Greaterbostonhomefinder.com Search Results

A rare opportunity to own one of Milton Hill's most distinguished homes. Set on nearly an acre just moments from Milton Village, this beautifully updated residence offers the space & versatility desired by the buyers of today. Designed to evolve with every stage of family life, the property features a 6 BR main home plus a newly completed 1 BR ADU, offering exceptional flexibility for extended family, guests, an au pair, private office or multigenerational living. Inside, generous gathering spaces, a chef's kitchen w/La Cornue range, formal & casual living areas, home office options & a finished 3rd floor provide room for families to grow, gather & entertain. Outside, enjoy a heated pool, pergola, wraparound deck & expansive fenced grounds designed for everything from childhood adventures to summer celebrations. Rich architectural detail blends seamlessly w/thoughtfully modern, yet classic updates. Minutes to Milton Academy, Milton Village, parks, restaurants & an easy commute.

7 Beds ⋅ 8 Baths ⋅ 73552866 MLS

A rare opportunity to own one of Milton Hill's most distinguished homes. Set on nearly an acre just moments from Milton Village, this beautifully updated residence offers the space & versatility desired by the buyers of today. Designed to evolve with every stage of family life, the property features a 6 BR main home plus a newly completed 1 BR ADU, offering exceptional flexibility for extended family, guests, an au pair, private office or multigenerational living. Inside, generous gathering spaces, a chef's kitchen w/La Cornue range, formal & casual living areas, home office options & a finished 3rd floor provide room for families to grow, gather & entertain. Outside, enjoy a heated pool, pergola, wraparound deck & expansive fenced grounds designed for everything from childhood adventures to summer celebrations. Rich architectural detail blends seamlessly w/thoughtfully modern, yet classic updates. Minutes to Milton Academy, Milton Village, parks, restaurants & an easy commute.

75 Canton Ave, Milton

Listing courtesy of Listing Agent: Sarah Glovsky from Listing Office: The Charles Realty.

$4,150,000

Milton Hill! Escape the ordinary and step into the extraordinary! French architecture meets modern luxury in the latest stunning Dev Group design. With grand features, an oasis-like outdoor area and smart-house system, it’s more than just a home—it’s a lifestyle. Say hello to your own personal sanctuary! Delivery date estimated at August 2025

6 Beds ⋅ 6 Baths ⋅ 73247341 MLS

Milton Hill! Escape the ordinary and step into the extraordinary! French architecture meets modern luxury in the latest stunning Dev Group design. With grand features, an oasis-like outdoor area and smart-house system, it’s more than just a home—it’s a lifestyle. Say hello to your own personal sanctuary! Delivery date estimated at August 2025

3 Hutchinson St, Milton

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

$3,500,000

There is a particular feeling that comes with finding the right home — recognition. And so it is with 103 Canton Ave, the feeling you’ve always known it. Set on a rare 2.65 acres, this residence carries a quiet confidence. The entry hall signals something significant ahead with each gathering space unfolding like a revelation. 6+ bedrooms, 4.5 renovated baths, and a floor plan that accommodates the full arc of life. The kitchen — custom cabinetry, Wolf and Sub-Zero — is the heart, as it always is. Floor-to-ceiling windows in the living room frame a bluestone terrace and expansive lawn. Light moves through this room in a way that reminds you why people fall in love with established addresses. Beneath its good bones: updated HVAC, electrical, roof, plumbing. The investment is sound; the comfort is modern. An oversized 2-car garage and mudroom complete the picture. Easy access to Milton Academy, Glover School, the trolley. This is the kind of home you explore once and already miss.

6 Beds ⋅ 5 Baths ⋅ 73508697 MLS

There is a particular feeling that comes with finding the right home — recognition. And so it is with 103 Canton Ave, the feeling you’ve always known it. Set on a rare 2.65 acres, this residence carries a quiet confidence. The entry hall signals something significant ahead with each gathering space unfolding like a revelation. 6+ bedrooms, 4.5 renovated baths, and a floor plan that accommodates the full arc of life. The kitchen — custom cabinetry, Wolf and Sub-Zero — is the heart, as it always is. Floor-to-ceiling windows in the living room frame a bluestone terrace and expansive lawn. Light moves through this room in a way that reminds you why people fall in love with established addresses. Beneath its good bones: updated HVAC, electrical, roof, plumbing. The investment is sound; the comfort is modern. An oversized 2-car garage and mudroom complete the picture. Easy access to Milton Academy, Glover School, the trolley. This is the kind of home you explore once and already miss.

103 Canton Ave, Milton

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

$3,100,000

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.

7 Beds ⋅ 5 Baths ⋅ 73374837 MLS

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

Listing courtesy of Listing Agent: Jackie O Real Estate Team from Listing Office: Keller Williams Realty Boston-Metro | Back Bay.

$3,099,000

Beautifully renovated and appointed 5-bedroom, 3.5-bath home in coveted Indian Cliffs Estates set on just under an acre of impeccably manicured grounds. This exceptional home features a spectacular 784 sq ft great room with 14-ft vaulted coffered ceilings, a dramatic 14-ft fieldstone fireplace, and custom mouldings, finishes and lighting throughout. The chef’s kitchen showcases a 9 foot island, custom Scandia cabinetry, Sub-Zero refrigerator, and a 48” Wolf dual-fuel 6-burner range with griddle and double ovens. Spacious, sun-filled interiors include a luxurious primary suite, finished basement, finished attic, ample storage, and flexible living space throughout. The private backyard retreat offers a resort-style salt water pool, spa, expansive patio, and lush landscaping perfect for entertaining. Ideally located less than one mile from Wollaston Golf Club, Milton Academy, Milton High, and Blue Hills Reservation. A rare turnkey opportunity in one of Milton’s premier neighborhoods.

5 Beds ⋅ 4 Baths ⋅ 73524569 MLS

Beautifully renovated and appointed 5-bedroom, 3.5-bath home in coveted Indian Cliffs Estates set on just under an acre of impeccably manicured grounds. This exceptional home features a spectacular 784 sq ft great room with 14-ft vaulted coffered ceilings, a dramatic 14-ft fieldstone fireplace, and custom mouldings, finishes and lighting throughout. The chef’s kitchen showcases a 9 foot island, custom Scandia cabinetry, Sub-Zero refrigerator, and a 48” Wolf dual-fuel 6-burner range with griddle and double ovens. Spacious, sun-filled interiors include a luxurious primary suite, finished basement, finished attic, ample storage, and flexible living space throughout. The private backyard retreat offers a resort-style salt water pool, spa, expansive patio, and lush landscaping perfect for entertaining. Ideally located less than one mile from Wollaston Golf Club, Milton Academy, Milton High, and Blue Hills Reservation. A rare turnkey opportunity in one of Milton’s premier neighborhoods.

85 Old Farm Rd, Milton

Listing courtesy of Listing Agent: Jay Rooney from Listing Office: Jay Rooney.

$3,000,000

Complete rebuild was finished in 2013 to create this state-of-the-art office building on the border of popular Milton Village. This stellar location provides easy access for consumers in Milton and Lower Mills, Dorchester, and an easy 1.5 mile drive on Adams St to I-93. Two beautifully redone floors of modern office space include kitchens, conference rooms, executive office suites and large reception areas. The building is ADA compliant and fully sprinklered with state-of-the-art heating and cooling systems. An additional 3000 square feet in its concrete high-and-dry basement is available for additional use. Large 22-space parking plus 2 ADA spaces. New owner can lease building as is or develop the property further, subject to Town of Milton approvals.

6 Baths ⋅ 73198906 MLS

Complete rebuild was finished in 2013 to create this state-of-the-art office building on the border of popular Milton Village. This stellar location provides easy access for consumers in Milton and Lower Mills, Dorchester, and an easy 1.5 mile drive on Adams St to I-93. Two beautifully redone floors of modern office space include kitchens, conference rooms, executive office suites and large reception areas. The building is ADA compliant and fully sprinklered with state-of-the-art heating and cooling systems. An additional 3000 square feet in its concrete high-and-dry basement is available for additional use. Large 22-space parking plus 2 ADA spaces. New owner can lease building as is or develop the property further, subject to Town of Milton approvals.

17 Canton Ave, Milton

Listing courtesy of Listing Agent: John Maxfield from Listing Office: Maxfield & Company Real Estate.

$2,900,000

Perched atop prestigious Milton Hill and set on nearly an acre of beautifully landscaped grounds, this extraordinary estate offers over 7,500 square feet of refined living space. A dramatic atrium foyer welcomes guests into elegant interiors featuring rich hardwood floors, soaring ceilings, and exceptional craftsmanship throughout. Designed for both grand entertaining and everyday living, the home includes a chef’s kitchen, wood-paneled library, media room, and temperature-controlled wine cellar. The luxurious primary suite serves as a private retreat with natural light and a spa-inspired bath, while four additional bedrooms provide ample space for family and guests. Outdoors, a resort-style setting awaits with a sparkling pool, cabana, expansive patios, and manicured grounds ideal for entertaining or relaxation. Complete with a three-car garage and offering the perfect balance of privacy and convenience, this residence is just minutes from Boston, renowned schools, and amenities.

4 Beds ⋅ 6 Baths ⋅ 73534896 MLS

Perched atop prestigious Milton Hill and set on nearly an acre of beautifully landscaped grounds, this extraordinary estate offers over 7,500 square feet of refined living space. A dramatic atrium foyer welcomes guests into elegant interiors featuring rich hardwood floors, soaring ceilings, and exceptional craftsmanship throughout. Designed for both grand entertaining and everyday living, the home includes a chef’s kitchen, wood-paneled library, media room, and temperature-controlled wine cellar. The luxurious primary suite serves as a private retreat with natural light and a spa-inspired bath, while four additional bedrooms provide ample space for family and guests. Outdoors, a resort-style setting awaits with a sparkling pool, cabana, expansive patios, and manicured grounds ideal for entertaining or relaxation. Complete with a three-car garage and offering the perfect balance of privacy and convenience, this residence is just minutes from Boston, renowned schools, and amenities.

263 Adams St, Milton

Listing courtesy of Listing Agent: Michael Carucci from Listing Office: Serhant.

$2,900,000

To those who resist being a foregone conclusion — consider this the on-ramp. The move to the suburbs is often framed as a trade: more space, less edge. At 995 Brush Hill Road, that bargain was never struck. This 6,790-square-foot mid-century residence carries its cool quietly — without announcement, without apology. The kitchen sets the tone with top tier appliances, a resort-scale fireplace, generous pantry and walls of glass dissolving the line between inside and out. Ceilings rise with intention, leaving room for light, art, and good times. Outdoors a generous deck hugs the landscape as though it was always meant to be. And for those whose other collection has horsepower, a new 6-car garage arrives as the final, considered gesture—designed for the discerning, built for the serious. There is room here for collections of every kind. This house doesn't ask what you'll do with the space. It assumes you already know. Mid-century bones. Modern sensibility. Milton, at its most compelling.

4 Beds ⋅ 4 Baths ⋅ 73504839 MLS

To those who resist being a foregone conclusion — consider this the on-ramp. The move to the suburbs is often framed as a trade: more space, less edge. At 995 Brush Hill Road, that bargain was never struck. This 6,790-square-foot mid-century residence carries its cool quietly — without announcement, without apology. The kitchen sets the tone with top tier appliances, a resort-scale fireplace, generous pantry and walls of glass dissolving the line between inside and out. Ceilings rise with intention, leaving room for light, art, and good times. Outdoors a generous deck hugs the landscape as though it was always meant to be. And for those whose other collection has horsepower, a new 6-car garage arrives as the final, considered gesture—designed for the discerning, built for the serious. There is room here for collections of every kind. This house doesn't ask what you'll do with the space. It assumes you already know. Mid-century bones. Modern sensibility. Milton, at its most compelling.

995 Brush Hill Rd, Milton

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

$2,850,000

Quintessential New England Home in one of the most desirable neighborhoods in Milton. This 5 bedroom, 3 full bath and 1 half bathroom is an entertainers dream with a beautifully appointed chef's kitchen with Wolf and Sub-Zero appliances, . This beautifully appointed home has abundant natural light, soaring ceilings with multiple entertainment areas throughout the home. This idyllic home is set on almost 3 private acres. Continue your entertaining on the very generous deck or retreat to your extensive backyard patio with a built in gas fireplace. This home is just minutes from the world renowned Milton Academy, fine dining and less than 30 minutes to downtown Boston or Providence.

5 Beds ⋅ 4 Baths ⋅ 73342706 MLS

Quintessential New England Home in one of the most desirable neighborhoods in Milton. This 5 bedroom, 3 full bath and 1 half bathroom is an entertainers dream with a beautifully appointed chef's kitchen with Wolf and Sub-Zero appliances, . This beautifully appointed home has abundant natural light, soaring ceilings with multiple entertainment areas throughout the home. This idyllic home is set on almost 3 private acres. Continue your entertaining on the very generous deck or retreat to your extensive backyard patio with a built in gas fireplace. This home is just minutes from the world renowned Milton Academy, fine dining and less than 30 minutes to downtown Boston or Providence.

80 Brierbrook, Milton

Listing courtesy of Listing Agent: Stephen Kraunelis from Listing Office: Gibson Sotheby's International Realty.

$2,750,000

Step into timeless elegance with this stunning brick manor-style residence, where classic architecture meets modern luxury. This exceptional home boasts a spectacular chef’s kitchen, featuring gleaming marble countertops, custom cabinetry, and top-of-the-line appliances—perfect for both grand entertaining and everyday living. Inside, you’ll find a harmonious blend of formal sophistication and inviting comfort. Expansive living spaces flow effortlessly, offering refined details such as intricate moldings, architecturally details, and rich hardwood floors, while maintaining a warm and relaxing atmosphere throughout. With intimate niches and multi functional spaces, this one will not disappoint! Whether hosting lavish gatherings or enjoying quiet moments by the fireplace, this property is designed to impress and embrace. A true masterpiece that combines elegance, functionality, and serenity. ...Come take a look, its 30 Highland Lane, what more needs to be said!

5 Beds ⋅ 6 Baths ⋅ 73469328 MLS

Step into timeless elegance with this stunning brick manor-style residence, where classic architecture meets modern luxury. This exceptional home boasts a spectacular chef’s kitchen, featuring gleaming marble countertops, custom cabinetry, and top-of-the-line appliances—perfect for both grand entertaining and everyday living. Inside, you’ll find a harmonious blend of formal sophistication and inviting comfort. Expansive living spaces flow effortlessly, offering refined details such as intricate moldings, architecturally details, and rich hardwood floors, while maintaining a warm and relaxing atmosphere throughout. With intimate niches and multi functional spaces, this one will not disappoint! Whether hosting lavish gatherings or enjoying quiet moments by the fireplace, this property is designed to impress and embrace. A true masterpiece that combines elegance, functionality, and serenity. ...Come take a look, its 30 Highland Lane, what more needs to be said!

30 Highland Ln, Milton

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

$2,680,000

This stunning 4-bedroom, 4.5-bath home with a 2-car garage is nestled on 1.8 beautifully landscaped acres in one of Milton’s most desirable neighborhoods. Perfectly suited for both everyday living and entertaining, the home offers spacious and sun-filled living areas throughout. The well -appointed chef’s kitchen features an eat-in breakfast area and cozy seating nook, flowing seamlessly into a large family room with a striking floor-to-ceiling stone fireplace. The luxurious primary suite boasts a second stone fireplace, a spa-like bath, a private deck overlooking the lawn, and a large walk-in closet with a dressing area. The finished basement offers flexible additional living space! Outside, enjoy a spacious deck, professionally designed gardens, a charming gazebo, and sweeping lawns, that include room for a pool and direct access to 125+ miles of scenic trails. A country like setting only 7 miles to Boston. Welcome home.

4 Beds ⋅ 5 Baths ⋅ 73420642 MLS

This stunning 4-bedroom, 4.5-bath home with a 2-car garage is nestled on 1.8 beautifully landscaped acres in one of Milton’s most desirable neighborhoods. Perfectly suited for both everyday living and entertaining, the home offers spacious and sun-filled living areas throughout. The well -appointed chef’s kitchen features an eat-in breakfast area and cozy seating nook, flowing seamlessly into a large family room with a striking floor-to-ceiling stone fireplace. The luxurious primary suite boasts a second stone fireplace, a spa-like bath, a private deck overlooking the lawn, and a large walk-in closet with a dressing area. The finished basement offers flexible additional living space! Outside, enjoy a spacious deck, professionally designed gardens, a charming gazebo, and sweeping lawns, that include room for a pool and direct access to 125+ miles of scenic trails. A country like setting only 7 miles to Boston. Welcome home.

218 Woodland Rd, Milton

Listing courtesy of Listing Agent: Katie Norton from Listing Office: William Raveis R.E. & Home Services.

$2,650,000

Welcome to 191 Adams Street, a fully reimagined sprawling Ranch offering effortless first-floor living, stylish updates, and spaces made for entertaining. Every room has been thoughtfully redone, creating a bright, open floor plan that feels inviting from the moment you walk in. The stunning kitchen features new appliances, a generous workspace, and a seamless connection to the living and dining rooms, where scenic views of Hutchinson Field and the Boston skyline steal the show. The finished lower level adds incredible flexibility with a bedroom, full bath, office, and multiple living areas ideal for guests, extended family, a gym, or media room. Step outside to an expansive patio and huge backyard perfect for cookouts, yard games, and summer nights. An attached garage, easy highway access, nearby restaurants, shopping, and the bike path complete this move-in-ready gem! PRIVATE SHOWINGS ONLY!

4 Beds ⋅ 3 Baths ⋅ 73550784 MLS

Welcome to 191 Adams Street, a fully reimagined sprawling Ranch offering effortless first-floor living, stylish updates, and spaces made for entertaining. Every room has been thoughtfully redone, creating a bright, open floor plan that feels inviting from the moment you walk in. The stunning kitchen features new appliances, a generous workspace, and a seamless connection to the living and dining rooms, where scenic views of Hutchinson Field and the Boston skyline steal the show. The finished lower level adds incredible flexibility with a bedroom, full bath, office, and multiple living areas ideal for guests, extended family, a gym, or media room. Step outside to an expansive patio and huge backyard perfect for cookouts, yard games, and summer nights. An attached garage, easy highway access, nearby restaurants, shopping, and the bike path complete this move-in-ready gem! PRIVATE SHOWINGS ONLY!

191 Adams St, Milton

Listing courtesy of Listing Agent: Kim Powers from Listing Office: Coldwell Banker Realty - Milton.

$2,575,000

Leave your worries at the door and follow your bliss—20 Herrick Drive is that rare home where every day feels lighter and brighter. Set on one of Milton’s premier cul-de-sacs and embraced by conservation land, the acre lot offers privacy that is increasingly hard to find. Lofty spaces elevate the experience while generous windows and glass doors draw in the sun’s warmth and light. A home office supports modern requirements. The expansive family room is designed to gather comfortably. Flexible options for a guest suite or live-in arrangement. A renovated primary bath offers everyday comfort. The inground pool and bluestone terrace promise long summer afternoons with plenty of lawn for play, gardening, or peace. An oversized garage, newer windows and modern HVAC are all here. With the trolley, restaurants, Glover School, Milton Academy and Turner’s Pond close at hand, convenience becomes part of the lifestyle. If you’ve been waiting for a home that simply feels right—this is your moment.

5 Beds ⋅ 4 Baths ⋅ 73458908 MLS

Leave your worries at the door and follow your bliss—20 Herrick Drive is that rare home where every day feels lighter and brighter. Set on one of Milton’s premier cul-de-sacs and embraced by conservation land, the acre lot offers privacy that is increasingly hard to find. Lofty spaces elevate the experience while generous windows and glass doors draw in the sun’s warmth and light. A home office supports modern requirements. The expansive family room is designed to gather comfortably. Flexible options for a guest suite or live-in arrangement. A renovated primary bath offers everyday comfort. The inground pool and bluestone terrace promise long summer afternoons with plenty of lawn for play, gardening, or peace. An oversized garage, newer windows and modern HVAC are all here. With the trolley, restaurants, Glover School, Milton Academy and Turner’s Pond close at hand, convenience becomes part of the lifestyle. If you’ve been waiting for a home that simply feels right—this is your moment.

20 Herrick Dr, Milton

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

$2,550,000

You've been looking for a while. You can stop now. 7 Phyllis Lane was custom-built by a trusted local builder as a forever home. And it shows. Ten-foot ceilings, custom millwork, built-ins. Hardieplank siding, Harvey windows, hydro air heating...infrastructure chosen for longevity and efficiency, not just aesthetics. The kitchen just works: massive island, Thermador appliances, Cambria quartz, sliders to the patio and fire pit. A main-level bedroom flexes as office or guest room. Upstairs, the primary suite delivers: soaking tub, steam shower, custom walk-in closet. Two bedrooms share a jack-and-jill; a fourth has its own bath. A spacious den and sitting room mean everyone has somewhere to land. The lower level flexes for whatever comes next...teen suite, au pair, in-laws. Premium white oak floors, high-end fixtures & finishes, Graff plumbing in plated gold. Carefully chosen details. Cunningham Park locale, top-tier schools, local dining, easy Boston access. You know this is the one.

5 Beds ⋅ 5 Baths ⋅ 73525582 MLS

You've been looking for a while. You can stop now. 7 Phyllis Lane was custom-built by a trusted local builder as a forever home. And it shows. Ten-foot ceilings, custom millwork, built-ins. Hardieplank siding, Harvey windows, hydro air heating...infrastructure chosen for longevity and efficiency, not just aesthetics. The kitchen just works: massive island, Thermador appliances, Cambria quartz, sliders to the patio and fire pit. A main-level bedroom flexes as office or guest room. Upstairs, the primary suite delivers: soaking tub, steam shower, custom walk-in closet. Two bedrooms share a jack-and-jill; a fourth has its own bath. A spacious den and sitting room mean everyone has somewhere to land. The lower level flexes for whatever comes next...teen suite, au pair, in-laws. Premium white oak floors, high-end fixtures & finishes, Graff plumbing in plated gold. Carefully chosen details. Cunningham Park locale, top-tier schools, local dining, easy Boston access. You know this is the one.

7 Phyllis Lane, Milton

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

$2,550,000

Stunning 2014 shingle-style contemporary filled with light, thoughtful design, and quality amenities. With more than 4,500 sq. ft. of living space, the open-concept first floor features a chef’s kitchen with Jenn-Air appliances, quartz countertops, a generous island with gas range, and pantry. The dining room opens to a sleek IPE deck, while the living room with fireplace offers a warm gathering space. There is a home study/office, first floor laundry, a half bath, and a luxurious first-floor suite with dual walk-ins, steam shower, and soaking tub that completes the first level. Upstairs are three spacious bedrooms with a shared double-sink bath. A private suite above the garage with walk-in and full bath offers flexible use—au pair, in-law, or guest retreat. Quality shines through with Marvin Integrity windows, Rinnai hot water, three HVAC systems (five zones), white oak floors and Emtek hardware. Very close to Milton Academy, this home blends modern convenience with timeless style.

5 Beds ⋅ 4 Baths ⋅ 73426168 MLS

Stunning 2014 shingle-style contemporary filled with light, thoughtful design, and quality amenities. With more than 4,500 sq. ft. of living space, the open-concept first floor features a chef’s kitchen with Jenn-Air appliances, quartz countertops, a generous island with gas range, and pantry. The dining room opens to a sleek IPE deck, while the living room with fireplace offers a warm gathering space. There is a home study/office, first floor laundry, a half bath, and a luxurious first-floor suite with dual walk-ins, steam shower, and soaking tub that completes the first level. Upstairs are three spacious bedrooms with a shared double-sink bath. A private suite above the garage with walk-in and full bath offers flexible use—au pair, in-law, or guest retreat. Quality shines through with Marvin Integrity windows, Rinnai hot water, three HVAC systems (five zones), white oak floors and Emtek hardware. Very close to Milton Academy, this home blends modern convenience with timeless style.

141 Gun Hill St, Milton

Listing courtesy of Listing Agent: Christman Johnsson Group from Listing Office: Hammond Residential Real Estate.

$2,515,000

Recently reimagined by Design Construction Plus of Wellesley, this exceptional 4-bedroom, 3.5-bath home blends classic New England charm with sophisticated modern design across three finished levels beneath a timeless gambrel roofline. Sunlight fills the home through oversized windows, highlighting soaring ceilings, designer lighting, and curated finishes throughout. The open-concept living area features a dramatic stone fireplace and flows seamlessly into a chef’s kitchen with a quartz waterfall island, custom cabinetry, and premium Wolf, Thermador, and Liebherr appliances. Spa-inspired baths, a private en suite office, six heating zones, three zones of central air, updated systems, integrated sound, and exterior lighting add comfort and convenience. Ideally located near Glover Elementary, parks, shopping, dining, and commuter access, this turnkey Milton home offers timeless architecture, luxury finishes, and modern living.

4 Beds ⋅ 4 Baths ⋅ 73525151 MLS

Recently reimagined by Design Construction Plus of Wellesley, this exceptional 4-bedroom, 3.5-bath home blends classic New England charm with sophisticated modern design across three finished levels beneath a timeless gambrel roofline. Sunlight fills the home through oversized windows, highlighting soaring ceilings, designer lighting, and curated finishes throughout. The open-concept living area features a dramatic stone fireplace and flows seamlessly into a chef’s kitchen with a quartz waterfall island, custom cabinetry, and premium Wolf, Thermador, and Liebherr appliances. Spa-inspired baths, a private en suite office, six heating zones, three zones of central air, updated systems, integrated sound, and exterior lighting add comfort and convenience. Ideally located near Glover Elementary, parks, shopping, dining, and commuter access, this turnkey Milton home offers timeless architecture, luxury finishes, and modern living.

196 Canton Ave, Milton

Listing courtesy of Listing Agent: Scott Farrell & Partners from Listing Office: Compass.

$2,500,000

Welcome to a home where quality meets versatility. This stunning young Gambrel is a true standout, offering a seamless flow for both daily living and entertaining. The heart of the first floor is a custom white kitchen with quartz countertops, a large island, and a gas stove, all open to a cozy living room with a fireplace. The main level also features a formal dining room with patio access, a dedicated office, and a convenient en-suite bedroom. Upstairs, the luxurious primary suite boasts two walk-in closets and a private bathroom. You'll find two additional en-suite bedrooms and a second laundry room for ultimate convenience. A versatile bonus room above the three-car garage, complete with a full bathroom, is ideal for a family room, home office, or an in-law suite. The finished, walk-out basement adds more functional space, including another full bathroom. Situated on a beautiful, fenced acre lot, this home also features durable Hardi-plank siding and a 3-car garage - a rare find!

4 Beds ⋅ 8 Baths ⋅ 73428702 MLS

Welcome to a home where quality meets versatility. This stunning young Gambrel is a true standout, offering a seamless flow for both daily living and entertaining. The heart of the first floor is a custom white kitchen with quartz countertops, a large island, and a gas stove, all open to a cozy living room with a fireplace. The main level also features a formal dining room with patio access, a dedicated office, and a convenient en-suite bedroom. Upstairs, the luxurious primary suite boasts two walk-in closets and a private bathroom. You'll find two additional en-suite bedrooms and a second laundry room for ultimate convenience. A versatile bonus room above the three-car garage, complete with a full bathroom, is ideal for a family room, home office, or an in-law suite. The finished, walk-out basement adds more functional space, including another full bathroom. Situated on a beautiful, fenced acre lot, this home also features durable Hardi-plank siding and a 3-car garage - a rare find!

16 Hallen Avenue, Milton

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

$2,450,000

Imagine coming home to a private Milton enclave where timeless elegance meets everyday livability. Set on over an acre, 50 Marine Road offers grand living spaces designed for comfort, longevity, & flexibility. With 3 separate staircases, the layout is ideal for multi-generational living/au pair suite. Inside, 9 fireplaces and rich millwork reflect the home’s classic character, with substantial infrastructure updates including a young roof and heating system, 400-amp electrical service, copper downspouts, and new water, sewer, and gas lines. The sun-filled kitchen with island anchors the home, while a sunroom, elegant office with fireplace, and versatile bonus rooms provide endless possibilities. Outdoors, lush grounds surround a pool, hot tub, & stone patios, creating a private setting for entertaining or retreat. Surrounded by newer homes on a coveted cul-de-sac, this rare estate blends elegance, substance, and the lifestyle that defines Milton living—just minutes to Milton Academy.

7 Beds ⋅ 6 Baths ⋅ 73423979 MLS

Imagine coming home to a private Milton enclave where timeless elegance meets everyday livability. Set on over an acre, 50 Marine Road offers grand living spaces designed for comfort, longevity, & flexibility. With 3 separate staircases, the layout is ideal for multi-generational living/au pair suite. Inside, 9 fireplaces and rich millwork reflect the home’s classic character, with substantial infrastructure updates including a young roof and heating system, 400-amp electrical service, copper downspouts, and new water, sewer, and gas lines. The sun-filled kitchen with island anchors the home, while a sunroom, elegant office with fireplace, and versatile bonus rooms provide endless possibilities. Outdoors, lush grounds surround a pool, hot tub, & stone patios, creating a private setting for entertaining or retreat. Surrounded by newer homes on a coveted cul-de-sac, this rare estate blends elegance, substance, and the lifestyle that defines Milton living—just minutes to Milton Academy.

50 Marine Rd, Milton

Listing courtesy of Listing Agent: Beth Rooney from Listing Office: .

$2,300,000

Step into the timeless elegance of this fabulous Antique Colonial, where historic charm meets modern sophistication. Soaring ceilings and sunlit open spaces create an inviting flow throughout, showcasing period details perfectly blended with contemporary updates. At the heart of the home is a designer chef’s kitchen, thoughtfully crafted with high-end finishes, custom cabinetry, and expansive workspaces—ideal for cooking, gathering, and entertaining in style. Outside, the property continues to impress with an expansive yard offering endless possibilities for play, gardening, or outdoor hosting. Anchoring the grounds is an original barn, rich with character and bursting with potential. Whether envisioned as a party venue, entertainment hub, or future recreation room, it adds a rare and remarkable dimension to the home.This is more than a residence—it’s a unique opportunity to own a beautifully preserved piece of history with all the comforts and conveniences of modern living.

4 Beds ⋅ 3 Baths ⋅ 73481833 MLS

Step into the timeless elegance of this fabulous Antique Colonial, where historic charm meets modern sophistication. Soaring ceilings and sunlit open spaces create an inviting flow throughout, showcasing period details perfectly blended with contemporary updates. At the heart of the home is a designer chef’s kitchen, thoughtfully crafted with high-end finishes, custom cabinetry, and expansive workspaces—ideal for cooking, gathering, and entertaining in style. Outside, the property continues to impress with an expansive yard offering endless possibilities for play, gardening, or outdoor hosting. Anchoring the grounds is an original barn, rich with character and bursting with potential. Whether envisioned as a party venue, entertainment hub, or future recreation room, it adds a rare and remarkable dimension to the home.This is more than a residence—it’s a unique opportunity to own a beautifully preserved piece of history with all the comforts and conveniences of modern living.

260 Canton Ave, Milton

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

$2,215,000

Nestled in Milton’s sought-after Hillside neighborhood, this exceptional Federal-style Colonial offers the perfect blend of classic charm, quality renovations, & ideal livability. Thoughtfully improved & meticulously cared for, the home offers 3400 sq ft of living space, including a floor-through living room, dining room, two inviting dens - with 8 ft ceilings, four fireplaces and windows galore. The sunlit kitchen opens to a breakfast nook and newly converted four-season sunroom, creating a natural connection to the outdoors. Upstairs offers four generously sized bedrooms including primary suite with en-suite bath and pristine family bath. A large and inviting family / bonus room with a gas fireplace and bar completes the lower level. Set on a private, professionally landscaped .92-acre lot, the outdoor setting is magnificent; with heated in-ground pool, expansive level lawn, and fenced privacy, this is a true lifestyle property and a turnkey opportunity for a forever home in Milton.

4 Beds ⋅ 3 Baths ⋅ 73490877 MLS

Nestled in Milton’s sought-after Hillside neighborhood, this exceptional Federal-style Colonial offers the perfect blend of classic charm, quality renovations, & ideal livability. Thoughtfully improved & meticulously cared for, the home offers 3400 sq ft of living space, including a floor-through living room, dining room, two inviting dens - with 8 ft ceilings, four fireplaces and windows galore. The sunlit kitchen opens to a breakfast nook and newly converted four-season sunroom, creating a natural connection to the outdoors. Upstairs offers four generously sized bedrooms including primary suite with en-suite bath and pristine family bath. A large and inviting family / bonus room with a gas fireplace and bar completes the lower level. Set on a private, professionally landscaped .92-acre lot, the outdoor setting is magnificent; with heated in-ground pool, expansive level lawn, and fenced privacy, this is a true lifestyle property and a turnkey opportunity for a forever home in Milton.

23 Parkwood Dr, Milton

Listing courtesy of Listing Agent: Peggy Gemelli from Listing Office: Gibson Sotheby's International Realty.

$2,200,000

Nestled in the foothills of the Blue Hills Reservation, with access to 7,000+ acres of protected land and miles of hiking trails, and close to Wollaston Golf Cub, this beautifully updated 5-bedroom, 4.5-bath home offers space, flexibility, and a peaceful setting just 10 miles from Boston. Set on nearly an acre and abutting conservation land, the backyard provides a private retreat ideal for everyday living and entertaining. The home features 5 bedrooms, including two primary suites, offering versatility for guests, extended family, or changing needs. A fully renovated primary bath, and thoughtful updates throughout make the home move-in ready. A modern kitchen, dedicated home office, and finished lower level with space for a playroom, gym, and media room complete the layout. Enjoy outdoor living with a new deck, covered deck, patio, and fire pit—all in a serene, natural setting.

5 Beds ⋅ 5 Baths ⋅ 73504726 MLS

Nestled in the foothills of the Blue Hills Reservation, with access to 7,000+ acres of protected land and miles of hiking trails, and close to Wollaston Golf Cub, this beautifully updated 5-bedroom, 4.5-bath home offers space, flexibility, and a peaceful setting just 10 miles from Boston. Set on nearly an acre and abutting conservation land, the backyard provides a private retreat ideal for everyday living and entertaining. The home features 5 bedrooms, including two primary suites, offering versatility for guests, extended family, or changing needs. A fully renovated primary bath, and thoughtful updates throughout make the home move-in ready. A modern kitchen, dedicated home office, and finished lower level with space for a playroom, gym, and media room complete the layout. Enjoy outdoor living with a new deck, covered deck, patio, and fire pit—all in a serene, natural setting.

5 Mark Ln, Milton

Listing courtesy of Listing Agent: Beth Rooney from Listing Office: eXp Realty LLC - Corporate Office.

$2,100,000

There are homes that welcome you, and then there are homes that claim you. From the moment you step inside, this Milton Hill original announces itself—high ceilings, sweeping wall spaces, hefty moldings, an irresistible personality. Set on a lush acre, this residence has only grown more compelling with each refinement. Grand wall spaces beg for the art you've been waiting to hang, while a sense of graciousness moves through every room like a long exhale. A renovated eat-in kitchen is beautiful and deeply livable—mornings full of promise, evenings that stretch long. Every thoughtful update (windows, electrical, roof) honors what the house has always known about itself. Interior life unfolds over 4,300sf, 5+ bedrooms and 3.5 baths. And just beyond your door: Milton Academy, Glover School, Steel & Rye, the trolley. This is a home for someone who understands that where you live shapes how you live — a backdrop for the art, the dinners, the mornings in the garden, a life available here.

5 Beds ⋅ 4 Baths ⋅ 73497233 MLS

There are homes that welcome you, and then there are homes that claim you. From the moment you step inside, this Milton Hill original announces itself—high ceilings, sweeping wall spaces, hefty moldings, an irresistible personality. Set on a lush acre, this residence has only grown more compelling with each refinement. Grand wall spaces beg for the art you've been waiting to hang, while a sense of graciousness moves through every room like a long exhale. A renovated eat-in kitchen is beautiful and deeply livable—mornings full of promise, evenings that stretch long. Every thoughtful update (windows, electrical, roof) honors what the house has always known about itself. Interior life unfolds over 4,300sf, 5+ bedrooms and 3.5 baths. And just beyond your door: Milton Academy, Glover School, Steel & Rye, the trolley. This is a home for someone who understands that where you live shapes how you live — a backdrop for the art, the dinners, the mornings in the garden, a life available here.

213 School St, Milton

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

$2,100,000

Beautifully maintained 5-bedroom, 3.5-bath home located in one of the most desirable Hillside neighborhoods in Milton. This pristine property is in impeccable condition and features numerous recent updates, including newly renovated primary and main bathrooms, updated windows, and a newer roof.The home is surrounded by gorgeous landscaping that enhances its curb appeal and provides a serene outdoor setting. Enjoy exceptional amenities including a private tennis court and a 2-car attached garage. Situated on over an acre lot, adjacent to the Blue Hills and its abundance of trails to explore! A short distance to Wollaston CC and Milton Academy as well as close proximity to Boston and Logan Airport (8 miles)…A rare opportunity to own a move-in-ready home in a sought-after Milton location

5 Beds ⋅ 4 Baths ⋅ 73485700 MLS

Beautifully maintained 5-bedroom, 3.5-bath home located in one of the most desirable Hillside neighborhoods in Milton. This pristine property is in impeccable condition and features numerous recent updates, including newly renovated primary and main bathrooms, updated windows, and a newer roof.The home is surrounded by gorgeous landscaping that enhances its curb appeal and provides a serene outdoor setting. Enjoy exceptional amenities including a private tennis court and a 2-car attached garage. Situated on over an acre lot, adjacent to the Blue Hills and its abundance of trails to explore! A short distance to Wollaston CC and Milton Academy as well as close proximity to Boston and Logan Airport (8 miles)…A rare opportunity to own a move-in-ready home in a sought-after Milton location

57 Brierbrook St, Milton

Listing courtesy of Listing Agent: Timothy E. Driscoll from Listing Office: South Shore Sotheby's International Realty.

$2,050,000

Rarely does a home so admired come to market! Timeless character and thoughtful updates of this story book home shine through its detailed woodwork, cozy nooks and connected layout. The flow of the open kitchen, dining, and family room create a perfect setting for gatherings big and small. Upstairs, a spacious landing, updated baths, and central air provide comfort and convenience, while the serene primary suite offers a calming retreat at day’s end. An attached two car garage and adjacent loft, convenient mudroom, and a lower level rec room provide flexibility and great storage space to simplify daily life. A charming front porch swing and backyard patio invite morning coffee and evening conversation. A quiet path that leads directly to Shields Park will bring a smile in every season. The home is just steps to schools, Turner’s Pond, coffee shops, restaurants and public transportation. Don't let the opportunity to live in this home in one of Milton's finest neighborhoods pass you by!

5 Beds ⋅ 3 Baths ⋅ 73451463 MLS

Rarely does a home so admired come to market! Timeless character and thoughtful updates of this story book home shine through its detailed woodwork, cozy nooks and connected layout. The flow of the open kitchen, dining, and family room create a perfect setting for gatherings big and small. Upstairs, a spacious landing, updated baths, and central air provide comfort and convenience, while the serene primary suite offers a calming retreat at day’s end. An attached two car garage and adjacent loft, convenient mudroom, and a lower level rec room provide flexibility and great storage space to simplify daily life. A charming front porch swing and backyard patio invite morning coffee and evening conversation. A quiet path that leads directly to Shields Park will bring a smile in every season. The home is just steps to schools, Turner’s Pond, coffee shops, restaurants and public transportation. Don't let the opportunity to live in this home in one of Milton's finest neighborhoods pass you by!

32 Columbine Rd, Milton

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

$2,000,000

Set on over 1.4 acres in one of Milton’s most picturesque settings, 268 Highland Street is a timeless brick-front Colonial where elegance, warmth, and unforgettable gatherings have defined this home for decades. From the slate roof and copper downspouts to the sweeping green lawns and mature landscape, every detail reflects classic New England charm. Inside, beautifully updated kitchens and baths blend seamlessly with gracious living spaces designed for entertaining and everyday comfort. A stunning home office overlooks the patio and expansive backyard, creating an inspiring work-from-home retreat. Beyond the main residence sits an extraordinary three-story barn—offering endless possibilities for creative space, storage, hobby use, or potential future ADU opportunities. Rarely does a property offer this combination of character, land, flexibility, and legacy just minutes from Boston.

3 Beds ⋅ 3 Baths ⋅ 73523755 MLS

Set on over 1.4 acres in one of Milton’s most picturesque settings, 268 Highland Street is a timeless brick-front Colonial where elegance, warmth, and unforgettable gatherings have defined this home for decades. From the slate roof and copper downspouts to the sweeping green lawns and mature landscape, every detail reflects classic New England charm. Inside, beautifully updated kitchens and baths blend seamlessly with gracious living spaces designed for entertaining and everyday comfort. A stunning home office overlooks the patio and expansive backyard, creating an inspiring work-from-home retreat. Beyond the main residence sits an extraordinary three-story barn—offering endless possibilities for creative space, storage, hobby use, or potential future ADU opportunities. Rarely does a property offer this combination of character, land, flexibility, and legacy just minutes from Boston.

268 Highland St, Milton

Listing courtesy of Listing Agent: Beth Rooney from Listing Office: eXp Realty LLC - Corporate Office.

$1,985,000

Timeless elegance meets modern sophistication in this distinguished Cunningham Park residence. This 5 bed, 4 bath brick-front Colonial stands proudly on a corner lot in one of Milton’s most desirable neighborhoods, offering a layout designed for both elegant entertaining and everyday comfort. The first floor features formal living and dining rooms, a thoughtfully designed kitchen with island and dining area, and a bright family room that extends to a spacious deck and expansive backyard. Upstairs, the serene primary suite with spa-like bath is joined by three additional bedrooms and a full bath. A finished loft provides flexible space for a home office, playroom, or lounge, while the lower level offers a recreation room ideal for movies or games plus an additional bedroom and a flex room currently used as a gym. Designer finishes elevate the interiors, while a two-car garage, manicured grounds, and commanding curb appeal complete this rare offering of classic style and modern ease.

5 Beds ⋅ 4 Baths ⋅ 73429965 MLS

Timeless elegance meets modern sophistication in this distinguished Cunningham Park residence. This 5 bed, 4 bath brick-front Colonial stands proudly on a corner lot in one of Milton’s most desirable neighborhoods, offering a layout designed for both elegant entertaining and everyday comfort. The first floor features formal living and dining rooms, a thoughtfully designed kitchen with island and dining area, and a bright family room that extends to a spacious deck and expansive backyard. Upstairs, the serene primary suite with spa-like bath is joined by three additional bedrooms and a full bath. A finished loft provides flexible space for a home office, playroom, or lounge, while the lower level offers a recreation room ideal for movies or games plus an additional bedroom and a flex room currently used as a gym. Designer finishes elevate the interiors, while a two-car garage, manicured grounds, and commanding curb appeal complete this rare offering of classic style and modern ease.

4 Cunningham Lane, Milton

Listing courtesy of Listing Agent: Ricardo Rodriguez & Associates Group from Listing Office: Coldwell Banker Realty - Boston.

$1,930,000

Nestled in the beautiful town of Milton, Massachusetts, 108 Indian Spring Rd presents a single-family residence that exudes timeless appeal, ready to welcome its next chapter. The generous living area, encompassing 3597 sq. ft. offers a canvas for both grand entertaining and intimate gatherings; here, the rhythm of daily life finds its perfect harmony. The residence includes five bedrooms, each providing a private sanctuary for rest and rejuvenation. Two full bathrooms and two half bathrooms are thoughtfully positioned to enhance convenience and comfort for everyone. Lower level features 1784 sq ft of unfinished space too. The expansive 41,251 square foot lot offers endless possibilities for outdoor enjoyment & recreation with an inground pool. Ready for New Buyers an exceptional opportunity living experience in a coveted location with a 2 Car Garage. Fabulous Indian Cliffs location minutes to Schools, Restaurants, Wollaston Golf Club & all Major Routes. See you at the Open Houses.

5 Beds ⋅ 4 Baths ⋅ 73431658 MLS

Nestled in the beautiful town of Milton, Massachusetts, 108 Indian Spring Rd presents a single-family residence that exudes timeless appeal, ready to welcome its next chapter. The generous living area, encompassing 3597 sq. ft. offers a canvas for both grand entertaining and intimate gatherings; here, the rhythm of daily life finds its perfect harmony. The residence includes five bedrooms, each providing a private sanctuary for rest and rejuvenation. Two full bathrooms and two half bathrooms are thoughtfully positioned to enhance convenience and comfort for everyone. Lower level features 1784 sq ft of unfinished space too. The expansive 41,251 square foot lot offers endless possibilities for outdoor enjoyment & recreation with an inground pool. Ready for New Buyers an exceptional opportunity living experience in a coveted location with a 2 Car Garage. Fabulous Indian Cliffs location minutes to Schools, Restaurants, Wollaston Golf Club & all Major Routes. See you at the Open Houses.

108 Indian Spring Rd, Milton

Listing courtesy of Listing Agent: Francine Jeffers from Listing Office: Kelley & Rege Properties, Inc..

$1,910,000

Designed to grow with you, this beautifully maintained, young home offers nearly 4,000 square feet of flexible living space on a spectacular 1.6-acre lot. The thoughtfully designed floor plan includes a first-floor primary suite, an additional first-floor bedroom, and two spacious bedrooms upstairs—ideal for a variety of lifestyles and living arrangements. At the heart of the home is a stunning custom kitchen by Faneuil Kitchens, opening to inviting spaces perfect for everyday living and entertaining. A bright living room with a dramatic two-sided fireplace creates a warm and welcoming gathering place, while oversized windows frame views of the beautifully landscaped grounds.Whether you're hosting holidays, working from home, accommodating guests, or simply looking for a home that will serve you for years to come, this exceptional property offers the space, flexibility, and setting to make it all possible!

4 Beds ⋅ 4 Baths ⋅ 73532795 MLS

Designed to grow with you, this beautifully maintained, young home offers nearly 4,000 square feet of flexible living space on a spectacular 1.6-acre lot. The thoughtfully designed floor plan includes a first-floor primary suite, an additional first-floor bedroom, and two spacious bedrooms upstairs—ideal for a variety of lifestyles and living arrangements. At the heart of the home is a stunning custom kitchen by Faneuil Kitchens, opening to inviting spaces perfect for everyday living and entertaining. A bright living room with a dramatic two-sided fireplace creates a warm and welcoming gathering place, while oversized windows frame views of the beautifully landscaped grounds.Whether you're hosting holidays, working from home, accommodating guests, or simply looking for a home that will serve you for years to come, this exceptional property offers the space, flexibility, and setting to make it all possible!

282 Highland St, Milton

Listing courtesy of Listing Agent: Beth Rooney from Listing Office: eXp Realty LLC - Corporate Office.

$1,899,000

Discover the ease of living in the distinguished Adams design at Wolcott Woods, a premier 55+ community just outside Boston. This thoughtfully crafted home features a bright, open layout, stunning fireplace and a living room with dramatic cathedral ceilings. The chef’s kitchen connects seamlessly to a sunlit breakfast nook and private deck, perfect for morning coffee or casual entertaining. The first-floor primary suite offers a peaceful retreat, while the upstairs loft and guest bedroom provide comfortable space for visitors or hobbies. A walk-out lower level adds flexibility, with the potential to finish for even more living area.

2 Beds ⋅ 3 Baths ⋅ 73473373 MLS

Discover the ease of living in the distinguished Adams design at Wolcott Woods, a premier 55+ community just outside Boston. This thoughtfully crafted home features a bright, open layout, stunning fireplace and a living room with dramatic cathedral ceilings. The chef’s kitchen connects seamlessly to a sunlit breakfast nook and private deck, perfect for morning coffee or casual entertaining. The first-floor primary suite offers a peaceful retreat, while the upstairs loft and guest bedroom provide comfortable space for visitors or hobbies. A walk-out lower level adds flexibility, with the potential to finish for even more living area.

69 Wolcott Woods Lane Unit 69, Milton

Listing courtesy of Listing Agent: Dot Collection from Listing Office: Access.

$1,895,000

Step into timeless elegance with this beautifully preserved 1928 Colonial, brimming with charm and character at every turn. Perfectly situated in the heart of highly desirable Milton Hill, this exceptional home blends classic architectural detail with modern living. Soaring ceilings and sun-drenched rooms create an inviting, airy atmosphere throughout. The open-concept kitchen and family room offer the ideal space for both everyday living and entertaining, seamlessly connecting style and function. Spanning three thoughtfully designed levels, this home provides abundant living space to grow, relax, and gather. Outside, enjoy an expansive, private yard on a peaceful dead-end street—perfect for outdoor entertaining, play, or quiet retreat. Start your day or unwind in the evening on the charming covered front porch, taking in the beauty of this quintessential New England setting. A rare opportunity to own a truly special home in an unbeatable location—this is Milton living at its finest.

4 Beds ⋅ 3 Baths ⋅ 73515241 MLS

Step into timeless elegance with this beautifully preserved 1928 Colonial, brimming with charm and character at every turn. Perfectly situated in the heart of highly desirable Milton Hill, this exceptional home blends classic architectural detail with modern living. Soaring ceilings and sun-drenched rooms create an inviting, airy atmosphere throughout. The open-concept kitchen and family room offer the ideal space for both everyday living and entertaining, seamlessly connecting style and function. Spanning three thoughtfully designed levels, this home provides abundant living space to grow, relax, and gather. Outside, enjoy an expansive, private yard on a peaceful dead-end street—perfect for outdoor entertaining, play, or quiet retreat. Start your day or unwind in the evening on the charming covered front porch, taking in the beauty of this quintessential New England setting. A rare opportunity to own a truly special home in an unbeatable location—this is Milton living at its finest.

50 W Side Rd, Milton

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