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$985,000
5 Beds 2 Baths SOLD Status 73431794 MLS 3,312 SqFt.
Very well built, turn of the century two family home situated very close proximity to Blue Hill Reservation and 1.5 miles from Milton/ Beth Israel Deaconess. This home boasts craftsmanship details and hardwood floors throughout, rear covered decks, laundry hookups on each unit level, a private yard and very strong income. The 1st floor unit consists of an eat-in kitchen, large family room, formal dining, two bedrooms, one full bath and a small front entrance farmer's porch. The second floor offers a full kitchen leading to an open concept dining room/ living room combination space and opposite the common area, there are three generous sized bedrooms and an office. There is a third floor walk-up which currently offers the potential for additional storage and/ or living space and/ or the potential to create an in-law or 3rd unit. The 3rd floor space is not included in GLA, room or bath counts. A two car garage and long driveway offer ample parking for 6-8 cars. SEE OH SCHEDULE!

320 Blue Hills Parkway, Milton

$1,930,000
5 Beds 4 Baths SOLD Status 73431658 MLS 3,597 SqFt.
Nestled in the beautiful town of Milton, Massachusetts, 108 Indian Spring Rd presents a single-family residence that exudes timeless appeal, ready to welcome its next chapter. The generous living area, encompassing 3597 sq. ft. offers a canvas for both grand entertaining and intimate gatherings; here, the rhythm of daily life finds its perfect harmony. The residence includes five bedrooms, each providing a private sanctuary for rest and rejuvenation. Two full bathrooms and two half bathrooms are thoughtfully positioned to enhance convenience and comfort for everyone. Lower level features 1784 sq ft of unfinished space too. The expansive 41,251 square foot lot offers endless possibilities for outdoor enjoyment & recreation with an inground pool. Ready for New Buyers an exceptional opportunity living experience in a coveted location with a 2 Car Garage. Fabulous Indian Cliffs location minutes to Schools, Restaurants, Wollaston Golf Club & all Major Routes. See you at the Open Houses.

108 Indian Spring Rd, Milton

$845,000
1 Beds 2 Baths SOLD Status 73431231 MLS 1,460 SqFt.
The Residences at Milton Landing pairs unmatched convenience with a riverfront location at the edge of the Neponset River estuary. Come discover this expansive 1,460-square-foot one-bedroom plus den, where a full renovation showcases thoughtful, sophisticated design, amplified by natural light from premium southwest-facing windows. Highlights include a bespoke open-concept kitchen, two updated full baths, built-ins, and well-appointed closets. The versatile den functions as a home office or guest space. Practical comforts add to the appeal, especially garage parking, concierge service, elevator access, a fitness center, and a community room. For dining, Madre—just downstairs—offers fresh bites and river views, a luxury within easy reach. At your doorstep, enjoy trolley service into Boston, vibrant restaurants, and recreational opportunities along the Neponset River Greenway trail. More than a home, this residence offers a lifestyle—comfortable, stylish, and effortlessly elevated.

88 Wharf St Unit 511, Milton

$1,000,000
3 Beds 2 Baths SOLD Status 73431000 MLS 2,722 SqFt.
A charming and versatile home in the heart of Milton that blends modern updates with classic character. The beautifully updated kitchen features sleek countertops, stainless steel appliances, and ample cabinetry, making it a perfect hub for everyday living and entertaining.This spacious residence offers multiple living areas, including a lower-level office or den with its own separate entrance—ideal for remote work, a guest suite, or potential in-law setup. The third floor presents an exciting opportunity for expansion with generous unfinished space, ready to be transformed to meet your needs.Step outside to a large, private yard with room to garden, play, or simply unwind. Located near schools, parks, and commuter routes, this home offers the perfect combination of comfort, flexibility, and convenience. A rare find in a sought-after Milton location!

398 Blue Hills Parkway, Milton

$1,985,000
5 Beds 4 Baths SOLD Status 73429965 MLS 4,746 SqFt.
Timeless elegance meets modern sophistication in this distinguished Cunningham Park residence. This 5 bed, 4 bath brick-front Colonial stands proudly on a corner lot in one of Milton’s most desirable neighborhoods, offering a layout designed for both elegant entertaining and everyday comfort. The first floor features formal living and dining rooms, a thoughtfully designed kitchen with island and dining area, and a bright family room that extends to a spacious deck and expansive backyard. Upstairs, the serene primary suite with spa-like bath is joined by three additional bedrooms and a full bath. A finished loft provides flexible space for a home office, playroom, or lounge, while the lower level offers a recreation room ideal for movies or games plus an additional bedroom and a flex room currently used as a gym. Designer finishes elevate the interiors, while a two-car garage, manicured grounds, and commanding curb appeal complete this rare offering of classic style and modern ease.

4 Cunningham Lane, Milton

$715,000
4 Beds 2 Baths SOLD Status 73429351 MLS 1,395 SqFt.
This home is ideally located in a sought-after Milton neighborhood, just a short walk to schools, parks, and playgrounds. A great opportunity for those looking to settle in a convenient and welcoming community. The first floor features a family room that opens to a deck overlooking a flat, fully usable backyard—perfect for outdoor activities and gatherings. A spacious kitchen with maple cabinets, along with a living room and dining room accented by hardwood floors, complete the main level. Upstairs, you’ll find three bedrooms, all with hardwood floors, as well as a generous hall closet for added storage. The property offers two full bathrooms, including a handicapped-accessible bath on the first floor. A lift attached to the back deck ensures full accessibility to the main level. With solid features and a prime location, this home is ready for your updates and personal touches. A great opportunity to create the Milton home you’ve been waiting for!

70 Warren Ave, Milton

$1,300,000
4 Beds 4 Baths SOLD Status 73429173 MLS 3,195 SqFt.
Spacious contemporary colonial home with pond views in the backyard, and within close proximity to Turner's Pond & walking trails, Schools, bus stop, T-station, hospital, and Milton Village. This modern home offers an open living concept with 4 large bedrooms, 3.5 modernized bathrooms, and hardwood flooring thruout. Family room with a brick fireplace, cathedral ceiling, and sliders leading to the exterior deck. Beautiful chef's kitchen with Jenn-Air stainless steel appliances, granite countertop, kitchen island, tiled flooring & backsplash. Formal dining room with wet bar that's great for entertaining. With 2 oversized primary bedrooms offering full bathrooms & walk-in-closets, you'll have to decide if you wish to sleep in the 1st floor or the 2nd floor. Beautiful full bathroom in the upstairs master bedroom with a soaking tub, private shower, double vanity, and radiant floor heating. Much potential in the walk-out basement for increased living space, and there's a 2-car garage.

290 Central Ave, Milton

$2,500,000
4 Beds 8 Baths SOLD Status 73428702 MLS 5,722 SqFt.
Welcome to a home where quality meets versatility. This stunning young Gambrel is a true standout, offering a seamless flow for both daily living and entertaining. The heart of the first floor is a custom white kitchen with quartz countertops, a large island, and a gas stove, all open to a cozy living room with a fireplace. The main level also features a formal dining room with patio access, a dedicated office, and a convenient en-suite bedroom. Upstairs, the luxurious primary suite boasts two walk-in closets and a private bathroom. You'll find two additional en-suite bedrooms and a second laundry room for ultimate convenience. A versatile bonus room above the three-car garage, complete with a full bathroom, is ideal for a family room, home office, or an in-law suite. The finished, walk-out basement adds more functional space, including another full bathroom. Situated on a beautiful, fenced acre lot, this home also features durable Hardi-plank siding and a 3-car garage - a rare find!

16 Hallen Avenue, Milton

$1,025,000
3 Beds 3 Baths SOLD Status 73428679 MLS 1,682 SqFt.
Located in my favorite neighborhood (I grew up in it), this incredible Cape has been totally remodeled. The first floor has a generous foyer open to a vast living room with a fireplace. There is a dining room and a beautiful white kitchen with a huge island, quartz countertops, and stainless steel appliances. There is a laundry area and a half bathroom. The dining room has sliding doors that lead to an inviting deck. The second floor features a primary bedroom with two closets and a new bathroom. There are two additional guest bedrooms, each with closets and hardwood flooring. There is a walk-up attic. There are new windows throughout. Outside is a newly seeded 1/4 acre corner lot. There is also a one-car garage. Two efficient Mitsubishi electric heat pumps service the home, and the house offers two-zone central air conditioning. There is also a new 200-amp circuit breaker panel with a second-floor subpanel. It is time for you to create new memories living on Hawthorn Rd. Do not miss!

36 Hawthorn Road, Milton

$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

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