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$735,000
4 Beds 2 Baths 73385021 MLS
Feeling blue about the real estate market? Here’s your rare chance to own a charming Philadelphia-style attached single-family home in one of Milton’s most convenient and quiet pockets, Pleasant Street, nestled between Brook Road and Centre Street. This thoughtfully laid out home offers flexibility for all stages of life. The first floor bedroom, full bath, and cozy den make it perfect for those seeking one level living without sacrificing space. With 4 bedrooms and 2 full baths spread across 3 levels, there’s plenty of room for guests, a home office, or multi-generational living. Investors take note this property offers excellent flexibility for long-term value with updated roof and windows, gas heating, central air and vinyl siding offering peace of mind with low maintenance ownership. Enjoy being just minutes from Milton Academy, Cunningham Park and East Milton Square, with easy access to shops, dining, and outdoor recreation. This gem might be the cure you've been waiting for!

641 Pleasant St, Milton

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

$754,000
3 Beds 2 Baths 73393744 MLS
ALL OFFERS DUE TODAY 6/24 BY 2PM Nestled in the heart of one of Milton's most sought-after neighborhoods, you will find that this home seamlessly combines timeless charm with unparalleled convenience. Situated just moments from East Milton Square, you'll find yourself within easy reach of vibrant shopping destinations, delightful dining experiences, and swift highway access for effortless commuting. This neighborhood is a sanctuary for outdoor enthusiasts and a wide range of buyers. Cunningham Park, a local treasure, offers year-round recreation, from serene nature trails and a welcoming dog park to the joy of ice skating in the winter months. With schools and parks just a short trip away, the area strikes the ideal balance between relaxation and active living.Don't let this opportunity pass you by. Embrace the chance to call this desirable property your new home—a harmonious blend of comfort, modern convenience, and an unbeatable location that truly caters to every lifestyle!

349 Pleasant Street, Milton

Listing courtesy of Listing Agent: Sharon Kelley Ryan from Listing Office: Coldwell Banker Realty - Milton.

$830,000
3 Beds 2 Baths 73390146 MLS
Beautiful East Milton home, nestled on a tree-lined street with a wide array of neighborhood amenities at your finger tips! Easy walking distance within a few blocks of several popular restaurants, coffee shops, fitness options.... and of course - stalwart local "Fruit Center" grocery store. This lovely home features three bedrooms, a terrific layout, a lovely three season front porch, 1 & 1/2 baths, garage parking and amazing curb appeal. Updates include a new roof, updated full bath, newer Gas heating & HW systems, windows - all you have to do is move in and enjoy! Milton is one of the most sought-after communities in the area with top schools, only 8 miles from Boston and is consistently rated one of the best towns in the country! This could be just the opportunity you have been waiting for!

102 Franklin St, Milton

Listing courtesy of Listing Agent: Kerry Dowlin from Listing Office: Coldwell Banker Realty - Dorchester.

$809,000
3 Beds 2 Baths 73374331 MLS
If you’ve been dreaming of a home in Milton that gives you comfort, convenience, and a fantastic neighborhood, 203 Church St is the one! The curb appeal of this property is undeniable. From the newly installed siding to the perfectly manicured landscaping, this home makes a statement before you even step inside. Once inside, you’ll love the flexible layout that is a blank canvas ready for your personal touch. Whatever your style, 203 Church St is ready for you to make it your own. This home is just a stone’s throw away from Andrew’s Park, one of the area’s best-loved green spaces, and just minutes from East Milton Square, where you can enjoy a cocktail at Novara, grab groceries at The Fruit Center, or pick up your morning coffee. But it’s not just about where you live—it’s who you live among. This is a community where neighbors know each other’s names, wave from the porch, and come together to make 203 Church St a special place to call home!

203 Church St, Milton

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

$2,000,000
3 Beds 5 Baths 73368114 MLS ['Wolcott Woods'] BLDG.
Stunning and rarely available, one of only five free-standing Cushing designs at Wolcott Woods, the award-winning, premier 55+ community in suburban Boston. Perfectly sited on a private cul-de-sac, this home offers breathtaking views from the Grand Room centered around a fireplace, a massive kitchen island, and a spacious dining area. One of the community’s most sought-after designs, this residence features two luxurious Owner’s Suites (one on each level) and the added convenience of laundry rooms on both floors, providing flexible and comfortable living options. For moments of quiet, the first-floor den with tranquil views and an upstairs home office offer private retreats. The second floor also includes a guest bedroom, a spacious loft, and a full bath, making it ideal for hosting family and friends. The finished walk-out lower level with hardwood floors, built in cabinet, wine refrigerator and a half bath adds versatility with additional living space and exceptional storage.

67 Wolcott Woods Lane Unit 67, Milton

Listing courtesy of Listing Agent: Greta Gustafson from Listing Office: LandVest, Inc..

$670,000
2 Beds 2 Baths 73356688 MLS
A well-curated home is thoughtfully designed, prioritizing intentional choices and creating a space that feels functional and beautiful. The unexpected offering at 2A Viola is the definition of well-curated, and its dedicated owner has transformed the space through meticulous renovations, reimagining every corner—without cutting any corners. This condo combines the warmth and comforts of a single-family home with a refined finish and a list of improvements to put any homebuyer at ease. The new kitchen is truly timeless, featuring high-end wood cabinetry and carefully chosen fixtures. An open living/dining area, 2 bedrooms, updated full bath, laundry area, and enclosed porch round out the main level. Downstairs, find an incredible flex space with a new spa-style bathroom and ample closets. Be surprised by attributes rarely found in a condo—neighborhood setting, a homey vibe, tons of storage, outdoor space, and 2-car garage. Easy access to parks, shopping/dining, and top-rated schools!

2 Viola Street Unit 2A, Milton

Listing courtesy of Listing Agent: Erin Feeney from Listing Office: Ceres Real Estate.

$1,220,000
3 Beds 3 Baths 73400747 MLS
East Milton Gem! A perfect blend of classic charm and modern elegance awaits in this beautiful home. Step into the four-season foyer wrapped in windows, and you’ll be drawn into an impressive open floor plan that’s sure to captivate. This Pottery Barn-inspired home features a warm, fireplaced living room flowing seamlessly into a stylish kitchen with grey cabinetry, granite countertops, stainless steel appliances, and an island perfect for entertaining. The dining area opens to a fenced backyard with a newly installed paver patio and pergola ideal for summer gatherings. The first floor also includes a laundry room and half bath. Exceptional details shine with crown moldings, gleaming hardwood floors, light fixtures, and stylish bathrooms. Energy-efficient heating, central A/C with smart thermostats, attic and basement storage, maintenance-free siding, new front stairs, driveway, and oversized shed. Just steps from East Milton Square, shops, dining, and 8 miles to Boston. DON'T MISS IT!

8 Howe St, Milton

Listing courtesy of Listing Agent: Ernad Preldzic from Listing Office: RE/MAX 360.

$2,650
2 Beds 1 Baths 73394543 MLS
Spacious Top-Floor 2-Bedroom in a Three-Family Home – Prime Location!Welcome to your new rental home! Enjoy the privacy and quiet of the top floor, with ample natural light and a roomy layout ideal for relaxing or entertaining.This bright and spacious unit in a three-family home offers the perfect blend of comfort and convenience. Two generously sized bedrooms, bathroom with step-in shower, washer/dryer stack in the unit and off-street parking. Just minutes from the highway for an easy commute. There's also your own exclusive use deck to enjoy those summer nights. Please note the BA is off the second bedroom. This unit would be ideal for a single person or couple.

392 Reedsdale Unit 3, Milton

Listing courtesy of Listing Agent: Kerry Elinskas from Listing Office: Coldwell Banker Realty - Hingham.

$3,800
3 Beds 2 Baths 73389144 MLS
No broker fee! Beautifully updated apartment in a meticulously maintained two-family home located in the highly desirable and convenient neighborhood of Milton. This spacious two-floor unit lives more like a single-family home and features 3 bedrooms, an office and 1.5 bathrooms. Recent renovations include stylish new light fixtures, modern kitchen and bathroom flooring, refinished hardwood floors, upgraded windows, and fresh paint throughout. Enjoy the charm of tall ceilings, abundant natural light, a private outdoor porch and a four-season sunroom. Attic storage available. Conveniently close to public transportation and local amenities. Showings are now available, and applications are being reviewed for a September 1 move-in! Excellent references and credit - no pets please!

18 Hawthorn Road Unit 2, Milton

Listing courtesy of Listing Agent: MacKinnon & Co from Listing Office: Compass.

$1,375,000
4 Beds 2 Baths 73381570 MLS
Move right in! Well kept 4 bedroom, 1 1/2 bath center entrance Colonial tucked away on a quiet, tree-lined circle in an ideal Milton Center location. Just minutes from Cunningham/Collicott Schools, Cunningham Park and Milton Academy. Picture yourself creating deliciousness in the beautifully renovated chef's kitchen (quartz counters/island/stainless appliances including a Bertazzoni induction stove) which flows seamlessly into both the dining room (w/coffee bar) and sunroom. A fireplace and built-in shelving make the front-to-back living room an ideal place to relax and entertain off-season (the inviting rear deck with hot tub overlooking the back yard is perfect the rest of the year!). New Andersen windows/doors; Sunnova solar panels with EV charger; finished basement; attached garage with plenty of driveway parking. Easy access to E. Milton Sq., 93/95/3 & downtown Boston. Deep double lot may offer expansion possibilities. Seller welcomes offers with requests for buyer concessions.

50 Badger Cir., Milton

Listing courtesy of Listing Agent: Jay Balaban from Listing Office: Gibson Sotheby's International Realty.

$735,000
2 Beds 2 Baths 73373137 MLS ['Ice House'] BLDG.
Introducing the newly constructed Icehouse on the Parkway Condominiums! This luxurious building boasts beautiful Quartz countertops, white shaker cabinets with stainless steel appliances. In-unit laundry with a Electrolux washer and dryer included. Generous-sized tiled bathrooms, custom designed closets, Hydro Air AC, and Navian energy-efficient tankless heat/hot water systems in every unit. The building features an elevator, fitness room, and comfortable common areas. Adjacent walking trails lead to the historic Popes Pond. The building pays homage to the once thriving ice harvesting businesses in the area (see attachment for a brief history). All units come with a designated storage space, and underground parking is available for an additional cost.

485 Blue Hills Parkway Unit 34, Milton

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: Coldwell Banker Realty - Duxbury.

$1,067,000
3 Beds 3 Baths 73372922 MLS
New price and motivated sellers! Discover the perfect blend of timeless charm and modern updates in this beautifully renovated move-in-ready Dutch Colonial, ideally located in Milton's Pine Brook neighborhood. Tucked away on a quiet dead-end street, this home offers the kind of peace and convenience buyers dream of, just a few lots down from the scenic Pine Tree Brook Path and Milton High School. Inside, enjoy a sun-filled living room with a gas fireplace, a custom kitchen, formal dining room, a mudroom with custom built-in closets, and a luxurious primary bath with heated marble floors, your toes will thank you all winter long. And when it’s time to enjoy the outdoors, the fully fenced-in patio is ideal for entertaining or relaxing. Need extra space? The detached garage has been transformed into a versatile bonus room, perfect for a home office, gym, or creative studio. This is more than just a house, it’s the lifestyle you’ve been waiting for.

73 Harold Street, Milton

Listing courtesy of Listing Agent: Meghan Ruivo from Listing Office: Jane Coit Real Estate, Inc..

$1,285,000
3 Beds 3 Baths 73379010 MLS
This one covers all the bases! Upstairs offers the privacy of two bedrooms, one with its own office, and the full bath of the original Cape-style home, while the main level has been architecturally reimagined and rebuilt with all new systems, windows, and an open floor plan. Living is easy with the dreamy, center island kitchen, the gas fireplace in the dining-living room, first-floor laundry and primary bedroom with ensuite bath and walk-in closet. Effortlessly slide between work and home with the convenient office off the kitchen. Then let the good times roll in the sensational family room addition, out onto the composite deck and into the enviable quarter-acre yard, just in time for summer barbeques, games, or gardening with a charming shed. Bonus points: storage abounds, and the basement has potential! This one is a home run, on a quiet, cul-de-sac next to conservation and walking trails, near Milton Academy and schools in the sought- after Cuningham area and all things Milton!

35 Orchard Road, Milton

Listing courtesy of Listing Agent: Leslie Will from Listing Office: Coldwell Banker Realty - Milton.

$945,000
5 Beds 2 Baths 73390339 MLS
Rarely does a property of this stature come to the market. This Classic Greek Revival 4/5 bedroom home has been in the same family for over 6 decades. Solidly built in 1859 to stand the test of time with superior craftsmanship and materials, impressive architectural details including soaring ceilings, large original windows, exquisite original molding, front curved staircase, rooms made for entertaining including a large eat-in kitchen, an abundance of sunlight, back staircase, and generous storage space. With some TLC, 167 Brook Road offers endless possibilities. Graciously set back on a flat level 1/3 acre. Situated on bike path, near public park, public and private schools, with access to public transportation, all major highways, 9 miles from Boston. This special gem awaits its new steward to write the next chapter. Shown by Appointment Only.

167 Brook Rd, Milton

Listing courtesy of Listing Agent: Matthew Freeman from Listing Office: Coldwell Banker Realty - Milton.

$502,400
1 Beds 1 Baths 73349031 MLS ['Ice House'] BLDG.
Introducing the newly constructed Icehouse on the Parkway Condominiums! This luxurious building boasts beautiful Quartz countertops, white shaker cabinets with stainless steel appliances. In-unit laundry with a Electrolux washer and dryer included. Generous-sized tiled bathrooms, custom designed closets, Hydro Air AC, and Navian energy-efficient tankless heat/hot water systems in every unit. The building features an elevator, fitness room, and comfortable common areas. Adjacent walking trails lead to the historic Popes Pond. The building pays homage to the once thriving ice harvesting businesses in the area (see attachment for a brief history). All units come with a designated storage space, and underground parking is available for an additional cost.

485 Blue Hills Parkway Unit 19, Milton

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: Coldwell Banker Realty - Duxbury.

$645,000
2 Beds 2 Baths 73384869 MLS ['Ice House'] BLDG.
Introducing the newly constructed Icehouse on the Parkway Condominiums! This luxurious building boasts beautiful Quartz countertops, white shaker cabinets with stainless steel appliances. In-unit laundry with a Electrolux washer and dryer included. Generous-sized tiled bathrooms, custom designed closets, Hydro Air AC, and Navian energy-efficient tankless heat/hot water systems in every unit. The building features an elevator, fitness room, and comfortable common areas. Adjacent walking trails lead to the historic Popes Pond. The building pays homage to the once thriving ice harvesting businesses in the area (see attachment for a brief history). All units come with a designated storage space, and underground parking is available for an additional cost.

485 Blue Hills Parkway Unit 36, Milton

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: Coldwell Banker Realty - Duxbury.

$1,058,000
6 Beds 3 Baths 73393151 MLS
Rare opportunity to own a two-family in highly desirable Milton! Perfect for investors or owner-occupants looking to offset the mortgage with rental income. The first-floor unit features 2 bedrooms, a sunroom or office, and a private patio—freshly painted and updated. The second and third floors offer a spacious 4-bedroom plus office, 2-bath layout with a huge deck off the living room—ideal for entertaining. Both units have hardwood floors throughout, and the property features blown-in insulation, a newer roof (2020), full dormer on top floor, and great natural light. Off-street parking (garage) and a private driveway add to the appeal. Located near top-rated schools, shops, parks, restaurants, and public transit. Great rental history and potential make this a smart investment in one of Greater Boston’s most sought-after towns!

88 Brush Hill Road, Milton

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

$625,000
2 Beds 2 Baths 73364522 MLS ['Ice House'] BLDG.
Introducing the newly constructed Icehouse on the Parkway Condominiums! This luxurious building boasts beautiful Quartz countertops, white shaker cabinets with stainless steel appliances. In-unit laundry with a Electrolux washer and dryer included. Generous-sized tiled bathrooms, custom designed closets, Hydro Air AC, and Navian energy-efficient tankless heat/hot water systems in every unit. The building features an elevator, fitness room, and comfortable common areas. Adjacent walking trails lead to the historic Popes Pond. The building pays homage to the once thriving ice harvesting businesses in the area (see attachment for a brief history). All units come with a designated storage space, and underground parking is available for an additional cost.

485 Blue Hills Parkway Unit 24, Milton

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: Coldwell Banker Realty - Duxbury.

$1,850,000
6 Beds 4 Baths 73356233 MLS
This is the One! Meticulously maintained & restored Colonial in one of Milton's finest locations nestled on a landscaped 17,800 ft lot w/ 2 car garage, fenced yard, patio & firepit. Inside you'll find a traditional floorplan with a perfect blend of character & modern amenities. Elegant formal dining room w/ hardwood floors, chair rail & Crown mouldings leads to the completely redesigned Chef's kitchen w/ Custom cabinetry, quartz counters, center island & peninsula open to a sun splashed family room. 2 First floor office spaces, 6 bedrooms (or 4 plus 2 room au-pair w full bath) including luxurious Primary w/ 2 closets including walk in closet, full bath w/ 48" marble vanities, soaking tub & spa shower w/ rainwater & side fixtures, Prime location close to schools, Milton Hospital, Library, Milton Academy & Blue Hills. Want to walk through this home in High-Definition & 3D? Visit https://tinyurl.com/164HighlandMilton

164 Highland St, Milton

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

$1,225,000
3 Beds 2 Baths 73380966 MLS
Set on a picturesque, tree-lined street in one of Milton’s most sought-after neighborhoods The Columbines. This move in ready home offers space for modern living and entertaining. With an ideal layout which includes a kitchen that opens to a sun-filled family room plus a front to back living room. Upstairs you’ll find three generously sized bedrooms, including a primary with a rare walk-in closet. The finished lower level provides flexible living space ideal for a playroom, home office, or guest space. Step outside to a fenced in quarter acre lot ready for summer gatherings, playing fetch with Scout and enjoy crisp fall nights around a fire pit. Just a short stroll to the trolley for easy access to Boston, Shields Playground for recreation, and the beloved Steel & Rye restaurant for dining. Outdoor lovers will enjoy quick access to the Neponset River Green Trail and its scenic views the perfect city escape. With tasteful updates throughout we guarantee it will not disappoint!

1 Columbine Rd, Milton

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

$960,000
4 Beds 3 Baths 73371198 MLS
Lovingly maintained single-family home features four bedrooms, three bathrooms, and a two-car garage. It is situated in a beautiful, tree-lined, highly desirable neighborhood. The first floor offers a cozy fireplace in the living room, a separate dining area off the kitchen, which includes stainless steel appliances and granite countertops, and a sunny den with a slider leading out to a deck and paved patio. This home also features four zones of air conditioning with mini-splits throughout. Three spacious bedrooms and a full bath are also on this first floor. On the second floor, a primary bedroom and bathroom await you. This inviting area feels like a retreat with sunlight and privacy. The basement features laundry, a tool room, a full bath, and a large space to add a workout room or an art studio, wherever your vision takes you!

25 Kevin Road, Milton

Listing courtesy of Listing Agent: Daniel Tully from Listing Office: Symphony Properties.

$1,450,000
4 Beds 4 Baths 73344196 MLS
Welcome to 4 Carisbrooke Rd, a beautiful home located in the sought after Blue Hills area of Milton. Spanning over 4,000 square feet of living space on almost half an acre lot, it has 4 bedrooms & 4 full bathrooms! Make your way through the foyer & explore the first floor that has a formal dining room, sitting room, living room with vaulted ceilings with fireplace. On the first floor is also the spacious kitchen with granite counters, a full bathroom and laundry as well. Make your way upstairs to 4 bedrooms & 2 full bathrooms, including the large primary bedroom with walk in closet & en suite bathroom. Head upstairs to the finished attic which can be a movie, game, or whatever your lifestyle needs! Head all the way down to the basement w/ 2 bonus rooms & access to the backyard as well. Garage is extremely spacious, heated &equipped with EV charger. With Houghton's Pond around the corner, easy access to the highway, shopping & all that Blue Hills has to offer- don't wait

4 Carisbrooke Road, Milton

Listing courtesy of Listing Agent: Beatrice Murphy from Listing Office: Lamacchia Realty, Inc..

$732,000
2 Beds 2 Baths 73349007 MLS ['Ice House'] BLDG.
Introducing the newly constructed Icehouse on the Parkway Condominiums! This luxurious building boasts beautiful Quartz countertops, white shaker cabinets with stainless steel appliances. In-unit laundry with a Electrolux washer and dryer included. Generous-sized tiled bathrooms, custom designed closets, Hydro Air AC, and Navian energy-efficient tankless heat/hot water systems in every unit. The building features an elevator, fitness room, and comfortable common areas. Adjacent walking trails lead to the historic Popes Pond. The building pays homage to the once thriving ice harvesting businesses in the area (see attachment for a brief history). All units come with a designated storage space, and underground parking is available for an additional cost.

485 Blue Hills Parkway Unit 51, Milton

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: Coldwell Banker Realty - Duxbury.

$6,900
5 Beds 6 Baths 73401253 MLS
Serene living at its finest. Wonderful colonial in Milton with the ambience of a private pastoral setting all within steps to Boston in the exclusive Brush Hill Neighborhood, you'll love this spacious home overlooking a manicured 40,000 sq ft lot and gardens. Bright and thoughtfully laid out with space for all. Chef's kitchen with center island, pendant and recessed lights, granite counters and stainless appliances. Formal Living & Dining areas with fireplace, detailed built-ins and hardwood floors. 5 Total bedrooms, 4 full and 2 half baths including multiple suites. Generous primary suite will walk in closet and full bath. Attached 1000+ sq ft 2 level in-law suite with full kitchen, open living & dining areas, 1.5 baths and laundry room. Attached and detached garages provide 4 bays and ample storage. 3 comfortable zones of Air conditioning and multiple heating zones keep everyone cozy. Your own oasis minutes from Boston & commuter rail - schedule your showing today!

34 Brush Hill Ln Unit 34, Milton

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

$1,375,000
4 Beds 4 Baths 73384179 MLS
When asked, “Why this house?”, the clear answer was and still is, “location”. Set in Milton’s desirable Columbine neighborhood, 51 Rustlewood offers proximity to Milton schools, Milton Academy, Turner’s Pond, and trolley access. Owners jumped right in, expanding to a rare 4-bedroom, 3.5-bath home with room for all. The coveted primary suite now includes a walk-in closet and sumptuous bath, choices smart and current. Expansion came easily with a complete 3rd floor takeover, including cathedral ceilings, recessed lighting, bedroom, full bathroom, lounge area and generous storage. A flexible first-floor office easily serves as a den or 5th bedroom. The eat-in kitchen with newer stainless-steel appliances opens to a fenced backyard and brick patio, perfect for play and outdoor entertainment. A screened porch off the living room, recessed lighting, newer windows, newer roof, gas heat, wired for EV, lower level recreation space complete the picture. Now the better question is, “Why wait?”!

51 Rustlewood Rd, Milton

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

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