Houses for Sale near Fenway High School

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  /38

  $1,700,000

  • 4 Beds
  • 2.5 Baths
  • 3,188 Sq Ft

  22 Kenilworth St, Roxbury, MA 02119

  Historic charm meets modern living in this 4BR/2.5BA 1860 brick single-family nestled at the foot of Fort Hill. With 2,100 sf of living space, the main level of this home features an open kitchen with Quartzite counters, Samsung white glass appliances, electrified island, tiled backsplash, and four fireplaces. The second floor offers three bedrooms and a stylish bath with double vanity, tile

  Brian Perry Gibson Sotheby's International Realty

  22 Kenilworth St, Roxbury, MA 02119
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  /37

  $3,095,000

  • 7 Beds
  • 4.5 Baths
  • 5,123 Sq Ft

  327 Franklin St, Newton, MA 02458

  Gorgeous light-filled Victorian on idyllic sought-after street has been transformed to provide modern comfort with timeless elegance. Chef’s kitchen with granite farmhouse sink, banquette seating, and butler’s pantry. Soaring ceilings, frameless glass showers, mahogany woodwork, central AC, museum-quality detail, modern mudroom, oversized windows, five-zone heat. Open design 1st floor apartment

  The Margie and Jon Team Gibson Sotheby's International Realty

  327 Franklin St, Newton, MA 02458
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  /41

  $4,687,000 Open Sun 1PM - 2:30PM

  • 6 Beds
  • 7.5 Baths
  • 7,149 Sq Ft

  21 Lovett Rd, Newton Center, MA 02459

  Elegance and craftsmanship define this stunning new-construction home on a quiet Newton cul-de-sac. A grand mahogany pivot door opens to soaring ceilings, open living/dining areas, and a Cristallo quartzite powder room. The family room with linear fireplace flows to a breakfast nook and chef’s kitchen with custom cabinetry, quartz island, butler’s pantry, and top-tier Sub-Zero, Wolf & Miele

  Rozita Tabatabaei William Raveis R.E. & Home Services

  21 Lovett Rd, Newton Center, MA 02459
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  /41

  $1,425,000

  • 4 Beds
  • 3.5 Baths
  • 3,195 Sq Ft

  290 Central Ave, Milton, MA 02186

  Spacious contemporary colonial home with pond views in the backyard, and within close proximity to Turner's Pond & walking trails, Schools, bus stop, T-station, hospital, and Milton Village. This modern home offers an open living concept with 4 large bedrooms, 3.5 modernized bathrooms, and hardwood flooring thruout. Family room with a brick fireplace, cathedral ceiling, and sliders leading to the

  Christine Do Keller Williams Realty

  290 Central Ave, Milton, MA 02186
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  /17

  $1,195,000

  • 1 Bed
  • 1 Bath
  • 1,390 Sq Ft

  111 Beach St Unit 5C, Boston, MA 02111

  Dramatic Duplex Penthouse Loft in the vibrant Leather District, steps from the Financial District, Seaport, and South Station with rental garage parking available nearby. This striking residence showcases soaring ceilings, exposed brick and beam detail, a sleek gas fireplace, and an airy open-concept layout spread across two levels. The chef’s kitchen features stainless steel appliances, granite

  Antonio Khoury Compass

  111 Beach St Unit 5C, Boston, MA 02111
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  /42

  $719,000

  • 4 Beds
  • 1 Bath
  • 1,292 Sq Ft

  46 Southbourne Rd, Jamaica Plain, MA 02130

  PRICE IMPROVEMENT! Step into a fairytale setting! Come see this rare opportunity to own a single-family home tucked away in the historic Woodbourne Neighborhood of JP: a lush hidden hamlet of quiet tree-lined streets & timeless charm. Cherished by the same owner for the past 50 years, this corner situated gem offers 4 bedrooms, 1 full bath, hardwood floors, high ceilings throughout, plenty of

  Sheila Gallagher Donahue Real Estate Co.

  46 Southbourne Rd, Jamaica Plain, MA 02130
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  /30

  $1,785,000

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  7 Kemble Place, Boston, MA 02127

  Spectacular 2022 ground-up new construction, 4-bed, 3.5 bath single family with garage parking & 3 private decks on desirable East Side.This thoughtfully designed home has a fantastic floor plan highlighted by sprawling living space, high ceilings & show-stopping floor-to-ceiling windows. The expansive open concept living space feat. a high-end kitchen with Miele appliances, quartz counters,

  Arianna Brown Compass

  7 Kemble Place, Boston, MA 02127
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  /32

  $2,250,000 Open Sun 12PM - 1:30PM

  • 5 Beds
  • 4.5 Baths
  • 2,460 Sq Ft

  33 Webster Ave Unit 33, Cambridge, MA 02141

  Modern living in the vicinity of Cambridge’s vibrant tech and cultural corridor, Kendall square! This attractive newly built 5-bed 4.5-bath detached home with garage space is thoughtfully designed, capturing natural light through skylights and striking architectural windows, elevating your living experience. The open light-filled living areas feature a Japandi-inspired interior with oak + cable

  Sandrine Deschaux RE/MAX Real Estate Center

  33 Webster Ave Unit 33, Cambridge, MA 02141
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  /30

  $1,200,000

  • 3 Beds
  • 2.5 Baths
  • 1,756 Sq Ft

  7 Lorenzo St, Dorchester, MA 02122

  Enjoy this beautifully renovated, open-concept rental home in Neponset Circle, close to parks, shopping, dining, and convenient access to 93. This 3-bedroom, 2.5-bathroom property boasts 10-foot ceilings on the main floor, filling the space with natural light through large windows. The first floor features an electric fireplace, crown molding, hardwood floors, and a high-end kitchen equipped with

  Shane Brady Keller Williams Realty

  7 Lorenzo St, Dorchester, MA 02122
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  /23

  $1,125,000

  • 3 Beds
  • 2.5 Baths
  • 1,475 Sq Ft

  89 Baxter St, Boston, MA 02127

  Single Family! Sun filled, stylish and versatile, this updated 3-bed, 2.5-bath West Side home in South Boston blends character with modern comfort. The spacious living room with fireplace and custom built-ins flows to the kitchen with granite countertops, stainless steel appliances, gas cooking, custom cabinetry and sunroom—ideal for dining, a home office, or cozy retreat. Step outside to a

  Gina Morda Corcoran Property Advisors

  89 Baxter St, Boston, MA 02127
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  /24

  $6,785,000

  • 6 Beds
  • 3.5 Baths
  • 4,379 Sq Ft

  12 Berkeley St, Cambridge, MA 02138

  The Earnest Longfellow House offers a rare opportunity to customize your Queen Anne Victorian dream home on one of West Cambridge’s most sought-after streets. NOTE: some listing images are renderings of the property showing the potential after renovation based on the Historical Approval in place. Set on a large corner lot walkable to Harvard Square, this historic residence comes with fully

  Michael Glenmullen Coldwell Banker Realty - Cambridge

  12 Berkeley St, Cambridge, MA 02138
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  /22

  $839,000

  • 2 Beds
  • 2.5 Baths
  • 988 Sq Ft

  45 Ward St, Boston, MA 02127

  Welcome to a true South Boston rarity, a single-family home offering space, privacy, and convenience all in one. Step inside to find freshly refinished hardwood floors and an open living, dining, and kitchen layout that flows seamlessly onto your spacious private deck, perfect for entertaining or relaxing outdoors. Upstairs, the primary suite provides a comfortable retreat, accompanied by a

  Chris Fitzpatrick

  45 Ward St, Boston, MA 02127
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  /19

  $995,000

  • 2 Beds
  • 2.5 Baths
  • 1,426 Sq Ft

  176 School St Unit C, Boston, MA 02119

  Discover your urban oasis at the final available townhouse residence at 176 School Street! This beautifully crafted 2-bedroom, 2.5-bath townhouse combines modern luxury with everyday convenience. Enter through your own private garage and ascend a dedicated staircase to a sun-splashed kitchen outfitted with top-of-the-line Thermador appliances—perfect for the home chef. The generous garage

  Adams & Co. Team Real Broker MA, LLC

  176 School St Unit C, Boston, MA 02119
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  /38

  $8,800,000

  • 9 Beds
  • 5.5 Baths
  • 5,734 Sq Ft

  84 Garden St, Cambridge, MA 02138

  Built in 1922 and designed by Putnam & Chandler this is Cambridge’s grandest Tudor Revival home. Perched on a terrace above the street and enveloped in lush greenery and fencing, the residence offers rare privacy on .31 acres of curated gardens. The landscape, reminiscent of a secluded European country estate, offers a combination of tranquility and proximity to Harvard Square. Every detail

  Cathleen Lane Gibson Sotheby's International Realty

  84 Garden St, Cambridge, MA 02138
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  /42

  $4,599,600

  • 6 Beds
  • 4.5 Baths
  • 5,397 Sq Ft

  85 Naples Rd, Brookline, MA 02446

  Experience the pinnacle of luxury living in this fully gut-renovated single-family home on prestigious Naples Road in the heart of Coolidge Corner, Brookline. Blending timeless architectural charm with modern sophistication, this residence showcases exquisite details including copper gutters, elegant turrets, and designer finishes throughout. A private elevator provides effortless access across

  Aurel Garban Gibson Sotheby's International Realty

  85 Naples Rd, Brookline, MA 02446
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  /27

  $4,995,000 Open Sat 12:30PM - 1:30PM

  • 6 Beds
  • 4.5 Baths
  • 4,212 Sq Ft

  67 Inman St, Cambridge, MA 02139

  Mid-Cambridge | An 1880 Mansard Victorian with rare presence: grand yet human in scale, renovated stem to stern with uncommon design integrity. The interiors lean more deVOL than developer—sophisticated, warm, and thoughtfully composed. Sunlight skims across white oak herringbone floors, handmade tile, and unlacquered brass fixtures and fittings, while the kitchen’s reclaimed oak farmhouse table

  Lauren Holleran Team Gibson Sotheby's International Realty

  67 Inman St, Cambridge, MA 02139
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  /36

  $669,000

  • 2 Beds
  • 2 Baths
  • 1,468 Sq Ft

  49 Heath St Unit 1, Somerville, MA 02145

  Spacious and sun-filled, this recently updated condo in sought-after Winter Hill offers two plus bedrooms and two full baths. The modern kitchen is equipped with energy-efficient Samsung stainless steel appliances, including a dishwasher, stove, and microwave. A stylishly renovated bathroom, oversized private deck, in-unit laundry, and abundant storage further enhance the home. Two parking spaces

  Drew Varallo Leopold & McMasters Realty

  49 Heath St Unit 1, Somerville, MA 02145
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  /28

  $3,395,000

  • 4 Beds
  • 4 Baths
  • 2,380 Sq Ft

  4 Strong Place, Boston, MA 02114

  Tucked away on a hidden gaslit lane, this single-family home epitomizes Beacon Hill charm while offering modern comforts. Gut-renovated in 2020 and designed to perfection, this impeccably finished 4-bed, 4-bath, four-floor residence provides over 2,300 sq. ft. of reimagined space in a classic Boston setting. The open main level features a seamless living, dining, and kitchen layout that flows to

  Bell Petrini Group Coldwell Banker Realty - Boston

  4 Strong Place, Boston, MA 02114
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  /12

  $15,500,000

  • 6 Beds
  • 8 Baths
  • 7,059 Sq Ft

  94 Mount Vernon St, Boston, MA 02108

  A landmark opportunity on Beacon Hill’s iconic Mt. Vernon Street - this wide, five-story NEW CONSTRUCTION single family overlooks Louisburg Square and has a rare private rear entry from famed Acorn Street. Behind the classic brick facade lies a full gut renovation with all new structural framing, high-end finishes, and an elevator to every level. Enjoy city views from the roof deck or unwind on

  Beth Dickerson Gibson Sotheby's International Realty

  94 Mount Vernon St, Boston, MA 02108
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  /36

  $749,000 Open Sat 12PM - 1:30PM

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft

  38 Hazelmere Rd, Roslindale, MA 02131

  This charming two-bedroom, one-bath home has so much to offer with its additional square footage: a three-season sunroom, attached garage with automatic door opener, finished basement, and a separate bonus building in the backyard--beyond the outdoor patio--that makes a perfect meditation room, artist's studio, or completes almost any vision you may have! Nestled on a dead-end street near

  Mike Wood Compass

  38 Hazelmere Rd, Roslindale, MA 02131
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  /35

  $4,995,000

  • 7 Beds
  • 5.5 Baths
  • 6,193 Sq Ft

  371 Walnut St, Brookline, MA 02445

  This 7BD, 5.5BA c1880 Greek Revival reflects historic character while embracing a meticulous, modern renovation. Set on a landscaped .96AC lot, this stately 6,100+SF residence has been thoughtfully expanded & updated to enhance today’s modern living. Soaring ceilings, bespoke millwork & 5 FP highlight the architecture, while clean, timeless finishes offer understated elegance. Gracious entry

  Hilary Maddox Team Compass

  371 Walnut St, Brookline, MA 02445
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  /41

  $1,375,000

  • 3 Beds
  • 2.5 Baths
  • 2,320 Sq Ft

  24 Sachem St, Roxbury Crossing, MA 02120

  Welcome to 24 Sachem St, a custom-built home crafted in 2004. This Mission Hill brick single-family residence blends atraditional exterior w/ a contemporary open floor plan. Enter through double mahogany doors to a stunning interiorfeaturing a cherry wood staircase & birch flooring. The modern kitchen w/ marble countertops opens to a dining & livingroom w/gas fireplace. Sliding doors lead to a

  The Collective Compass

  24 Sachem St, Roxbury Crossing, MA 02120
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  /36

  $4,995,000

  • 5 Beds
  • 5 Baths
  • 5,010 Sq Ft

  59 Hyde Ave, Newton, MA 02458

  This enthralling c1890 Colonial Revival estate marks the confluence of timeless architectural elegance and craftsmanship with modern-day luxury and glamour. Brilliantly updated and restored with a curator’s eye for detail, the property is distinguished by beamed ceilings, leaded glass windows and doors, a stunning veranda, and exquisite woodwork including a spectacular foyer and curved staircase.

  Elisabeth Preis Compass

  59 Hyde Ave, Newton, MA 02458
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  /35

  $850,000

  • 3 Beds
  • 1.5 Baths
  • 1,767 Sq Ft

  139 Newfield St, West Roxbury, MA 02132

  Beautiful three-bedroom raised ranch on desirable cul-de-sac in West Roxbury’s sought-after Brook Farm neighborhood. Home features open-concept design with the living area flowing to the dining area and an eat-in kitchen opening to a spacious three-season porch, perfect for entertaining or relaxing. Home also offers a large family room, multiple home offices, and 1.5 tiled baths. Central AC,

  Brian Kenneally Keller Williams Realty

  139 Newfield St, West Roxbury, MA 02132
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  /27

  $1,499,000

  • 3 Beds
  • 4 Baths
  • 1,909 Sq Ft

  18 Loring St, Boston, MA 02127

  NEW PRICE! SELLER IS ALSO OPEN TO DISCUSSING BUY DOWN OPTIONS! Come see this single! Every detail has been carefully considered to offer modern comforts while maintaining timeless appeal. Step inside to discover a light-filled, open-concept layout featuring a stunning kitchen with sleek finishes, stainless steel appliances, integrated fridge and a spacious dining room perfect for entertaining.

  Carlisle Group Compass

  18 Loring St, Boston, MA 02127
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  /38

  $10,995,000

  • 5 Beds
  • 7 Baths
  • 6,020 Sq Ft

  18 Marlborough St, Boston, MA 02116

  Sophisticated Single Family townhouse just steps from the iconic Boston Public Garden on the coveted first block of Marlborough Street. Completely gut renovation in 2012 adding 2 Car Garage and Elevator is a stately center entrance Brownstone opens to a gracious foyer, setting the tone for refined living. An elevator services all levels, including the garage entry. The parlor level features a

  Beth Dickerson Gibson Sotheby's International Realty

  18 Marlborough St, Boston, MA 02116
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  /20

  $3,500,000 Open Thu 12PM - 1PM

  • 4 Beds
  • 3.5 Baths
  • 2,983 Sq Ft

  55 Museum St, Cambridge, MA 02138

  Exclusive 3.875% financing available for qualified buyers!** In partnership with a local bank, this limited offer brings back near-pandemic-era affordability—making ownership in Harvard Square more accessible. Rarely available, this brand-new ground-up single-family home combines elegance and sustainability with solar panels, energy-efficient HVAC, and EV charging. The open-concept first floor

  Jessica Ferris Cutter Luxe Living LLC

  55 Museum St, Cambridge, MA 02138
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  /27

  $1,099,000

  • 4 Beds
  • 2 Baths
  • 2,152 Sq Ft

  8 Thornley St, Dorchester, MA 02125

  Stunningly preserved Colonial blends historic charm w/ modern updates nestled in coveted Savin Hill! Timeless beauty 8 rms, 4 beds, 2 baths, crown molding, oversized windows & hardwd flrs. Welcome in through enchanting wrought iron inset door & you’re greeted by original parquet floors, refurbished decorative staircase, soaring 10.5ft ceilings & mudroom alcove. Mindfully upgraded custom kitchen

  Paul Cirignano The Synergy Group

  8 Thornley St, Dorchester, MA 02125
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  /17

  $5,950,000

  • 4 Beds
  • 4.5 Baths
  • 4,138 Sq Ft

  16 W Cedar St, Boston, MA 02108

  This beautiful townhouse, built during the late Federal period by Cornelius Coolidge, is situated on one of Beacon Hill's most picturesque streets. Renowned for its arched entryways, elegant fanlights, and first-floor triple windows, this row of townhouses exudes historic charm. The property features a tranquil garden, accessible via a door leading to Cedar Lane Way, which has been showcased on

  Sally Brewster Brewster & Berkowitz R. E.

  16 W Cedar St, Boston, MA 02108
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  /37

  $3,450,000

  • 3 Beds
  • 4 Baths
  • 2,706 Sq Ft

  52 River St, Boston, MA 02108

  Nestled in Beacon Hill, 52 River Street is a rare single-family home that beautifully combines historic charm with modern comfort. This elegant home features sun-filled living spaces, rich hardwood floors, and fireplaces. The open-concept living and dining area is perfect for entertaining, while the updated kitchen provides easy access to the property's crown jewel: a private outdoor patio. This

  The Mazer Group Compass

  52 River St, Boston, MA 02108
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  /28

  $899,900

  • 4 Beds
  • 2 Baths
  • 1,550 Sq Ft

  69 Presentation Rd, Brighton, MA 02135

  Back on the Market! Nestled at 69 Presentation Rd, Boston, MA, this beautifully updated single-family residence offers the perfect blend of modern comfort and classic charm in one of Brighton’s most coveted neighborhoods. Built in 1955 and thoughtfully reimagined in 2025, this home presents a rare opportunity to enjoy turnkey living while establishing roots in a peaceful, residential setting. Set

  Tina Hill RE/MAX On the Charles

  69 Presentation Rd, Brighton, MA 02135
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  /35

  $2,200,000 Open Sun 12PM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,444 Sq Ft

  53 Snow Hill St, Boston, MA 02113

  RARELY Available Single-Family in Boston's North End/Waterfront! Fully renovated in 2017, this modern home features 3 beds, 2.5 baths, and high-end finishes throughout. Chef’s kitchen with custom cabinetry and waterfall Calacatta stone island opens to a private patio with gas fire pit and grill—perfect for entertaining. Built-ins plus tons of thoughtful storage maximize this beautiful space.

  Toni Gilardi Gibson Sotheby's International Realty

  53 Snow Hill St, Boston, MA 02113
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  /13

  $634,900

  • 2 Beds
  • 1 Bath
  • 590 Sq Ft

  260 Sidney St Unit 3R, Cambridge, MA 02139

  Discover the allure of this sunlit penthouse with two spacious bedrooms in a charming brick building near Central Square. The kitchen combines style and functionality with granite countertops, stainless steel appliances, and a convenient desk nook. Enjoy your private deck, ideal for outdoor dining and relaxation. The L-shaped living area offers a distinct dining space, complemented by warm maple

  Aranson Maguire Group Compass

  260 Sidney St Unit 3R, Cambridge, MA 02139
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  /21

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 1,982 Sq Ft

  152 Saratoga St, Boston, MA 02128

  A city retreat like no other. This rare 4-level single-family redefines East Boston living with 3 bedrooms, 2.5 baths, and nearly 2,000 sqft including a finished lower level. Completely gut renovated in 2019, everything from the windows, siding, and roof to the kitchen, heating system, tankless hot water, electric panel, and everything in between was replaced. Designed for modern lifestyles, the

  Team ROVI Real Broker MA, LLC

  152 Saratoga St, Boston, MA 02128
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  /17

  $4,480,000

  • 7 Beds
  • 9 Baths
  • 8,056 Sq Ft

  44 Lovett Rd, Newton Center, MA 02459

  Experience refined luxury in this brand-new Modern Colonial, offering seven spacious en-suite bedrooms. Perfectly sited on a 15,714 SF lot in one of the area’s most prestigious neighborhoods, this residence seamlessly combines timeless architecture with contemporary design and high-end finishes. Step inside to soaring ceilings, an open and elegant floor plan, and abundant natural light that

  Alex Kuzakovsky Luna Luxury Realty

  44 Lovett Rd, Newton Center, MA 02459
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  /19

  $4,175,000

  • 5 Beds
  • 7 Baths
  • 7,523 Sq Ft

  42 Bow Rd, Newton, MA 02459

  RIGHT BY NEWTON CENTRE! This exceptional new Colonial showcases 5 bedrooms and 5 full bathrooms with an open, sun-filled layout designed for today’s lifestyle. The main level features a gourmet kitchen equipped with high-end appliances, custom cabinetry, a spacious island that flows seamlessly into the dining and living areas, and a beautiful, large walk-in pantry. A versatile additional room

  Alex Kuzakovsky Luna Luxury Realty

  42 Bow Rd, Newton, MA 02459
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  /28

  $2,390,000

  • 3 Beds
  • 2.5 Baths
  • 2,666 Sq Ft

  5 Hammond St, Chestnut Hill, MA 02467

  Majestic and elegant center entrance brick single family colonial on large corner lot in Ward school district. Conveniently located near Commonwealth Avenue, Chestnut Hill, Newton Center and Boston College with easy access to Mass Pike to downtown Boston. Gracious entry foyer, French doors and arched entries to rooms. Three plus bedrooms, 2.5 bathrooms, living room with original wood detail,

  Mary Lochner Hurwitz Coldwell Banker Realty - Brookline

  5 Hammond St, Chestnut Hill, MA 02467
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  /35

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 3,172 Sq Ft

  104 Stratford St, West Roxbury, MA 02132

  Welcome to this Elegant Colonial located on a beautiful treelined street in the sought after area of Bellevue Hill. The home is boasting a blend of classic charm and modern comfort. Step into the large welcoming foyer leading you to the impressive fireplaced living room with french doors, wood beam ceiling, rich wood molding, built in bookshelf, and large front window allowing for amazing

  Mike Flynn The Delamere Flynn Group, LLC

  104 Stratford St, West Roxbury, MA 02132
• 

  

  /42

  $9,950,000

  • 6 Beds
  • 4.5 Baths
  • 6,788 Sq Ft

  158 Brattle St, Cambridge, MA 02138

  Designed by William Ralph Emerson, a prominent architect and relative of Ralph Waldo Emerson, this proud c.1884 Colonial Revival house is beautifully sited together with a c.1840 Italianate carriage house on two separate lots of almost a half an acre just outside of Harvard Square. Both the house and carriage house were extensively renovated in 1998 and have been updated periodically since. The

  Monahan Barker Team LandVest, Inc., Ipswich

  158 Brattle St, Cambridge, MA 02138
• 

  

  /40

  $2,800,000

  • 5 Beds
  • 5 Baths
  • 4,500 Sq Ft

  206 Franklin St, Newton, MA 02458

  This home is on the prettiest street in Newton! 206 Franklin Street is an architectural jewel on a private half acre lot and is a commuters dream into Boston with a drive time of 8 minutes. This storied home presents a special opportunity for a trophy single-family residence in Newton Centre location & retains several original architectural details including soaring ceiling height, intricate

  Aditi Jain Redfin Corp.

  206 Franklin St, Newton, MA 02458

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