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$825,000
3 Beds ⋅ 2 Baths ⋅ 73554096 MLS
***Multiple Offers - Deadline is Monday at 12pm***Offered for the first time in 47 years, this well-loved home presents a rare opportunity to reimagine a classic property in one of Milton's most desirable neighborhoods. Filled with retro charm and endless potential, this 3-bedroom, 1.5-bath home offers the perfect canvas to create a sophisticated, one-of-a-kind residence. The custom kitchen features granite countertops, stainless steel appliances, gas cooking, and quality cabinetry, while hardwood floors run throughout much of the home. An impressive family room addition showcases vaulted ceilings with exposed beams, expansive windows, and a cozy wood stove, creating a warm gathering space filled with natural light. The finished lower level includes new luxury vinyl plank flooring, a half bath, and a large storage area with a cedar closet offering potential for future expansion. Outside, enjoy a beautifully landscaped half-acre lot with mature plantings and a 2-car garage. Don't miss your chance to experience the perfect blend of style and comfort that is 27 Trout Brook Avenue! Ideally located within striking distance to Milton High School, the Blue Hills Reservation, and major highways. This home isn't just a place to live; it's a place to love!

27 Trout Brook Ave, Milton

Listing courtesy of Listing Agent: Ben and Kate Real Estate from Listing Office: Keller Williams Realty Signature Properties.
$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.
$2,995,000
4 Beds ⋅ 3 Baths ⋅ 73550784 MLS
Welcome to 191 Adams Street, a fully reimagined sprawling Ranch offering effortless first-floor living, stylish updates, and spaces made for entertaining. Every room has been thoughtfully redone, creating a bright, open floor plan that feels inviting from the moment you walk in. The stunning kitchen features new appliances, a generous workspace, and a seamless connection to the living and dining rooms, where scenic views of Hutchinson Field and the Boston skyline steal the show. The finished lower level adds incredible flexibility with a bedroom, full bath, office, and multiple living areas ideal for guests, extended family, a gym, or media room. Step outside to an expansive patio and huge backyard perfect for cookouts, yard games, and summer nights. An attached garage, easy highway access, nearby restaurants, shopping, and the bike path complete this move-in-ready gem! PRIVATE SHOWINGS ONLY!

191 Adams St, Milton

Listing courtesy of Listing Agent: Kim Powers from Listing Office: Coldwell Banker Realty - Milton.
$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..
$1,195,000
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.
$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.
$1,699,900
6 Beds ⋅ 5 Baths ⋅ 73529479 MLS
One of Milton's most desirable neighborhoods. Extensively updated in 2023, this property underwent a comprehensive gut renovation, including all-new plumbing, electrical systems, heating system, roof and numerous high-quality improvements throughout, offering the perfect blend of modern efficiency and timeless charm.The spacious kitchen and living areas provide excellent functionality for both everyday living and entertaining. The walk-out basement, offering tremendous potential for a future Accessory Dwelling Unit (ADU), in-law suite, guest quarters, home office, or additional income-producing space, subject to local approvals. The direct exterior access creates endless possibilities for multi-generational living or investment opportunities. Located near top-rated schools, parks, shopping, restaurants, and major commuter routes.

52 Ridgewood Rd, Milton

Listing courtesy of Listing Agent: Rebecca Huang from Listing Office: William Raveis R.E. & Home Services.
$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.
$674,900
3 Beds ⋅ 1 Baths ⋅ 73469207 MLS
Opportunity knocks in one of Milton’s most desirable neighborhoods! This classic home at 7 Parkway Crescent offers incredible potential for buyers looking to renovate, customize, and build equity. Set on a spacious lot in a quiet, established area, the property features a flexible floor plan with generous room sizes, hardwood floors, and plenty of natural light. Conveniently located near schools, parks, shopping, and major routes, this property combines a prime location with tremendous upside potential. Don’t miss this rare chance to invest in Milton. The occupant of this house has a life estate.

7 Parkway Cres, Milton

Listing courtesy of Listing Agent: Fermin Group from Listing Office: Century 21 North East.

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