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$895,000
3 Beds ⋅ 2 Baths ⋅ 73574978 MLS
Set in a convenient Milton location, this classic English Colonial combines timeless character with significant recent improvements. The seller has invested significantly in the property with a NEW ROOF, NEW HEATING AND HOT WATER SYSTEMS, NEW FENCE, NEW DRIVEWAY, gas fireplace and newly updated appliances, allowing the next owner to focus on making the home their own. Step inside to a bright, inviting eat in kitchen featuring a breakfast bar and peninsula, plenty of room for a dining table or can also be used as flexible space for homework nook, a home office or whatever your lifestyle calls for. Direct access from the kitchen leads to the back deck, driveway and a fenced yard, making the outdoor space an easy extension of everyday living. From the kitchen, the floor plan flows naturally into the formal dining room and spacious living room, where a gas fireplace creates a warm focal point. Hardwood floors, crown molding and wainscoting add the timeless details that give this home its character. A convenient half bath completes the first floor. Upstairs are three well-proportioned bedrooms and a full bath. Continue to the finished third floor for valuable bonus space that can adapt as your needs change, whether used as a home office, playroom, gym, creative space or guest retreat. The basement offers high ceilings, newer washer and dryer, excellent storage and direct access to the garage. AND THEN THERE IS THE LOCATION! For buyers who love the conveniences of city living but are ready for more space, this part of Milton offers a great balance. East Milton Square and neighborhood favorites are just minutes away, with coffee shops, restaurants, fitness options and everyday conveniences close at hand. The Fruit Center Marketplace is a local favorite for everything from everyday groceries to quality meats, seafood, prepared foods, wine and specialty items, while nearby Julianne's, Novara and Abby Park add plenty of options for dining close to home. Cunningham Park provides acres of green space and recreation nearby, while easy access to I 93 makes commuting into Boston, heading to the South Shore or getting out of town especially convenient. With its classic Colonial character, inviting living space, garage and substantial recent improvements already completed, 1200 Brook Road is ready for its new owners. Come see why this Milton home may be the one you’ve been waiting for. Easy to show!

1200 Brook Road, Milton

Listing courtesy of Listing Agent: The Residential Group from Listing Office: Coldwell Banker Realty - Brookline.
$999,900
4 Beds ⋅ 3 Baths ⋅ 73574898 MLS
Beautifully Renovated 5 Bedroom Colonial - Where Classic Charm Meets Modern Elegance. Step into timeless sophistication in this tastefully updated home. Newly redesigned to blend traditional character with contemporary luxury. Sun-drenched interiors showcase a grand foyer, coffered ceilings, & gleaming hardwood floors. Brand-new kitchen features granite counters, stainless steel appliances, and ample space for entertaining. Upstairs offers 5-6 generously sized bedrooms with room for everyone, a home office, or adjoining nursery. Luxurious primary suite includes a private bath with expansive closet space. Enjoy formal dining, a dedicated sitting room, and 3 spacious levels of living plus an additional fully finished basement ideal for a media room, play room, or home gym. Renovated Inside & Out ...Completely Turn-Key! Prime Milton location with top-rated schools, a quick drive to downtown Boston, and steps to public transportation.

84 Blue Hills Parkway, Milton

Listing courtesy of Listing Agent: Tatiana Diaz from Listing Office: William Raveis R.E. & Home Services.
$849,000
3 Beds ⋅ 1 Baths ⋅ 73574820 MLS
This is the One! Welcome to 133 Gulliver St - An inviting 3-bedroom, 1,402 sq ft home in one of Milton’s most desirable neighborhoods. Set on a quiet street in the heart of Milton Center - walk to schools and parks. Comfortable main level includes a front to back fireplaced living room, formal dining room with chair rail and crown molding and a large family room that overlooks the spacious level fenced yard. Utilities include: 200 Amp electric, Efficient Gas heating and Hot water with tons of basement storage. Classic Milton Character in an ideal and walkable location. This one won't last!

133 Gulliver St, Milton

Listing courtesy of Listing Agent: Mikel Defrancesco from Listing Office: William Raveis R.E. & Home Services.
$1,795,000
4 Beds ⋅ 5 Baths ⋅ 73573740 MLS
Located in Milton’s desirable Columbine neighborhood, this fully renovated four-bedroom Dutch Colonial offers exceptional design and incredible indoor-outdoor living. The magazine-worthy interior features a classic New England-style kitchen with soapstone countertops and Wolf and Sub-Zero appliances. A spacious breakfast nook with French doors to the backyard and formal dining room with patio access create an ideal setting for entertaining. The home offers two full and three half baths, plus finished attic and lower-level spaces. The showstopping garage doubles as an inviting lounge with a gas fireplace, wet bar and half bath while retaining its garage functionality. Complete with central air, gas heat and a backyard designed for gathering. Close to Kelly Field, Turner’s Pond, Glover School and Milton Academy, and minutes to the Trolley Line for convenient access to Boston. This is the one-of-a-kind Milton dream home you’ve been waiting for—completely finished and truly move-in ready.

22 Windsor Rd, Milton

Listing courtesy of Listing Agent: Colleen Foulsham from Listing Office: FC Realty Group.
$2,149,000
4 Beds ⋅ 4 Baths ⋅ 73573816 MLS
Welcome to a spacious four-bedroom Colonial offering privacy, luxury, and exceptional flexibility in a beautiful setting close to Boston. Featuring TWO primary suites, including a newly constructed first-floor primary with private deck access, walk-in closet, and spa-like bath with dual vanities, soaking tub, and accessible shower. The renovated chef’s kitchen showcases Sub-Zero, Wolf, and Thermador appliances, quartz countertops, and a large island. Enjoy the flexibility of one-floor living with first-floor laundry, dining room, family room, and home office. Upstairs offers a second primary suite with custom walk-in closet and luxurious ensuite, two additional bedrooms, and additional full bath. Outside, entertain on the large composite deck and screened room overlooking the private yard. Additional features include a two-car garage with EV charger, finished basement, walk-up attic, and proximity to Blue Hills Reservation and Mary Wakefield Arboretum. A rare Milton-area opportunity combining space, privacy, luxury, and convenience.

1375 Brush Hill Rd, Milton

Listing courtesy of Listing Agent: Foster/ Harrington Team from Listing Office: Coldwell Banker Realty - Milton.
$1,595,000
4 Beds ⋅ 4 Baths ⋅ 73573253 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.
$1,095,000
4 Beds ⋅ 2 Baths ⋅ 73573212 MLS
It's one of those magical streets...Brae Burn Road. In the the heart of East Milton but tucked away from it all. It's the kind of neighborhood where kids free range play, neighbors are known and a sense of community just happens. Light and bright, the tasteful modern decor of this inviting home allows you to settle in without too much heavy lifting. The fireplaced living room is front to back and transitions to a screened porch perfect for those early fall evenings. The updated quartz kitchen has ample white cabinetry and a sizeable island for seating and prep. The square dining room accommodates family & friends, and a china cabinet awaits your favorite things. The elusive 4th bedroom is HERE, and two updated full baths make the ready hour less hurried. The lower level offers a spacious family room for movie night, and a separate playroom space can maintain it's purpose or transition to a home office. Newer gas boiler, central air, great outdoor space including a fully fenced yard with play space, and composite deck add to the list of pluses. Walkable to Cunningham/Collicot schools, Cunningham Park and the restaurants, coffee shops and retail of East Milton Square. A truly special home in a location you've been longing for!

24 Brae Burn Rd, Milton

Listing courtesy of Listing Agent: Cahill+Co. Team from Listing Office: William Raveis R.E. & Home Services.
$4,495,000
5 Beds ⋅ 8 Baths ⋅ 73573141 MLS
A striking new construction residence at Brush Hill, thoughtfully designed with timeless architecture, elevated finishes, and today’s most sought-after amenities. The exterior makes an immediate impression with custom-colored LP Smart Siding, CertainTeed architectural shingles, partial brick façades, and elegant brick and bluestone entryways. Marvin windows and doors enhance both aesthetics and energy efficiency while filling the home with natural light. Outdoor living is seamlessly integrated with a built-in grill and outdoor Sonos speakers, ideal for entertaining.Inside, the home blends sophistication and comfort across every level. Six-inch engineered hardwood floors flow throughout, complemented by custom moldings, built-ins, and both gas and wood-burning fireplaces. The chef’s kitchen serves as the heart of the home, featuring a custom-designed kitchen and hood, Sub-Zero and Wolf appliance package, a 48” column refrigerator/freezer combination, 48” Wolf induction range, Cove dishwasher, and quartz countertops.A fully appointed butler’s pantry adds exceptional functionality with an additional oven, microwave, water bottle dispenser, Miele coffee system, and Thermador wine refrigerator—perfect for entertaining and everyday convenience.Designed with wellness and recreation in mind, the home includes three bathrooms with heated floors, a private sauna with red light therapy, a dedicated gym, and a finished basement bar. An optional TrackMan golf simulator offers a unique and elevated recreational experience.Additional features include a whole-house Sonos sound system, prewired alarm and camera system, and full-house water filtration—delivering comfort, security, and peace of mind. This exceptional new construction at Brush Hill offers a rare combination of luxury, lifestyle, and thoughtful design.

688 Brush Hill Road, Milton

Listing courtesy of Listing Agent: Scott Farrell & Partners from Listing Office: Compass.
$1,195,000
4 Beds ⋅ 3 Baths ⋅ 73570461 MLS
Welcome to 88 Elm Street, a spacious and inviting 4-bedroom, 2.5-bath home offering over 3,000 square feet of living space in Milton’s desirable Elmiver Park neighborhood. With generous room sizes, two fireplaces, hardwood floors and a flexible floor plan, this home offers plenty of space to gather, entertain, and make your own. At the heart of the home is a large, well-appointed kitchen featuring granite countertops, stainless steel appliances, abundant cabinetry, and plenty of space for meal prep and casual dining. A dining room just off the kitchen provides a dedicated space for meals and entertaining, while the spacious family room with custom built-ins provides a comfortable place to gather and unwind. In addition to the four upstairs bedrooms, there is a wonderful bonus living space, offering endless possibilities. Create an au pair suite, in-law setup, private guest space, home office, hobby room, or simply make it your own. The spacious finished lower level adds even more room to spread out, complete with its own fireplace and half bath. Whether used as a family room, playroom, home gym, media room, or entertaining space, this space has plenty of possibilities to fit your needs. Outside, a large deck and paver patio overlook the expansive, fully fenced-in yard, creating an inviting setting for outdoor dining, entertaining, gardening, pets, or simply relaxing at home. A rear garage provides plenty of additional storage for bikes, tools, lawn equipment, and more. Set in a welcoming Milton neighborhood, 88 Elm Street is just 0.2 miles from Milton High School and close to nearby walking trails, Milton Center and everyday conveniences. With generous living space inside and out, flexible options for extended family or guests, and a location that puts so much of Milton within easy reach, this home has so much to offer. Showings begin at Commuter Open House Wednesday Sept. 2nd.

88 Elm St, Milton

Listing courtesy of Listing Agent: Susan Solis from Listing Office: Keller Williams Realty Signature Properties.
$11,900,000
5 Beds ⋅ 7 Baths ⋅ 73570207 MLS
Privately gated and exquisitely appointed, 540 Harland Street presents a rare opportunity to own an extraordinary equestrian estate set on approximately 8 acres within the Blue Hills Reservation. Surrounded by protected natural beauty and offering direct riding access to approximately 7,000 acres of preserved landscape, this exceptional property combines complete privacy, sophisticated living, and an unparalleled connection to the outdoors—yet remains conveniently close to Boston.The approximately 8,250-square-foot main residence is designed for grand-scale living and effortless entertaining, featuring five bedrooms, five full baths, and two half baths, complemented by soaring 10-foot ceilings throughout. The spectacular chef’s kitchen is outfitted with premium Wolf appliances, while a dedicated home gym and state-of-the-art home theater elevate the everyday experience. An in-home elevator provides seamless access throughout the residence.Outdoor living is equally impressive, with a 350-square-foot patio and a fully equipped Wolf outdoor kitchen, creating an exceptional setting for entertaining, dining, and enjoying the surrounding landscape.The estate’s remarkable carriage house adds an extraordinary layer of versatility, offering an 8–16+ car garage and approximately 1,750 square feet of guest living space above. Ideal for car enthusiasts, collectors, guests, or extended family, this separate structure provides an exceptional combination of utility and luxury.At the heart of the property’s equestrian amenities is an approximately 2,000-square-foot state-of-the-art multi-stall equestrian center, thoughtfully complemented by an adjacent exercise pen. The direct access to miles of protected Blue Hills terrain allows riders to leave the property on horseback and immediately experience one of the region’s most spectacular natural settings.This is far more than a luxury residence—it is a private equestrian compound and lifestyle estate, offering an extraordinary level of scale, privacy, amenities, and access to protected land rarely found in Greater Boston. A truly distinctive retreat where refined living and the freedom of the countryside exist in perfect harmony.

540 Harland St, Milton

Listing courtesy of Listing Agent: Signature Collective Team from Listing Office: Serhant.
$1,050,000
3 Beds ⋅ 3 Baths ⋅ 73568972 MLS
61 Elm Street is move-in ready and ideally located in Milton’s desirable "Elmiver Park" neighborhood, with Milton High School just two streets over! This bright, beautifully maintained home has been exceptionally well cared for, and it shows. Freshly painted with newly refinished hardwood floors, newer windows, and thoughtful updates throughout, there’s truly nothing to do but move in. The open-concept first floor features a fireplaced living room, dining area with a built-in china cabinet, an updated kitchen with stainless steel appliances, and a convenient half bath. Step outside to a private backyard with a brick patio—perfect for relaxing, entertaining, or outdoor dining. An irrigation system makes it easy to keep both the front and back yards looking their best. Upstairs, you’ll find three bedrooms, a full bath, and a spacious landing. The finished lower level provides valuable additional space with a large playroom or family room, laundry area, and a bathroom with shower. A new 2025 Navien combination boiler and water heater is located in a clean, well-maintained mechanical space.The location is hard to beat. Milton High School is just two streets over, while Pierce Middle School, Milton Academy, Milton Public Library, Town Hall, and BID Milton Hospital are within a mile of this home. Public transportation is also easily accessible, including bus service and the Red Line trolley, with convenient access to Routes 128/95, 24, and 3. With Boston less than 8 miles away and Logan Airport within 13 miles, 61 Elm Street offers the best of both worlds—a welcoming Milton neighborhood with exceptional access to Boston. Beautifully maintained, updated, move-in ready, and close to everything—61 Elm Street is ready to welcome its next owner.

61 Elm Street, Milton

Listing courtesy of Listing Agent: Robinson / Rull Team from Listing Office: William Raveis R.E. & Home Services.
$699,000
3 Beds ⋅ 2 Baths ⋅ 73567961 MLS
Welcome to this classic three-bedroom, one-and-a-half-bath Colonial in one of Milton’s desirable neighborhoods. Lovingly maintained by the same owner for over 40 years, this home offers hardwood floors throughout most living areas and bedrooms, newer windows, blown-in wall insulation, 200-amp electrical service, and a gas heating system installed in May 2022. The inviting living room features a fireplace, while the formal dining room showcases a beautiful built-in china cabinet. An enclosed three-season porch provides additional space to relax and enjoy the changing seasons. Set on a .19-acre lot, the property offers a spacious backyard abutting conservation land, providing added privacy. Additional features include a generously sized shed, gutters with leaf filters, and a roof replaced primarily with 50-year shingles in 2005, with a portion repaired in 2017. A wonderful opportunity to make this well-maintained home your own! Conveniently located near public transportation, major routes, and highway access, making commuting to Boston easy.

66 Ferncroft Rd, Milton

Listing courtesy of Listing Agent: Diane M. Marchione from Listing Office: Conway - Hingham.
$839,000
3 Beds ⋅ 2 Baths ⋅ 73563860 MLS
Welcome to 37 Nahanton Avenue, a charming Colonial offering an exciting opportunity to own in sought-after Milton. Filled with natural light, this 3-bedroom, 1.5-bath home features beautiful hardwood floors, central air, newer heating system and a warm, inviting living room that leads to a charming screened in porch and overlooks tranquil back yard. The comfortable floor plan offers wonderful potential to update, personalize, and create a home that truly reflects your style. Outside, the property offers space to relax, garden, entertain, or enjoy summer gatherings. Set in an established residential neighborhood, this home provides the perfect balance of suburban living and convenience, with easy access to Milton’s schools, parks, shopping, dining, major routes, and Boston.Whether you're a first-time buyer, downsizer, or simply looking for a home you can make your own, 37 Nahanton Avenue is an opportunity not to be missed. Bring your vision and discover the possibilities this Milton gem has to offer!

37 Nahanton Ave, Milton

Listing courtesy of Listing Agent: Julie Joyce from Listing Office: Coldwell Banker Realty - Milton.
$2,995,000
5 Beds ⋅ 6 Baths ⋅ 73560323 MLS
Welcome to your brand new construction home in the beautiful town of Milton. Thoughtfully designed with over 5,300 square feet of refined living space, this custom built residence offers 5 bedrooms, 4 full baths, 2 half baths & an attached 2 car garage w/ extra storage. Entering through the arched front doorway you are greeted by an extensive open layout w/ high ceilings, natural light, a spacious dining room, and an oversized chef's kitchen featuring: taj mahal quartz counters, Thermador panelized appliances, a custom built venetian plaster vent hood, Mouser custom cabinetry & a massive pantry w/ a custom built door for easy loading direct from the garage. The 1st floor continues w/ a large living room area including a venetian plaster electric fireplace, custom built-ins, an extra office or 1st floor bedroom flex space. The second level features a stunning primary suite bedroom w/ a parquet ipe private deck & a spa-inspired en-suite bath w/ a large wet-room shower and tub. Three guest bedrooms all include walk in closets and hardwood flooring. A dedicated laundry room and two more full baths complete the 2nd floor. The finished lower level offers flexible space for a media room, playroom, home gym area, wellness center, and/or an extra bedroom w/ a full bath. The exterior includes a fully landscaped yard, composite privacy fence, a massive Ipe deck, and irrigation. A 1 year builder warranty is included as well. Come see this custom designed home built by one of the best custom home builders in the area!

33 Harbor View Park, Milton

Listing courtesy of Listing Agent: The Quirk Group from Listing Office: Coldwell Banker Realty - Boston.
$939,900
3 Beds ⋅ 4 Baths ⋅ 73559960 MLS
Refreshed and Reimagined center-entrance Colonial in desirable Milton, offering three bedrooms, two full baths, and two half baths. This thoughtfully updated home features a spacious primary ensuite and a sun-filled bonus sunroom—ideal for a home office, reading nook, or relaxation space. The refined open-concept kitchen blends beauty and function with quartz countertops, a pot filler, and a custom island with microwave drawer, offering seamless flow for entertaining. Additional attic space and an open basement provide exceptional potential for future expansion, ADU (Additional Dwelling Unit) just open space for personal customization. A two-car garage with additional parking completes the package. Ideally located near trolley access, the Red Line, Blue Hills Reservation, and the Neponset River Trail, this home delivers the perfect blend of elegance, comfort, and commuter convenience.

80 Blue Hills Parkway, Milton

Listing courtesy of Listing Agent: Shawn Burgess from Listing Office: Compass.
$995,000
4 Beds ⋅ 2 Baths ⋅ 73559489 MLS
Get ready to feel right at home at 128 Pleasant Street! Set on a charming corner lot in a convenient Milton location, this bright and welcoming home brings together classic character, easy living, and the kind of everyday comfort buyers love. Step inside and you’re greeted by sun-filled rooms, well-maintained hardwood floors, and a warm, natural flow that makes the home feel instantly inviting. The open dining area leads right into a bright kitchen with recessed lighting and new stainless steel appliances, creating the perfect setup for weeknight dinners, weekend hosting, and everything in between. With four bedrooms, ductless mini-split A/C, comfortable living space, and a three-season porch that adds the perfect spot for morning coffee or a quiet evening unwind, there’s room here to spread out and enjoy. Out back, a wood deck overlooks the yard and garden space, offering just the right setting for grilling, relaxing, and making the most of the seasons. Bright, charming, well cared for, and wonderfully convenient — 128 Pleasant Street is the kind of Milton home that feels good from the moment you walk in. Come see for yourself!

128 Pleasant St, Milton

Listing courtesy of Listing Agent: Matthew Freeman from Listing Office: Coldwell Banker Realty - Milton.
$999,999
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.
$4,995,000
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.
$645,000
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.

52 Meagher Ave, Milton

Listing courtesy of Listing Agent: Pedro Garcia from Listing Office: Garcia Realty, LLC.
$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.
$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.
$987,000
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.
$1,895,000
8 Beds ⋅ 5 Baths ⋅ 73509983 MLS
Welcome to 147 Canton Avenue, a home where timeless elegance, 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.
$3,845,000
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.

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