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$1,125,000
3 Beds 2 Baths NEW Status 73556667 MLS 2,303 SqFt.
Welcome to 48 Marilyn Road, a charming 1940 Colonial-style home in the highly sought-after Columbine neighborhood. This sun-drenched three-bedroom, one-and-a-half-bath residence features freshly refinished hardwood floors throughout, an updated half bath, and excellent storage. The inviting living room serves as the heart of the home, showcasing custom built-ins and a beautiful fireplace that creates a warm, cozy gathering space. A walk-up attic and expansive basement provide exciting possibilities for future use. The finished basement adds over 400 square feet of living space, featuring a family room with a fireplace and wet bar that provides a comfortable space to gather, entertain and unwind. Bring your imagination! Outside, the private backyard provides a peaceful retreat, perfect for relaxing or entertaining, while the one-car garage offers convenient parking and additional storage. Blending timeless character with thoughtful updates, this exceptional home is ready to welcome its next owners.

48 Marilyn Rd, Milton

$725,000
2 Beds 2 Baths ACTIVE Status 73554434 MLS 1,159 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). This unit come with a designated storage space, and underground parking.

485 Blue Hills Parkway Unit 42, Milton

$825,000
3 Beds 2 Baths UNDER AGREEMENT Status 73554096 MLS 1,877 SqFt.
***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

$3,500,000
5 Beds 5 Baths ACTIVE Status 73553103 MLS 5,700 SqFt.
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

$4,500,000
7 Beds 8 Baths ACTIVE Status 73552866 MLS 6,404 SqFt.
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

$1,675,000
4 Beds 4 Baths ACTIVE Status 73552638 MLS 3,288 SqFt.
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

$1,499,900
4 Beds 4 Baths ACTIVE Status 73552355 MLS 2,621 SqFt.
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

$4,995,000
5 Beds 5 Baths ACTIVE Status 73551180 MLS 4,310 SqFt.
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

$875,000
4 Beds 2 Baths CONTINGENT Status 73550789 MLS 1,460 SqFt.
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

$2,995,000
4 Beds 3 Baths ACTIVE Status 73550784 MLS 4,643 SqFt.
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

$749,900
4 Beds 2 Baths PRICE CHANGED Status 73550682 MLS 1,492 SqFt.
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

$1,185,000
4 Beds 3 Baths ACTIVE Status 73550414 MLS 1,907 SqFt.
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

$1,249,000
5 Beds 3 Baths CONTINGENT Status 73550347 MLS 2,369 SqFt.
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

$949,000
4 Beds 3 Baths ACTIVE Status 73547798 MLS 1,593 SqFt.
Big opportunity, hard-to-beat location, and endless possibilities at 146-148 Warren Ave. Set on a fun, tucked-away dead-end street near Kelly Field, this side-by-side two-family offers the space, flexibility, and neighborhood feel that so many buyers are looking for. Live in one unit and rent the other, bring extended or multi-generational family together while still enjoying separation, or add a strong Milton property to your portfolio. Each side feels more like its own home, offering privacy, functionality, a day-to-day living. The location is a major win, with Kelly Field, tennis courts, playgrounds, open fields, Pierce Middle School, and Glover School all nearby. Outside, a spacious backyard with a shared deck and separate parking for each unit adds even more appeal. Ready to rent, easy to own, and full of long-term upside, this is a two-family that makes sense today and for years to come!

146-148 Warren Ave, Milton

$745,000
2 Beds 2 Baths ACTIVE Status 73547281 MLS 1,193 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). This unit come with a designated storage space, and 1 underground parking space.

485 Blue Hills Parkway Unit 44, Milton

$699,000
4 Beds 2 Baths UNDER AGREEMENT Status 73547061 MLS 1,945 SqFt.
Idyllically set in a neighborhood where people move in and never leave and that's exactly what you'll find on Dyer Ave. Generations have called this address home and now it's time for its next chapter. The space is here, three levels ready for your vision. This one needs work so if you're only after turn-key, keep scrolling. But for those who want to build equity and make it their own, don't miss out. Contractors, investors, DIY dreamers this is your canvas with solid bones high ceilings, generous rooms and a fabulous farmer's porch. A fresh coat of paint, refinished hardwood floors and a kitchen renovation that can open the whole first level up is what we are envisioning. Set amid lush greenery on a level lot, see why so many plant roots in this neighborhood. Schools, Kelly Field and the Trolley are all just minutes away making for an easy Boston commute. Affordable and full of potential, this is the place to be! Don't let this one slip by!

82 Dyer Ave, Milton

$1,225,000
4 Beds 3 Baths ACTIVE Status 73546456 MLS 3,006 SqFt.
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

$1,195,000
4 Beds 2 Baths CONTINGENT Status 73546064 MLS 2,218 SqFt.
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

$1,349,000
5 Beds 3 Baths ACTIVE Status 73539896 MLS 2,980 SqFt.
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

$899,900
3 Beds 2 Baths CONTINGENT Status 73541229 MLS 1,760 SqFt.
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

$1,595,000
4 Beds 4 Baths UNDER AGREEMENT Status 73540395 MLS 3,803 SqFt.
A true architectural statement, this custom contemporary blends iconic Mid-Century Modern design with refined European sensibility. Perfectly situated on a private acre, it’s a masterclass in light, volume, and timeless style. Dramatic angled beam ceilings and expansive walls of glass frame the sky and landscape, creating a seamless connection between indoors and out. Thoughtful renovations honor the home's original architectural integrity while introducing a fresh, sophisticated aesthetic. A chef's kitchen opens to dining room, designed for everyday living and elegant entertaining. The primary suite is a private sanctuary featuring custom Italian wardrobe systems and a spa-inspired bath. A media room, beautifully renovated baths, four to six flexible bedrooms provide versatility & potential for an au pair or guest suite. A covered patio overlooks terraced yard. Direct proximity to Longwood Medical area, Milton Academy, Fairmont commuter T station. It's a property that stands alone.

285 Brush Hill Rd, Milton

$835,000
3 Beds 2 Baths UNDER AGREEMENT Status 73540243 MLS 1,850 SqFt.
Welcome to this classic center-entrance Colonial where charm meets comfortable modern living. This nicely maintained home features a spacious over-sized living room with a cozy gas fireplace and attached reading nook, the perfect spot to relax. The kitchen includes stainless steel appliances, granite counters and opens seamlessly to the dining room with a charming built-in hutch. A convenient 1/2 bath completes the first floor. Upstairs, you’ll find three spacious bedrooms plus a versatile bonus space ideal for a nursery, home office or creative retreat. The walk-up attic presents additional finished space along with room to expand. The lower level extends the living area with a finished room perfect for a playroom or office, a washer/dryer and plenty of storage. With classic details and flexible spaces, this Colonial offers timeless appeal and room to grow. A wonderful home filled with warmth and character. 10 minutes walk to trolley into Boston! Come see this gem!

7 St. Mary's Rd., Milton

$1,895,000
4 Beds 5 Baths ACTIVE Status 73538357 MLS 4,398 SqFt.
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

$1,199,999
4 Beds 2 Baths UNDER AGREEMENT Status 73538210 MLS 3,194 SqFt.
Blending timeless character with modern versatility, this charming Milton home showcases beautiful original dark woodwork and a classic fireplace mantel. The spacious eat-in kitchen offers abundant cabinetry and a large butler’s pantry for exceptional storage and prep space. A first-floor den provides the option of a fifth bedroom, ideal for guests, a home office, or multigenerational living. The expansive third floor offers endless possibilities as a family room or office, featuring four skylights, exposed beams, ceiling fans, wall-to-wall carpeting, and built-in bookcases, with space to create two rooms if desired. Outside, the fully fenced backyard provides a private setting for entertaining, pets, and outdoor enjoyment. Set on a quiet dead-end street with convenient access to public transportation, downtown Boston, dining, bike trails, and recreational amenities.

14 Brookside Park, Milton

$899,000
3 Beds 3 Baths UNDER AGREEMENT Status 73537745 MLS 1,570 SqFt.
Offer accepted- open houses cancelled. Lovingly maintained by the same family since 1949, this charming 3-bedroom home offers a rare opportunity to own a piece of Milton history. Set on a beautiful private lot abutting peaceful woodlands, the home blends timeless character with thoughtful updates. The updated kitchen opens seamlessly to the main living areas, while the stunning family room with soaring vaulted ceilings and abundant natural light creates the perfect space to gather and entertain. Recent improvements include mini-split systems (2019), a new roof, new chimney, and upgraded 200-amp electrical service (2023-2024). Enjoy the serenity of your backyard retreat while being just moments from Milton Village with shops, restaurants, parks, and MBTA transit. Offering the perfect balance of privacy, convenience, and pride of ownership, this is a truly special home in one of Milton's most desirable locations.

30 School Street, Milton

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