Milton Real Estate

Nestled in the heart of Norfolk County, Milton, Massachusetts, is a picturesque town that beautifully blends suburban charm with a rich historical tapestry. Known for its rolling hills and scenic landscapes, Milton offers residents a serene escape from the hustle and bustle of nearby Boston, while still providing convenient access to the vibrant city life.

With a population of just over 27,000, Milton boasts a close-knit community feel, where friendly neighbors and local businesses thrive. The town is renowned for its exceptional public schools, making it an ideal place for families looking to settle down. Educational institutions like Milton Academy, one of the oldest independent schools in the country, add to the town’s reputation for academic excellence.

Outdoor enthusiasts will find plenty to love in Milton. The town is home to the stunning Blue Hills Reservation, a sprawling area perfect for hiking, biking, and enjoying nature. With miles of trails and breathtaking views, it’s a haven for those who appreciate the great outdoors. Additionally, the charming Milton Village offers quaint shops, delightful dining options, and a vibrant community atmosphere.

Milton’s rich history is evident in its well-preserved architecture and local landmarks. The town’s historic district features beautiful colonial homes that tell the story of its past, while modern developments seamlessly integrate into the landscape.

Whether you’re drawn to Milton for its top-rated schools, beautiful parks, or strong sense of community, this charming town offers a unique blend of tranquility and accessibility that makes it a wonderful place to call home. Experience the best of suburban living in Milton, where history meets modernity in perfect harmony.

Newest Listings in Milton

$1,325,000

8 Beds ⋅ 4 Baths ⋅ 73575852 MLS

Renovated two family in desirable Milton location, close to schools parks and an array of commute options. 29 Laurel Road is an unmatched opportunity for the savvy end user buyer or investor. Live multi-generational and owner occupy, off-set your mortgage payment with a tenant or hold as an investment opportunity with a promising return. Both units are turnkey, freshly painted and floors refinished. Modern living is easy with the open flow of the renovated quartz and stainless kitchens that blend seamlessly into the main living areas. Versatility in beds and baths abounds in Unit 1, with 3 spacious bedrooms and 1 full bath on the main level and a bonus 4th bedroom in the lower level with it's own full bath, kitchenette and sitting area- perfect for an extended stay guest or ADU potential. Unit 2 spans two floors and has 4 bedrooms, including an upper level sunny master suite with additional ensuite full bath. A separate home office in Unit 2 makes work from home a breeze. Outdoors you'll find a level yard, separate rear porches and a spacious 2 car garage. Separately metered utilities, central air, gas heat, a renovated laundry area and exclusive storage closets make it easy to just move in and maximize your investment on Day 1. Walkable to Kelly Field, schools and easily accessible to multiple public transit options. Make a visit to 29 Laurel and see for yourself the possibilities!

29 Laurel Rd, Milton

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

$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..

$895,000

3 Beds ⋅ 2 Baths ⋅ 73574978 MLS

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

1200 Brook Road, Milton

Listing courtesy of Listing Agent: The Residential Group from Listing Office: Coldwell Banker Realty - Brookline.

$725,000

3 Beds ⋅ 2 Baths ⋅ 73574911 MLS

You thought you needed a single-family home in Milton—until this condo hit the market. Offering 1,800+ sq ft of living space across two levels, 3+ bedrooms, 2 full baths, 3 off-street parking spaces and multiple outdoor spaces, this 2nd and 3rd floor CONDO is move-in-ready and delivers the space and everyday functionality of a single family home at an unbeatable price point. The main level features two generously sized bedrooms, a full bath and a separate office/flex space ideal for working from home, hobbies or a playroom. The kitchen is appointed with granite countertops and stainless steel appliances, while in-unit laundry and central air add everyday convenience. Upstairs, the oversized primary suite creates a private retreat of its own, complete with an en suite bath and multiple spacious walk-in closets. The bedroom also features a spacious sitting area that can be used as a home gym, 2nd home office, or rec room. Ample storage throughout is another standout. The home features 2 private decks and access to a shared backyard on a corner lot. The location offers the best of Milton in multiple directions: enjoy the shops, restaurants and conveniences of East Milton Square, recreation at Cunningham Park, and miles of hiking, biking and running trails at the Blue Hills Reservation. With easy highway access and Boston just 10 miles away.

80 Pleasant St. Unit 2, Milton

Listing courtesy of Listing Agent: Elizabeth Trofatter from Listing Office: William Raveis R.E. & Home Services.

$999,900

4 Beds ⋅ 3 Baths ⋅ 73574898 MLS

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

84 Blue Hills Parkway, Milton

Listing courtesy of Listing Agent: Tatiana Diaz from Listing Office: William Raveis R.E. & Home Services.

$849,000

3 Beds ⋅ 1 Baths ⋅ 73574820 MLS

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

133 Gulliver St, Milton

Listing courtesy of Listing Agent: Mikel Defrancesco from Listing Office: William Raveis R.E. & Home Services.

$1,200,000

7 Beds ⋅ 3 Baths ⋅ 73574773 MLS

Open this weekend — Saturday, September 12, 12:00–2:00 p.m. and Sunday, September 13, 1:00–3:00 p.m. A rare three-family on Blue Hills Parkway, in the Milton Public Schools district, between the Neponset bike path and the Blue Hills Reservation. Mattapan Station, local buses, and the highway are a short hop; Tucker School is next door, Churchill’s is down the parkway, and trails and neighborhood parks are out the door. Three units: two 3-bedrooms and one 1-bedroom. The first floor is vacant and opens to a large lower level — a natural owner’s suite with room for extra bedrooms and a bath. Units 2 and 3 are occupied, so you can live on one floor and keep income on the others. Hard to find this much flexibility in Milton, this close to the reservation and the T. Come through Saturday or Sunday and see it for yourself.

197 Blue Hills Pkwy, Milton

Listing courtesy of Listing Agent: Rogerio Rodriguez from Listing Office: Gibson Sotheby's International Realty.

$725,000

3 Beds ⋅ 2 Baths ⋅ 73574274 MLS

You thought you needed a single-family home in Milton—until this condo hit the market. Offering 1,800+ sq ft of living space across two levels, 3+ bedrooms, 2 full baths, 3 off-street parking spaces and multiple outdoor spaces, this move-in-ready home delivers the space and everyday functionality of a house at an unbeatable price point. The main level features two generously sized bedrooms, a full bath and a separate office/flex space ideal for working from home, hobbies or a playroom. The kitchen is appointed with granite countertops and stainless steel appliances, while in-unit laundry and central air add everyday convenience. Upstairs, the oversized primary suite creates a private retreat of its own, complete with an en suite bath and multiple spacious walk-in closets. The bedroom also features a spacious sitting area that can be used as a home gym, 2nd home office, or rec room. Ample storage throughout is another standout. The home features 2 private decks and access to a shared backyard on a corner lot. The location offers the best of Milton in multiple directions: enjoy the shops, restaurants and conveniences of East Milton Square, recreation at Cunningham Park, and miles of hiking, biking and running trails at the Blue Hills Reservation. With easy highway access and Boston just 10 miles away.

80 Pleasant St. Unit 2, Milton

Listing courtesy of Listing Agent: Elizabeth Trofatter from Listing Office: William Raveis R.E. & Home Services.

$1,795,000

4 Beds ⋅ 5 Baths ⋅ 73573740 MLS

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

22 Windsor Rd, Milton

Listing courtesy of Listing Agent: Colleen Foulsham from Listing Office: FC Realty Group.

$2,149,000

4 Beds ⋅ 4 Baths ⋅ 73573816 MLS

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

1375 Brush Hill Rd, Milton

Listing courtesy of Listing Agent: Foster/ Harrington Team from Listing Office: Coldwell Banker Realty - Milton.

$1,899,000

4 Beds ⋅ 3 Baths ⋅ 73573617 MLS

Where in Milton can you find a single-family home offering this much space, land, and lifestyle at this price? This exceptional property checks all the boxes. Set alongside the private golf course at Wollaston Country Club, this home offers over 4,000+ sq. ft. of living space, 4+ rooms, and over an acre of land. The open-concept kitchen flows seamlessly into the private backyard, complete with an in-ground pool perfect for entertaining and enjoying the outdoors. Turnkey and move-in ready, all that’s left to do is bring your belongings and make this spacious Milton home your own.

901 Randolph Ave, Milton

Listing courtesy of Listing Agent: Kimberly Ruiz from Listing Office: eXp Realty LLC - Corporate Office.

$1,595,000

4 Beds ⋅ 4 Baths ⋅ 73573253 MLS

Completely and tastefully renovated from top to bottom, this stunning Colonial is set back from the main road on a private lot near the scenic Blue Hills Reservation. Offering 4 bedrooms, 4 full baths, and a beautifully finished lower level with a wet bar, full bath, and in-law potential, this turnkey home blends timeless charm with modern luxury. The open-concept main level features a designer kitchen with quartz countertops, farmhouse sink, LG Studio appliances, center island, coffee/bar area, and spacious living and dining areas. The luxurious primary suite offers a fireplace and oversized tiled shower, and double vanity. Major updates include a new 30-year roof, radon mitigation system, heat pump mini-splits, ERV, new indirect water heater, updated plumbing and electrical, EV charger, hardwood floors, redesigned kitchen and baths, second-floor laundry, new fencing, landscaping, and more. One-year American Home Shield home warranty included.

1262 Randolph Ave, Milton

Listing courtesy of Listing Agent: Danny Zheng from Listing Office: Keller Williams Realty.

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