Milton Real Estate

Nestled in the heart of Norfolk County, Milton, Massachusetts, is a picturesque town that beautifully blends suburban charm with a rich historical tapestry. Known for its rolling hills and scenic landscapes, Milton offers residents a serene escape from the hustle and bustle of nearby Boston, while still providing convenient access to the vibrant city life.

With a population of just over 27,000, Milton boasts a close-knit community feel, where friendly neighbors and local businesses thrive. The town is renowned for its exceptional public schools, making it an ideal place for families looking to settle down. Educational institutions like Milton Academy, one of the oldest independent schools in the country, add to the town’s reputation for academic excellence.

Outdoor enthusiasts will find plenty to love in Milton. The town is home to the stunning Blue Hills Reservation, a sprawling area perfect for hiking, biking, and enjoying nature. With miles of trails and breathtaking views, it’s a haven for those who appreciate the great outdoors. Additionally, the charming Milton Village offers quaint shops, delightful dining options, and a vibrant community atmosphere.

Milton’s rich history is evident in its well-preserved architecture and local landmarks. The town’s historic district features beautiful colonial homes that tell the story of its past, while modern developments seamlessly integrate into the landscape.

Whether you’re drawn to Milton for its top-rated schools, beautiful parks, or strong sense of community, this charming town offers a unique blend of tranquility and accessibility that makes it a wonderful place to call home. Experience the best of suburban living in Milton, where history meets modernity in perfect harmony.

Newest Listings in Milton

$725,000

2 Beds ⋅ 2 Baths ⋅ 73554434 MLS ⋅ ['Ice House'] BLDG.

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). This unit come with a designated storage space, and underground parking.

485 Blue Hills Parkway Unit 42, Milton

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: South Shore Sotheby's International Realty.

$3,500,000

5 Beds ⋅ 5 Baths ⋅ 73553103 MLS

Welcome to 16 Longmeadow Road, a custom-built masterpiece showcasing exceptional architectural detail at every turn. A dramatic two-story foyer with grand staircase and soaring ceilings sets the tone for this five-bedroom, four-and-a-half-bath residence in the highly sought-after Indian Cliffs Estates. The luxurious primary suite spans 500 square feet and features a spa-inspired ensuite with whirlpool tub, steam shower, and dual walk-in closets. The gourmet eat-in kitchen is a chef's dream, with a center island featuring a gas stove, dual sinks, and French doors flooded with natural light—flowing seamlessly into the formal dining room and sophisticated lounge complete with fireplace and wet bar, creating an entertainer's paradise. An additional living room with 11-foot tray ceiling, fireplace, and custom media cabinetry offers the perfect retreat. The home features a guest suite with separate entrance—ideal for an au pair, multi-generational living, or a private office sanctuary. Throughout, five walk-in closets, multiple linen closets, and a cedar closet provide unparalleled storage. The three-car garage and expansive rear patio with private well irrigation complete this exceptional property. Situated on nearly one acre and just 300 yards from Wollaston Golf Club, this residence offers both privacy and prestige.

16 Longmeadow Rd, Milton

Listing courtesy of Listing Agent: Emily Edwards from Listing Office: Gibson Sotheby's International Realty.

$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.

$4,500,000

7 Beds ⋅ 8 Baths ⋅ 73552866 MLS

A rare opportunity to own one of Milton Hill's most distinguished homes. Set on nearly an acre just moments from Milton Village, this beautifully updated residence offers the space & versatility desired by the buyers of today. Designed to evolve with every stage of family life, the property features a 6 BR main home plus a newly completed 1 BR ADU, offering exceptional flexibility for extended family, guests, an au pair, private office or multigenerational living. Inside, generous gathering spaces, a chef's kitchen w/La Cornue range, formal & casual living areas, home office options & a finished 3rd floor provide room for families to grow, gather & entertain. Outside, enjoy a heated pool, pergola, wraparound deck & expansive fenced grounds designed for everything from childhood adventures to summer celebrations. Rich architectural detail blends seamlessly w/thoughtfully modern, yet classic updates. Minutes to Milton Academy, Milton Village, parks, restaurants & an easy commute.

75 Canton Ave, Milton

Listing courtesy of Listing Agent: Sarah Glovsky from Listing Office: The Charles 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.

$875,000

4 Beds ⋅ 2 Baths ⋅ 73550789 MLS

Nestled on a quiet dead-end street in the sought-after Cunningham Park neighborhood, this charming bungalow offers the perfect blend of comfort, value, and space. From the moment you arrive, you'll appreciate the peaceful setting and welcoming curb appeal.Inside, the home features surprisingly spacious living areas filled with warmth and character, creating an inviting atmosphere for everyday living and entertaining. The thoughtful layout maximizes every square foot, offering comfortable rooms and plenty of flexibility to fit your lifestyle.Step outside and discover one of the property's standout features—a deep, expansive backyard with endless potential for gardening, play, outdoor gatherings, or simply relaxing in your own private retreat. The generous open space surrounding the home provides a rare sense of privacy and room to breathe.Whether you're a first-time buyer, downsizing, or looking for an affordable opportunity in a desirable neighborhood, this delightful bungalow the one!

22 Bradford Rd, Milton

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

$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.

$749,900

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.

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