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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.

$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.

$3,099,000

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.

$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.

$2,650,000

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.

$2,550,000

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.

$2,515,000

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.

$2,300,000

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.

$2,000,000

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.

$1,910,000

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.

$1,895,000

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.

$1,890,000

Step back in time with this stunning 12 room Victorian masterpiece-a perfect blend of timeless elegance and modern comfort. This turn-key home features three levels of living with 5 spacious bedrooms and 3 bathrooms, offering room for everyone. From the moment you enter, you'll be captivated by the incredible solid woodwork, ornate architectural details and period charm that define every space. High ceilings, intricate trim and large windows bathe the home in natural light, while modern updates-thoughtfully integrated throughout-ensure effortless living. Whether your're entertaining guests on the stately covered porch or enjoying quiet evenings by the fireplace, this Victorian gem delivers both grandeur and warmth in equal measure. With its meticulous preservation and complete updates, this home is truly a one-of-a-kind treasure ready for you to move right in and enjoy. See attached list of improvements which includes central air, solar panels, hardscaping and boiler.

5 Beds ⋅ 3 Baths ⋅ 73508119 MLS

Step back in time with this stunning 12 room Victorian masterpiece-a perfect blend of timeless elegance and modern comfort. This turn-key home features three levels of living with 5 spacious bedrooms and 3 bathrooms, offering room for everyone. From the moment you enter, you'll be captivated by the incredible solid woodwork, ornate architectural details and period charm that define every space. High ceilings, intricate trim and large windows bathe the home in natural light, while modern updates-thoughtfully integrated throughout-ensure effortless living. Whether your're entertaining guests on the stately covered porch or enjoying quiet evenings by the fireplace, this Victorian gem delivers both grandeur and warmth in equal measure. With its meticulous preservation and complete updates, this home is truly a one-of-a-kind treasure ready for you to move right in and enjoy. See attached list of improvements which includes central air, solar panels, hardscaping and boiler.

30 Magnolia Rd, Milton

Listing courtesy of Listing Agent: Kathleen Huntington from Listing Office: Coldwell Banker Realty - Milton.

$1,815,000

Set on a prominent corner lot in Milton, this turnkey residence blends classic Garrison architecture with elevated modern design. Renovated in 2020, it features Hardie Board siding, a new roof, underground electrical service, updated plumbing, and a Navien on-demand water heater. The kitchen is crafted for both everyday living and entertaining, offering quartz countertops, a gas cooktop, double ovens, and custom cabinetry. Each bedroom enjoys direct bath access, including a luxurious primary suite with heated marble floors, dual vanities, an oversized shower, two walk-in closets, and a private roof deck. A top-level family or game room adds flexibility, while the finished lower level includes a wet bar and full bath ideal for media, guests, or fitness. Three-zone gas HVAC, composite decking, an outdoor gas line for grilling, a lofted garage with mudroom access, and mature arborvitae privacy create a home you will truly love.

5 Beds ⋅ 5 Baths ⋅ 73476915 MLS

Set on a prominent corner lot in Milton, this turnkey residence blends classic Garrison architecture with elevated modern design. Renovated in 2020, it features Hardie Board siding, a new roof, underground electrical service, updated plumbing, and a Navien on-demand water heater. The kitchen is crafted for both everyday living and entertaining, offering quartz countertops, a gas cooktop, double ovens, and custom cabinetry. Each bedroom enjoys direct bath access, including a luxurious primary suite with heated marble floors, dual vanities, an oversized shower, two walk-in closets, and a private roof deck. A top-level family or game room adds flexibility, while the finished lower level includes a wet bar and full bath ideal for media, guests, or fitness. Three-zone gas HVAC, composite decking, an outdoor gas line for grilling, a lofted garage with mudroom access, and mature arborvitae privacy create a home you will truly love.

6 Brewster Road, Milton

Listing courtesy of Listing Agent: Kevin Struzziero from Listing Office: Lamacchia Realty, Inc..

$1,750,000

Versatility is the name of the game! Set on a private lane on one of Milton's most spectacular lots with lush garden views from every window. This tastefully renovated home started off as a small 2 bedroom house built in 1905. Previous owners thoughtfully added on over time resulting in this expansive Colonial. What sets this house apart is it's 1,036 sqft townhouse style ADU which so seamlessly integrates it feels like a natural extension of the home. A few of the additional home features include high ceilings, custom built ins, 3 working fireplaces, central air, updated windows, walk up attic, one car attached garage and separate 3 bay garage. Set just 8 miles south of Boston, with the commuter rail minutes away and Back Bay less than 15 minutes by train, you get the feel of a private country retreat without sacrificing a minute of city access. Stop by one of our open houses, we'd love to introduce you to this exceptional home and the welcoming community that surrounds it!

5 Beds ⋅ 6 Baths ⋅ 73506486 MLS

Versatility is the name of the game! Set on a private lane on one of Milton's most spectacular lots with lush garden views from every window. This tastefully renovated home started off as a small 2 bedroom house built in 1905. Previous owners thoughtfully added on over time resulting in this expansive Colonial. What sets this house apart is it's 1,036 sqft townhouse style ADU which so seamlessly integrates it feels like a natural extension of the home. A few of the additional home features include high ceilings, custom built ins, 3 working fireplaces, central air, updated windows, walk up attic, one car attached garage and separate 3 bay garage. Set just 8 miles south of Boston, with the commuter rail minutes away and Back Bay less than 15 minutes by train, you get the feel of a private country retreat without sacrificing a minute of city access. Stop by one of our open houses, we'd love to introduce you to this exceptional home and the welcoming community that surrounds it!

34 Brush Hill Ln, Milton

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

$1,750,000

Welcome to 12 Morton Terrace! A meticulously maintained and updated, charming craftsman home, situated on a quiet side street in the highly sought after Milton Hill neighborhood. With 5 bedrooms, 2 full and 1 half baths, along with a modern kitchen, this house checks all the boxes. Take in the beauty of spacious rooms with gleaming hardwood floors throughout, many windows for tons of bright natural sunlight. In addition, the seller recently installed solar panels and new energy efficient heating and cooling systems. This house is a must see!

5 Beds ⋅ 3 Baths ⋅ 73491249 MLS

Welcome to 12 Morton Terrace! A meticulously maintained and updated, charming craftsman home, situated on a quiet side street in the highly sought after Milton Hill neighborhood. With 5 bedrooms, 2 full and 1 half baths, along with a modern kitchen, this house checks all the boxes. Take in the beauty of spacious rooms with gleaming hardwood floors throughout, many windows for tons of bright natural sunlight. In addition, the seller recently installed solar panels and new energy efficient heating and cooling systems. This house is a must see!

12 Morton Terrace, Milton

Listing courtesy of Listing Agent: John Shea from Listing Office: Duhallow Real Estate.

$1,675,000

A true architectural statement, this custom contemporary blends iconic Mid-Century Modern design with refined European sensibility. Perfectly situated on a private acre, it’s a masterclass in light, volume, and timeless style. Dramatic angled beam ceilings and expansive walls of glass frame the sky and landscape, creating a seamless connection between indoors and out. Thoughtful renovations honor the home's original architectural integrity while introducing a fresh, sophisticated aesthetic. A chef's kitchen opens to dining room, designed for everyday living and elegant entertaining. The primary suite is a private sanctuary featuring custom Italian wardrobe systems and a spa-inspired bath. A media room, beautifully renovated baths, four to six flexible bedrooms provide versatility & potential for an au pair or guest suite. A covered patio overlooks terraced yard. Direct proximity to Longwood Medical area, Milton Academy, Fairmont commuter T station. It's a property that stands alone.

4 Beds ⋅ 4 Baths ⋅ 73540395 MLS

A true architectural statement, this custom contemporary blends iconic Mid-Century Modern design with refined European sensibility. Perfectly situated on a private acre, it’s a masterclass in light, volume, and timeless style. Dramatic angled beam ceilings and expansive walls of glass frame the sky and landscape, creating a seamless connection between indoors and out. Thoughtful renovations honor the home's original architectural integrity while introducing a fresh, sophisticated aesthetic. A chef's kitchen opens to dining room, designed for everyday living and elegant entertaining. The primary suite is a private sanctuary featuring custom Italian wardrobe systems and a spa-inspired bath. A media room, beautifully renovated baths, four to six flexible bedrooms provide versatility & potential for an au pair or guest suite. A covered patio overlooks terraced yard. Direct proximity to Longwood Medical area, Milton Academy, Fairmont commuter T station. It's a property that stands alone.

285 Brush Hill Rd, Milton

Listing courtesy of Listing Agent: Sandra Keller from Listing Office: Coldwell Banker Realty - Milton.

$1,650,000

Timeless elegance welcomes you the moment you reach the inviting front porch of 67 Frothingham Street. This beautifully maintained home is a blend of classic charm and modern comfort. Inside, you’ll find a gracious foyer, a charming staircase, rich hardwood floors, central air conditioning & an abundance of natural light. The main level is ideal for everyday living & entertaining, with a formal dining room with pocket doors, the kitchen, half bath, laundry area & mudroom. The private backyard patio is ideal for relaxing or hosting friends. On the 2nd floor you'll find four bedrooms & a full bath. The 3rd floor primary suite offers a full bath with a double vanity & ample closet space. Set in a welcoming neighborhood, this home is close to Milton Academy, Turner’s Pond & Milton’s highly regarded public schools. Variety of commuting options available. Don't miss out on the opportunity to own a move-in ready home that truly has it all: space, character & an unbeatable location!

5 Beds ⋅ 3 Baths ⋅ 73491050 MLS

Timeless elegance welcomes you the moment you reach the inviting front porch of 67 Frothingham Street. This beautifully maintained home is a blend of classic charm and modern comfort. Inside, you’ll find a gracious foyer, a charming staircase, rich hardwood floors, central air conditioning & an abundance of natural light. The main level is ideal for everyday living & entertaining, with a formal dining room with pocket doors, the kitchen, half bath, laundry area & mudroom. The private backyard patio is ideal for relaxing or hosting friends. On the 2nd floor you'll find four bedrooms & a full bath. The 3rd floor primary suite offers a full bath with a double vanity & ample closet space. Set in a welcoming neighborhood, this home is close to Milton Academy, Turner’s Pond & Milton’s highly regarded public schools. Variety of commuting options available. Don't miss out on the opportunity to own a move-in ready home that truly has it all: space, character & an unbeatable location!

67 Frothingham St, Milton

Listing courtesy of Listing Agent: Robinson / Rull Team from Listing Office: William Raveis R.E. & Home Services.

$1,650,000

Exquisitely crafted and newly built, this stunning single-family home is located in the prestigious gated community of The Mansions at Brush Hill—an association offering breathtaking grounds, privacy, security gates, tennis-pickle-basketball court and full landscape maintenance. Designed for modern living, it features an open-concept layout with soaring ceilings and abundant natural light. The gourmet kitchen offers quartz countertops, an oversized island, custom cabinetry, stainless-steel appliances, and a double oven, flowing into a bright dining and sitting area. The living room features built-ins, a fireplace, and deck access. A first-floor office adds flexibility. Upstairs includes a luxurious primary suite with spa-like bath and walk-in closet, additional bedrooms, and laundry. The finished lower level offers a spacious family room with backyard access and entry to the two-car garage. Minutes to Boston, train, and highways.

4 Beds ⋅ 4 Baths ⋅ 73488741 MLS

Exquisitely crafted and newly built, this stunning single-family home is located in the prestigious gated community of The Mansions at Brush Hill—an association offering breathtaking grounds, privacy, security gates, tennis-pickle-basketball court and full landscape maintenance. Designed for modern living, it features an open-concept layout with soaring ceilings and abundant natural light. The gourmet kitchen offers quartz countertops, an oversized island, custom cabinetry, stainless-steel appliances, and a double oven, flowing into a bright dining and sitting area. The living room features built-ins, a fireplace, and deck access. A first-floor office adds flexibility. Upstairs includes a luxurious primary suite with spa-like bath and walk-in closet, additional bedrooms, and laundry. The finished lower level offers a spacious family room with backyard access and entry to the two-car garage. Minutes to Boston, train, and highways.

333 Brush Hill Rd, Milton

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

$1,635,000

Tucked into Milton’s sought-after Columbine neighborhood, this beautifully-built Colonial has the kind of character & warmth that’s hard to replicate. Thoughtfully designed & carefully maintained from the very beginning, it’s a home that feels both impressive & genuinely welcoming. The fireplaced living room feels elegant without trying too hard, French doors open to a family room lined with windows that overlook the gracious backyard. The dining room is perfectly scaled for holidays, celebrations, or a spontaneous dinner with friends. The chef's kitchen, anchored by a sunny breakfast nook, is the kind of space people naturally gather in. Oversized windows fill the home with natural light throughout the day. Upstairs, an airy open landing connects three generous bedrooms, including a front-to-back primary suite with a walk-in closet & private bath that was just completely renovated. Fully fenced-in/landscaped back yard with a large patio is the cherry on top of this extraordinary home.

3 Beds ⋅ 3 Baths ⋅ 73519195 MLS

Tucked into Milton’s sought-after Columbine neighborhood, this beautifully-built Colonial has the kind of character & warmth that’s hard to replicate. Thoughtfully designed & carefully maintained from the very beginning, it’s a home that feels both impressive & genuinely welcoming. The fireplaced living room feels elegant without trying too hard, French doors open to a family room lined with windows that overlook the gracious backyard. The dining room is perfectly scaled for holidays, celebrations, or a spontaneous dinner with friends. The chef's kitchen, anchored by a sunny breakfast nook, is the kind of space people naturally gather in. Oversized windows fill the home with natural light throughout the day. Upstairs, an airy open landing connects three generous bedrooms, including a front-to-back primary suite with a walk-in closet & private bath that was just completely renovated. Fully fenced-in/landscaped back yard with a large patio is the cherry on top of this extraordinary home.

60 Marilyn Rd, Milton

Listing courtesy of Listing Agent: Arianna Brown from Listing Office: Compass.

$1,600,000

Prominently positioned on Pleasant Street, this custom 1927 home is rich in character and timeless architectural detail while offering wonderful opportunities for personalization. The home blends the charm of yesterday with a thoughtful addition featuring a spacious dining area and family room with a dramatic floor-to-ceiling fieldstone fireplace and striking beamed ceiling—creating a warm and inviting gathering space. Hardwood floors run throughout the home, complemented by classic yesteryear detailing that reflects the craftsmanship of the era. An expansive deck overlooks the beautiful 1.80-acre property, complete with walking trails and natural surroundings ideal for outdoor enjoyment. A barn offers space for one-car parking, storage, or workshop potential. Perfectly located for commuters and convenient to area amenities, this distinctive Milton property presents a rare opportunity to restore, customize, and create your dream home in a sought-after setting.

4 Beds ⋅ 2 Baths ⋅ 73484306 MLS

Prominently positioned on Pleasant Street, this custom 1927 home is rich in character and timeless architectural detail while offering wonderful opportunities for personalization. The home blends the charm of yesterday with a thoughtful addition featuring a spacious dining area and family room with a dramatic floor-to-ceiling fieldstone fireplace and striking beamed ceiling—creating a warm and inviting gathering space. Hardwood floors run throughout the home, complemented by classic yesteryear detailing that reflects the craftsmanship of the era. An expansive deck overlooks the beautiful 1.80-acre property, complete with walking trails and natural surroundings ideal for outdoor enjoyment. A barn offers space for one-car parking, storage, or workshop potential. Perfectly located for commuters and convenient to area amenities, this distinctive Milton property presents a rare opportunity to restore, customize, and create your dream home in a sought-after setting.

207 Pleasant Street, Milton

Listing courtesy of Listing Agent: DeWolfe Group from Listing Office: Gibson Sotheby's International Realty.

$1,580,000

Refined, fully renovated 4,300 sq ft residence offering timeless design, elevated finishes, and immediate move-in readiness. The open floor plan is anchored by a beautifully crafted kitchen with Thermador appliances and an oversized quartz island, seamlessly connecting living and dining spaces ideal for both everyday living and elegant entertaining.The thoughtfully designed layout offers 5 bedrooms & 3 baths, including a desirable first-floor bedroom ideal for guests, au pair, or home office. The serene primary suite features a spa-inspired bath and walk-in closet, complemented by three additional generously sized bedrooms and a versatile third-floor bonus room for media, fitness, or guest use. Additional highlights include a mudroom, laundry area, attached 2-car garage with direct entry, private backyard with patio, and all new systems, incl. an energy-efficient heat pump with EV-charger ready capability.

5 Beds ⋅ 3 Baths ⋅ 73459704 MLS

Refined, fully renovated 4,300 sq ft residence offering timeless design, elevated finishes, and immediate move-in readiness. The open floor plan is anchored by a beautifully crafted kitchen with Thermador appliances and an oversized quartz island, seamlessly connecting living and dining spaces ideal for both everyday living and elegant entertaining.The thoughtfully designed layout offers 5 bedrooms & 3 baths, including a desirable first-floor bedroom ideal for guests, au pair, or home office. The serene primary suite features a spa-inspired bath and walk-in closet, complemented by three additional generously sized bedrooms and a versatile third-floor bonus room for media, fitness, or guest use. Additional highlights include a mudroom, laundry area, attached 2-car garage with direct entry, private backyard with patio, and all new systems, incl. an energy-efficient heat pump with EV-charger ready capability.

405 Blue Hill Avenue, Milton

Listing courtesy of Listing Agent: Gary Morton from Listing Office: Real Estate Professionals.

$1,575,000

Perched at the pinnacle of luxury, this exceptional 2-bedroom, 2-bath penthouse offers an elevated lifestyle with two garage parking spaces and a truly rare private rooftop terrace showcasing sweeping views of the Neponset River Estuary and ever-changing, painted sky vistas. Inside, light-filled living spaces invite effortless entertaining and quiet relaxation, while the sprawling primary en-suite provides a serene retreat with generous proportions and comfort. A concierge building enhances daily living with a fitness center, library, and on-site restaurant, offering everyday convenience with a boutique-hotel feel. Outside your door, miles of walking and bike trails await, with the Milton Yacht Club nearby for weekends on the water. Just minutes to the Trolley and easy access to downtown Boston, with Milton Village and Milton Academy just outside your door. This is more than a home, it’s your elevated escape. Truly Milton living at it's finest.

2 Beds ⋅ 2 Baths ⋅ 73517093 MLS ⋅ ['Milton Landing'] BLDG.

Perched at the pinnacle of luxury, this exceptional 2-bedroom, 2-bath penthouse offers an elevated lifestyle with two garage parking spaces and a truly rare private rooftop terrace showcasing sweeping views of the Neponset River Estuary and ever-changing, painted sky vistas. Inside, light-filled living spaces invite effortless entertaining and quiet relaxation, while the sprawling primary en-suite provides a serene retreat with generous proportions and comfort. A concierge building enhances daily living with a fitness center, library, and on-site restaurant, offering everyday convenience with a boutique-hotel feel. Outside your door, miles of walking and bike trails await, with the Milton Yacht Club nearby for weekends on the water. Just minutes to the Trolley and easy access to downtown Boston, with Milton Village and Milton Academy just outside your door. This is more than a home, it’s your elevated escape. Truly Milton living at it's finest.

88 Wharf Street Unit 604, Milton

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

$1,570,000

Breathe in. Breathe out. At 30 Ridge Rd there’s plenty of room to stretch out. This 4-bedrm, 2.5-bath home is set in Milton’s coveted Columbine neighborhood, noted for its tree-lined winding roads. There’s much to ground you: a renovated eat-in kitchen with generous storage, island, new appliances, an easy flow. A mudroom and walk-in closet bring order to the seasons and all their accompanying gear. Multiple sitting areas create space for the rhythm of the day—morning coffee or cozy evenings. The spacious primary suite offers an ensuite bath designed for two. 3 additional bedrooms share a bright hall bath and laundry access. A lower-level offers hang out space and sauna. The deck and leafy yard invite you to step outside and exhale. C/A keeps things cool and comfortable throughout summer. A 2-car garage will feel especially satisfying after a New England winter. 30 Ridge Rd offers the balance so many seek: comfort, function, and a setting that feels just right. Come find your flow.

4 Beds ⋅ 3 Baths ⋅ 73490615 MLS

Breathe in. Breathe out. At 30 Ridge Rd there’s plenty of room to stretch out. This 4-bedrm, 2.5-bath home is set in Milton’s coveted Columbine neighborhood, noted for its tree-lined winding roads. There’s much to ground you: a renovated eat-in kitchen with generous storage, island, new appliances, an easy flow. A mudroom and walk-in closet bring order to the seasons and all their accompanying gear. Multiple sitting areas create space for the rhythm of the day—morning coffee or cozy evenings. The spacious primary suite offers an ensuite bath designed for two. 3 additional bedrooms share a bright hall bath and laundry access. A lower-level offers hang out space and sauna. The deck and leafy yard invite you to step outside and exhale. C/A keeps things cool and comfortable throughout summer. A 2-car garage will feel especially satisfying after a New England winter. 30 Ridge Rd offers the balance so many seek: comfort, function, and a setting that feels just right. Come find your flow.

30 Ridge Rd, Milton

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

$1,570,000

Where timeless Colonial charm meets modern sophistication in the heart of the Columbines, this beautifully renovated & expanded home truly stands out! The thoughtful transformation seamlessly blends classic architecture with high-quality, modern updates throughout. This 4-bedroom, 2.5-bath home offers a bright, open layout with formal living and dining room, ideal for everyday living & effortless entertaining. The stunning kitchen is the heart of the home, featuring quartzite countertops, stainless steel appliances, quality cabinetry, and large island. Open to the main living areas, it flows seamlessly to the backyard—creating the perfect indoor-outdoor connection. A dedicated home office, mudroom, and first-floor laundry add exceptional functionality. Upstairs, the spacious primary suite is a serene private retreat, offering a private bath and generous closet space, along with 3 additional bedrooms & full bath. The backyard with stone patio is perfect for relaxing or entertaining.

4 Beds ⋅ 3 Baths ⋅ 73479934 MLS

Where timeless Colonial charm meets modern sophistication in the heart of the Columbines, this beautifully renovated & expanded home truly stands out! The thoughtful transformation seamlessly blends classic architecture with high-quality, modern updates throughout. This 4-bedroom, 2.5-bath home offers a bright, open layout with formal living and dining room, ideal for everyday living & effortless entertaining. The stunning kitchen is the heart of the home, featuring quartzite countertops, stainless steel appliances, quality cabinetry, and large island. Open to the main living areas, it flows seamlessly to the backyard—creating the perfect indoor-outdoor connection. A dedicated home office, mudroom, and first-floor laundry add exceptional functionality. Upstairs, the spacious primary suite is a serene private retreat, offering a private bath and generous closet space, along with 3 additional bedrooms & full bath. The backyard with stone patio is perfect for relaxing or entertaining.

44 Allen Cir, Milton

Listing courtesy of Listing Agent: Robinson / Rull Team from Listing Office: William Raveis R.E. & Home Services.

$1,552,500

Welcome to 7 Russell Street, a home rooted in history. Long before modern Milton took shape, this home was built on the site of the former Governor Hutchinson estate and was originally the gardener James Morrissey’s house. Only two families have ever owned this home, and that kind of stewardship shows. Thoughtfully curated gardens surround the home, designed for year-round beauty and lovingly maintained. Inside, original hardwood floors, multiple fireplaces, and a 4-bedroom, 2.5-bath layout blend historic charm with modern updates. Located on Milton Hill, you’re minutes to Lower Mills’ dining & river paths, a short stroll to Turner’s Pond or Glover Elementary, and steps to the trolley into Boston. Homes with this kind of story are rare. 7 Russell St truly is where history feels like home.

4 Beds ⋅ 3 Baths ⋅ 73497661 MLS

Welcome to 7 Russell Street, a home rooted in history. Long before modern Milton took shape, this home was built on the site of the former Governor Hutchinson estate and was originally the gardener James Morrissey’s house. Only two families have ever owned this home, and that kind of stewardship shows. Thoughtfully curated gardens surround the home, designed for year-round beauty and lovingly maintained. Inside, original hardwood floors, multiple fireplaces, and a 4-bedroom, 2.5-bath layout blend historic charm with modern updates. Located on Milton Hill, you’re minutes to Lower Mills’ dining & river paths, a short stroll to Turner’s Pond or Glover Elementary, and steps to the trolley into Boston. Homes with this kind of story are rare. 7 Russell St truly is where history feels like home.

7 Russell St, Milton

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