Milton MA Historical Real Estate, Homes for Sale

2 Beds ⋅ 2 Baths ⋅ NEW Status ⋅ 73601212 MLS ⋅ 1,056 SqFt.

Welcome to 50 Sheldon Street, Unit 1, ideally situated in desirable East Milton! This modern 2-bedroom, 2-bathroom home offers 1,056 square feet of comfortable living space with a thoughtful layout and stylish finishes throughout. The kitchen features white shaker cabinetry, stainless steel appliances, natural stone countertops, and a convenient coffee bar/mudroom just off the kitchen providing additional storage. The generously sized second bedroom is positioned at the front of the unit, creating excellent separation and privacy from the spacious primary suite at the rear. The primary suite features an en-suite bathroom and two closets, including a walk-in. Additional highlights include forced-air heating and central air conditioning for year-round comfort, plus the added convenience of two off-street parking spaces and private basement storage. A wonderful opportunity to enjoy comfortable, low-maintenance living in a sought-after East Milton location!

50 Sheldon St Unit 1, Milton

$965,000

6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 73600442 MLS ⋅ 2,775 SqFt.

Welcome to this beautiful and spacious 6-bedroom, 4-bathroom home located in the highly desirable town of Milton, Massachusetts! Offering the perfect combination of space, comfort, and convenience, this home is ideal for families, entertaining, and everyday living. Featuring generously sized 6 bedrooms 4 full bathrooms, and plenty of living space, this property has room for everyone. Step outside and enjoy a large backyard, perfect for summer gatherings, outdoor entertaining, relaxing, or creating your own private outdoor oasis. Additional highlights include a potential ADU in the rear of home what once was a over sized shed and garage can now be used for another dwelling/living space. convenient off-street parking, proximity to excellent schools, and an unbeatable location close to shopping, restaurants, parks, and a variety of local amenities. Enjoy everything Milton has to offer while having the space and comfort to truly feel at home.

96 Houston Ave, Milton

$8,900,000

7 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 73599988 MLS ⋅ 10,707 SqFt.

AUCTION: Bidder registration deadline: 7 Dec. Starting bids expected between $4M-6M.Nearly 20 private acres in the heart of Milton, just 20 minutes from downtown Boston, make this turn-of-the-century estate a truly rare offering. Land holdings of this scale have all but disappeared this close to the city, and this estate along storied Highland Street preserves the sense of space and seclusion that once defined Boston’s great country houses. Built around 1900, the residence carries enduring New England character, while a multi-residence configuration adds flexibility for guests. Beyond the grounds, the 7,000-acre Blue Hills Reservation extends the feeling of open land, with downtown Boston’s dining, culture, and waterfront an easy drive away. Property and opportunity details provided by seller or others; buyer to verify.

241 Highland Street, Milton

$850,000

4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73599006 MLS ⋅ 2,808 SqFt.

***EXCELLENT OFFER ACCEPTED, OPEN HOUSES CANCELLED*** Deeply cherished and thoroughly enjoyed by same owners since 1972, the original 1922 single story bungalow was GREATLY expanded with a massive 2 story colonial addition in 1987 creating a most unexpected combination of old and newer space totaling nearly 3,000 square feet of living area. With 10 rooms you'll have myriad living options including 1st or 2nd floor primary; perhaps a good fit for multi-generation living. See attached floor plan for room layout and flow. I don't think you'll find another quite like it in Milton! Yes, the kitchen is adorable but will need updating. Fireplace likely does not function. French door to the side deck requires attention and probably so do 50 more things. Definitely work to be done here, but should not be considered a true gut renovation. You will be hard-pressed to find more above-grade space for the money. Interior is freshly painted, though exterior is in need of EXTENSIVE restoration and some forms of financing will be affected. Full basement under the bungalow section has remnants of interior walls and partitions, which have been partially torn down. You'll need to start over if you intend to finish it. Laundry is in basement, but ample room to bring upstairs. The 1899 subdivision plan (attached) refers to the neighborhood as Mount Pleasant. Important updates: carpeting 2026; boiler 2025; roof and skylight replaced 2024; oil tank 2023; replacement windows 2012. Garage structure in poor condition. Strongly suggest you watch the short narrated video tour to better understand the flow and overall condition of this unique property, but you should really come visit. PLEASE make any offers valid for minimum 24 hours.

20 Mathaurs Street, Milton

$598,999

3 Beds ⋅ 3 Baths ⋅ BACK ON MARKET Status ⋅ 73593760 MLS ⋅ 1,209 SqFt.

Welcome to 70 Brush Hill Road, a fully renovated home in one of Greater Boston’s most sought-after suburbs. The main living area features a coffered ceiling with dentil crown molding, recessed lighting, built-in speakers and polished, large-format marble-look tile throughout the living room and kitchen area. Floating custom cabinetry with brushed-gold hardware frames a stone feature wall, complemented by brass sconces, arched openings and built-in shelving beneath the staircase.The first-floor primary suite offers single-level living and flexibility for intergenerational households, with refinished hardwood floors, a beamed tray ceiling, custom built-ins and a private bath. Upstairs, cathedral ceilings with exposed wood beams, dentil crown molding and refinished hardwood continue the craftsmanship. The bath features a walk-in shower with floor-to-ceiling tile, rain showerhead, handheld wand, built-in bench, niche and river-stone floor.A dream for dog lovers: a stone-clad pet wash station with handheld sprayer in the lower level, a custom pet closet for leashes and supplies, and a yard with plenty of room to run.The backyard is built for entertaining, with a stone outdoor kitchen and stainless grill, a sunken fire pit with built-in stone seating, granite steps, paver walkways and tons of open space.The lower level is a blank canvas awaiting the buyer’s finishes. It already includes a laundry area with front-load washer and dryer, a powder room with wall-hung toilet and trough sink, and a bonus room with built-in bench seating, sconces and recessed lighting. Finish it as a media room, gym, office or guest space.Milton not only offers highly regarded schools, but quick access to Boston and nearby trails and outdoor recreation. Come see it today!

70 Brush Hill Rd Unit 70, Milton

$839,000

3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73593447 MLS ⋅ 1,454 SqFt.

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

$1,379,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73591215 MLS ⋅ 2,552 SqFt.

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

$799,000

3 Beds ⋅ 1 Baths ⋅ CONTINGENT Status ⋅ 73591196 MLS ⋅ 1,576 SqFt.

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

$969,000

4 Beds ⋅ 2 Baths ⋅ PRICE CHANGED Status ⋅ 73591193 MLS ⋅ 1,768 SqFt.

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

$630,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73590212 MLS ⋅ 1,660 SqFt.

NO CONDO FEE, A FULL GUT RENOVATION, AND EVERY MAJOR SYSTEM NEW IN 2025. This Milton, MA condo gives you new-construction living without the monthly dues. The open-concept kitchen has quartz countertops and stainless steel appliances, and it flows into a sunny dining and living area with hardwood floors. Two bedrooms and two full baths sit on the main level. Downstairs, the finished lower level adapts to a home office, media room, or play space. A bonus room is ready for a home gym, with extra storage and in-unit laundry. The like-new furnace, central A/C, windows, and water heater (all 2025) mean no big-ticket replacements on the horizon. Step out to your private deck or the shared patio. You also get two exclusive side-by-side parking spaces. Pets are welcome, and shops, parks, and highway access are minutes away. Move-in ready. Schedule your showing today.

172-174 Blue Hill Ave Unit 174, Milton

$3,249,000

6 Beds ⋅ 4 Baths ⋅ CONTINGENT Status ⋅ 73589772 MLS ⋅ 6,074 SqFt.

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

$739,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73589512 MLS ⋅ 1,392 SqFt.

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

$625,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73589069 MLS ⋅ 2,097 SqFt.

You'll love this spacious Milton condo with 2,000+ square feet across two levels and a garage plus three additional parking spots. The main level is full of original character. Coffered ceilings, bay windows, and gleaming hardwood floors set the tone in the living room, which flows into a sunny dining area. The kitchen is the heart of it all, with a large center island, granite counters, a gas range, stainless appliances, and recessed lighting. A main-level bedroom with a walk-in closet sits near a full bath. There's also a den that opens to a private front balcony overlooking the trees, plus a home office and a bright laundry room with walls of windows and a back deck. Head upstairs and the space really opens up. The primary suite is over 300 square feet with vaulted ceilings, recessed lights, a mini-split, and two walk-in closets. The primary bath has a double vanity, a soaking tub, and a separate shower. A second bedroom rounds out the upper level. Three bedrooms, two full baths, an office, and a den give you room to work from home, host guests, or just spread out. All this in a classic shingle-style home on historic Brush Hill Road, with easy access to the Blue Hills, Legacy Place, Route 138, I-93 and I-95 and the T. Come see it in person, You'll be glad you did...

162 Brush Hill Rd Unit 2, Milton

$1,150,000

3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73588638 MLS ⋅ 2,014 SqFt.

Welcome to this centrally located, beautifully renovated Colonial, ideally situated within a short walking distance of the Milton Public Library and Milton Academy.The first floor features a bright, open-concept layout with a spacious kitchen boasting an oversized center island, a dining area with a sliding door leading to the exterior composite deck, a convenient half bathroom, and a welcoming living room with a charming brick fireplace.The second floor offers three comfortable bedrooms and two full bathrooms, including a private en-suite bathroom in the primary bedroom.The finished walk-out basement provides versatile additional living space, with one area ideal for a home gym or game room and another perfect for entertaining, relaxing, or family activities.Outside, enjoy the large composite deck overlooking the beautiful yard—an ideal setting for outdoor dining, gatherings, or simply relaxing.This beautifully renovated home offers a wonderful combination of location, modern updates, versatile living space, and outdoor enjoyment. This is a must-see!

32 Centre St, Milton

$769,000

3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73588158 MLS ⋅ 1,395 SqFt.

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

$749,000

3 Beds ⋅ 1 Baths ⋅ UNDER AGREEMENT Status ⋅ 73587170 MLS ⋅ 1,326 SqFt.

SUNDAY OPEN HOUSE CANCELLED! Classic charm meets an exceptional Milton location in this beautifully maintained 1903 farmhouse. Set on a picturesque 6000sqft lot, this inviting 3 bedroom, 1 bath home blends timeless character with the ease of everyday living. A welcoming front porch creates an idyllic setting for morning coffee and relaxing afternoons, while private outdoor spaces are perfect for entertaining friends and add to the home's appeal. Inside are warm, comfortable living spaces filled with natural light and thoughtful updates. The stylish kitchen provides a functional heart of the home, while 3 well-proportioned bedrooms offer flexibility for family, guests, or a home office. The home's classic architectural details and handsome exterior create the kind of curb appeal that is increasingly difficult to find. The location is truly special- just moments from Shields Park, with convenient access to the trolley for an easy connection to Boston. Enjoy the best of Milton's vibrant neighborhood amenities with popular restaurants, cafes and shops all within walking distance. A wonderful opportunity to own a distinctive piece of Milton's history in one of it's most desirable and convenient neighborhoods.

12 Capen St, Milton

$889,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73587033 MLS ⋅ 1,450 SqFt.

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

$1,150,000

8 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73586409 MLS ⋅ 2,785 SqFt.

Tenants have lease until End of Nov. Discover this beautifully updated 2-family home in one of Milton’s most desirable locations! This spacious three-story property is perfect for both investors and owner-occupants. The first floor has been fully renovated, showcasing a modern kitchen with stainless steel appliances, quartz countertops, and a bright open layout. The second unit extends across two levels, with generous bedrooms, ample storage, and a third-floor bonus retreat featuring a wet bar—ideal for entertaining or creating a private suite. Location highlights: set on Brush Hill Rd, the home offers quick access to I-93, making commutes to Boston and Cambridge effortless. Enjoy proximity to Blue Hills Reservation for outdoor recreation, top-rated Milton schools, local shops, and restaurants. With strong rental potential, versatile living options, and a prime location, this updated multi-family is a rare find in Milton. Move right in and start enjoying everything this home.

112 Brush Hill Rd, Milton

$899,000

4 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73585759 MLS ⋅ 2,043 SqFt.

Sometimes you just need the facts. Here they are. As close to new construction as you'll find. Completely gutted and redesigned in 2019 for today's ideal layout with updated wiring, plumbing, siding, a newer roof, windows and a newer heating system with central air. The heart of the home is a large open kitchen anchored by a Thermador range. Two full levels of living give you options. Grow into it or lock the door and travel in the off season without a second thought. Four bedrooms, two full baths and a dedicated laundry room are spread across the second and third floors. Parking is easy, with a one car garage plus two driveway spaces. Location? Right in the center of town! Steps from the Milton Public Library, which is so much more than a library. It's a true community hub with everything from mah jong groups to book clubs. Or escape into the city on the trolley just down the street on Central Ave. Tired of the Milton Academy commute? Say no more. This is the perfect weekday home base. Everything is done. SHOWINGS BEGIN IMMEDIATELY, so don't sit on the fence with this one.

440 Central Ave Unit 2, Milton

$1,395,000

3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73584614 MLS ⋅ 2,307 SqFt.

Welcome to 19 Edward Avenue, a beautifully updated home nestled in one of Milton’s most cherished neighborhoods. Tucked away on one of the town's most secluded streets, this special location offers a wonderful sense of community where neighbors become friends, locals gather for impromptu lemonade stands, and walks to Cunningham Park are part of everyday life. Just moments from vibrant East Milton Square, you'll enjoy easy access to local favorites, dining, shopping, and recreation. Inside, a welcoming foyer leads to a spacious living room with a wood-burning fireplace, an inviting four-season sunroom with vaulted ceiling and slate flooring, an open, sun-filled kitchen and dining area perfect for everyday living and entertaining, both with direct access to the tranquil backyard. Upstairs are 3 generous bedrooms and 2 full baths, including a coveted primary suite. Thoughtfully updated throughout with timeless finishes, this home is move-in ready. Outside, the private backyard oasis features a beautifully maintained yard and patio, creating the perfect setting to relax, entertain, and enjoy all this exceptional home and neighborhood has to offer.

19 Edward Avenue, Milton

$779,000

2 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73584152 MLS ⋅ 1,206 SqFt.

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

$975,000

4 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73583997 MLS ⋅ 1,896 SqFt.

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

$1,850,000

4 Baths ⋅ ACTIVE Status ⋅ 73583711 MLS ⋅ 7,713 SqFt.

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

$829,999

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73582555 MLS ⋅ 1,460 SqFt.

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

$1,249,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73581867 MLS ⋅ 2,079 SqFt.

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

$1,795,000

4 Beds ⋅ 3 Baths ⋅ PRICE CHANGED Status ⋅ 73581598 MLS ⋅ 4,772 SqFt.

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

$1,300,000

3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73579718 MLS ⋅ 3,658 SqFt.

Exceptional space, flexibility and outdoor living await at 17 Hallen Avenue. Set on an expansive 40,000-square-foot lot, this sprawling Milton ranch offers 3,658 SF of total living area, an in-ground swimming pool, attached 2-car garage and driveway parking for up to 6 additional vehicles.The 1,941 SF main level features all 3 bedrooms and 2 full bathrooms, providing the convenience of primarily one-level living. The main level offers 8 rooms, including a spacious living room, dining room, eat-in kitchen, enclosed sunroom and a versatile bonus room with multiple access points, including direct access to the garage. Two fireplaces, central air, a main-level laundry area and generous storage add to the home’s functionality.The finished 1,717 SF lower level provides exceptional additional living space with 4 rooms, including a second eat-in kitchen, a large entertainment room and two additional bonus rooms, plus a second laundry area and additional crawl-space storage. The lower level also offers direct backyard access and interior access to the main level. With its second kitchen, full bathroom, laundry facilities and flexible layout, this level offers excellent potential for an in-law or multigenerational living arrangement, or possible ADU conversion, subject to applicable zoning, permitting and approvals.Additional storage is available in the spacious attic storage area and large outdoor shed. Outside, the expansive grounds and in-ground swimming pool create an outstanding setting for entertaining, recreation and summer enjoyment.Ideally situated in Milton, the property combines suburban space with exceptional proximity to Boston—approximately 10 miles from Downtown Boston—while remaining close to Milton Academy, Wollaston Golf Club, East Milton Square, Novara, Abby Park and many of Milton’s local amenities. Nature lovers and outdoor enthusiasts will appreciate nearby Blue Hills Reservation, offering hiking, year-round recreation and seasonal skiing.17 Hallen Avenue offers a rare combination of 12 rooms, two kitchens, two laundry areas, flexible multigenerational living space, abundant parking, generous storage, a pool and a substantial lot—all with convenient access to Boston.

17 Hallen Ave, Milton

$999,000

5 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73579278 MLS ⋅ 2,462 SqFt.

Motivated seller - don't miss out! This is the best opportunity in Milton. 27 Glendale Road has an updated kitchen, with large island, stainless steel appliances & an open concept dining area.Close to Milton Schools & Cunningham Park.Plus, a spacious primary suite with large close and glass enclosed shower stall. Also, this home has Central AC, 5 bedrooms, a partially finished basement and a one car garage. Lastly, this home has an in ground pool!Ready for new owners!!

27 Glendale Road, Milton

$1,249,000

4 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73578361 MLS ⋅ 2,273 SqFt.

Welcome to 10 Hazel Street, a beautifully updated 4-bedroom home tucked away on one of Milton’s quintessential side streets, offering the perfect blend of classic New England character and modern comfort. At the heart of the home is a brand-new kitchen featuring custom white cabinetry, quartz countertops, a stylish tile backsplash, Bosch range, Thermador drawer microwave, Summit beverage refrigerator, and generous workspace for everyday living and entertaining. The kitchen flows naturally into the home’s inviting living spaces, where high ceilings, hardwood floors, crown moldings, and abundant natural light preserve the warmth and character of the original home. The flexible floor plan includes four bedrooms and two full baths, with plumbing already in place for a potential third full bath. The primary suite features a walk-in closet and adjoining office, creating an ideal work-from-home space or an opportunity to add an additional bath. The finished lower level provides even more versatility for a family room, playroom, gym, or additional home office. Outside, the fenced and beautifully landscaped backyard feels like a private retreat, complete with a spacious patio, mature plantings, irrigation, and plenty of room to entertain or unwind. A substantial carriage house provides exceptional storage and adds to the property’s classic charm. Additional features include central air conditioning, tankless systems, heated bathroom flooring, and thoughtful updates throughout. Ideally situated close to Cunningham Park, neighborhood schools, and the shops and restaurants of East Milton Square, 10 Hazel Street delivers character, location, and modern updates in one of Milton’s most convenient neighborhood settings.

10 Hazel Street, Milton

$899,000

3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73577397 MLS ⋅ 2,517 SqFt.

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

$949,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73577111 MLS ⋅ 2,155 SqFt.

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

$759,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73575577 MLS ⋅ 1,124 SqFt.

REDUCED to sell! Must see! Move into 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. Spacious living area, private yard, drive way and one-car garage located under plus 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. Desirable top school district. 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. Move in ready!

65 Sassamon Ave, Milton

$949,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73574898 MLS ⋅ 3,328 SqFt.

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. Open House This Sat, Oct 31 11:00 - 12:30

84 Blue Hills Parkway, Milton

$1,175,000

7 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 73574773 MLS ⋅ 2,860 SqFt.

***Price Reduced*** View By appointment anytime. Rare three-family on Blue Hills Parkway in the Milton Public Schools district, between the Neponset bike path and Blue Hills Reservation. Tucker School is right next door; Churchill’s is down the parkway; Mattapan Station, local buses, and highway access are a short hop. Trails and neighborhood parks are out the front door.Three units: first-floor 2-bedroom (currently configured as a 3-bedroom); second-floor 3-bedroom; and a third floor 1-bedroom. The first-floor unit is vacant and opens to a large lower level. Use the lower level as office space,kiddy play-rooms, maybe take up a hobby — or expand the 1st Floor unit into the massive sq footage on the lower level. A giant 1st & ground 2-floor owner’s suite come to mind. (Bonus 3/4 bath & laundry hookup -- already there) Build yourself some wealth. Units 2 and 3 are occupied, so you can live on the first floor, keep the rental income from top 2 apartments, while you figure out what to do with all that space, work on your timeline. Hard to find this much flexibility in Milton this close to the Reservation, highway, schools and public transportation. Units 2 and 3 are market rate. Bespoke showings need a minimum 24-hour notice to accommodate the children's nap schedules. Come through on a weekend open house, or schedule a private tour anytime. Many possibilities and now at an improved price.

197 Blue Hills Pkwy, Milton

$2,149,000

4 Beds ⋅ 4 Baths ⋅ UNDER AGREEMENT Status ⋅ 73573816 MLS ⋅ 3,804 SqFt.

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

$1,145,000

4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73570461 MLS ⋅ 3,275 SqFt.

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.

88 Elm St, Milton

$1,185,000

3 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73566740 MLS ⋅ 3,182 SqFt.

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

$1,050,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73565687 MLS ⋅ 1,900 SqFt.

Fresh floors, fresh photos, and a fresh reason to take a look. The hardwood at 45 Wendell Park has just been refinished, and with the rooms empty, you can see exactly what makes this house special. Only two families have ever called it home, and that kind of care shows everywhere you look. Step inside and the main level opens up. Glowing floors, generous light, and rich original woodwork carry from room to room. The kitchen was updated a decade ago with timeless choices that still feel current today. Upstairs, four well proportioned bedrooms fill the sleeping level. The finished attic adds flexible space above, and two dedicated offices keep work out of the dining room. Out front, the porch looks across the street to the park, a perfect spot for morning coffee and a wave to the neighbors. Out back, a patio sits level with the house and yard, so it’s an easy walk from kitchen to grill to pool. The pool was refurbished in 2023 with a new liner, steps, and filter, and has its own changing room off the deck. The big projects are already done: roof and siding in 2016, a 2011 boiler, a 2021 hot water heater, a repointed chimney with a new liner, and a new garage door. You get to move in and enjoy it.Saw it before? Come see it again. Haven’t seen it yet? Now is the time.

45 Wendell Park, Milton

$965,000

4 Beds ⋅ 2 Baths ⋅ PRICE CHANGED Status ⋅ 73559489 MLS ⋅ 1,688 SqFt.

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

$699,999

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73557060 MLS ⋅ 1,124 SqFt.

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

$4,800,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73551180 MLS ⋅ 4,310 SqFt.

Set off a lovely cul-de-sac, this restored Greek Revival sits on 4+ acres of open field, rare this close to Boston, stretching out rather than closing in. The expansive field: open, level, and bordering the 7,000 acre Blue Hills Reservation, accessible and yours to explore. A buildable lot: room to expand, a family compound, simply hold as open space, you decide. Fine millwork and French doors speak to fine craftsmanship. The kitchen is anchored by top appliances and built for serious cooking. A well-appointed mudroom keeps the everyday beautifully managed. A glass-walled garden room with fireplace, woodland views and stillness. Modern systems (geothermal heating/cooling, solar array, EV charger) reflect a commitment to sustainability. Privacy and peace without sacrificing reach: commuter rail, Rts 128/95, and Logan Airport all close. Access to Milton's public and the area's prestigious independent schools. This is where sophistication, sanctuary, and the wide-open sky meet.

1632 Canton Ave, Milton

$949,000

4 Beds ⋅ 3 Baths ⋅ UNDER AGREEMENT Status ⋅ 73547798 MLS ⋅ 1,593 SqFt.

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

146-148 Warren Ave, Milton

$635,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 73544814 MLS ⋅ 1,123 SqFt.

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

$975,000

3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73543043 MLS ⋅ 1,628 SqFt.

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

$5,995,000

7 Beds ⋅ 10 Baths ⋅ ACTIVE Status ⋅ 73519804 MLS ⋅ 9,320 SqFt.

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

$3,200,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 73511555 MLS ⋅ 4,310 SqFt.

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

$3,950,000

6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 73506861 MLS ⋅ 8,764 SqFt.

Set down a meandering, tree-lined drive, this spectacular turn-of-the-century Manor estate in Milton is a truly rare offering. From the moment you step into the welcoming foyer, elegance abounds. Three gracious floors of seamless living provide an exceptional balance of grand scale and warmth, featuring multiple bedroom suites and generous gathering spaces designed to accommodate both everyday living and memorable entertaining. This is a home where families gather, laughter fills the rooms, and life’s most cherished moments are made. A true architectural gem, the residence showcases exquisite period details including thick dentil moldings, rich hardwood floors, and finely preserved craftsmanship throughout. The home has undergone a thoughtful, major renovation that honors its historic character while seamlessly incorporating modern comforts and functionality. Privately sited on an impressive 7.32 acres, the grounds offer serenity, space, and a sense of timeless estate living.

650 Canton Ave, Milton

$649,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 73469207 MLS ⋅ 1,560 SqFt.

Opportunity knocks in one of Milton’s most desirable neighborhoods! This classic home at 7 Parkway Crescent offers incredible potential for buyers looking to renovate, customize, and build equity. Set on a spacious lot in a quiet, established area, the property features a flexible floor plan with generous room sizes, hardwood floors, and plenty of natural light. Conveniently located near schools, parks, shopping, and major routes, this property combines a prime location with tremendous upside potential. Don’t miss this rare chance to invest in Milton. The occupant of this house has a life estate.

7 Parkway Cres, Milton

$799,000

3 Beds ⋅ 2 Baths ⋅ UNDER AGREEMENT Status ⋅ 73048556 MLS ⋅ 1,487 SqFt.

Coveted Cunningham Park neighborhood, a rare offering! Classic center entrance straight front colonial with an oversized attached 2 car garage. Stunning details such as custom fluted woodworking, hardwood floors throughout, lovely fireplace, picture window looking out to large, open, leveled private backyard with shed. Three generously sized bedrooms, two with dressing rooms. Staircase to large attic. New upgrades include fresh paint throughout, brand new driveway, some electrical, professional landscaping, partially finished addition with new windows and door to backyard, and custom crystal lighting. Sunday open house from 11:30-1:30pm!

46 Century Lane, Milton

Browse All Milton MA Historical Properties for Sale

Milton Historical Real Estate

How much is your home worth?

How much is your home worth?