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$1,285,000
3 Beds 3 Baths SOLD Status 73379010 MLS 2,064 SqFt.
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

$1,100,000
4 Beds 3 Baths SOLD Status 73378952 MLS 2,370 SqFt.
We are excited to present this beautiful colonial, with four bedrooms , three baths and 2 fireplaces , one of which is located in the master suite. It has a two car garage with tons of storage. It has an amazing deck space off the back of the house and the large eat in kitchen. This home sits on a spectacularly quaint dead end street and located at the end of a long private driveway. The outside of the home and the grounds have been meticulously kept and create amazing privacy and curb appeal . There is a large unfinished basement with plenty of height and room to expand . The first level of this home, flows beautifully with an office, a living room, dining room, and a large mudroom off the spacious kitchen . The second level has 4 bedrooms and 2 full baths. This beauty is ripe for its next owner and being sold as is. Open House Sunday 25th, from 12-1:30

1262 Randolph Ave, Milton

$875,000
3 Beds 2 Baths SOLD Status 73378730 MLS 1,596 SqFt.
Opportunity knocks in one of East Milton’s most sought-after neighborhoods! Set on a generous lot, this property offers the perfect canvas for your vision. While the home is in need of significant renovation, it’s bursting with possibilities — whether you’re looking to restore its original charm, expand, or start fresh. With plenty of room to grow and a location that can’t be beat, this is a rare chance to break into the East Milton market at an affordable price point. The surrounding area is known for its tree-lined streets and strong community feel, making it the ideal spot to invest and build equity. Bring your ideas, your contractor, and your imagination — and transform this diamond in the rough into the home of your dreams. This is more than a project — it’s an opportunity. Don’t miss it!

39 Otis Street, Milton

$3,100,000
7 Beds 5 Baths SOLD Status 73374837 MLS 7,312 SqFt.
Once in a lifetime opportunity to own this home w/expert craftsmanship, discover the timeless elegance of the historic Dr. Amos Holbrook House. Built around1800, this distinguished Federal-style residence offers over 7,300 square feet of living space, featuring seven spacious bedrooms & four & a half bathrooms. Set on a generous 2.56-acre lot, the property boasts a blend of historical charm & modern comfort. Original architectural details have been meticulously preserved, reflecting the home's rich heritage, complete w/hand painted frescos, original inlaid hardwood floors, rare pentagonal bay window in the family room, 7 fireplaces & a very special barn + greenhouse w/possibilities. Nestled directly across from the scenic Governor Hutchinson's Field, residents can enjoy breathtaking views of the Neponset River marshes, the city of Boston skyline & Harbor. This private & exceptional estate offers a unique opportunity to own a piece of Massachusetts history.

203 Adams St, Milton

$700,000
3 Beds 2 Baths SOLD Status 73374674 MLS 1,507 SqFt.
Classic Crosby Colonial located minutes to downtown Boston in one of Milton's most desirable neighborhoods. This charming 3 bedroom, 1.5 bath home has been well maintained by the same family for over 60 years! The main level features a spacious front to back living room with traditional fireplace, a sunny dining room with built-in corner cabinet, half bath, large eat-in kitchen, and a 150sf mudroom off the attached garage. French doors open to a large rear deck overlooking a private fenced yard, perfect for outdoor dining and warm-weather entertaining. A classic center staircase leads to the second level where you’ll find three generous bedrooms, two walk-in closets, and a full bath. A walk-up attic offers excellent storage or expansion potential, while the massive basement provides even more flexible space. The Milton Academy neighborhood boasts charming tree lined streets and convenience to parks, schools, public transit, commuter routes, restaurants, shops, and much more!

32 Centre St, Milton

$809,000
3 Beds 2 Baths SOLD Status 73374331 MLS 1,733 SqFt.
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

$600,000
2 Beds 1 Baths SOLD Status 73373716 MLS 1,442 SqFt.
All offers due Monday, May 19 at 5 PM. MILTON -- Impeccably updated and move-in ready, this gorgeous, low-maintenance 2-bed condo on the first floor of a 2-family home offers comfort, convenience, and quality. Enjoy a beautifully renovated kitchen and bath, gleaming hardwood floors, updated systems, and central air. Set in a peaceful setting with mature landscaping, this home provides easy access to East Milton Square, Cunningham Park, and The Blue Hills Reservation. Ideal for those seeking a simplified lifestyle without sacrificing space or location. A rare opportunity to enjoy town amenities with room to breathe. 3 dedicated parking spots, common yard fenced on three sides, and porches off both the front and back are private to each unit.

80 Pleasant St Unit 1, Milton

$1,740,000
3 Beds 3 Baths SOLD Status 73373554 MLS 2,764 SqFt.
Just love a rare Milton Hill Greek Revival, exuding commanding presence and stability, set on nearly 1/2 acre of verdant canvas inviting parties, play, and pups. Architectural details include tall pilasters, soaring ceilings, and pedimented windows pulling light into every room. Move through the library-style entry hall over finely finished hardwoods to a fully renovated chef’s kitchen: oversized island, 6-burner cooktop, and open concept sink-right-in lounge. French doors spill onto a screened porch, a 3-season sanctuary for morning coffee or summer dinners. Upstairs 3 bedrooms are joined by a walkthrough office/sitting room with separate private outside entrance, connecting to a southwest facing sun porch floating in the treetops. 2 renovated baths, new HVAC and full-house electrical updates. Dream bigger with 3rd floor expansion potential. Prime location is just a stone’s throw to Milton Academy, trolley, Steel & Rye. Experience how effortlessly modern living inhabits timeless bones

185 School St, Milton

$1,210,000
3 Beds 4 Baths SOLD Status 73373536 MLS 1,520 SqFt.
Finally, a Milton home with all the right stuff! In the right hands, the magic always happens. 45 Cliff Road has undergone a magical, recent, and inspired transformation for some lucky buyers … starting with a new kitchen which brings in so much light to the new open floor plan. A center island gives the cook plenty of room to work. A south facing breakfast bar overlooks the generously fenced yard. Pretty living room has a beamed ceiling and recessed lighting perfect for sinking into day or night. An extra sitting room can be whatever you need … the sliding French doors can offer peace and privacy. 3 new bathrooms, oh my! This very rare offering in Milton has new: roof, kitchen and baths, HVAC, electrical, plumbing and windows throughout. A 2-car garage, sundeck and stone terrace complete the picture. Opportunity to finish the lower level with good ceiling height. Close to the trolley, Shields Park and a wonderful group of neighbors. Do you need another reason to see this beauty?

45 Cliff Rd, Milton

$735,000
2 Beds 2 Baths SOLD Status 73373137 MLS 1,193 SqFt.
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

$1,025,000
4 Beds 2 Baths SOLD Status 73373092 MLS 1,870 SqFt.
This spacious residence offers the perfect blend of classic character and modern amenities. Step inside to discover a thoughtfully renovated interior featuring a stunning new kitchen with contemporary cabinetry, stylish countertops, and premium appliances. The adjacent living room is anchored by an inviting fireplace, creating a warm gathering space for family and friends. The main level is bathed in natural light thanks to brand new energy-efficient windows throughout. Recessed lighting adds a contemporary touch while illuminating the home's beautiful details. Upstairs, you'll find four generous bedrooms offering plenty of space for family or guests. Both bathrooms have been fully updated with elegant fixtures and finishes. The partially finished basement adds valuable living space, complete with its own fireplace. Recent upgrades include the conversion from oil to gas heating and the addition of central AC.

30 Buckingham Road, Milton

$1,067,000
3 Beds 3 Baths SOLD Status 73372922 MLS 1,679 SqFt.
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

$1,030,000
3 Beds 3 Baths SOLD Status 73372240 MLS 2,306 SqFt.
NEW PRICE! $1,049,000. BRAND NEW GAS HEATER TOO! IF YOU'RE LOOKING FOR LAND THIS IS YOUR HOME! 20,199 SQ FT LOT! If you’re looking for a home in a fabulous neighborhood on a beautiful lot & a Two Car Garage you have found it. This home is perfectly sited on a fenced in 0.46-acre yard. This prime location is minutes to Wollaston Golf Club, Milton Academy, Blue Hills, Route 93 and much more. This spacious Split-entry home features 3 bedrooms 2.5 baths, with 2,306 square feet of living space. The main level offers an open floor plan with a Fireplaced Living Room, Formal Dining Rm, a 15 x 24 Eat in Kitchen, Sunroom/ Office, Three bedrooms & Two Baths. The Lower level features a Fireplaced Family Room, a Kitchenette/ Laundry Room, Bonus Room and a Half Bath. Enjoy summer gatherings on the deck and the fabulous yard. All this and more awaits you!

88 Hilltop St, Milton

$1,490,000
4 Beds 4 Baths SOLD Status 73371210 MLS 4,031 SqFt.
Dream Home is Now More Affordable! Located in the exclusive, gated Mansions at Brush Hill—an intimate 17-home community on 18 park-like acres—this free-standingresidence (4 beds, 3.5 baths) offers unmatched luxury. A chef’s kitchen boasts custom cabinetry, quartz counters, and premium appliances, while a sunlit living room features a fireplace andatrium doors to a private deck. First-floor office or formal sitting room. The 2nd floor hosts a spacious master suite with a spa-inspired bath & walk-in closet. An enormous family/playroomopens to the backyard, plus a 2-car garage. Enjoy the privacy of a yard with resort-style perks: landscaped grounds, tennis/pickleball courts, pet-friendly trails, and included maintenance.Ideally locate

333 Brush Hill Rd Unit Z2, Milton

$960,000
4 Beds 3 Baths SOLD Status 73371198 MLS 2,716 SqFt.
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

$3,400,000
5 Beds 7 Baths SOLD Status 73370362 MLS 5,104 SqFt.
At 152 Adams Street, the Neponset River is your personal canvas—sunrises, seasons, and sky, all unfolding outside your windows. Perched on a 1.38-acre parcel of gently sloping grounds, this Milton Hill estate is one of the rare properties to offer panoramic vistas. A full-scale renovation in 2017 overhauled the home’s systems—electrical/plumbing/HVAC/building envelope—while preserving its soul through curated updates, including thoughtful floor plan enhancements and interior finishes, like windows to frame every sunrise and custom millwork that whispers of the craftsmanship of a bygone era. The result is a home that balances formality with the casual expectations of today's living, creating a natural flow for both quiet mornings and large-scale entertaining. Outside, a sprawling lawn leads to the river's edge, and natural treeline creates a serene enclosure. Yet the home is intimately connected to town life, Milton Village and Lower Mills shopping and dining are but a short stroll away

152 Adams Street, Milton

$1,795,000
3 Beds 5 Baths SOLD Status 73369252 MLS 3,416 SqFt.
Better than new 3 bedroom/4.5 bathroom townhouse in the tranquil Wolcott Woods. First floor of this home boasts primary suite, laundry room, private office, top of the line kitchen with Sub-Zero refrigeration and Wolf stove, fireplaced living and dining areas. The open-concept floor plan provides an inviting space for entertaining quests or everyday living. The second floor has 2 en-suite bedrooms, sitting area and walk-in storage. Finished walk-out lower level has a terrific family/game room, a second home office, full bath, craft room and exercise space. Enjoy sitting on your deck overlooking the wonder of the Blue Hills Reservation. This bucolic 55+ community offers several recreational options with easy access to shopping, restaurants, highways and airport.

54 Wolcott Woods Ln Unit 54, Milton

$812,000
3 Beds 1 Baths SOLD Status 73368244 MLS 1,352 SqFt.
Welcome to this charmingl 3-bedroom, 1-bath colonial nestled in one of Milton’s most sought-after, tree-lined neighborhoods. From the moment you step inside, you’ll feel right at home in the inviting sunroom—an ideal spot to unwind and enjoy gentle summer breezes.The cozy, fireplaced living room offers the perfect setting for relaxing evenings and flows seamlessly into a classic dining room, perfect for gathering with family and friends. The beautifully renovated kitchen is light-filled and thoughtfully designed, featuring crisp white shaker cabinets, gleaming quartz countertops, and a charming eat-in bar—combining both style and functionality.Upstairs, you’ll find three comfortable bedrooms with rich hardwood floors and the enduring character that makes this home truly special.Don’t miss the opportunity to make this timeless treasure yours!

133 Church Street, Milton

$1,320,000
4 Beds 3 Baths SOLD Status 73368197 MLS 2,556 SqFt.
Handsome Dutch Colonial in one of Milton’s most coveted neighborhoods. Substantially renovated in 2021, Boasting 4 bedrooms and 2.5 baths, this residence beautifully marries period details with modern updates. Step inside to discover a warm and inviting atmosphere highlighted by a classic wood-burning fireplace and gleaming hardwood floors that flow throughout the home. Open and flexible floor-plan plus not one but two options for work from home! The stunning chef's kitchen features custom cabinetry and designer appliances, making it perfect for both cooking and entertaining. Each bedroom offers ample space and natural light including the primary bedroom complete w/ spa like ensuite bath & TWO walk-in closets!, while the updated bathrooms provide a touch of luxury. Enjoy the character of this timeless home, complete w/ high ceilings and elegant moldings. Outside, the landscaped yard invites relaxation and outdoor gatherings. This gem is a must-see!

5 Meredith Circle, Milton

$2,000,000
3 Beds 5 Baths SOLD Status 73368114 MLS 3,592 SqFt.
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

$1,325,000
3 Beds 2 Baths SOLD Status 73367190 MLS 1,743 SqFt.
This timeless Crosby Colonial beautifully combines classic charm with modern updates, located in one of the area's most sought-after neighborhoods. Enjoy your own private oasis with a large screened-in porch, a secluded patio with a Japanese soaking tub, and direct access to Shields Park, perfect for outdoor living. Inside, the bright spacious layout features a fireplaced living room, formal dining room, and an updated kitchen. A sunny first-floor office or reading room offers flex space for work or relaxation. The lower-level family room, complete with its own fireplace, adds extra space for gatherings. Upstairs, there are 3 generously sized BR's with ample closet space, plus a walk-up 3rd floor with great potential for expansion. Recent updates include a freshly painted exterior, a brand-new roof, and an attached garage w/ an EV charger. This home blends timeless curb appeal with modern convenience, making it move-in ready for its next chapter! Close to the T, parks & restaurants!

12 Columbine Road, Milton

$985,000
3 Beds 2 Baths SOLD Status 73367143 MLS 2,462 SqFt.
Leaving the city has never been easier—or more appealing—when you land in East Milton, one of the town’s most sought-after neighborhoods. Here, walkability is everything: coffee shops, parks, and everyday essentials are just steps from your door, making convenience part of your daily routine. Add in quick access to the highway and public transportation, and it’s easy to see why people love it here. This expansive Colonial offers the space and flexibility to grow for years to come. The second floor features two spacious bedrooms, with the option to convert one into two rooms for a more traditional layout. Downstairs, a large family room with a wall of sliders floods the space with natural light and frames views of the green backyard—proof that a little nature can brighten any day. Lovingly cared for by long-time owners, this home is ready for its next chapter and new memories. Don’t miss your chance to make it yours!

49 Wood St, Milton

$910,000
4 Beds 2 Baths SOLD Status 73367106 MLS 1,622 SqFt.
Welcome to Crown Street, located in one of Milton’s most lively and welcoming neighborhoods! This well- appointed and well-kept side entrance Colonial offers four true corner bedrooms and eat-in kitchen. There's finally that extra space everyone’s always looking for but can rarely be found. The current owners have cared for this home with the kind of attention and pride you don’t see every day, featuring newer windows, roof, heating system, and recently added mini-splits. Outside, enjoy a private yard with patio in a tight-knit community where neighbors offer a wave or helping hand, kids ride bikes and summer kicks off with an ice cream social and ends with an annual block party. Walk to all schools, hop on nearby public transit, or escape to nature with Pope’s Pond trail and the Blue Hills Reservation just minutes away. Located 8 miles south of Boston, it’s easy to see why Milton is such a dream spot to plant roots. This standout property is not to be missed. Showings start on Friday!

52 Crown St, Milton

$2,500,000
5 Beds 4 Baths SOLD Status 73366909 MLS 4,307 SqFt.
Thoughtfully updated Milton Hill gem offers the rare combination of easy access to neighborhood amenities & a feeling of privacy. Just 0.3mi to the Milton station, Lower Mills shops & restaurants, this expanded center entrance Colonial delights with rich character details. Radiating from the gracious foyer with elegant stairway & wainscoting are the living room with 3 exposures & handsome fireplace, the den with corner bookcases & dining room with original china cabinet. The eat-in kitchen offers direct access & good sightlines to the back deck & landscaped fenced yard. Renovated in 2023, the kitchen with large center island was smartly configured to provide a good working triangle while maximizing storage & counterspace. The 2nd fl hosts the primary suite with 4-piece bath & good closets, 3 additional BRs, a study & hallway bath. The 3rd fl comprises a 5th BR with sitting area & full bath. A finished basement & 2-car garage complete this lovely Milton classic. A must see!

70 Morton Rd, Milton

$1,250,000
4 Beds 4 Baths SOLD Status 73366831 MLS 3,078 SqFt.
Welcome to 481 Eliot Street! Classic brick colonial located in popular Columbine-Cliff neighborhood. Step through front entrance and be wowed by fine woodwork and French doors leading to over-sized foyer. Note high ceilings, stunning staircase, beamed ceiling, front-to-back living room with fireplace and adjacent sunroom/office. Generous dining room for entertaining, butler's pantry, eat-in-kitchen provides plenty of counter space with center island for meal prep and room for family gatherings. Second floor offers primary bedroom with ensuite, two additional bedrooms and full bath. There is more...third floor features fourth bedroom and full bath with soaking tub. Perfect spot for au pair/teens/study area. Home perfectly sited on lot with good setback, two car garage and patio in rear yard. Located close to the bike trail, trolley, commuter rail, Shields Park, restaurants and easy drive to Blue Hills Reservation.

481 Eliot Street, Milton

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