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$799,000
3 Beds 2 Baths 73537398 MLS
Get ready to fall in love with this sweet and stylish Cape bursting with personality! Step inside and you're instantly welcomed by rich hardwood floors and sun-splashed rooms that make every space feel bright, cheerful, and full of life. This home has that perfect mix of cozy charm and open, airy vibes.Location? It doesn't get much better. Set in a popular, convenient neighborhood, this gem abuts the scenic Neponset River Bike Path and is just moments from the Capen Street Red Line trolley stop, offering easy access to Boston, recreation, and the outdoors.Outside, an expansive tree-lined backyard with an in-ground pool creates the perfect setting for summer barbecues, pool parties, yard games, and relaxing evenings on the deck.Adorable, affordable, and move-in ready, this is a home that delivers charm, convenience, and feel-good energy from the moment you arrive. Glover School District, Shields Park, Turner’s Pond, Bike Path, Trolley access…what could be better? Come see for yourself!

71 Capen St, Milton

Listing courtesy of Listing Agent: Matthew Freeman from Listing Office: Coldwell Banker Realty - Milton.

$725,000
3 Beds 2 Baths 73529240 MLS
Located in one of Milton's most cherished neighborhoods, where tree lined streets, strong community ties, and convenience come together. Tucked on the corner of Eliot Cir and across from Willoughby Road, this clean lined, sun filled Arts and Crafts condo was gut renovated in 2020 and it shows. Open floor plan living with dedicated spaces gives you flexibility to work from home, host, or just breathe. Modern finishes throughout, and natural light that earns its keep. But here's what will really get your attention: the average electric bill is $100 a month. THAT'S IT. Electric heat pumps, triple pane windows, and heavily insulated walls and roof deliver comfort in every season, no drafts and no surprises. Deeded patio out back and ample basement storage round things out nicely. Hop on the Neponset Trail and ride it straight into Central Village, where coffee shops, a bakery, and the infamous Steel & Rye are waiting. Stop by one of our open houses or schedule a private showing!

583 Eliot St Unit 583, Milton

Listing courtesy of Listing Agent: Cahill+Co. Team from Listing Office: William Raveis R.E. & Home Services.

$749,000
3 Beds 2 Baths 73517484 MLS
Every now and then, a home comes along that simply feels like it's the one. This side entrance Dutch Colonial welcomes you with high ceilings and rich woodwork, where one room leads naturally to the next. Three bedrooms plus a quiet office overlooking the treetops, make working from home that much more enjoyable. The screened in porch is hidden behind a canopy of trees, filtering sunlight over a climbing rose bush soon to be in full bloom. Milton is the sort of town people discover and never quite get over. Stone walls, tree lined streets and neighbors who still know each other's names. This location gives you the beauty of being minutes from the Blue Hills Reservation offering acres of trails, skyline views, and the kind of outdoor escape that makes every season feel worth staying for. The Trolley connects directly to Ashmont Station on the Red Line, putting all of Boston within reach without ever pulling you away from any of it. This is your chance to try Milton on for size!

15 Crown St, Milton

Listing courtesy of Listing Agent: Cahill+Co. Team from Listing Office: William Raveis R.E. & Home Services.

$1,525,000
6 Beds 8 Baths 73510632 MLS
Milton — Rare Opportunity! This beautifully renovated (2016) duplex offers 10 rooms, 6 bedrooms, 4full baths & 2 half baths. The main level features a spacious kitchen with stainless steel appliances, granite countertops, and an open-concept living and dining area, along with convenient first-floor laundry. The second floor includes two bedrooms and two full baths, while the third-floor bedroom offers a private retreat complete with a walk-in closet. Enjoy a generous yard perfect for outdoor entertaining. The unfinished basement provides ample storage and potential for future expansion. Ideally located with easy highway access and close proximity to Milton Academy and local public schools. Set in the heart of Milton, this home is just moments from Blue Hills Reservation scenic trails, Cunningham Park ballfields and pool, and the shops and dining of East Milton Square, including Abby Park, Novara, The Fruit Center Marketplace, The Cue & Nutshell.

403-405 Reedsdale Rd, Milton

Listing courtesy of Listing Agent: Paul Rege from Listing Office: Kelley & Rege Properties, Inc..

$1,890,000
5 Beds 3 Baths 73508119 MLS
Step back in time with this stunning 12 room Victorian masterpiece-a perfect blend of timeless elegance and modern comfort. This turn-key home features three levels of living with 5 spacious bedrooms and 3 bathrooms, offering room for everyone. From the moment you enter, you'll be captivated by the incredible solid woodwork, ornate architectural details and period charm that define every space. High ceilings, intricate trim and large windows bathe the home in natural light, while modern updates-thoughtfully integrated throughout-ensure effortless living. Whether your're entertaining guests on the stately covered porch or enjoying quiet evenings by the fireplace, this Victorian gem delivers both grandeur and warmth in equal measure. With its meticulous preservation and complete updates, this home is truly a one-of-a-kind treasure ready for you to move right in and enjoy. See attached list of improvements which includes central air, solar panels, hardscaping and boiler.

30 Magnolia Rd, Milton

Listing courtesy of Listing Agent: Kathleen Huntington from Listing Office: Coldwell Banker Realty - Milton.

$1,600,000
4 Beds 2 Baths 73484306 MLS
Prominently positioned on Pleasant Street, this custom 1927 home is rich in character and timeless architectural detail while offering wonderful opportunities for personalization. The home blends the charm of yesterday with a thoughtful addition featuring a spacious dining area and family room with a dramatic floor-to-ceiling fieldstone fireplace and striking beamed ceiling—creating a warm and inviting gathering space. Hardwood floors run throughout the home, complemented by classic yesteryear detailing that reflects the craftsmanship of the era. An expansive deck overlooks the beautiful 1.80-acre property, complete with walking trails and natural surroundings ideal for outdoor enjoyment. A barn offers space for one-car parking, storage, or workshop potential. Perfectly located for commuters and convenient to area amenities, this distinctive Milton property presents a rare opportunity to restore, customize, and create your dream home in a sought-after setting.

207 Pleasant Street, Milton

Listing courtesy of Listing Agent: DeWolfe Group from Listing Office: Gibson Sotheby's International Realty.

$900,000
3 Beds 2 Baths 73535732 MLS
Welcome to this beautifully maintained and charming Colonial, where classic character meets modern convenience. Relax on the spacious front porch or entertain on the private back patio surrounded by lush gardens filled with peonies, allium, lilies, and stunning roses.Inside, you'll find a spacious updated chef’s kitchen featuring granite countertops, custom cabinetry, and abundant storage. Just off the kitchen is an oversized dining room, perfect for family gatherings and entertaining. The inviting living room offers a comfortable space to relax and unwind.The second floor features a generous primary suite with double closets and the convenience of second-floor laundry, plus two additional bedrooms. The third floor offers two versatile bonus rooms ideal for a home office, playroom, or guest space. Conveniently located near schools, shopping, dining, and major commuter routes, this move-in-ready home is an opportunity you won’t want to miss.

570 Eliot Street, Milton

Listing courtesy of Listing Agent: Sharon Kelley Ryan from Listing Office: Coldwell Banker Realty - Milton.

$2,550,000
5 Beds 5 Baths 73525582 MLS
You've been looking for a while. You can stop now. 7 Phyllis Lane was custom-built by a trusted local builder as a forever home. And it shows. Ten-foot ceilings, custom millwork, built-ins. Hardieplank siding, Harvey windows, hydro air heating...infrastructure chosen for longevity and efficiency, not just aesthetics. The kitchen just works: massive island, Thermador appliances, Cambria quartz, sliders to the patio and fire pit. A main-level bedroom flexes as office or guest room. Upstairs, the primary suite delivers: soaking tub, steam shower, custom walk-in closet. Two bedrooms share a jack-and-jill; a fourth has its own bath. A spacious den and sitting room mean everyone has somewhere to land. The lower level flexes for whatever comes next...teen suite, au pair, in-laws. Premium white oak floors, high-end fixtures & finishes, Graff plumbing in plated gold. Carefully chosen details. Cunningham Park locale, top-tier schools, local dining, easy Boston access. You know this is the one.

7 Phyllis Lane, Milton

Listing courtesy of Listing Agent: Erin Feeney from Listing Office: Ceres Real Estate.

$905,000
3 Beds 2 Baths 73537274 MLS
The one you've been waiting for! Beautiful and versatile 3-bed, 1.5-bath Colonial on a spacious corner lot offering classic charm and modern updates in one of Milton's most desirable neighborhoods. Gorgeous hardwood floors throughout. The main level features a front-to-back living room with wood-burning fireplace opening to deck and backyard, formal dining room, and an updated kitchen with quartz countertops, center island, tile backsplash, and new range and microwave. A perfectly positioned half bath completes the first floor. Upstairs offers 3 spacious bedrooms and a classically designed full bath. Sliders off the living area lead to a 26' x 16' cedar deck with lush, manicured landscaping and summer privacy. Partially finished basement with cedar closet - ideal for home office, gym or playroom. Gas heat, attached garage and 100-amp electric. Convenient to the Blue Hills, top-rated schools, public transportation and commuter routes.

35 Craig Street, Milton

Listing courtesy of Listing Agent: Leslie MacKinnon from Listing Office: Compass.

$3,099,000
5 Beds 4 Baths 73524569 MLS
Beautifully renovated and appointed 5-bedroom, 3.5-bath home in coveted Indian Cliffs Estates set on just under an acre of impeccably manicured grounds. This exceptional home features a spectacular 784 sq ft great room with 14-ft vaulted coffered ceilings, a dramatic 14-ft fieldstone fireplace, and custom mouldings, finishes and lighting throughout. The chef’s kitchen showcases a 9 foot island, custom Scandia cabinetry, Sub-Zero refrigerator, and a 48” Wolf dual-fuel 6-burner range with griddle and double ovens. Spacious, sun-filled interiors include a luxurious primary suite, finished basement, finished attic, ample storage, and flexible living space throughout. The private backyard retreat offers a resort-style salt water pool, spa, expansive patio, and lush landscaping perfect for entertaining. Ideally located less than one mile from Wollaston Golf Club, Milton Academy, Milton High, and Blue Hills Reservation. A rare turnkey opportunity in one of Milton’s premier neighborhoods.

85 Old Farm Rd, Milton

Listing courtesy of Listing Agent: Jay Rooney from Listing Office: Jay Rooney.

$3,500,000
6 Beds 5 Baths 73508697 MLS
There is a particular feeling that comes with finding the right home — recognition. And so it is with 103 Canton Ave, the feeling you’ve always known it. Set on a rare 2.65 acres, this residence carries a quiet confidence. The entry hall signals something significant ahead with each gathering space unfolding like a revelation. 6+ bedrooms, 4.5 renovated baths, and a floor plan that accommodates the full arc of life. The kitchen — custom cabinetry, Wolf and Sub-Zero — is the heart, as it always is. Floor-to-ceiling windows in the living room frame a bluestone terrace and expansive lawn. Light moves through this room in a way that reminds you why people fall in love with established addresses. Beneath its good bones: updated HVAC, electrical, roof, plumbing. The investment is sound; the comfort is modern. An oversized 2-car garage and mudroom complete the picture. Easy access to Milton Academy, Glover School, the trolley. This is the kind of home you explore once and already miss.

103 Canton Ave, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.

$2,515,000
4 Beds 4 Baths 73525151 MLS
Recently reimagined by Design Construction Plus of Wellesley, this exceptional 4-bedroom, 3.5-bath home blends classic New England charm with sophisticated modern design across three finished levels beneath a timeless gambrel roofline. Sunlight fills the home through oversized windows, highlighting soaring ceilings, designer lighting, and curated finishes throughout. The open-concept living area features a dramatic stone fireplace and flows seamlessly into a chef’s kitchen with a quartz waterfall island, custom cabinetry, and premium Wolf, Thermador, and Liebherr appliances. Spa-inspired baths, a private en suite office, six heating zones, three zones of central air, updated systems, integrated sound, and exterior lighting add comfort and convenience. Ideally located near Glover Elementary, parks, shopping, dining, and commuter access, this turnkey Milton home offers timeless architecture, luxury finishes, and modern living.

196 Canton Ave, Milton

Listing courtesy of Listing Agent: Scott Farrell & Partners from Listing Office: Compass.

$878,500
4 Beds 2 Baths 73532316 MLS
This wonderful Milton single family home is truly a classic, with seemingly endless features and updates showing true pride of ownership. It all starts with incredible curb appeal and a wide, updated front porch with composite decking, leading directly into a spacious foyer. The main living level offers high ceilings and great natural light throughout. Large living room connected to dining area with built in cabinet. Thoughtfully updated kitchen and half bath for guests. French doors provide easy access to the private rear deck, massive yard and garage. On the upper floors, this home offers four full bedrooms, with the opportunity to finish additional attic area on the third floor for a 5th bedroom or office area. While this turn key home is truly exceptional, the location simply can't be beat. Amazing neighborhood, with easy access to Milton Village, the Red Line Extension, commuter rail, and so much more!

44 Houston Avenue, Milton

Listing courtesy of Listing Agent: ResCo Team from Listing Office: Gibson Sotheby's International Realty.

$895,000
3 Beds 2 Baths 73533670 MLS
Presenting a distinguished single-family in the heart of town at 29 Buckingham Rd. This property spans 1700 square feet of meticulously designed living space, offering an exceptional opportunity for discerning homeowners. Features include three well-proportioned bedrooms, hardwood floors and a fireplace in the living room. The bonus room on the first floor is designed for a variety uses. The property includes one full bathroom and one half bathroom, and a lower level with the possibility of establishing additional living space. Further enhancing the property's appeal is a single-car garage, offering secure parking and additional storage solutions. The generous 6,129 square foot lot provides ample outdoor space for various activities. View virtual and 3D tours by clicking the house with the orange roof in the menu bar.

29 Buckingham Rd, Milton

Listing courtesy of Listing Agent: Thomas O'Neill Jr. from Listing Office: The Firm.

$1,635,000
3 Beds 3 Baths 73519195 MLS
Tucked into Milton’s sought-after Columbine neighborhood, this beautifully-built Colonial has the kind of character & warmth that’s hard to replicate. Thoughtfully designed & carefully maintained from the very beginning, it’s a home that feels both impressive & genuinely welcoming. The fireplaced living room feels elegant without trying too hard, French doors open to a family room lined with windows that overlook the gracious backyard. The dining room is perfectly scaled for holidays, celebrations, or a spontaneous dinner with friends. The chef's kitchen, anchored by a sunny breakfast nook, is the kind of space people naturally gather in. Oversized windows fill the home with natural light throughout the day. Upstairs, an airy open landing connects three generous bedrooms, including a front-to-back primary suite with a walk-in closet & private bath that was just completely renovated. Fully fenced-in/landscaped back yard with a large patio is the cherry on top of this extraordinary home.

60 Marilyn Rd, Milton

Listing courtesy of Listing Agent: Arianna Brown from Listing Office: Compass.

$1,280,000
4 Beds 2 Baths 73537459 MLS
Curb appeal that stops you in your tracks. This classic 1929 Colonial sits proudly on a corner lot in Milton's coveted Columbines neighborhood, where tree lined streets and lush colorful gardens and flowers greet you before you even reach the front door. Step inside and the light does the talking, sun filled rooms all day long, with gleaming hardwood floors carrying that warmth from room to room. Every space here is a generous size with high ceilings and endless character. This easy, livable layout that gives you room to spread out, entertain, and comfortably live. If you know Milton, then you know how special this location is, it's the whole package. Located across the street from Kelly Field and Playground an 11 acre park. Plus you are minutes to Turner's Pond, Glover school and an easy stroll to the Trolley Line, ideal for those commuting into the city. If you are looking for updated, neighborhood plus amenities, I am here to tell you, you can have it all!

3 Windsor Rd, Milton

Listing courtesy of Listing Agent: Cahill+Co. Team from Listing Office: William Raveis R.E. & Home Services.

$1,370,000
3 Beds 3 Baths 73508336 MLS ['Woodmere Condominiums'] BLDG.
Set on beautifully manicured grounds, this rarely offered Adams end-unit townhome blends luxury with ease of living. A welcoming front porch opens to soaring 22-foot ceilings and sun filled open spaces. The gourmet kitchen features quartz island and countertops, custom cabinetry, and Jenn Air appliances, flowing seamlessly into the formal dining room with a tray ceiling and an inviting living room with a gas fireplace and private deck access. The first-floor primary suite offers a walk-in closet and spa-inspired marble bathroom. A flexible den/office, first-floor laundry, and mud room add practicality, while an attached two-car garage provides convenience. Upstairs, two spacious bedrooms, a loft, nook, family room and full bath offer versatile living spaces. Meticulously designed, this home combines elegance, function and comfort in a highly desirable location with thoughtful details and an ideal layout.

23 Woodmere Drive Unit 23, Milton

Listing courtesy of Listing Agent: Barry Cohen from Listing Office: Coldwell Banker Realty - Newton.

$1,125,000
2 Beds 2 Baths 73519579 MLS ['Woodmere Condominium'] BLDG.
Some homes are built. This one was considered. Every detail. A grand entry that sets the tone — warm, unhurried, quietly assured—with a welcome that signals something better is ahead. 2 bedrooms and 2 full baths. A dedicated home office because some things shouldn't be a compromise. A designer kitchen anchored by a considerable island and top appliances — the kind of space that makes cooking feel like a choice, not a chore. A laundry room that brings organization to daily life. A gas fireplace that earns its place in the room. A private deck for summer evenings and the slow art of the grill. An oversized two-car garage designed for cars that dare to dream bigger. New construction quality without the wait. Mature landscaping softens the edges and grounds the space in something that feels like home. Clean lines. Fresh finishes. No compromises. Lock and leave or settle in and stay. Either way, this is living at its most effortless.

29 Woodmere Dr Unit 29, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.

$7,500
4 Beds 3 Baths 73480546 MLS
Welcome to this well-loved Emerson Woods contemporary, privately set in one of Milton’s finest neighborhoods! Soaring cathedral ceilings on first and second floors and large picture windows offer views of nature in all directions. The newly renovated kitchen opens onto a large family family room with a floor-to-ceiling stone double facing fireplace. Sliding glass doors lead to a wrap around deck perfect for entertaining! A finished lower level is well designed for a home office or game room. This bucolic setting is ideal for any commute, minutes from Boston, and provides easy access to private and public schools. The property includes all furnishings. Showings may begin immediately. A lease term less than 12 months may be considered.

4 Crestview Ln, Milton

Listing courtesy of Listing Agent: Meredith Hall from Listing Office: Coldwell Banker Realty - Milton.

$949,900
3 Beds 2 Baths 73516528 MLS
Highly desirable East Milton Square location on a picturesque tree-lined street. This well-maintained 3 bedroom, 2 bathroom Colonial offers a light-filled interior with hardwood floors throughout and timeless charm. The updated kitchen features white cabinetry, stainless steel appliances, gas cooking, and a wine fridge, while the mudroom adds everyday convenience. Built-ins and a wood-burning fireplace enhance the home’s warmth and character. Enjoy relaxing on the inviting farmer’s porch or entertaining in the fenced backyard with a paver patio. Ideally located near highways, shopping, restaurants, Boston, and Milton’s highly regarded public school system, making this an excellent commuter location.

94 Grafton Ave, Milton

Listing courtesy of Listing Agent: Ashley Brennan from Listing Office: Gibson Sotheby's International Realty.

$1,750,000
5 Beds 6 Baths 73506486 MLS
Versatility is the name of the game! Set on a private lane on one of Milton's most spectacular lots with lush garden views from every window. This tastefully renovated home started off as a small 2 bedroom house built in 1905. Previous owners thoughtfully added on over time resulting in this expansive Colonial. What sets this house apart is it's 1,036 sqft townhouse style ADU which so seamlessly integrates it feels like a natural extension of the home. A few of the additional home features include high ceilings, custom built ins, 3 working fireplaces, central air, updated windows, walk up attic, one car attached garage and separate 3 bay garage. Set just 8 miles south of Boston, with the commuter rail minutes away and Back Bay less than 15 minutes by train, you get the feel of a private country retreat without sacrificing a minute of city access. Stop by one of our open houses, we'd love to introduce you to this exceptional home and the welcoming community that surrounds it!

34 Brush Hill Ln, Milton

Listing courtesy of Listing Agent: Cahill+Co. Team from Listing Office: William Raveis R.E. & Home Services.

$1,475,000
4 Beds 3 Baths 73508478 MLS
Want to live on a quiet cul-de-sac and still be 6 miles from downtown Boston? Welcome to 13 Cantwell Road in Milton's Columbine neighborhood. This home delivers space, style, and character that's increasingly hard to find. A welcoming entrance and graceful staircase set the stage from the moment you arrive. Hardwood floors and timeless charm carry throughout. The main level offers a living room, den, dining area, and kitchen bathed in natural light through large, elegant windows. Four bedrooms and 2.5 baths offer room for everyone to spread out. The primary suite features soaring ceilings, an en suite bath, dedicated laundry, and multiple closets. A partially finished basement adds flexible space for a home office, gym, or playroom. The Milton Trolley is within walking distance, connecting you to the Red Line and the city with ease. Shields Park, the Neponset River Trail and Turners Pond are all a short walk away. This is Milton living at its finest.

13 Cantwell Rd, Milton

Listing courtesy of Listing Agent: Bridget Conroy from Listing Office: Coldwell Banker Realty - Milton.

$1,400,000
3 Beds 2 Baths 73504843 MLS
On a picturesque tree-lined street in the treasured Columbines neighborhood a classic Garrison Colonial is ideally situated with nearness to Glover and Pierce schools, Milton Academy, Turner's Pond, parks and playing fields, and the Central and Milton Village restaurants and shops. This handsome home greets you with a timeless layout of light-filled elegant living and dining rooms with bay windows and built-ins, a chef's kitchen with double ovens and paneled appliances, and a sun room ready for work, play, or leisure. Three generously sized bedrooms are anchored by a gracious landing, and a walk-up attic lends itself to convenient storage. A finished lower level with full sized windows and a second fireplace provides the extra living space missing in other homes you've seen. Central AC keeps you comfortable indoors and the expansive deck is perfect for entertaining and enjoying meals throughout spring, summer, and fall. It's the quintessential Milton home in the most admired setting!

47 Standish Rd, Milton

Listing courtesy of Listing Agent: Lauren Greeley from Listing Office: Coldwell Banker Realty - Milton.

$1,300,000
3 Beds 2 Baths 73513892 MLS
Renewed and expanded in 2016 and thoughtfully updated since, this Milton home blends classic charm with modern convenience- simply unpack and enjoy. The sun-filled main level features high ceilings, a spacious living room with wood-burning fireplace, updated kitchen with island seating and stainless appliances, and an inviting dining area with corner built-in. From here, step outside to the sizable deck and level backyard which make everyday living and entertaining easy. A dedicated first-floor office adds everyday functionality, while the bright sunroom provides the perfect flex space. Upstairs offers three well-proportioned bedrooms with ample closet space and central air. The lower level provides excellent potential with good ceiling height and flexible usable space ready to be finished. Recent notable updates include installation of central AC, recessed lighting, custom kitchen built-in, and fresh paint throughout most of the home- making this a true turn-key opportunity.

39 Park St, Milton

Listing courtesy of Listing Agent: Abigail Marjollet from Listing Office: Ceres Real Estate.

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