Refine Search
Sort by
$1,480,000
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.

$1,575,000
2 Beds 2 Baths 73517093 MLS ['Milton Landing'] BLDG.
Perched at the pinnacle of luxury, this exceptional 2-bedroom, 2-bath penthouse offers an elevated lifestyle with two garage parking spaces and a truly rare private rooftop terrace showcasing sweeping views of the Neponset River Estuary and ever-changing, painted sky vistas. Inside, light-filled living spaces invite effortless entertaining and quiet relaxation, while the sprawling primary en-suite provides a serene retreat with generous proportions and comfort. A concierge building enhances daily living with a fitness center, library, and on-site restaurant, offering everyday convenience with a boutique-hotel feel. Outside your door, miles of walking and bike trails await, with the Milton Yacht Club nearby for weekends on the water. Just minutes to the Trolley and easy access to downtown Boston, with Milton Village and Milton Academy just outside your door. This is more than a home, it’s your elevated escape. Truly Milton living at it's finest.

88 Wharf Street Unit 604, Milton

Listing courtesy of Listing Agent: Kim Powers from Listing Office: Coldwell Banker Realty - Milton.

$2,600
2 Beds 1 Baths 73569693 MLS
This beautiful, charming apartment awaits! This spacious 5-room, 2-bedroom, 1-bathroom apartment is located on the first floor of a well-maintained multifamily home.The remodeled kitchen features stainless steel appliances, including a gas range, dishwasher, and refrigerator, along with newer plank flooring. Both the living and dining rooms are full of character, showcasing beautiful original details such as coffered ceilings and a built-in hutch.The two bedrooms feature refinished hardwood floors. Laundry is included and conveniently located in the rear hallway just off the kitchen. A rear sunroom serves as a common area and rear entrance. Tenants may enjoy the front porch, while the backyard is a shared common area.

68 Houston Unit 1, Milton

Listing courtesy of Listing Agent: Edward Desilets from Listing Office: ETCH Realty, LLC.

$880,000
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.

$3,750
3 Beds 1 Baths 73543227 MLS
Enjoy all Milton has to offer just minutes from Boston!. Townhouse style large 1,713 square foot apartment consisting of the 2nd and 3rd floor of a beautiful 2 family home. Private office to work from home! Oak hardwood floors. Crown moldings. Built in china cabinet. Full sized laundry units included. Eat in kitchen with walk in pantry. Natural gas cooking with 5 burner cooktop. Quartz counters. Microwave and disposal. Refrigerator included. 3rd floor 28 foot media room with electric built in fireplace. Natural gas cooking, heat and hot water. Wall AC unit. Private rear deck overlooking back yard. Rent includes 4-5 car off street parking and water /sewer. Plenty of extra storage in the basement if needed.

17 Laurel Rd Unit 2, Milton

Listing courtesy of Listing Agent: Joseph Bean from Listing Office: Joe Bean Real Estate.

$1,385,000
5 Beds 5 Baths 73533982 MLS
Set in one of Milton's most desirable neighborhoods, this thoughtfully designed home offers exceptional space, flexibility, and upscale finishes throughout. At its heart is a high-end chef's kitchen featuring premium appliances, custom cabinetry, and generous gathering space for everyday living and entertaining. A rare first-floor primary suite provides ideal accommodations for guests, multigenerational living, or single-level convenience, while the second floor features four additional bedrooms including a luxurious primary suite. The finished lower level with half bath adds approximately 500 square feet of versatile living space perfect for a media room, playroom, gym, or home office. Enjoy private outdoor space ideal for relaxing or entertaining, along with convenient access to the scenic walking and hiking trails of the Blue Hills Reservation. Meticulously maintained and built just 10 years ago, this home combines comfort, functionality, and timeless appeal.

37 Sassamon Ave, Milton

Listing courtesy of Listing Agent: Robin Shea from Listing Office: Principal Real Estate Partners.

$1,910,000
4 Beds 4 Baths 73532795 MLS
Designed to grow with you, this beautifully maintained, young home offers nearly 4,000 square feet of flexible living space on a spectacular 1.6-acre lot. The thoughtfully designed floor plan includes a first-floor primary suite, an additional first-floor bedroom, and two spacious bedrooms upstairs—ideal for a variety of lifestyles and living arrangements. At the heart of the home is a stunning custom kitchen by Faneuil Kitchens, opening to inviting spaces perfect for everyday living and entertaining. A bright living room with a dramatic two-sided fireplace creates a warm and welcoming gathering place, while oversized windows frame views of the beautifully landscaped grounds.Whether you're hosting holidays, working from home, accommodating guests, or simply looking for a home that will serve you for years to come, this exceptional property offers the space, flexibility, and setting to make it all possible!

282 Highland St, Milton

Listing courtesy of Listing Agent: Beth Rooney from Listing Office: eXp Realty LLC - Corporate Office.

$1,275,000
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.

$4,500
4 Beds 3 Baths 73517375 MLS
Well-maintained and recently updated 4-bedroom, 2.5-bath Colonial rental located on scenic Brush Hill Road in desirable Milton. This spacious home offers a warm and inviting layout with generous living and dining areas, hardwood floors, great natural light, and a functional kitchen. The upper levels feature four bedrooms, including a spacious third-level private bedroom with its own private bathroom, ideal for a primary suite or guest space. The home also includes a bonus room that can be used as a private office, reading room, study area, or flex space. Enjoy the convenience of off-street parking, a porch, and a corner-lot setting. Conveniently located within walking distance to Tucker Elementary School, with easy access to parks, shopping, public transportation, and major routes. Available August 1. Strong rental opportunity in a sought-after Milton location

208 Brush Hill Road, Milton

Listing courtesy of Listing Agent: Lindsey & Associates Realty Team from Listing Office: Keller Williams Realty Boston-Metro | Back Bay.

$915,000
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.

$2,000,000
3 Beds 3 Baths 73523755 MLS
Set on over 1.4 acres in one of Milton’s most picturesque settings, 268 Highland Street is a timeless brick-front Colonial where elegance, warmth, and unforgettable gatherings have defined this home for decades. From the slate roof and copper downspouts to the sweeping green lawns and mature landscape, every detail reflects classic New England charm. Inside, beautifully updated kitchens and baths blend seamlessly with gracious living spaces designed for entertaining and everyday comfort. A stunning home office overlooks the patio and expansive backyard, creating an inspiring work-from-home retreat. Beyond the main residence sits an extraordinary three-story barn—offering endless possibilities for creative space, storage, hobby use, or potential future ADU opportunities. Rarely does a property offer this combination of character, land, flexibility, and legacy just minutes from Boston.

268 Highland St, Milton

Listing courtesy of Listing Agent: Beth Rooney from Listing Office: eXp Realty LLC - Corporate Office.

$765,000
4 Beds 2 Baths 73547061 MLS
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

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

$2,100,000
5 Beds 4 Baths 73497233 MLS
There are homes that welcome you, and then there are homes that claim you. From the moment you step inside, this Milton Hill original announces itself—high ceilings, sweeping wall spaces, hefty moldings, an irresistible personality. Set on a lush acre, this residence has only grown more compelling with each refinement. Grand wall spaces beg for the art you've been waiting to hang, while a sense of graciousness moves through every room like a long exhale. A renovated eat-in kitchen is beautiful and deeply livable—mornings full of promise, evenings that stretch long. Every thoughtful update (windows, electrical, roof) honors what the house has always known about itself. Interior life unfolds over 4,300sf, 5+ bedrooms and 3.5 baths. And just beyond your door: Milton Academy, Glover School, Steel & Rye, the trolley. This is a home for someone who understands that where you live shapes how you live — a backdrop for the art, the dinners, the mornings in the garden, a life available here.

213 School St, Milton

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

$1,675,000
4 Beds 4 Baths 73540395 MLS
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

Listing courtesy of Listing Agent: Sandra Keller from Listing Office: Coldwell Banker Realty - Milton.

$880,000
3 Beds 1 Baths 73533488 MLS
Pretty as a picture, this warm and inviting 3-bedroom, 1-bath home with attached garage is set on a charming tree-lined street. The bright and cheerful living room is anchored by a wood-burning fireplace with an updated stone surround and rustic wood mantle, and the formal dining room flows into a timeless white/granite/ss open-plan kitchen, perfect for everyday living and entertaining. Upstairs you'll find 3 bedrooms, 2 with oversized closets, and a tastefully updated full bath. The yard is a private and peaceful oasis complimented by mature plantings, an irrigation system, and a new deck that extends the living space outdoors. Thoughtful updates and tasteful touches show throughout, with an attention to detail that will be appreciated for years to come. Ideally located near Blue Hills recreation, public transportation and major highways. This is a home you'll love coming back to.

17 Landon Road, Milton

Listing courtesy of Listing Agent: Kim Powers from Listing Office: Coldwell Banker Realty - Milton.

$729,000
1 Beds 2 Baths 73518950 MLS ['The Residences At Milton Landing'] BLDG.
Welcome to this sun-filled top-floor 1-bedroom, 2-bath residence at sought-after Milton Landing with garage parking. An updated kitchen opens to bright living spaces with beautiful hardwood floors, ideal for everyday living and entertaining. The spacious primary en suite offers a comfortable retreat, complemented by in-unit laundry for added convenience. Residents enjoy a concierge-hotel lifestyle with a fitness center, library, and on-site restaurant. Step outside to peaceful nature walks, bird watching, and miles of scenic biking trails, or water activities along the Neponset River, with hiking and equestrian recreation in the nearby Blue Hills. The trolley provides easy access to downtown Boston in minutes, connecting you to renowned universities, hospitals, world-class museums, dining, and theater. This is elevated living at its finest, offering the perfect blend of easy living, with nature and accessibility to city life just outside your door.

88 Wharf Street Unit 607, Milton

Listing courtesy of Listing Agent: Kim Powers from Listing Office: Coldwell Banker Realty - Milton.

$1,015,000
3 Beds 2 Baths 73540243 MLS
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

Listing courtesy of Listing Agent: MonaLisa Team from Listing Office: Compass.

$1,130,000
3 Beds 3 Baths 73536896 MLS
Some homes ask you to choose. This one doesn't. Set on a private half-acre corner lot, this three-bedroom, three-bath Milton home is move-in ready and freshly painted throughout. Hardwood floors run the length of the main level. The living and dining areas open to one another, anchored by a sunroom and a bright kitchen with granite counters and stainless steel appliances. A finished lower level with a full bath offers room to spread out. Guests. A place to gather. A home office that stays separate when it needs to. Separation without distance. Two fireplaces. An oversized two-car garage. Central air-conditioning. The everyday details are handled. A fully fenced yard with a stone patio, pond, and retractable awning. Quiet when you want it. Ready when you don't. Minutes from Milton Academy, the Blue Hills, Wollaston Golf Club, Houghton's Pond, and Route 93. Space, comfort, and room to grow are yours for the taking.

79 Hilltop St, Milton

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

$2,900,000
4 Beds 6 Baths 73534896 MLS
Perched atop prestigious Milton Hill and set on nearly an acre of beautifully landscaped grounds, this extraordinary estate offers over 7,500 square feet of refined living space. A dramatic atrium foyer welcomes guests into elegant interiors featuring rich hardwood floors, soaring ceilings, and exceptional craftsmanship throughout. Designed for both grand entertaining and everyday living, the home includes a chef’s kitchen, wood-paneled library, media room, and temperature-controlled wine cellar. The luxurious primary suite serves as a private retreat with natural light and a spa-inspired bath, while four additional bedrooms provide ample space for family and guests. Outdoors, a resort-style setting awaits with a sparkling pool, cabana, expansive patios, and manicured grounds ideal for entertaining or relaxation. Complete with a three-car garage and offering the perfect balance of privacy and convenience, this residence is just minutes from Boston, renowned schools, and amenities.

263 Adams St, Milton

Listing courtesy of Listing Agent: Michael Carucci from Listing Office: Serhant.

$900,000
3 Beds 2 Baths 73524024 MLS
7 room, 3 bedroom, 1 & 1/2 bath New England Colonial with a 1 car garage set on a cozy side street location in sought after East Milton. You will feel welcomed as you enter the front foyer and through the french doors to the comfortable fireplaced living room, formal dining room with built-in china cabinet and 1/2 bath. You will love the eat in kitchen with ample room for your table with plenty of cabinets, stainless steel appliances, recessed lighting, corian countertops, and a built-in desk station opening to an outside deck overlooking the backyard. Hardwood floors throughout the first and second floors. The second level has three generous sized bedrooms with a full bath. This gorgeous home has been tastefully updated along with a brand-new gas heating system and a newer roof. The basement has a spacious family room. Potential future expansion possibilities with the walk-up attic. Perfectly located with shopping, restaurants, Route 93 & all the area amenities minutes away.

25 Waldeck Road, Milton

Listing courtesy of Listing Agent: Robert T. Germaine from Listing Office: Germaine Realty LLC.

$720,000
2 Beds 2 Baths 73506801 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). All units come with a designated storage space, and underground parking.

485 Blue Hills Parkway Unit 21, Milton

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

$725,000
3 Beds 2 Baths 73486879 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). All units come with a designated storage space, and underground parking.

485 Blue Hills Parkway Unit 23, Milton

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

$2,650,000
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.

$875,000
3 Beds 3 Baths 73537745 MLS
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

Listing courtesy of Listing Agent: The Jenkins Group from Listing Office: Keller Williams Realty.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.