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10 Nahanton Ave, Milton
$839,000
3 Beds ⋅ 2 Baths ⋅ 73593447 MLS
Move-in ready and beautifully updated! This charming 3-bedroom, 1.5-bath Colonial was completely remodeled in 2019 and has been thoughtfully maintained with additional improvements throughout. Recent updates include a new roof (2023), added kitchen pantry storage, a new back door, and an updated garage door system (2024). The bright and sunny main level features a beautiful three-season sunroom, an updated kitchen with quartz countertops, custom cabinetry, a breakfast bar, and additional pantry storage. The living room and dining room are filled with natural light, while a convenient half bath and mudroom with built-in storage and seating complete the first floor. Upstairs, you'll find three bedrooms, including one with a custom California Closet, and a full bathroom. The home offers an impressive amount of storage throughout. Outside, enjoy a spacious, fully fenced in backyard with a lovely patio, perfect for entertaining or relaxing on summer evenings. Nestled in a desirable neighborhood bordering the Blue Hills Reservation and Wollaston Country Club, outdoor enthusiasts will love having direct access to the Blue Hills hiking and walking trails right from the neighborhood at the end of the street. All of this while being conveniently located near major highways, shopping, restaurants, and everyday amenities. Nothing to do but move in and enjoy!

10 Nahanton Ave, Milton

Listing courtesy of Listing Agent: Abigail Marjollet from Listing Office: Ceres Real Estate.
44 Ridgewood Rd, Milton
$2,890,000
5 Beds ⋅ 7 Baths ⋅ 73593368 MLS
A life without compromise awaits at 44 Ridgewood Rd in Milton, where exceptional new construction pairs architectural presence with thoughtful everyday ease. A grand kitchen, butler’s pantry, and dedicated dining room set the stage for memorable entertaining, while the dramatic living room impresses with soaring ceilings, expansive windows, and a commanding fireplace. A first-floor office/bedroom with ensuite bath adapts to changing needs. A mudroom off the two-car garage and designer powder room complete the main level. The luxurious primary suite offers two separate closets and an expansive, spa-inspired bath; every secondary bedroom features its own ensuite. With 9-foot ceilings, the finished lower level offers generous entertainment spaces, a wet bar, gym, sauna, full bath, and flexible office/guest space. An expansive deck overlooks the private backyard. From milestone celebrations to quiet mornings, this distinctive Milton home makes room for every part of life.

44 Ridgewood Rd, Milton

Listing courtesy of Listing Agent: Foster/ Harrington Team from Listing Office: Coldwell Banker Realty - Milton.
4 Hawthorn Rd, Milton
$1,379,000
4 Beds ⋅ 3 Baths ⋅ 73591215 MLS
Welcome to 4 Hawthorn Road, a distinguished Colonial nestled in Milton's sought-after Columbine neighborhood, where timeless New England charm meets exceptional modern living. Offering approximately 2,552 square feet of above-grade living space across three beautifully appointed levels, this four-bedroom, 2.5-bath home has been extensively improved with comfort, quality, and versatility in mind. The inviting main level showcases hardwood floors, a sun-filled living room with an electric fireplace, an elegant formal dining room, and a charming sunroom. The updated kitchen features granite countertops, a center island, upgraded cabinetry, stainless steel appliances, and generous storage, creating a welcoming space for everyday living and entertaining. The crown jewel of the home is the remarkable third-floor primary ensuite, completed in 2024. Designed as a private retreat, this expansive space features a comfortable sitting area, a sleek electric fireplace, a beautifully appointed bathroom with double vanity and tiled shower, convenient in-suite laundry, and enhanced insulation and soundproofing. Three additional bedrooms and a versatile study offer flexibility for family, guests, or a home office. Thoughtful improvements include upgraded electrical and plumbing, 200-amp electrical service, heat pumps and mini-splits, enhanced insulation, and a 14kW natural gas standby generator. Outside, a detached garage, fenced yard, patio, welcoming porch, and deck with newly installed mahogany deck boards provide inviting spaces to relax and entertain. Rich in architectural character and enhanced by substantial modern upgrades, 4 Hawthorn Road offers an exceptional opportunity to enjoy the charm of a classic Colonial with the comfort and convenience of today's lifestyle in one of Milton's most desirable neighborhoods.

4 Hawthorn Rd, Milton

Listing courtesy of Listing Agent: Frederick Hartford from Listing Office: Keller Williams Realty Boston South West.
6 Rowe St, Milton
$799,000
3 Beds ⋅ 1 Baths ⋅ 73591196 MLS
Opportunity Awaits!! Located in a desirable Milton neighborhood, this well-maintained Colonial offers plenty of potential for its new owners. A charming 3 Bedroom, 1 Bathroom home featuring hardwood floors throughout, high ceilings, a formal dining room with a built-in hutch cabinet, a relaxing den and a sunny living room with a beautiful brick fireplace, a one car garage under & a sun-filled 3 season porch overlooking a beautiful yard. Other attributes include a newer roof, newer driveway, newer water line, vinyl siding, a natural gas steam furnace & main bedroom with walk-in closets. A spacious walk-up attic creates the opportunity to finish it as a home office or bonus room. Also, a large walk-out ground level basement that can be finished for additional living area. This location is absolutely perfect. Walk to East Milton Square Shoppes, Markets & Restaurants. Near Cunningham Park which provides a playground, baseball fields, tennis & basketball courts, trails & a community pool. Close to Collicott Elementary School. Easy highway access & public transportation to Boston and the Cape.

6 Rowe St, Milton

Listing courtesy of Listing Agent: Jeffrey D. Sill from Listing Office: Reliant Real Estate, Inc..
48 Hawthorn Rd, Milton
$979,000
4 Beds ⋅ 2 Baths ⋅ 73591193 MLS
Single-family treasure in Milton’s highly coveted Columbine neighborhood! Set on a quiet street, this charming 1922 Colonial seamlessly pairs timeless period character with everyday functionality. A light-filled front porch welcomes you into an oversized foyer and a living room featuring original beamed, coffered ceilings and classic architectural details. The main level offers comfortable living spaces, a bright formal dining room ideal for hosting, an eat-in kitchen, and a convenient half bath. Upstairs, four generous bedrooms and a full bath provide ample room for family and guests. Tremendous expansion potential awaits in the full basement and walk-up attic—ready for a future home office, playroom, media room, or guest suite. Outside, enjoy a private yard perfect for play, gardening, and relaxing. Unbeatable location steps from Kelly Field, Shields Park, Turner’s Pond, Glover School, Milton Academy, and Milton Village, plus quick Boston access via the nearby Trolley Line.

48 Hawthorn Rd, Milton

Listing courtesy of Listing Agent: James Kopecky from Listing Office: Red Tree Real Estate.
341 Highland St, Milton
$3,249,000
6 Beds ⋅ 4 Baths ⋅ 73589772 MLS
Grand 7.5 acre Estate in ideal Milton location. 341 Highland Street is tucked away at the end of a long, private approach and opens up to impressive grounds and a stately brick Colonial with circular driveway. The secluded 7.5 acres has a flowing combination of lawn, gardens & woodlands, including walking trails. The 6-Bedroom, 3.5-bath home starts with a grand entry foyer with ornate woodwork & a layout made for entertaining. A stunning combination of French- & pocket-doors for separation link the formal living and dining space with the Chef's kitchen that has radiant heated floors, countertop range, wall oven & banquet-style table made for gathering with family & friends. Storage is a standout, w/built-ins in nearly every room & flexible rooms on both first & second floors that work as an office or bedroom. Window bench seats in living room & primary suite are the spots to curl up with coffee & a book. Primary bedroom has en-suite bath & huge walk in changing room with plenty of windows. Heated sunroom brings in light year-round, two staircases add flexibility & a whimsical dollhouse room on the third floor is a bonus. Updates include 212 new Andersen Permashield windows, 200-amp electrical, a newer furnace & many more modernizations. Generous laundry room. Outside, a stone patio, play area, hot tub & fire pit invite fun for every season. A majestic dogwood anchors the gardens & trails that wind through the property creating the feel of a private mini Blue Hills trek. Over 1500 SF of unfinished basement offers room to finish. Concept plans for an in ground pool have been drawn up by a landscape design firm. Developers - there is potential to divide land into separate lots - subject to zoning and town approvals. Buyers to conduct their own due diligence.

341 Highland St, Milton

Listing courtesy of Listing Agent: Vineburgh / DiMella Team from Listing Office: Charlesgate Realty Group, llc.
45 Decker St, Milton
$739,900
4 Beds ⋅ 2 Baths ⋅ 73589512 MLS
This is more than just a residence, this distinguished single-family colonial invites you into a warm, tight-knit community where neighbors look out for one another year-round. Perfectly blending classic charm with everyday functionality, this home is freshly painted ready for its next chapter. The main level features an inviting layout centered around a spacious living room, formal dining room, and an updated kitchen complete with granite countertops, a center island, and a striking designer backsplash. Upstairs, you will find 4-bedrooms and a full bathroom. A standout feature of this property is its exceptional versatility and privacy, highlighted by three-way side-to-side access and the rare convenience of stepping directly into the basement right off the driveway. The finished lower level offers a wonderful private retreat without ever having to leave home. Additional highlights include a fully fenced backyard, an attached garage, and an unbeatable location just moments from the playground, commuter train station, and top-rated schools.

45 Decker St, Milton

Listing courtesy of Listing Agent: Richard C. Maurice from Listing Office: Diamond Realty Professionals.
53 Aberdeen Rd, Milton
$769,000
3 Beds ⋅ 2 Baths ⋅ 73588158 MLS
Welcome to Milton! Opportunities like this don’t come around often. Lovingly maintained and thoughtfully updated, this beautiful 3-bedroom, 1.5-bath home is truly move-in ready and offers the perfect blend of original character, modern updates, and everyday comfort. Pride of ownership is evident throughout, with meticulous attention to detail—from the full restoration of the original brass and glass door hardware to the refinished original wood floors, finished in a beautiful natural satin sheen. The updated kitchen is both stylish and functional, featuring cherry cabinetry with updated modern fronts and hardware, granite countertops, newer designer GE Café appliances, newer porcelain tile flooring, and a charming greenhouse window that brings in an abundance of natural light. The home has been thoughtfully improved over the years, including a new metal roof on the main house in 2018 and an asphalt roof on the garage in 2021. The newer heating system was converted from oil to gas in 2024, and the water heater was replaced in 2017. Designer light fixtures, smooth-finish ceilings, and new recessed lighting in the living room add a refined touch throughout. Elfa closet systems provide smart and efficient storage in the bedrooms, and a newer washer adds to the convenience. A standout feature is the oversized two-car garage, offering privacy and flexibility beyond parking—with space for a workshop, studio, gym, storage, or potentially additional living space or an accessory dwelling, subject to zoning and permitting. The spacious bedrooms feature oversized walk-in closets, while the main level offers a convenient half bath. Outside, the modified farmer’s porch—with board-and-batten siding and a tongue-and-groove ceiling—creates a welcoming spot for morning coffee or relaxing at the end of the day. A generous deck provides plenty of room for summer entertaining, while the fenced rear yard offers space to enjoy the outdoors. On cooler evenings, gather around the working wood-burning fireplace and enjoy the warmth and character that make this house feel like home. Set in a desirable Milton neighborhood convenient to commuter rail, shopping, dining, and everyday amenities, this is the kind of home where you can move in, unpack, and simply enjoy. Beautifully maintained, thoughtfully updated, and ready for its next chapter—just in time for the holidays.

53 Aberdeen Rd, Milton

Listing courtesy of Listing Agent: Bill Lau from Listing Office: Windsor Real Estate LLC.
88 Decker St, Milton
$889,000
3 Beds ⋅ 2 Baths ⋅ 73587033 MLS
Fall in love with this beautifully renovated Cape, where sun-splashed rooms and open, airy living spaces create the perfect blend of comfort and style. Every detail of this magnificent renovation has been thoughtfully designed, offering modern updates while maintaining timeless charm. Step outside to enjoy the private Beacon Hill-style patio, an ideal setting for relaxing, entertaining, or enjoying your morning coffee. The home's bright interiors flow seamlessly from room to room, creating an inviting atmosphere filled with natural light. Conveniently located near the outstanding recreational opportunities of Blue Hills Reservation, Pope's Pond, and the exciting new Peverly Park, this home offers endless options for outdoor enjoyment and family fun. With a stellar location, a truly exceptional renovation, and incredible value, this is a rare opportunity you won't want to miss!

88 Decker St, Milton

Listing courtesy of Listing Agent: Matthew Freeman from Listing Office: Coldwell Banker Realty - Milton.
454 Eliot St, Milton
$779,000
2 Beds ⋅ 2 Baths ⋅ 73584152 MLS
Shelter. Home. They are not always the same thing. But here, what’s necessary and what’s intimate are built into one floor living on a sizable lot at the gateway of the Columbine/Cliff neighborhood. This mid-century ranch has never asked for more than it needed. Two bedrooms, 1.5 baths, 1,200 square feet arranged with the kind of clarity that comes from a floor plan actually lived in. Every room in its right place. A walk-up attic is storage today. It could be more, if someone decides it should be. A screened porch looks out over a private yard and 13,000 sf lot where green space and solitude go hand in hand. Garden or structure to your heart’s content or just admire with a good book being the primary focus. Recent roof and central air have you off to a great start. For the downsizer or small household, it's complete as it stands. For the next owner with ambition and a dream, it's an invitation. Either way, the shelter is already here, and a home is what you will imagine and create.

454 Eliot St, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.
23 Christopher Drive, Milton
$975,000
4 Beds ⋅ 2 Baths ⋅ 73583997 MLS
For the discerning buyer with vision, a spacious 9-room home in desirable East Milton awaits. Set on a residential side street, this well-loved property features 4–5 bedrooms, two full bathrooms, a two-car garage, and a level, fenced backyard on nearly a quarter-acre. The house lives considerably larger than you might expect, with generously proportioned rooms and abundant space at every turn. The main level features a huge front-to-back living room with a center fireplace, a kitchen brimming with possibility, a separate dining room with a built-in hutch, and a bright 4-season sunroom with an adjoining deck. The expansive, fenced 9,500+sf backyard provides ample room for gardening, sports, entertaining, or simply enjoying the outdoors. An office on this level offers flexibility and could serve as a fifth bedroom if desired, while a full bathroom adds convenience. Upstairs, you’ll find four exceptionally large corner bedrooms with excellent closet space, along with a second full bathroom. All hardwood floors throughout the home have just been refinished, and much of the interior has been freshly painted. Additional features include a large, wide-open unfinished basement, along with an attached two-car garage. Situated minutes from the restaurants and shops of East Milton Square, Cunningham Park, top schools, and major commuting routes, this is your chance to make a property with character and an enviable location truly your own.

23 Christopher Drive, Milton

Listing courtesy of Listing Agent: Donna Charpentier from Listing Office: William Raveis R.E. & Home Services.
68 Smith Rd, Milton
$1,850,000
4 Baths ⋅ 73583711 MLS
Exceptional land, restoration, and redevelopment opportunity on the Milton/Hyde Park line. Situated on approximately 1.23 acres in Milton, with additional land extending into Boston/Hyde Park as shown on the existing conditions plan, 68 Smith Rd features a substantial circa-1900 Colonial-style structure containing approximately 7,713 square feet per public record. Previously utilized as a school/institutional facility, the existing structure is not presently configured as a conventional residence, creating a unique opportunity for a buyer, builder, developer, or investor to explore restoration, renovation, or redevelopment of the site. The property offers substantial land area in a desirable Milton location with convenient access to Boston and surrounding communities. Property is being offered AS-IS. Existing structure is subject to a municipal order; buyer to independently verify current status. Seller and listing brokers make no representations or warranties regarding subdivision, buildability, number of lots, development yield, permitted use or feasibility of conversion to residential use. Existing conditions plan and additional property information are available through MLS documents. Buyer and buyer’s representatives are responsible for independently verifying zoning, utilities, lot configuration, living area, intended use, and all required municipal approvals.

68 Smith Rd, Milton

Listing courtesy of Listing Agent: Zachary Dieujuste from Listing Office: Lifestyle Realty Group LLC.
11 Austin St, Milton
$829,999
3 Beds ⋅ 2 Baths ⋅ 73582555 MLS
Motivated Seller! Ask about rate buy down! Discover a piece of Milton's heritage at 11 Austin St, a charming single-family residence built in 1910, offering 1460 square feet of thoughtfully designed living space. This property presents a unique opportunity to embrace a lifestyle characterized by classic charm and modern convenience. The home features three and half comfortable bedrooms, providing ample private space for relaxation, rejuvenation and a potential office space. With one full bathroom and an additional half bathroom, the property offers practical amenities for daily living. Experience the enduring appeal of a home designed for comfortable living, perfectly situated on a 3115 square foot lot, and close to the highway, nearby shopping, public transportation and more. Schedule your private viewing and envision the possibilities at this remarkable Milton address. The TV and soundbar is included in sale unless otherwise communicated.

11 Austin St, Milton

Listing courtesy of Listing Agent: Stephen Gousby from Listing Office: Gousby Realty Group LLC.
68 Avalon Rd, Milton
$1,249,000
4 Beds ⋅ 3 Baths ⋅ 73581867 MLS
Nestled in the highly coveted Columbine neighborhood, this picture-perfect home is overflowing with charm, character, and timeless detail. Perched high on the lot and surrounded by mature trees, it enjoys a wonderful treehouse-like setting, where nature fills every window and creates a peaceful sense of retreat.Lovingly maintained and thoughtfully renovated over the years, the home beautifully blends its original character with the comforts of modern living. Sunlight pours into the inviting rooms, highlighting the warm architectural details and creating spaces that feel both elegant and welcoming. Whether gathering with friends or enjoying a quiet evening at home, every room has a special warmth and personality. The enchanting backyard feels as though it was borrowed from Beacon Hill, offering a private oasis with charming landscaping and intimate outdoor spaces perfect for entertaining, gardening, or simply unwinding at the end of the day. Central air adds modern convenience, while the home's tasteful updates ensure it is move-in ready without sacrificing its soul. A rare opportunity to own a truly special home in one of the area's most beloved neighborhoods, this Columbine gem offers the perfect combination of charm, comfort, and character in a setting that feels worlds away, yet remains close to everything.

68 Avalon Rd, Milton

Listing courtesy of Listing Agent: Matthew Freeman from Listing Office: Coldwell Banker Realty - Milton.
901 Randolph Ave, Milton
$1,895,000
4 Beds ⋅ 3 Baths ⋅ 73581598 MLS
Come take a fresh look at 901 Randolph Ave. At its new price, this beautifully updated Milton home offers an exceptional combination of space, lifestyle and value. Inside, you’ll find a truly move-in-ready home with a beautifully updated kitchen featuring a 12-foot island, quartz countertops, Thermador appliances and an open floor plan. All three full baths have been fully renovated. Outside, extensive improvements include new windows, siding, garage doors and roof. But what truly sets this property apart is what awaits out back: more than an acre of land, a gorgeous deck, in-ground pool, built-in outdoor kitchen and a spectacular setting overlooking the 12th hole of Wollaston. Whether entertaining a crowd, spending summer afternoons by the pool or simply enjoying the view, this is a backyard designed to be enjoyed. With 4,772 SF and nothing left to do, this home offers an opportunity that deserves another look. The main-road location is balanced by a remarkably private backyard retreat, where the pool, outdoor kitchen and sweeping views of Wollaston create something truly special.

901 Randolph Ave, Milton

Listing courtesy of Listing Agent: Beth Rooney from Listing Office: eXp Realty LLC - Corporate Office.
631 Blue Hill Ave, Milton
$899,000
3 Beds ⋅ 3 Baths ⋅ 73577397 MLS
Privately sited on a beautiful one-acre parcel, this substantial home commands attention with its impressive scale, high ceilings, and spacious layout. Sun-filled rooms and expansive living areas create an inviting atmosphere while offering tremendous flexibility for today's lifestyle needs. Whether you're seeking space to grow, entertain, or customize to your personal vision, this property presents an extraordinary opportunity to unlock its full potential. A rare chance to own a home with incredible bones, exceptional privacy, and endless possibilities. Property is currently VA financed and potentially can transfer rate to VA financed buyer. Buyer and buyer agent to do all due diligence in this matter.

631 Blue Hill Ave, Milton

Listing courtesy of Listing Agent: Matthew Freeman from Listing Office: Coldwell Banker Realty - Milton.
61 Belcher Cir, Milton
$949,000
4 Beds ⋅ 2 Baths ⋅ 73577111 MLS
There's a particular kind of quiet that settles over a Victorian like this one, built in 1902 and still wearing its history proudly. Step onto the wrap around front porch and through a front door that has welcomed families for well over a century. This is a house that knows what it is. Inside, the bones tell the story, quarter sawn oak trim, a grand front staircase with a hand turned newel post and a good morning staircase leading to the second floor, French doors with their original beveled glass and wide plank oak floors that still glow. Three full levels of living offer four large corner bedrooms flooded with light from multiple exposures. This is your chance to start with a clean slate and design the chef's kitchen you've been dreaming about, choose your favorite Benjamin Moore colors or make a statement with Thibaut wallpaper in the front hall. The craftsmanship is already here. The vision is yours to add. Outside, the property sits on nearly a quarter acre and backs directly to Andrews Park, with tennis courts, playground, baseball fields and green space right out your back door. Mature trees wrap the lot and it's hard to believe you're this close to the cityscape. Add in the benefit of top ranked Milton Public Schools, with Milton High School consistently recognized among the best in Massachusetts. Pair that with proximity to the North Quincy Red Line station, the expressway and the shops and restaurants of East Milton Square, making this one of Milton's most connected and most desired addresses. This is a house built to be lived in for another hundred years. The only question is what you'll bring to it!

61 Belcher Cir, Milton

Listing courtesy of Listing Agent: Cahill+Co. Team from Listing Office: William Raveis R.E. & Home Services.
65 Sassamon Ave, Milton
$779,000
2 Beds ⋅ 2 Baths ⋅ 73575577 MLS
Welcome to this charming modern ranch-style home offering comfortable single-level living in a desirable Milton location. This well-maintained home features 2 bedrooms, 2 full bathrooms, newer furnace, newer water heater, refinished hardwood floors throughout, newer windows, central heat and air conditioning, and a bright, inviting interior. Functional floor plan includes spacious living areas. One-car garage located under, and additional storage. The expansive unfinished basement flexible space, presenting excellent expansion potential for future living areas, recreation space, a home office, fitness area, or workshop. Attractive curb appeal and a comfortable layout make this property truly stand out. Conveniently situated with easy highway access and close to local amenities, this home offers a wonderful opportunity to personalize and enjoy for years to come. Access to I-93, public transportation, Wollaston Golf course and the Blue Hills Reservation for year-round adventure.

65 Sassamon Ave, Milton

Listing courtesy of Listing Agent: Olivia Tjie from Listing Office: Redfin Corp..
84 Blue Hills Parkway, Milton
$999,890
4 Beds ⋅ 3 Baths ⋅ 73574898 MLS
Ask About Rate Buy-Down Incentives on this Property!! 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.
540 Harland St, Milton
$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.
355 Brush Hill Road, Milton
$1,185,000
3 Beds ⋅ 3 Baths ⋅ 73566740 MLS
Situated in Milton’s Brush Hill Estate area, this 9-room, mid-century home on nearly an acre offers 3182 square feet of living space and a wonderful opportunity to add your personal touches. The property includes a two-car garage and several well-maintained updates over the years, including an addition and a renovated finished lower level, all adding to its appeal. On the main level, the home features a semi-open living room with a fireplace, a well-appointed kitchen with S/S appliances and recessed lights, a dining room with built-ins, and a sunroom/den with a wall of windows. There’s also a breakfast area with a skylight and sliding door leading to a small deck for your convenience and easy maintenance. Three bedrooms, each with ample closet space, including a primary en-suite bedroom and a hallway bath, complete the main level. The finished lower level features a spacious family room with a second fireplace, a separate office with custom cabinetry, a laundry room, a mud room/pantry with an extra refrigerator and upright freezer, and direct access to the garage. The utility/mechanical room houses all the home's systems, including five heating zones and central air conditioning for year-round comfort. The expansive grounds include a patio area, an in-ground gunite swimming pool in need of some repairs, and three sheds providing extra storage for gardening tools and outdoor furniture. Move in now and make your desired alterations over time. Do not miss this unique opportunity. Enjoy easy access to the commuter rail, downtown Boston, Longwood Medical Area, the Neponset Bike Path, Blue Hills, Milton Academy, and more.

355 Brush Hill Road, Milton

Listing courtesy of Listing Agent: Christine Dillon from Listing Office: Coldwell Banker Realty - Newton.
45 Wendell Park, Milton
$1,050,000
4 Beds ⋅ 2 Baths ⋅ 73565687 MLS
Floors refinished this week! Come take a look. Only the second owners have ever called this house home, and that kind of stewardship is impossible to fake. It shows in every room. Warm floors, generous light, and rich original woodwork greet you at the door and carry through the main level. The kitchen was updated a decade ago with choices that were timeless then and still feel current now, the mark of an owner who renovated for the long haul rather than the trend. Out front, a welcoming porch looks across the street to the park, the kind of spot where mornings slow down and neighbors stop to talk. Out back, a patio sits level with both the house and the yard, an easy flow from kitchen to grill to pool. The pool itself was renovated three years ago, with a dedicated changing room right off the deck. Four well proportioned bedrooms anchor the sleeping level, while the finished attic adds flexible space above and two dedicated offices mean working from home never means working from the dining table.

45 Wendell Park, Milton

Listing courtesy of Listing Agent: Bridget Conroy from Listing Office: Coldwell Banker Realty - Milton.
37 Nahanton Ave, Milton
$799,000
3 Beds ⋅ 2 Baths ⋅ 73563860 MLS
Classic Colonial charm meets everyday comfort at 37 Nahanton Avenue. This inviting 3-bedroom, 1.5-bath home features sun-filled rooms, beautiful hardwood floors, and central air. The welcoming living room opens to a charming screened-in porch overlooking the backyard—a peaceful spot for morning coffee or unwinding at the end of the day. Outdoors, there’s room to garden, entertain, or simply relax.Conveniently located near Milton’s schools, parks, shopping, and dining, with easy access to major routes and Boston, this home offers both neighborhood charm and accessibility. Enjoy its character today while adding your own style over time. Discover the possibilities and make this Milton Colonial your own.

37 Nahanton Ave, Milton

Listing courtesy of Listing Agent: Julie Joyce from Listing Office: Coldwell Banker Realty - Milton.
33 Harbor View Park, Milton
$2,750,000
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.
128 Pleasant St, Milton
$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.
15 Churchill St, Milton
$699,999
3 Beds ⋅ 2 Baths ⋅ 73557060 MLS
Some homes announce themselves from the curb. This one saves the reveal for inside.Step through the mudroom into a wide, warm first floor where dark-stained beams cross the ceiling, hardwood floors run beneath a bay of windows, and thoughtful craftsmanship gives the home its character. At the center, a striking navy shaker kitchen pairs quartz countertops with a farmhouse sink beneath a triple window, gas cooking, and marble tile carried dramatically to the ceiling.The full bath is finished with hand-set stone chevron mosaic and a built-in niche. A separate half bath and first-floor laundry keep everyday life where it belongs on the living level. Upstairs, three bedrooms are laid out simply and efficiently, without wasted space.Outside, sliders open to a newly finished paver patio, stone fire pit, fresh sod, and a level yard wrapped in full privacy fencing. Four-car parking adds another layer of practicality. Minutes from the Mattapan trolley and Route 93, this is a home where strong design and real-life function meet.

15 Churchill St, Milton

Listing courtesy of Listing Agent: Tayla Andre from Listing Office: Thumbprint Realty, LLC.
106 Edge Hill Rd, 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.
1632 Canton Ave, Milton
$4,800,000
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.
52 Meagher Ave, Milton
$640,000
3 Beds ⋅ 2 Baths ⋅ 73544814 MLS
** OpenHouse Saturday 12 to 1:30pm ** 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.
55 Parkwood Drive, Milton
$5,995,000
7 Beds ⋅ 10 Baths ⋅ 73519804 MLS
Experience the pinnacle of Milton living at this 1915 French Colonial masterpiece. Set on nearly three acres at the foot of the Blue Hills Reservation, this legacy estate offers a rare blend of privacy and prestige. The grounds are an entertainer’s dream, featuring an in-ground pool, pool house, and a two-story, five-bay garage with an attached vintage greenhouse. Spanning 9,000+ sq. ft., the residence boasts seven bedrooms, ten bathrooms, and nine fireplaces. The main level offers grand formal spaces, including a mahogany-paneled library and a sophisticated office. The chef’s culinary suite is a masterwork of marble and high-end gas ranges. Retreat to the palatial primary wing—a four-room haven with dual baths and expansive views. The finished lower level adds versatility with twin fitness studios and a private lounge and office. Located eight miles from Boston and Logan, enjoy a country-manor lifestyle near world-class Milton Academy. A rare architectural gem. Welcome home!

55 Parkwood Drive, Milton

Listing courtesy of Listing Agent: Kevin G. Keating from Listing Office: Keating Brokerage.

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