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$1,100,000
4 Beds ⋅ 2 Baths ⋅ 73552983 MLS
Welcome to this inviting Colonial, ideally located in one of East Milton’s most desirable neighborhoods. With hardwood floors throughout the main and second floor staircase and hall, it awaits your personal touch. Enjoy the convenience of being just moments from local schools, directly across from Cunningham Park, and close to major highways, making commuting a breeze. You’ll also appreciate the nearby restaurants, shops, and amenities that make East Milton such a sought-after place.

106 Edge Hill Rd, Milton

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: South Shore Sotheby's International Realty.
$1,675,000
4 Beds ⋅ 4 Baths ⋅ 73552638 MLS
Completely and tastefully renovated from top to bottom, this stunning Colonial is set back from the main road on a private lot near the scenic Blue Hills Reservation. Offering 4 bedrooms, 4 full baths, and a beautifully finished lower level with a wet bar, full bath, and in-law potential, this turnkey home blends timeless charm with modern luxury. The open-concept main level features a designer kitchen with quartz countertops, farmhouse sink, LG Studio appliances, center island, coffee/bar area, and spacious living and dining areas. The luxurious primary suite offers a fireplace and oversized tiled shower, and double vanity. Major updates include a new 30-year roof, radon mitigation system, heat pump mini-splits, ERV, new indirect water heater, updated plumbing and electrical, EV charger, hardwood floors, redesigned kitchen and baths, second-floor laundry, new fencing, landscaping, and more. One-year American Home Shield home warranty included

1262 Randolph Ave, Milton

Listing courtesy of Listing Agent: Danny Zheng from Listing Office: Keller Williams Realty.
$1,499,900
4 Beds ⋅ 4 Baths ⋅ 73552355 MLS
Nestled in the heart of Milton's coveted Columbines neighborhood, 187 Hinckley Rd. offers the perfect blend of timeless charm, generous living space, and an unbeatable location. This 4-bedroom, 3.5-bath home features a warm, functional floor plan, spacious living areas, a partially finished lower level, and an unfinished walk-up attic offering exceptional expansion potential. Step outside to a private backyard ideal for entertaining, relaxing, and making lifelong memories. Just moments away, enjoy the convenience of walking to Glover Elementary, Pierce Middle School, Turner's Pond, Steel & Rye, and the trolley for easy access to Boston. The Columbines is celebrated for its tree-lined streets, welcoming neighbors, children playing outside, and traditions that make this one of Milton's most beloved communities. A rare opportunity to put down roots in a neighborhood you'll be proud to call home.

187 Hinckley Rd, Milton

Listing courtesy of Listing Agent: Brian Gagnon from Listing Office: Coldwell Banker Realty - Boston.
$4,995,000
5 Beds ⋅ 5 Baths ⋅ 73551180 MLS
Set off a lovely cul-de-sac, this restored Greek Revival sits on 4+ acres of open field, rare this close to Boston, stretching out rather than closing in. The expansive field: open, level, and bordering the 7,000 acre Blue Hills Reservation, accessible and yours to explore. A buildable lot: room to expand, a family compound, simply hold as open space, you decide. Fine millwork and French doors speak to fine craftsmanship. The kitchen is anchored by top appliances and built for serious cooking. A well-appointed mudroom keeps the everyday beautifully managed. A glass-walled garden room with fireplace, woodland views and stillness. Modern systems (geothermal heating/cooling, solar array, EV charger) reflect a commitment to sustainability. Privacy and peace without sacrificing reach: commuter rail, Rts 128/95, and Logan Airport all close. Access to Milton's public and the area's prestigious independent schools. This is where sophistication, sanctuary, and the wide-open sky meet.

1632 Canton Ave, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.
$739,900
4 Beds ⋅ 2 Baths ⋅ 73550997 MLS
This home has been cared for by the same family for many years and shows great pride in ownership. The site offers fenced in rear yard and large, detached newly rebuilt 2 car garage ; see firm remarks !!. Interior contains traditional layout with first floor lavatory, refinished original hardwood flooring, fireplace located in the living room,some built-ins . Four bedrooms and full bathroom are located in upper floor. This home has lots to offer ,all within walking distance to local parks,schools and MBTA transportation.

274 Blue Hills Pkwy, Milton

Listing courtesy of Listing Agent: Christopher Shea from Listing Office: Christopher Shea.
$799,000
4 Beds ⋅ 2 Baths ⋅ 73550682 MLS
Welcome to 29 Lawrence Road – 1st time on the market in over 50 years. This classic colonial with tons of character and opportunity sits right outside of Cunningham Park. This 4 bedroom with 1.5 baths offers a traditional layout with hardwood floors throughout most of the home. The 1st floor offers a nice fireplaced living room with a double set of French doors. One set of doors lead into the formal dinning room with built in cabinet. An eat in kitchen with plenty work and storage space. 1st floor also offers the 4th bedroom or home office. Upstairs features 3 bedrooms with hardwood floors and a full bath. Basement has a great tiled floor family room for extra living space if needed. Home in need of updating but well worth the effort in this fabulous neighborhood within easy walking distance of Cunningham Park. Make your appointment today before this incredible opportunity is gone.

29 Lawrence Rd, Milton

Listing courtesy of Listing Agent: James Mulvey from Listing Office: Bird Dog Real Estate, LLC.
$1,185,000
4 Beds ⋅ 3 Baths ⋅ 73550414 MLS
Nestled on one of Milton’s most picturesque streets, this classic center-entrance Colonial offers the perfect blend of timeless charm, exceptional space, and an unbeatable location. Just a short stroll to Glover Elementary School, the Milton Public Library, and all the amenities that make Milton such a special place to consider home, this property delivers both convenience and community. Lovingly maintained by its original owner, this four-bedroom home reflects pride of ownership throughout. Generous living spaces include a rarely available first-floor family room, providing the flexibility and comfort today’s buyers seek. The well-designed floor plan offers plenty of room for everyday living and entertaining, while the two-car garage adds valuable convenience. A wonderful opportunity to own a cherished home in one of Milton’s most sought-after neighborhoods, where classic Colonial architecture, an outstanding location, and years of meticulous care come together beautifully.

40 Cape Cod Ln, Milton

Listing courtesy of Listing Agent: Matthew Freeman from Listing Office: Coldwell Banker Realty - Milton.
$1,249,000
5 Beds ⋅ 3 Baths ⋅ 73550347 MLS
Peacefully tucked away at the end of a quiet dead end street in East Milton, this 5 bedroom home offers a rare combination of privacy and space. With both a living room and a family room on the first floor, there is plenty of space for everyday living or room to entertain. The eat in kitchen overlooks the backyard and flows seamlessly to the dining room. Upstairs, the expansive primary suite is a true retreat, featuring a gas fireplace, cozy sitting area, his and her closets and a private ensuite bath. Step out to the attached deck - an ideal spot to enjoy the tranquill surroundings. Four additional bedrooms provide ample space for family and guests. Each bedroom has generous sized closets and can easily fit queen size beds. The spacious heated basement presents an excellent opportunity for future finishing, perhaps a rec room or home gym! The attached 2 car garage is large enough to accommodate 2 SUV's + storage. Walking trail at the end of street leads to golf course.

44 Quarry Lane, Milton

Listing courtesy of Listing Agent: Kathy McDevitt from Listing Office: Kelley & Rege Properties, Inc..
$1,225,000
4 Beds ⋅ 3 Baths ⋅ 73546456 MLS
The home you've been waiting for! This classic Milton Colonial in the desirable Elmiver neighborhood offers exceptional space and flexibility for today's lifestyle, including multi-generational living. The spacious kitchen opens to a formal dining room and large family room with sliders to a generous deck overlooking a private backyard with a beautiful patio—perfect for entertaining. Featuring 4 bedrooms, 2 full baths, two fireplaces, and a finished lower level with a half bath and flexible bonus room ideal for an au pair, home office, guest, or in-law space. A thoughtful addition includes a second full bath, second-floor laundry, and office/flex space. Conveniently located near top-rated Milton schools, parks, Boston, and major highways, this home offers comfort, versatility, and an unbeatable community.

88 Elm St, Milton

Listing courtesy of Listing Agent: Robinson / Rull Team from Listing Office: William Raveis R.E. & Home Services.
$1,195,000
4 Beds ⋅ 2 Baths ⋅ 73546064 MLS
Offering exceptional curb appeal in Milton's Hospital Hill neighborhood, this colonial blends timeless charm with comfortable living space. Gleaming hardwood floors flow throughout the home. The first floor offers a front-to-back living room with fireplace, a bright sunroom, a formal dining room with a built-in china cabinet, an eat-in kitchen & a half bath. Upstairs, you'll find four corner bedrooms, a full bath and a walk-up attic for storage/expansion options. The partially finished basement provides additional living space, ideal for a playroom, home office or gym. The backyard is perfect for entertaining family & friends, featuring a patio and play structure. Well maintained & updated, the current owners have replaced the roof (2018), water heater (2023) and gas furnace (2024). Ideally located minutes from Milton Academy, Milton Hospital, Turner's Pond & Milton's highly regarded public schools and a convenient location for commuting to Boston. Don't miss out on this great home!

8 Clifton Road, Milton

Listing courtesy of Listing Agent: Robinson / Rull Team from Listing Office: William Raveis R.E. & Home Services.
$660,000
3 Beds ⋅ 2 Baths ⋅ 73544814 MLS
Welcome to 52 Meagher Ave Milton. This charming colonial property offers convenience and comfort featuring three bedrooms and one bathroom and half , this home is ideal for families, first-time buyers, or anyone seeking a beautiful home ** Open House Saturday 12 to 2pm **

52 Meagher Ave, Milton

Listing courtesy of Listing Agent: Pedro Garcia from Listing Office: Garcia Realty, LLC.
$1,349,000
5 Beds ⋅ 3 Baths ⋅ 73539896 MLS
Welcome home to this exceptional 5-bedroom, 3-bath residence that seamlessly blends timeless 1925 character with modern luxury of a 2015 substantial addition. Offering just under 3,000 square feet of living space, the home features a stunning kitchen with quartz countertops and new appliances. Beautifully done baths, radiant heat, air conditioning throughout, a spacious mudroom, versatile sunroom/home office, and convenient second-floor laundry enhance everyday living. House is now empty and move in ready. Bonus room in basement offers additional flexible living space. A substantial addition completed in 2014 creates the perfect balance of old-world charm and contemporary convenience. Ideally located within walking distance of East Milton Square's popular restaurants, cafés, and shops, near Andrews Park, and just minutes from Quincy Center Commuter Rai

24 Victory Avenue, Milton

Listing courtesy of Listing Agent: Jennifer Fortin from Listing Office: Frakes Realty.
$995,000
3 Beds ⋅ 2 Baths ⋅ 73543043 MLS
Pride of ownership abounds in this lovingly maintained center entrance colonial home featuring nine rooms with three bedrooms and 1 and 1/2 baths. The welcoming foyer leads you to the fireplaced living room and sunny den as well as the formal dining room with two corner hutches and the fully applianced kitchen with the granite countertop and wood cabinets. The beautiful three season room off the kitchen leads to a sunny deck overlooking the back yard and one car garage.Conveniently located near the shops and restaurants of East Milton Square with easy access to the highway for trips into Boston or down to the Cape.Time to make this move in ready home yours for a long time

20 Rowe Street, Milton

Listing courtesy of Listing Agent: Paul Hurley from Listing Office: Coldwell Banker Realty - Milton.
$899,900
3 Beds ⋅ 2 Baths ⋅ 73541229 MLS
Here’s your chance to be in your new home before the end of summer! Step inside this charming English Colonial and fall in love! The heart of the home is the bright eat-in kitchen, featuring a breakfast bar/peninsula, space for a table, a homework or dining nook + direct access to the back deck, driveway & fenced yard. From the kitchen, the floor plan flows seamlessly into the formal dining room and living room, showcasing a gas fireplace & timeless details including crown molding, wainscoting & hardwood floors. A convenient 1/2 bath completes the first floor. Upstairs are 3 spacious bedrooms, a full bath & a finished 3rd floor offering flexible space for an office, playroom, gym or guest retreat. Large basement w/high ceilings, new W&D & direct access to the garage. Restaurants & coffee shops in East Milton Square are minutes away + easy access to I-93 for a quick commute into Boston or all points South. Significant updates include a NEW ROOF, FENCE, HEATING & HOT WATER SYSTEMS.

1200 Brook Road, Milton

Listing courtesy of Listing Agent: The Residential Group from Listing Office: Coldwell Banker Realty - Brookline.
$1,895,000
4 Beds ⋅ 5 Baths ⋅ 73538357 MLS
Tucked away in Milton’s coveted Emerson Woods neighborhood, this beautifully maintained contemporary home offers exceptional space, flexibility & timeless design. Soaring ceilings, oversized windows, crown molding & a wood-burning fireplace create a bright, welcoming great room ideal for everyday living & entertaining. The chef’s kitchen features stone countertops, shaker cabinetry, a large center island, double ovens, a breakfast nook & dining area. A versatile first-floor suite with private entrance & full bath is perfect for guests, an au pair, or a primary bedroom option. Upstairs, the skylit primary suite is joined by two additional bedrooms, a loft & another full bath. The finished lower level offers flexibility for a gym, office, guest suite, or 5th bedroom. Enjoy outdoor living on the wraparound composite deck & brick patio, all in a peaceful setting close to top schools, local amenities, the Blue Hills Reservation & Milton Academy. Extensively renovated between 2012-2014.

375 Atherton Street, Milton

Listing courtesy of Listing Agent: David Green from Listing Office: Coldwell Banker Realty - Boston.
$1,400,000
4 Beds ⋅ 2 Baths ⋅ 73536730 MLS
Rarely does an opportunity arise on this coveted cul-de-sac one block from East Milton Square. This meticulously maintained Colonial offers exceptional living space with a spacious living room just off the kitchen, featuring cathedral ceiling with an abundance of natural light. Hardwood, marble, and tile flooring add timeless elegance throughout. The finished lower level provides versatile bonus space ideal for a media room, fitness area, home office, or playroom. Outdoor living is equally inviting, with a large brick patio overlooking the beautifully maintained grounds—perfect for relaxing, and hosting gatherings. Additional highlights include central air, heated two-car garage, and an irrigation system for effortless landscape maintenance. Offering potential for a first-floor primary suite and/or in-law accommodations, this home provides flexibility to meet a variety of lifestyle needs. Enjoy convenient access to Milton Square, local shops, restaurants, and public transportation.

17 Duggan Ln, Milton

Listing courtesy of Listing Agent: Brendan Henry from Listing Office: Redfin Corp..
$2,195,000
4 Beds ⋅ 4 Baths ⋅ 73531108 MLS
Welcome to 1375 Brush Hill Road, a spacious 4 bedroom colonial with two primary suites. Privacy and luxury in a beautiful rural setting, yet so close to the city and a variety of commuting options. Minutes to the Blue Hills Reservation and the Mary Wakefield Arboretum, this elegant colonial will greet you with charm, quality and attention to detail. The newly constructed first floor primary suite provides beautiful views of the private setting from sliders to the back deck. You'll also find an amazing primary bath with two sinks, a soaking tub & an accessible shower. The renovated kitchen is stunning with a Sub Zero refrigerator, Wolf ovens & a Thermador induction cooktop, quartz counters and a large island. One floor living is possible with first floor laundry, dining room, family room & a home office. Upstairs, there are two bedrooms, a full bath & the original primary suite. The first floor primary suite and the second floor primary suite each have a large walk in closet. Outside is a perfect spot for hosting family and friends with a large deck, a screen room and a private back yard. This home has all you've been looking for, plus a 2 car garage with an EV charger, a walk up attic & finished basement.

1375 Brush Hill Rd, Milton

Listing courtesy of Listing Agent: Robinson / Rull Team from Listing Office: William Raveis R.E. & Home Services.
$1,395,000
4 Beds ⋅ 4 Baths ⋅ 73531855 MLS
Welcome to 45 Foster Lane, a beautifully maintained four-bedroom home at the end of a coveted cul-de-sac in one of Milton's most desirable neighborhoods, just moments from East Milton Square. The bright and inviting floor plan features granite countertops, stainless steel appliances, gas cooking, hardwood floors, central air, and abundant natural light. The home offers four spacious bedrooms and three full baths, including a private primary suite with walk-in closet and en-suite bath. Outside, enjoy a resort-style backyard highlighted by a PermaCrete saltwater vinyl liner pool built by Easton Pool & Spa in 2020 and first enjoyed in 2021. Complete with an electric heater and expansive stamped concrete patio, the space is ideal for entertaining. A detached cabana with finished living space and a full bath adds exceptional flexibility for guests and poolside gatherings, creating a true private retreat.

45 Foster Lane, Milton

Listing courtesy of Listing Agent: Scott Farrell & Partners from Listing Office: Compass.
$699,000
4 Beds ⋅ 2 Baths ⋅ 73531370 MLS
Nothing to do but move right into this beautiful home featuring 4 spacious bedrooms and 1.5 baths. Gleaming hardwood floors run throughout the house, complemented by a gorgeous kitchen with stainless steel appliances, granite countertops, and a generously sized island. The open floor plan seamlessly connects the kitchen, dining room, and living room, creating the perfect space for entertaining and everyday living. All bedrooms are located on the second floor along with a full bathroom. The finished basement offers a large family room, plenty of storage closets for additional living space. The property also includes a one-car garage and a driveway that accommodates two cars. Conveniently located within walking distance to the elementary, middle, and high school.

45 Decker St, Milton

Listing courtesy of Listing Agent: Dee Rodrigues from Listing Office: Model Living RE.
$1,200,000
4 Beds ⋅ 2 Baths ⋅ 73519606 MLS
This spacious 9-room home on Hillside Street offers 4 bedrooms in one of Milton's most coveted settings, nestled at the edge of the Blue Hills Reservation. With miles of trails, open space, and stunning natural scenery right outside your door, the location is truly special. The generous layout gives buyers real flexibility to update and personalize, with good bones and a highly desirable address to build from. The property includes a pool currently in need of repair, presenting a great opportunity to create a standout outdoor space on your own terms. Milton is known for its excellent schools, beautiful neighborhoods, and easy access to Boston, and Hillside Road delivers all of it. For a buyer with vision and an eye for value, this is a rare chance to put your stamp on a property where nature and neighborhood come together beautifully.

1066 Hillside St, Milton

Listing courtesy of Listing Agent: Bridget Conroy from Listing Office: Coldwell Banker Realty - Milton.
$3,400,000
5 Beds ⋅ 5 Baths ⋅ 73511555 MLS
Set off a lovely cul-de-sac, surrounded by woodland and sky, this restored Greek Revival offers grace, modern sustainability, and space for you and yours. Fine millwork and French doors speak to fine craftsmanship. The kitchen is anchored by top appliances and built for serious cooking. A well-appointed mudroom keeps the everyday beautifully managed: a quiet workhorse. A glass-walled garden room with fireplace and woodland views offers needed stillness. A bluestone terrace flows to the private trailhead into the Blue Hills Reservation: 7,000 acres for hiking or exploration. Modern systems — geothermal heating/cooling, solar array, and EV charger — reflect a commitment to sustainability. On 2+ acres of natural beauty, find privacy and peace without sacrifice: the commuter rail, Rts 128/95, Logan Airport within easy reach. Access to Milton's public and the area’s prestigious independent schools makes the address practical and inspiring. This is where sophistication and sanctuary meet.

1632 Canton Ave, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.
$1,995,000
8 Beds ⋅ 5 Baths ⋅ 73509983 MLS
Welcome to 147 Canton Avenue, a home where historical significance, rich character, and grand proportions come together. From the moment you step into the expansive foyer with its soaring 10-foot ceilings, you can feel the warmth and history of a home that has been deeply loved. Designed for effortless living and entertaining, the main level boasts a stately front-to-back living room with a cozy fireplace, a dedicated office with custom built-ins, a generous formal dining room, and a kitchen that flows seamlessly into an adjoining family room. A practical laundry room, a half bath, and a deep walk-in foyer closet complete this floor. With eight bedrooms and three finished baths spread across the upper levels, there is no shortage of space: Situated on a sprawling, half-acre level lot, the outdoor oasis features a private patio and a relaxing hot tub. The home is equipped with efficient gas heating and an updated 200-amp electrical panel. The Milton Hill location is unbeatable!

147 Canton Avenue, Milton

Listing courtesy of Listing Agent: Kevin G. Keating from Listing Office: Keating Brokerage.
$3,895,000
5 Beds ⋅ 7 Baths ⋅ 73508385 MLS
This fully renovated Georgian Colonial offers exceptional living and entertaining in one of Milton’s most desirable neighborhoods. Privately set at the end of a cul-de-sac in Indian Cliff Estates, the home sits on 1.88 acres with a three-car attached garage. The main level features an eat-in kitchen, formal dining room, and a gracious living room that flows into a sitting area. A dramatic family room with cathedral ceilings and a floor-to-ceiling stone fireplace anchors the home, complemented by a wet bar and direct access to the indoor heated pool and hot tub. An elegant foyer with a curved staircase leads to five well-appointed bedrooms. The expansive lower level offers multiple flex spaces, including a home gym, recreation rooms, and a private theater. Designed for both everyday living and memorable entertaining, this home delivers a rare blend of space, privacy, and resort-style amenities.

90 Countryside Ln, Milton

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.
$3,500,000
6 Beds ⋅ 4 Baths ⋅ 73488165 MLS
Set behind a long approach offering the ultimate in wooded privacy and open lawn, 341 Highland is a classic Milton estate defined by land, light, and enduring craftsmanship. Substantial oak doors, rich paneling, French pocket doors between the living and dining rooms, and multiple fireplaces reflect the home's timeless character. The main living spaces balance scale with everyday comfort. A dedicated first floor office with private entrance off the circular drive and a playroom complement rooms suited for both formal entertaining and relaxed living. The primary suite anchors a generous private wing, while two staircases one with its own private entrance offer flexible circulation throughout. The finished third floor provides au pair quarters alongside space for hobbies, music and creative pursuits. Stone walls, patio areas, and an enclosed porch extend living into the landscape perfect for quiet mornings and memorable sunset views near the Blue Hills. Shown by private appointment only.

341 Highland St, Milton

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

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