES to a luxurious primary that includes an oversized walk-in closet & spa-like ensuite bath with soaking tub, rain-shower and dual vanities. YES to the chef's kitchen with waterfall center island, sleek quartz countertops, walk-in pantry & top-of-the-line appliances. YES to designer details like a grand foyer, gas fireplace & oversized windows that flood the home with natural light. YES to a 2-car attached garage with direct access to a dedicated mudroom. YES to the location and lifestyle. Tucked into one of Milton's favorite neighborhoods, you will be steps from Cunningham Park, public & private schools, and enjoy easy access to East Milton Square. There is no doubt that this home is a YES you won't regret!

48 Cypress Rd, Milton

$735,000
2 Beds 2 Baths SOLD Status 73424533 MLS 1,109 SqFt.
This is your chance to own a unit in a well managed boutique condo association. Located in Milton's Central Village, this inviting unit has 2 bedrooms, 2 full baths, in-unit laundry, central air conditioning and a deeded parking spot. The open concept layout offers hardwood floors, a beautiful kitchen with stainless steel appliances, a living area with a gas fireplace and a balcony with outdoor living space. The primary bedroom, walk in closet & ensuite are spacious. The second bedroom could also be used as a home office, guest room or den. A community room, water filtration system, bike storage and covered parking are other key features of this building. The lively Central Village location will keep you close to a variety of shops, Steele & Rye, the Red Line Trolley & the Neponset River Greenway Trail. Plus, you're just minutes to Downtown Boston, Milton Academy, Turners Pond and all major highways. Don't miss the opportunity for a rarely available unit at 36 Central Ave.

36 Central Ave Unit 3, Milton

$2,450,000
7 Beds 6 Baths SOLD Status 73423979 MLS 7,085 SqFt.
Imagine coming home to a private Milton enclave where timeless elegance meets everyday livability. Set on over an acre, 50 Marine Road offers grand living spaces designed for comfort, longevity, & flexibility. With 3 separate staircases, the layout is ideal for multi-generational living/au pair suite. Inside, 9 fireplaces and rich millwork reflect the home’s classic character, with substantial infrastructure updates including a young roof and heating system, 400-amp electrical service, copper downspouts, and new water, sewer, and gas lines. The sun-filled kitchen with island anchors the home, while a sunroom, elegant office with fireplace, and versatile bonus rooms provide endless possibilities. Outdoors, lush grounds surround a pool, hot tub, & stone patios, creating a private setting for entertaining or retreat. Surrounded by newer homes on a coveted cul-de-sac, this rare estate blends elegance, substance, and the lifestyle that defines Milton living—just minutes to Milton Academy.

50 Marine Rd, Milton

$830,000
3 Beds 2 Baths SOLD Status 73423068 MLS 1,410 SqFt.
Very desirable Badger Circle! Recent sales on street all well over 1 mill.This property boasts approx. 1400 sq.ft. of well-designed, finished living space, featuring 3 spacious bedrooms,1.5 baths(full- floor 2 &1/2 on lower level), a 1 car garage (under), central air,secruity AND an irrigation system.The main living area welcomes you w/ a generously sized living room,complete with a cozy fireplace,adjoining dining area that flows into the kitchen.A family room/sunroom off the back of the house(w/new windows) overlooks a recently installed outdoor patio & entertainment area-ideal for hosting summer barbecues or enjoying quiet evening outdoors!The lower level of this tri-level home has been partially gutted,new window installed & is ready for renovations, offering quick potential for ADDITIONAL & SIGNIFICANT increase of living space (would be total approx 2k s.f.)(see plan marked storage.)This property is being offered at a true value for the neighborhood!!

17 Badger Cir, Milton

$805,000
5 Beds 3 Baths SOLD Status 73422524 MLS 1,749 SqFt.
Step into this stunning, gut-renovated home offering 5 spacious bedrooms, 2 full bathrooms, and a convenient half bath perfectly designed for modern living. Every inch of this home has been thoughtfully updated, with attention to detail throughout.The main level boasts an open concept layout with gleaming hardwood floors, recessed lighting, and a stylish designer kitchen complete with quartz countertops, custom cabinetry, stainless steel appliances, and a large center island ideal for entertaining. The living and dining areas flow seamlessly for a bright and airy feel.Upstairs, you’ll find generously sized bedrooms with ample closet space, including a luxurious primary suite with a private full bath. The bathrooms are fully updated with high-end tile work, sleek vanities, and contemporary fixtures.

16 Blue Hill Ave, Milton

$965,000
3 Beds 2 Baths SOLD Status 73420800 MLS 2,468 SqFt.
Nestled at 62 Ferncroft Rd, Milton, MA, this single-family residence presents an attractive opportunity to own a piece of quintessential New England charm. The property is in great condition and ready to welcome its new owners. The living room offers an inviting space to unwind, enhanced by the sophisticated touch of crown molding. In the kitchen, culinary dreams become reality amidst stone countertops and a stylish backsplash, with crown molding adding a final flourish to this delightful space. The kitchen bar and peninsula create a versatile area for casual dining and social gatherings. The bathroom becomes a private spa with its luxurious soaking tub and tiled walk-in shower. A skylight infuses the bedroom with natural light. Outside, the property offers a variety of spaces to enjoy the outdoors, including a deck, patio, and an outdoor dining area perfect for al fresco meals.

62 Ferncroft Rd, Milton

$2,680,000
4 Beds 5 Baths SOLD Status 73420642 MLS 4,132 SqFt.
This stunning 4-bedroom, 4.5-bath home with a 2-car garage is nestled on 1.8 beautifully landscaped acres in one of Milton’s most desirable neighborhoods. Perfectly suited for both everyday living and entertaining, the home offers spacious and sun-filled living areas throughout. The well -appointed chef’s kitchen features an eat-in breakfast area and cozy seating nook, flowing seamlessly into a large family room with a striking floor-to-ceiling stone fireplace. The luxurious primary suite boasts a second stone fireplace, a spa-like bath, a private deck overlooking the lawn, and a large walk-in closet with a dressing area. The finished basement offers flexible additional living space! Outside, enjoy  a spacious deck, professionally designed gardens, a charming gazebo, and sweeping lawns, that include room for a pool and direct access to 125+ miles of scenic trails. A country like setting only 7 miles to Boston. Welcome home.

218 Woodland Rd, Milton

$990,000
4 Beds 2 Baths SOLD Status 73420278 MLS 2,700 SqFt.
Buyer got Cold Feet! This massive multi-family home, built in the 1920s, blends timeless character with thoughtful updates. Beautiful built-ins show off its charm and classic era details. Offering over 2,700 sq. ft. of living space, 1st unit has 2 bedrooms, 1 full bathroom and 2nd unit has 2 bedrooms, 1 full bathroom and 3 ADDITIONAL rooms to use as you wish! (see floor plan photos). Hardwood floors and soaring high ceilings enhance the open, airy feel. Inside both units you’ll find deceptively large rooms filled with natural light, while outside, each side of the home offers its own driveway for convenience. Over the past 20 years, many updates have been made, ensuring comfort and peace of mind. Step out onto your new deck and relax in the stunning backyard oasis, a true extension of the home—private, inviting, and designed for everyday enjoyment. A rare opportunity in Milton, this home is truly a must-see!

15 Belvoir Rd, Milton

$1,083,500
4 Beds 3 Baths SOLD Status 73419799 MLS 1,700 SqFt.
This stunning, gut renovated home offers 4 bedrooms, 3 full bathrooms, and approximately 1,700 sq ft of beautifully designed living space. The open-concept first floor is perfect for entertaining, featuring a stylish kitchen with island seating, an arched coffee/dry bar, and adjacent dining area. A mudroom with coat closet, walk-in pantry, and a versatile office or sitting room with French doors add function and charm. A spacious first-floor bedroom and nearby full bath make an ideal guest suite or family room. Upstairs, the primary suite boasts 9' ceilings, dual closets, a built-in bookcase, and en-suite bath. Two additional bedrooms and a third full bath complete the upper level. Enjoy a private backyard patio and ample off-street parking—this home is truly a must-see! All new electric, plumbing, HVAC, windows, roof, vinyl siding, hardwood floors, kitchen, bathrooms, etc!

40 Lafayette St, Milton

$975,000
4 Beds 2 Baths SOLD Status 73419278 MLS 1,560 SqFt.
Welcome Home to 99 Elm Street ! Classic and charming best describe this 3/4 bedroom, 2 full bath Cape. Located in one of Miltons most desirable neighborhoods, this home is perfect for the first time home buyer or the buyer looking to downsize and stay in Milton. This home has an inviting entry way which leads to a spacious fireplaced front room which could be used as a dining/living room. A renovated kitchen with stainless appliances leads to a comfortable den with access to the private back yard with deck and covered porch area. Great for entertaining and hosting your friends and family. Two spacious bedrooms on the first floor with a full bath and two spacious bedrooms on the second floor round out the versatile floor plan. The unfinished basement has so much potential. There is abundant natural light and gleaming hardwood floors throughout first floor. Charming exterior, well maintained landscaping and private backyard. This turn key property is ready for its next chapter.

99 Elm St, Milton

$1,675,000
3 Beds 4 Baths SOLD Status 73418229 MLS 2,576 SqFt.
This classic shingle-style three bedroom, three and a half bath town-home has wonderful natural light, great space, and relaxing views. The open floor plan provides a welcoming space for entertaining and ease of living. First floor highlights include fireplaced living room, well-appointed kitchen with a generous island, dining area, private primary suite, den/office, half bath, and laundry room. The two en-suite bedrooms and loft on the second floor are perfect for guests or a separate space to just relax. Two car attached garage, plantation shutters, spacious closets, high ceilings, pantry, and attic are just a few of the special features. A welcoming front porch and a relaxing back deck. The lower level provides the option to finish for additional living area. Set on 47-acres, Wolcott Woods, an Award-Winning 55+ community, abuts the Blue Hills Reservation. Easy access to shopping, restaurants, highways, universities and more.

53 Wolcott Woods Lane Unit 53, Milton

$735,000
2 Beds 2 Baths SOLD Status 73418014 MLS 1,286 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 41, Milton

$1,300,000
4 Beds 2 Baths SOLD Status 73417845 MLS 2,200 SqFt.
Stunning Property! Gorgeous 4-BR Home + HUGE TWO LEVEL GARAGE located in one of Milton’s hottest areas! The stylish front sunroom sets the tone for this superbly updated home. Featuring Gleaming hardwood floors, freshly painted interior, recessed lighting, and modern interior doors throughout. The sunlit fireplace living room offers cozy charm. The showstopping NEW sky-lit kitchen features quartz counters, granite island, sleek cabinetry, and brand new stainless-steel appliances, flowing seamlessly into the dining room with custom built-ins and a spacious family room—perfect for entertaining. First-floor full BA and flexible office/bedroom space. Upstairs offers 3 BRS and an updated full bath. Enjoy the new composite deck and stone firepit in the private fenced in yard. shed, and irrigation system. Walk to schools and library. Minutes to Boston. +/-1,300 sq ft, 2-LEVEL GARAGE is ideal for equipment storage with a studio/office, living or potential, already built, ADU/In-Law.

338 Thacher St, Milton

$950,000
5 Beds 2 Baths SOLD Status 73416152 MLS 2,630 SqFt.
Welcome to 418 Pleasant Street in Milton, a two-family gem that's as charming as it is versatile! This delightful duplex offers a perfect opportunity for both investors and those seeking a cozy home. The first unit features 2 bedrooms and 1 bath, while the second unit boasts 3 bedrooms plus 3 bonus rooms and 1 bath. With a total of 2,630 square feet, there's plenty of space to stretch out.Situated with easy access to Milton Marketplace, Starbucks, Cunningham Park, and more, you'll never be short of things to do or places to explore. Whether you're drawn to the investment potential or looking to make it your own, this charming abode has something for everyone! Get ready to turn the key and start your next adventure.

418 Pleasant St, Milton

$1,300,000
5 Beds 4 Baths SOLD Status 73414145 MLS 4,048 SqFt.
With over 4,000 sq. ft. of living space set on an 11, 286 sq. ft. lot this 5 bed, 3.5 bath historic home offers unmatched size and value. While Milton's average sale is at $512.00 per sq. ft. this home at $372.00 per square foot is priced to sell. Enjoy multiple 1st floor living areas, a kitchen with custom cabinets, a separate office area and expansive decks. The private primary suite features its own staircase, a walk-in closet, soaring ceilings, a deck and a unique primary bath. A top floor suite with kitchenette is ideal for guests or an au pair. There are garages for 3 cars and an attached building for storage and potential work space. The quiet cul-de-sac with its direct access to the Blue Hills Reservation and its bike and hiking trails provide comfort, privacy and peace of mind.

161 Sassamon Ave, Milton

$759,000
2 Beds 2 Baths SOLD Status 73412257 MLS 1,102 SqFt.
Hendries at Central Station is a newly built 38-unit condominium complex situated in the historic and vibrant Lower Mills neighborhood of Milton, MA. This top floor unit faces the courtyard and features sleek interiors with Bosch stainless steel appliances, quartz countertops, Pella windows, stylish modern flooring, in-unit stackable washer and dryer, and private balconies.Enjoy soaring ceilings and an open-concept layout, perfect for everyday living and entertaining. The spacious primary suite includes a walk-in closet and a luxurious en-suite bath with a glass-enclosed shower. A well-sized second bedroom offers generous closet space. Additional highlights include one deeded garage parking space and an unbeatable location. Just steps from the Central Station trolley stop and the Neponset River Greenway, you’ll have access to 8 miles of scenic trails leading to Pope John Paul II Park. Launch a kayak, hop on a bike, or explore the many nearby shops and restaurants in Lower Mills.

131 Eliot St Unit 407, Milton

$645,000
2 Beds 2 Baths SOLD Status 73411213 MLS 1,660 SqFt.
New Price Adjustment !!! 669,000*** Open House Sat & Sunday 10/11,10/12, 12-2pm *** BEST VALUE ON MARKET 1,660+- SQUARE FEET *** BEAUTIFUL NEW CONDOMINIUM CONVERSION 2024/2025... TWO LEVELS LIVING SPACE *** FINISHED LOWER LEVEL....HUGE OPEN SPACE FOR...RECREATIONAL AREA....HOME OFFICE ETC..OR POTENTIAL FOR 3RD BEDROOM.*** OPEN FLOOR PLAN *** TOP NOTCH STAINLESS STEEL APPLIANCES *** QUARTZ WATERFALL COUNTERTOPS *** SHAKER STYLE CABINETRY *** 2 FULL BATHROOMS **** 2 EXCLUSIVE OFF STREET PARKING & PLENTY OF ADDITIOANL OFF STREET PARKING*** OUT DOOR PATIO TO RELAX AND ENJOY *** PRIVATE OVERSIZED PORCH *** AMAZING SUNFILLED NATURAL SUNLIGHT *** CENTRAL AIR *** LOW CONDO FEE*** EVERY ATTENTION TO DETAIL BY DEVELOPER WELL PLANNED ***

172-174 Blue Hill Ave Unit 174, Milton

$2,375,000
5 Beds 5 Baths SOLD Status 73410628 MLS 4,244 SqFt.
Exceptional, fully-renovated, stately brick colonial on a quiet lane in the sought-after Columbine/Cliff neighborhood. This meticulously maintained residence spans over 4,000 SF, seamlessly blending modern luxury with timeless elegance and craftsmanship. The well-appointed kitchen is equipped with high-end appliances, custom cabinetry, and a peninsula island. The upper levels include five generously sized bedrooms, each providing comfort and privacy, including a primary suite with an en-suite bathroom and walk-in closet. The finished basement provides flexible space, including a gym, recreation room, and a full bath. And wait until you see the almost half-acre serene lot with an outdoor kitchen, spa, pool and custom patio. Make your way to the two-car carriage house with endless possibilities in the loft area. Come take a look, you won't want to leave!

76 Cliff Rd, Milton

$837,500
4 Beds 3 Baths SOLD Status 73409896 MLS 1,845 SqFt.
This well-maintained classic colonial in highly desirable Milton offers 4 generous bedrooms, PLUS bonus office, 1 full bath and 2 half baths, hardwood floors throughout with timeless character and many updates to windows, kitchen, baths, includes stainless steel kitchen appliances, Navien tankless hot water system (2021), and a brand-new roof (2025). The eat-in kitchen features a large island is adjacent to a cozy screened in porch and leads to a formal dining room and open-concept living room with fireplace and built-ins. Finished basement with ceramic tile includes a den with a 2nd fireplace, a heavy-duty laundry room, access to a double car garage and fenced in back yard. This home has more, a walk-up attic and. ADT security system included. Enjoy easy access to top private schools and direct access to Boston medical facilities, universities, entertainment and more. Don't miss this rare opportunity for suburban living with city access!

96 Brook Rd, Milton

$955,000
3 Beds 3 Baths SOLD Status 73408312 MLS 1,757 SqFt.
If convenience and walkability to coffee shops, restaurants and parks are top on your list then 67 Howe is a must see! Located walking distance to East Milton Square, Andrews Park and Crane Field/Belcher Cir this side entrance colonial is centrally located in one of Milton's most loved neighborhoods. Inside you'll be greeted by a neutral palette, dark hardwoods and a spacious flow that includes a fireplaced living room, accommodating dining room, kitchen with upgraded cabinetry and surfaces, and first floor home office. A sizable landing grounds the second floor with 3 bedrooms, and a finished third level with additional full bath offers 4th bedroom or guest room possibilities. A fully fenced yard and expansion opportunities with the basement offer more versatile spaces. Add a top notch public school system and quick access to the highway and public transportation to the long list of pluses. Make a visit to Howe Street before your weekend summer plans!

67 Howe St, Milton

$500,000
2 Beds 1 Baths SOLD Status 73407510 MLS 1,046 SqFt.
Enjoy the perfect blend of suburban charm and city convenience in this two-level unit located just minutes from the MBTA, Turner’s Pond, Shields Park, and the Neponset River bike path. Walk to local favorite restaurants like El Barrio and Steel & Rye. Set in a classic Greek Revival, this sun-filled condo features original molding, refinished wood floors, and updated appliances including a 2025 stove and 2024 refrigerator. The kitchen and bathroom offer an opportunity for updates. Includes surrounding yard space and a single-car garage with electricity—great for storage, a workshop, or potential studio. The spacious attic (approx. 800 SF) has two rooms, partial finish work, its own entrance, and electric—ideal for a future primary suite or ADU. A rare chance to own in a peaceful, well-connected neighborhood with growing amenities.

55 Maple St Unit B, Milton

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