Houses for Sale near Fenway High School

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  /18

  $599,999

  • 3 Beds
  • 1.5 Baths
  • 1,503 Sq Ft

  15 Newburg St Unit 1, Roslindale, MA 02131

  This move-in ready single-family alternative near the commuter rail is unique. It feels more like a single family than a condo. Great for a first-time home buyer or anyone looking to build equity with some minor changes over time. Also listed as condo: MLS # 73435962

  Mary Bennett Shore Road Realty - Cityside

  15 Newburg St Unit 1, Roslindale, MA 02131
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  /11

  $499,900

  • 4 Beds
  • 1 Bath
  • 1,190 Sq Ft

  305R Lexington St, East Boston, MA 02128

  ***DEAL ALERT*** Welcome to 305-R Lexington St! Super desirable Eagle Hill location. This 4 bed, 1 bath, single family home has been owned and loved by the same family for over 70 years! It's time for the next generation to take the reins and bring this property into the 21st century. Set back from the road with a fenced in yard. Solid bones. Dry basement. Updated to circuit breakers. Priced for

  Joseph Gindi Realty One Group Next Level

  305R Lexington St, East Boston, MA 02128
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  /17

  $649,900

  • 3 Beds
  • 1.5 Baths
  • 2,114 Sq Ft

  36 Oakridge St, Mattapan, MA 02126

  This well maintained larger colonial has been in the same family for over 80 years. A licensed professional roofing contractor has been hired to install a new roof, ask the list agent for details. The home has a comfortable front porch where you can sit and enjoy the neighborhood. The backyard offers room for a garden, grass to play on and a large patio area. The first floor offers an eat in

  Gerard Lally Christopher Shea

  36 Oakridge St, Mattapan, MA 02126
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  /30

  $699,000

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  15 Cornell St, Roslindale, MA 02131

  Most buyers move to the suburbs to find a backyard like the one at 15 Cornell St. Fully fenced in on a corner lot, the kids and pets can run free with no worries. This home has been brought back to life by the current owners with major upgrades such as a new heating system with a programmable wifi/smart thermostat, central ac, new windows and new appliances. Improvements weren't just limited to

  Michael Gilbert Stuart St James, Inc.

  15 Cornell St, Roslindale, MA 02131
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  /24

  $3,479,000

  • 4 Beds
  • 4.5 Baths
  • 2,560 Sq Ft

  193 W Springfield St, Boston, MA 02118

  One Word "Breathtaking" Be the First to Experience a Reimagined South End Single Family Townhome. Yes, 3 Deeded Parking Spaces w/Direct Access! 2 Side-Side & Bonus 3rd Spot. VISIONARY Design-Build Team Just Completed a TOTAL RENOVATION! New Doors, Windows, Plumbing & Electrical. Perfect Layout: 4 Beds/4.5 Baths across 2560 SF. Step Inside, Floor to Ceiling Marble Fireplace "The Showstopper."

  Collin Bray Century 21 Cityside

  193 W Springfield St, Boston, MA 02118
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  /26

  $519,000 Open Sun 2PM - 3PM

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  24 Belnel Rd, Boston, MA 02136

  Dreaming of a home of your own? Welcome to 24 Belnel Road — a charming 2-bedroom, 1-bath single-family home tucked away on a peaceful street in Hyde Park. Featuring classic details and a cozy layout, this home delivers the perfect blend of comfort and character.What really sets this property apart is the generous 4,400+ sq ft yard — a rare find in the city! Whether you're imagining a garden, a

  Brittany Morris eXp Realty

  24 Belnel Rd, Boston, MA 02136
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  /25

  $1,275,000 Open Sat 12PM - 1:30PM

  • 3 Beds
  • 2.5 Baths
  • 1,778 Sq Ft

  16 Mcbride St, Jamaica Plain, MA 02130

  Perfect single-family alternative! Light pours into this stunning front-facing townhouse, where contemporary design meets effortless living. The open floor plan is anchored by a sleek gas fireplace with herringbone tile surround and framed by a wall of oversized windows that fill the space with natural light. A designer kitchen shines with West Elm lighting, marble backsplash, and a spacious

  The Muncey Group Compass

  16 Mcbride St, Jamaica Plain, MA 02130
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  /19

  $669,000

  • 2 Beds
  • 1.5 Baths
  • 1,123 Sq Ft

  701 Vfw Pkwy, West Roxbury, MA 02132

  Check out 701 VFW Parkway in vibrant Boston as this SF residence presents a remarkable opportunity to establish roots in a coveted location. Within the 1123 square feet of living area, discover two comfortable bedrooms, offering restful retreats from the bustle of the day. The residence features both a full bathroom and a half bathroom, providing convenience and functionality for residents and

  Dana Kokoska Sterling Breakwater LLC

  701 Vfw Pkwy, West Roxbury, MA 02132
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  /20

  $5,000,000

  • 5 Beds
  • 4.5 Baths
  • 6,419 Sq Ft

  540 Chestnut Hill Ave, Brookline, MA 02445

  Beautifully restored 1900s French-style residence on an acre of land in Brookline’s coveted Fisher Hill. Over 6,000 sq ft of living space featuring five bedrooms and 4.5 bathrooms. Inviting foyer with fireplace & custom bookshelves, an impressive great room with 15’ ceilings & fireplace, an elegant living room with period details including a fireplace, and a dining room with French doors to a

  The Duffy Group Compass

  540 Chestnut Hill Ave, Brookline, MA 02445
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  /31

  $499,000

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft

  156A South St Unit 1L, Jamaica Plain, MA 02130

  Exceptionally well cared for 2 Bed/1 bath condo in spectacular JP locale. Currently enjoyed as a large 1 bed w/ formal living & dining rooms, the versatile flr plan can easily be utilized as a 2 bed. Well-appointed kitchen w/granite, breakfast bar, SS appliances & walk-in pantry. Off the kitchen is a large foyer perfect for a home office setup. Spacious primary bedroom in the rear w/ oversized

  Christian Iantosca Team Arborview Realty Inc.

  156A South St Unit 1L, Jamaica Plain, MA 02130
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  /23

  $1,495,000

  • 3 Beds
  • 3.5 Baths
  • 2,175 Sq Ft

  53 Jamaica St, Jamaica Plain, MA 02130

  Steps to the Arboretum, come dwell in this architecturally renovated story-book home with distinctive finishes and brimming with charm & beauty. Beyond the picket fence and flowering garden beds, enter this airy and light-filled home. The expansive living room and dining room flow seamlessly into the inviting cook’s kitchen. Just beyond, a bucolic deck nestles among the treetops. Sleeping

  Janet Deegan Coldwell Banker Realty - Boston

  53 Jamaica St, Jamaica Plain, MA 02130
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  /27

  $2,375,000

  • 4 Beds
  • 4 Baths
  • 3,003 Sq Ft

  133 Fayerweather St, Cambridge, MA 02138

  Welcome to 133 Fayerweather St, a fully electric townhome nestled on a tree-lined quiet residential street. This modern new construction home features an elegant 4-bed, 4-bath configuration, thoughtfully designed for contemporary open living. Upon entry, you're greeted with quality white oak floors, plentiful natural light, open see-through fireplace, and soaring ceilings. High-end Thermador

  Lisa Drapkin Compass

  133 Fayerweather St, Cambridge, MA 02138
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  /39

  $7,200,000

  • 5 Beds
  • 7.5 Baths
  • 9,136 Sq Ft

  99 Baldpate Hill Rd, Newton Center, MA 02459

  This contemporary masterpiece embodies modern luxury—deceivingly understated from the front yet unfolding into a stunning four-level estate of architectural brilliance. Custom built with every imaginable feature, the home showcases 18+ rooms of exquisite craftsmanship and design. Step through grand double doors into a world of custom millwork, built-ins, and refined finishes. The main level is

  Samantha Stumpo New Brook Realty Group, LLC

  99 Baldpate Hill Rd, Newton Center, MA 02459
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  /22

  $969,999 Open Wed 5PM - 6PM

  • 3 Beds
  • 2 Baths
  • 1,871 Sq Ft

  84 Romsey St Unit 3, Dorchester, MA 02125

  NEW PRICE! Don’t miss this stunning Savin Hill duplex penthouse offering exceptional value and modern sophistication. Renovated in 2017 and refreshed in 2025, this 3-bed, 2-bath home blends luxury with comfort. The open main level features bright living and dining areas, a chef’s kitchen with quartz waterfall countertops, custom cabinetry, and JennAir appliances, plus two spacious bedrooms, a

  Maria Del Carmen Vera-Diaz Compass

  84 Romsey St Unit 3, Dorchester, MA 02125
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  /26

  $749,000

  • 4 Beds
  • 1.5 Baths
  • 2,000 Sq Ft

  95 Newburg St, Roslindale, MA 02131

  Timeless elegance meets every day comfort in this gem! This well loved Home exudes old world charm. Enter the welcoming foyer & be captivated by the graceful staircase & classic details that echo a bygone era. Spacious living room opens into a bright, formal dining room, perfect for gatherings & special occasions. A convenient 1/2 bath is located on the main level while the eat in kitchen

  Patty McNulty McNulty REALTORS®

  95 Newburg St, Roslindale, MA 02131
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  /22

  $3,749,000

  • 5 Beds
  • 4.5 Baths
  • 4,711 Sq Ft

  15 Glenland Rd, Chestnut Hill, MA 02467

  Experience luxury in this newly completed custom home by a renowned local builder. Ideally situated in the highly desirable Brookline/Chestnut Hill neighborhood, this residence offers the perfect blend of upscale living and everyday comfort. The sun splashed main level features an open & airy layout with soaring ceilings & oversized windows that fill the space with natural light. An elegant

  Rjp Sells Coldwell Banker Realty - Brookline

  15 Glenland Rd, Chestnut Hill, MA 02467
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  /38

  $1,250,000

  • 5 Beds
  • 3 Baths
  • 3,493 Sq Ft

  21 Glenley Terrace, Brighton, MA 02135

  Beautifully updated 5-bed, 3-bath home with stunning panoramic views — the last house on a dead-end street! Immediately feel the spaciousness of the open-concept layout, seamlessly connecting the living room, dining, and show-stopping kitchen. The kitchen is a true centerpiece, featuring quartz countertops, generous center island, and sleek breakfast bar - ideal for entertaining. The dining room

  Michael Helsmoortel Coldwell Banker Realty - Brookline

  21 Glenley Terrace, Brighton, MA 02135
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  /32

  $959,900 Open Wed 3:30PM - 5PM

  • 3 Beds
  • 2 Baths
  • 1,551 Sq Ft

  24 Moseley St, Dorchester, MA 02125

  Nestled in Savin Hill. One of Dorchester’s most vibrant neighborhoods, this charming single-family home radiates pride in its ownership both inside and out. The meticulously designed floor plan boasts custom kitchen cabinetry, expansive countertops, and stainless steel appliances. Each room is elegantly decorated, featuring a formal living and dining room, three to four bedrooms, and 2 full

  Frank Gillespie Village Realty HM, LLC

  24 Moseley St, Dorchester, MA 02125
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  /13

  $990,000

  • 2 Beds
  • 1.5 Baths
  • 1,897 Sq Ft

  15 Russell St, Charlestown, MA 02129

  Single family good location with roof deck. Come and create your own single family. Total rehab needed.

  Joe McGonagle Century 21 Elite Realty

  15 Russell St, Charlestown, MA 02129
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  /7

  $2,365,000

  • 4 Beds
  • 5 Baths
  • 4,855 Sq Ft

  3 Glenoe Rd, Chestnut Hill, MA 02467

  Renovate or build new, on one of Brookline’s most desirable and picturesque streets and sought after neighborhoods. Existing GLA of nearly 5k sqft (988 finished basement), or build 4396 sqft by right on upper floors. Survey and existing conditions plans are available. Demo hold expires October 2025

  Jason Gell RE/MAX On the Charles

  3 Glenoe Rd, Chestnut Hill, MA 02467
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  /32

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,085 Sq Ft

  14 Converse St, Brighton, MA 02135

  Completely renovated from top to bottom, this 3-bed, 2-bath single-family home combines modern comfort with city convenience on a quiet, dead-end street. The home features a new kitchen, baths, plumbing, electrical (200 amp), insulation, and high-efficiency systems. The bright kitchen offers new low-energy appliances and opens to a redone deck overlooking a private, fenced-in yard with new gravel

  Ashley Perkins Gibson Sotheby's International Realty

  14 Converse St, Brighton, MA 02135
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  /32

  $739,000

  • 2 Beds
  • 2.5 Baths
  • 1,129 Sq Ft

  216 Havre St Unit 4, Boston, MA 02128

  Stunning Duplex Penthouse in East Boston! Built in 2021 by one of the area’s top builders, this home feels better than new. The main level offers an open layout with a two-toned kitchen, large quartz peninsula, hardwood floors, designer lighting, and a private deck with a half bath nearby — perfect for entertaining. Upstairs features two spacious bedrooms, including a serene primary suite with

  Stone Prum Corcoran Property Advisors

  216 Havre St Unit 4, Boston, MA 02128
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  /18

  $7,800,000

  • 5 Beds
  • 7 Baths
  • 3,765 Sq Ft

  62 Chestnut St, Boston, MA 02108

  Publicly available for the first time in over 50 years! Exquisite Fully Renovated Chestnut Street 5+ bedroom with Elevator. This Federal style single family offers an amazing layout with a parlor level eat-in kitchen with top-of-the-line appliances, large breakfast bar, marble mantle fireplace and a bright southern oriented bay window eating area. Parlor level has large formal dining room and a

  Michael Harper Coldwell Banker Realty - Boston

  62 Chestnut St, Boston, MA 02108
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  /32

  $1,249,900

  • 3 Beds
  • 2.5 Baths
  • 1,435 Sq Ft

  54 Oak St, Somerville, MA 02143

  54 Oak Street is a meticulously renovated single-family row house on the Cambridge line, steps to Inman Sq. This property is tailored for discerning individuals with an appreciation for quality and detail. Thoughtfully designed floor plan fosters both work and relaxation. The open kitchen/living area features premium appliances, quartz countertops, and tasteful cabinetry, providing an ideal

  Charles Ball Berkshire Hathaway HomeServices Commonwealth Real Estate

  54 Oak St, Somerville, MA 02143
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  /27

  $649,900

  • 2 Beds
  • 1 Bath
  • 1,334 Sq Ft

  2 Pleasant St Unit 3, Boston, MA 02125

  Stunning Penthouse in Savin Hill. Beautifully updated 2 bed, 1 bath home on a tree-lined street in the sought-after Savin Hill neighborhood. This bright and spacious home features a rare double parlor with a wood-burning fireplace, high ceilings, and gleaming hardwood floors throughout. The updated eat-in kitchen includes SS appliances, granite counters, and a full-size W/D in the pantry. The

  Chris Poulos Coldwell Banker Realty - Boston

  2 Pleasant St Unit 3, Boston, MA 02125
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  /28

  $889,000 Open Sat 12PM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  697 E 6th St Unit 3, Boston, MA 02127

  Perfect for Entertaining in City Point! This rare 1,200-square-foot corner unit offers the ultimate South Boston lifestyle—just three blocks from Pleasure Bay & M Street beaches. The spacious, sun-splashed living & dining area (currently featuring a pool table) showcases charming bay windows, ideal for hosting family and friends. The eat-in kitchen has stainless steel appliances, and three

  Paula Maher Capital Residential Group, LLC

  697 E 6th St Unit 3, Boston, MA 02127
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  /34

  $769,999 Open Sat 11AM - 12:30PM

  • 5 Beds
  • 2 Baths
  • 2,065 Sq Ft

  223 Neponset Ave Unit 2, Boston, MA 02122

  The space you’ve been searching for in the neighborhood you love, welcome to 223 Neponset Ave, Unit 2! This rare FIVE bed, 2 bath condo spans 2,065 sq ft across two spacious levels. With the feel of a single family home, this condo features a bright, updated kitchen, open dining and living areas, three large bedrooms, two full bathrooms and laundry on the main level. Upstairs offers two

  Brigid Murphy Access

  223 Neponset Ave Unit 2, Boston, MA 02122
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  /27

  $2,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,963 Sq Ft

  236 Walnut St, Brookline, MA 02445

  Sophisticated Pill Hill residence in a Romanesque puddingstone row house designed by Henry Ives Cobb c. 1887, blends beautiful period detail with discerning finish and design offering recessed windows with built-in shutters, five original tile fireplaces, and impeccable renovations. First floor features an elegant foyer, living room with custom bookshelves and bay window, dining room with French

  Susan and Jen Rothstein Team Hammond Residential Real Estate

  236 Walnut St, Brookline, MA 02445
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  /38

  $5,195,000

  • 7 Beds
  • 8 Baths
  • 6,560 Sq Ft

  40 Heath Hill St, Brookline, MA 02445

  An exquisite stucco residence nestled in the coveted Chestnut Hill neighborhood of Brookline. Its hilltop location with stunning terraced grounds provides seasonal views of the reservoir and iconic Boston skyline. This property boasts a clay tennis court and completely renovated interior with a geothermal HVAC system and heated 3-car garage. The cook's kitchen with breakfast area and French doors

  Mizner+ Montero Gibson Sotheby's International Realty

  40 Heath Hill St, Brookline, MA 02445
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  /41

  $649,000

  • 4 Beds
  • 2.5 Baths
  • 1,690 Sq Ft

  114 Wrentham St Unit 1, Dorchester Center, MA 02124

  Free standing, detached single family style condo located on a quiet side street close to Ashmont T, dining, shopping, and Route 93. With nearly 1700 square feet of living space, not including the full basement, this home features 3 levels of living with a large, well equipped kitchen with gas cooking, stainless appliances, lots of cabinet space, and extensive work surfaces. Huge living room with

  Eric Gould Coldwell Banker Realty - Dorchester

  114 Wrentham St Unit 1, Dorchester Center, MA 02124
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  /33

  $4,600,000

  • 5 Beds
  • 7 Baths
  • 5,693 Sq Ft

  64 Walker St Unit 66, Charlestown, MA 02129

  A sanctuary of nature in the heart of the city, where the bustle fades & tranquility blooms. This exceptional residence offers approx. 5,693sf w/ 5 beds & 7 baths in one of Boston’s most historic neighborhoods. Featuring timeless craftsmanship, this homes includes sun-filled interiors, detailed millwork, crown moldings, & wide-plank hardwood floors, a grand living & dining space that centers on a

  Ricardo Rodriguez Coldwell Banker Realty - Boston

  64 Walker St Unit 66, Charlestown, MA 02129
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  /39

  $1,150,000

  • 7 Beds
  • 3.5 Baths
  • 3,200 Sq Ft

  19 Nixon St, Dorchester Center, MA 02124

  Prime Dorchester Location....Beautifully colonial just steps from Shawmut subway. This home offers 7 spacious bedrooms, 3.5 baths, and office spaces ideal for additional living or work-from-home. Updates include new roof and siding (2019) and a renovated living area with finished basement (2015). Interior highlights feature a granite kitchen, hardwood floors, high ceilings, and a thoughtful

  Emthanh Nguyen CRK Group, LLC

  19 Nixon St, Dorchester Center, MA 02124
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  /35

  $1,250,000 Open Sat 12PM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,621 Sq Ft

  2 Brewer St, Jamaica Plain, MA 02130

  Fantastic opportunity to own a versatile two-family townhouse in central Jamaica Plain steps from Centre St and next to the Brewer Street Tot Lot. This property features an income-producing 1 bedroom garden level unit and a spacious 2 bedroom, 1.5 bath, 1 office main unit. The stunning upper floors feature a dramatic layout with a extra high ceiling, skylights, oversized windows, split-level

  Brilliant Places Team Gibson Sotheby's International Realty

  2 Brewer St, Jamaica Plain, MA 02130
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  /22

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

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

  55 Museum St Unit 55, 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 Unit 55, Cambridge, MA 02138
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  /24

  $449,999 Open Sat 10:30AM - 11:30AM

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft

  28 Hansborough St Unit 2, Boston, MA 02124

  Limited Time Incentive!!! Seller offering a 2-1 rate buydown with an acceptable offer. This newly designed 2-bedroom, 1-bathroom unit, offers an open floor plan, soaring ceilings, and oversized windows that flood the space with natural light.The inviting living area seamlessly connects to a stylish and functional open-concept kitchen, with a Juliet balcony —ideal for both everyday living and

  Alex Walsh Access

  28 Hansborough St Unit 2, Boston, MA 02124
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  /40

  $1,350,000 Open Sun 12PM - 1PM

  • 4 Beds
  • 3 Baths
  • 2,539 Sq Ft

  276 Cornell St, Roslindale, MA 02131

  Modern luxury meets unbeatable location in this custom-built showstopper just minutes from Roslindale Village, Centre Street, and the Commuter Rail. Originally crafted as the builder’s own home, it’s loaded with high-end finishes, smart Lutron Caseta lighting, and sleek contemporary style throughout. The open layout is all about flow—perfect for entertaining and effortless everyday living. A

  Kris Macdonald Insight Realty Group, Inc.

  276 Cornell St, Roslindale, MA 02131
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  /42

  $12,900,000

  • 5 Beds
  • 8 Baths
  • 7,777 Sq Ft

  57 Hancock St, Boston, MA 02114

  Grand iconic corner building has just undergone a complete restoration into one of the finest single family homes on Beacon Hill. An extremely rare corner home has stood in this location since 1870 and still posses the papyrus capitals on the entryway columns to mark the style. This sun filled corner property maintains three exposures, 65 windows, ceiling heights ranging from 9-11 to 11-7, three

  Glenn Forger Olde Forge Realty

  57 Hancock St, Boston, MA 02114
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  /3

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,108 Sq Ft

  100 Itasca St, Mattapan, MA 02126

  Raised Ranch offering a unique split-entry layout with two full levels of living space. This home features 4 spacious bedrooms and 2 full bathrooms, designed for both entertaining and cozy family living. Inside, enjoy a formal living room, dining room, and kitchen, plus a lower-level family room and office, providing flexible space for today’s lifestyle. The open layout creates seamless flow for

  Lindsey & Associates Realty Team Keller Williams Realty Boston-Metro | Back Bay

  100 Itasca St, Mattapan, MA 02126
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  /30

  $1,299,000

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  430 E 8th St, Boston, MA 02127

  Incredible Opportunity by the Beach - Detached Single-Family on Southie's East Side. 500 feet from Carson Beach & scenic S.Boston Harborwalk. Rare SF is a perfect blend of coastal living & city convenience. A prime lot, features 2-beds, 2-full baths, fenced-in yard w/patio, ideal for entertaining or relaxing in the salty ocean air. Main level boasts a spacious kitchen w/vaulted ceilings, bright

  Vineburgh DiMella Team Charlesgate Realty Group, llc

  430 E 8th St, Boston, MA 02127
• 

  

  /36

  $850,000

  • 5 Beds
  • 2 Baths
  • 1,938 Sq Ft

  40 Humphreys St, Dorchester, MA 02125

  **JOIN US THIS FRIDAY OCT 17 FROM 4-6 PM FOR A FREE BLOCK PARTY -- LIVE MUSIC, GAMES & GOODIES** Nestled on sought-after Humphreys St, this spacious single-family home blends original charm of the early 1900s with modern updates & convenience across 4 levels of living. Set on a rare oversized lot, the fully fenced driveway offers ample parking or outdoor entertaining space. Inside, a grand

  Jessica Oknin Gibson Sotheby's International Realty

  40 Humphreys St, Dorchester, MA 02125

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