Homes for Sale in Middlesex County MA with 5-Bedrooms

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  /27

  $1,100,000

  • 7 Beds
  • 3 Baths
  • 3,427 Sq Ft

  41 Winthrop St, Everett, MA 02149

  Rare opportunity in the heart of revitalized Everett! Oversized, fully vacant 3-family on a corner lot offering incredible flexibility for investors, owner-occupants, or house hackers. Features a 1-car garage + 3 driveway spaces, separate updated utilities, replacement windows, newer roof/siding, hardwood floors, tall ceilings, abundant natural light, and generous storage throughout. First &

  Richard Harkins EWK Realty

  41 Winthrop St, Everett, MA 02149
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  /42

  $2,199,000

  $386K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 5,248 Sq Ft

  2 Emerald Dr, Hopkinton, MA 01748

  Welcome to Emerald Drive, an exclusive enclave of 8 exquisite modern farmhouse-style homes on a private cul-de-sac in sought-after Hopkinton. This breathtaking 5,248 SF residence is a masterpiece of craftsmanship, blending timeless elegance with contemporary luxury. Step into a sunlit open floor plan featuring designer millwork, soaring ceilings, and rich hardwood floors. The gourmet chef’s

  Katie McBride REMAX Executive Realty

  2 Emerald Dr, Hopkinton, MA 01748
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  /29

  $1,025,000

  $125K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 2,925 Sq Ft

  114 Haverhill St, North Reading, MA 01864

  Become an homeowner AND investor! Extremely Rare 3 Family in the heart of North Reading. Only steps from Ryers, Flint Library, and Ipswich River Park, not to mention just a block from all 4 schools (Hilltop Nursery school, Batch elementary, Middle and High schools). This unicorn property is completely updated, laundry for each individual unit and has 6 off street parking spaces. Newer Heating and

  Shawn McEntee Classified Realty Group

  114 Haverhill St, North Reading, MA 01864
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  /27

  $3,250,000

  $150K PRICE DROP

  • 15 Beds
  • 10 Baths
  • 6,191 Sq Ft

  266-274 River St, Waltham, MA 02453

  We are excited to offer this compelling opportunity for investors. The property is made up of ten apartment units. Five 2-bedroom / 1-bathroom apartments, five 1-bedroom / 1-bathroom apartments side by side and a 15 spot parking area behind the building. Ideally located near the Charles River and within close proximity to Moody Street’s restaurants, shopping, and the MBTA Commuter Rail, this

  Kevin Benzinger Boston Realty Advisors

  266-274 River St, Waltham, MA 02453
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  /7

  $2,499,000

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,120 Sq Ft

  8 Twillingate Rd, Sudbury, MA 01776

  New Construction, to be built on final lot in established neighborhood. This stunning modern Farmhouse offers exceptional craftsmanship and attention to detail throughout. Get in early and take advantage of the opportunity to customize and create your dream home Thoughtfully designed with modern living in mind, this spacious home features a Chef's kitchen that opens to a dramatic

  Libby Rankin Hamill Berkshire Hathaway HomeServices Stephan Real Estate

  8 Twillingate Rd, Sudbury, MA 01776
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  /34

  $4,150,000

  $275K PRICE DROP

  • 5 Beds
  • 6.5 Baths
  • 8,500 Sq Ft

  11 Winthrop Cir, Weston, MA 02493

  An award-winning architect brings sophisticated modern design to Weston at 11 Winthrop Circle. This extraordinary home offers 8,500 sq. ft. of sun-filled living space with an open floor plan, expansive windows, and beautiful contemporary mill work. The Poggenpohl kitchen flows seamlessly into a stunning family room with fireplace, perfect for everyday living and entertaining. Elegant living and

  Sheryl Simon Gibson Sotheby's International Realty

  11 Winthrop Cir, Weston, MA 02493
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  /20

  $1,195,000

  • 5 Beds
  • 2 Baths
  • 2,614 Sq Ft

  601 Main St, Watertown, MA 02472

  PRISTINE OVERSIZED TWO FAMILY featuring bright eat-in-kitchens, large living rooms, formal dining rooms w/built-ins', hardwood flooring throughout, natural gas heating, newer roof, large relaxing front porch, ample off street parking and more! Walk to public transportation and shops! A real find!

  Dave DiGregorio Jr. Coldwell Banker Realty - Waltham

  601 Main St, Watertown, MA 02472
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  /35

  $1,095,000

  $155K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 1,950 Sq Ft

  62 Thomas St, Belmont, MA 02478

  Rarely available, turnkey duplex-style two-family situated right outside Belmont Center. Both units feature a living room, large kitchen and half bath on the lower floor, two bedrooms and full bath on the middle, and a 3rd bedroom on the upper level. Conveniently located around the corner from Town Field, this property is walking distance to Wellington, Belmont Center commuter rail stop and

  David Hurley Berkshire Hathaway HomeServices Commonwealth Real Estate

  62 Thomas St, Belmont, MA 02478
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  /23

  $2,288,000

  • 6 Beds
  • 3 Baths
  • 2,419 Sq Ft

  66 Walden St, Cambridge, MA 02140

  Rare North Cambridge two-family on a corner lot, in a prime location, just 0.3 miles to Porter Square and the Red Line. Philadelphia-style layout offers true owner-occupant appeal: the upper unit spans the 2nd and 3rd floors with 3 beds, 2 full baths, spacious living room, formal dining room, central AC, in-unit laundry, eat-in kitchen, and a covered front porch. The lower unit is a spacious 3

  Sage Jankowitz Cambridge Sage Inc.

  66 Walden St, Cambridge, MA 02140
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  /27

  $549,900

  • 5 Beds
  • 2 Baths
  • 1,788 Sq Ft

  25 Prospect St, Ashland, MA 01721

  Nestled in a highly desirable neighborhood within a top-rated school system, this spacious single-family home offers an exceptional opportunity to create your dream living space. Featuring an inviting open-concept layout, the home provides seamless flow between the main living, dining, and kitchen areas—perfect for both everyday living and entertaining. Offering 5 generously sized bedrooms and 2

  Rodrigo Azevedo Pablo Maia Realty

  25 Prospect St, Ashland, MA 01721
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  /36

  $6,500,000

  • 5 Beds
  • 9 Baths
  • 11,820 Sq Ft

  41 Skating Pond Rd, Weston, MA 02493

  Privately set on 2.42 acres in Weston’s highly coveted South Side Country Club area, 41 Skating Pond Road offers over 11,000 sf of exceptional living space, recently renovated to the highest standard of fit & finish. The residence features 5 en suite bedrooms, 7 full baths, 2 half baths & attached 3 car garage. A dramatic 2 story foyer fills the home with natural light, while refined interiors

  Collin Sullivan William Raveis R.E. & Home Services

  41 Skating Pond Rd, Weston, MA 02493
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  /36

  $2,590,000

  • 5 Beds
  • 5.5 Baths
  • 4,590 Sq Ft

  6 Revolutionary Rd, Lexington, MA 02421

  Looking for new construction that feels anything but cookie-cutter? This beautifully crafted home offers a fresh take on the classic Cape, blending character & quality construction. A shingled exterior w/stone veneer & extensive hardscape introduces the home’s timeless style, while inside, bright, spacious living areas feature refined finishes, custom millwork & an easy, livable flow. The

  Coleman Group William Raveis R.E. & Home Services

  6 Revolutionary Rd, Lexington, MA 02421
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  /21

  $1,099,000

  • 6 Beds
  • 3.5 Baths
  • 2,970 Sq Ft

  28 Washington St, Stoneham, MA 02180

  Great condo conversion or owner-occupant opportunity with strong income potential. Live in one unit while the other helps offset your mortgage, or explore expansion potential. Located near downtown Stoneham, shops, schools, restaurants, parks, public transportation, the Tri-Community Greenway, and quick access to I-93. This oversized two-family offers 6 bedrooms and 3.5 bathrooms across ~2,970 sq

  Adam Cutter Massachusetts Bay Realty Advisors, LLC

  28 Washington St, Stoneham, MA 02180
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  /25

  $15,800,000

  • 5 Beds
  • 8 Baths
  • 12,704 Sq Ft

  157 Brattle St, Cambridge, MA 02138

  Set among the stately residences of historic Brattle Street, this completely renovated & pristine home offers approximately 9,594 square feet of elegant living space on a rare 0.41-acre corner lot in sought-after West Cambridge—moments from Harvard Squar/Charles River. Beautiful private yard w/ sports court, outdoor kitchen,heated garage. The interior blends timeless architectural character w/

  Cort LaBonte Coldren Coopersmith Gr Compass

  157 Brattle St, Cambridge, MA 02138
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  /24

  $11,999,000

  • 30 Beds
  • 15 Baths
  • 22,992 Sq Ft

  183 Harvard St, Cambridge, MA 02139

  Exceptional opportunity to acquire The Allen Block, a historic 15-unit brick rowhouse portfolio in the heart of Cambridge. Located at 177–183 Harvard Street, the property consists of five Mansard-style attached buildings, each containing three units (1 one-bedroom, 1 two-bedroom, and 1 three-bedroom) for a total of 15 apartments. The property also includes unfinished attic space and high-ceiling

  Farah Fakih Coldwell Banker Realty - Boston

  183 Harvard St, Cambridge, MA 02139
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  /15

  $1,775,000

  • 5 Beds
  • 5 Baths
  • 3,191 Sq Ft

  356 Linwood Ave, Newtonville, MA 02460

  This gorgeous new construction home is on a Newtonville side street under a mile to the Newton public elementary, middle and high schools, a 1/3 mile to Albemarle Field with a playground, community pool and sports fields, and only 1/2 mile to the Newtonville village & commuter rail station. It offers a flexible floor plan & central AC throughout. The open living spaces include a dining room, a

  Montgomery Carroll Group Compass

  356 Linwood Ave, Newtonville, MA 02460
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  /3

  $775,000

  • 5 Beds
  • 2 Baths
  • 2,112 Sq Ft

  31 Luke Rd Unit A, Everett, MA 02149

  Spacious 2 unit opportunity in the heart of Everett across from a beautiful neighborhood park and just steps to public transportation with quick access to Boston. This property offers tremendous potential for investors, owner-occupants, or contractors looking to add value in one of Greater Boston’s fastest-growing communities. Generous living space, strong rental potential, and a highly

  Jason Saphire www.HomeZu.com

  31 Luke Rd Unit A, Everett, MA 02149
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  /41

  $3,139,900

  New Construction $455K PRICE DROP

  • 5 Beds
  • 6.5 Baths
  • 7,317 Sq Ft

  6 Clifford Ln, Weston, MA 02493

  Welcome to Trails End! A luxury subdivision on a private dead-end street. Compare the value, this home is offered at $437 psf vs the average new home in Weston is over $700 psf. This is our third offering and is a spectacular 14 room modern farmhouse style. Enter into a welcoming foyer and open floor plan featuring a chefs kitchen and oversize island Breakfast area opens up to a large family room

  Gary Litchfield Mass. Real Estate Solutions, LLC

  6 Clifford Ln, Weston, MA 02493
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  /4

  $2,100,000

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

  8 Arlington Cir, Natick, MA 01760

  Step into your dream home—brand new construction designed with both luxury and functionality in mind. This thoughtfully crafted residence features a convenient first-floor bedroom and full bathroom, perfect for guests or multigenerational living, while the expansive primary suite offers a private retreat with generous space and comfort. Nestled in an A+ neighborhood, the home boasts an

  Justin Brown High End Homes Realty Group LLC

  8 Arlington Cir, Natick, MA 01760
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  /16

  $2,500,000

  • 6 Beds
  • 3 Baths
  • 3,159 Sq Ft

  17 Orrin St, Cambridge, MA 02138

  Handsome three-family property on a larger lot. Current leases in place through May 31, 2027 for units 1 & 3, and through September 1, 2026 for unit 2. The building features three sunny, floor-through units, each offering high ceilings, hardwood floors, kitchen pantries, and separate systems. Front and rear decks are included with each unit. The property also includes a full unfinished basement,

  Maggie Dee + Charles Cherney Team Compass

  17 Orrin St, Cambridge, MA 02138
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  /28

  $5,900,000

  $300K PRICE DROP

  • 5 Beds
  • 7 Baths
  • 11,300 Sq Ft

  741 Boston Post Rd, Weston, MA 02493

  A modern masterpiece born of a dramatic barn conversion, completed in 2023. This one-of-a-kind residence blends rustic charm & contemporary luxury. Featuring soaring ceilings, a 20' high wall of windows, exposed beams, and sun-drenched living spaces. The dreamy kitchen includes modern cabinetry, Miele appliances and an enormous quartz-wrapped island. The living areas flow effortlessly to outdoor

  Amy Rutkowski A. Rutkowski Realty, Inc.

  741 Boston Post Rd, Weston, MA 02493
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  /38

  $2,195,000

  $104K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 5,006 Sq Ft

  276 High St, Winchester, MA 01890

  Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

  Kim Covino Compass

  276 High St, Winchester, MA 01890
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  /33

  $1,150,000

  • 5 Beds
  • 3 Baths
  • 2,186 Sq Ft

  63-65 Harvard St, Winchester, MA 01890

  Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home.

  Beth Sager Group Keller Williams Realty Boston Northwest

  63-65 Harvard St, Winchester, MA 01890
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  /38

  $1,799,900

  • 5 Beds
  • 4 Baths
  • 2,964 Sq Ft

  30-32 Oakland St, Newton, MA 02458

  Tucked along a quiet residential street in Newton Corner, this 2-family home has been thoughtfully reimagined from the inside out. A gut renovation made into a chic urban retreat offering modern finishes, flexible living space, and exceptional commuter convenience. The sun-filled, open-concept living spaces create an effortless flow for everyday living & entertaining. The kitchens serve as the

  Paul Cirignano The Synergy Group

  30-32 Oakland St, Newton, MA 02458
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  /42

  $1,599,000

  $100K PRICE DROP

  • 8 Beds
  • 4 Baths
  • 3,464 Sq Ft

  227-229 Newton St, Waltham, MA 02453

  Four Family investment property with an HUGE garage with 10x10 garage doors and an ample parking lot? Four rental units all separately metered. Two top floor apartments are occupied and have lead certificates and are on Tenant at Wills and two bottom floor units are Vacant. There are two forms of egress out of the parking lot, one driveway on Newton St. The other driveway is on Gorham St.

  Michelle Zona Aloha Heights Real Estate

  227-229 Newton St, Waltham, MA 02453
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  /42

  $915,000

  $34K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 2,496 Sq Ft

  11 Harmony Ln, Framingham, MA 01702

  Don’t miss this exceptional opportunity to own a modern two-family duplex tucked away on a quiet dead-end street. Situated on a very large lot offering excellent potential for future expansion making it a standout opportunity for both investors & owner-occupants. Each unit features 3 bedrooms & 1.5 baths, along with separate utilities for convenience & efficiency. The layout includes

  Dina Goncalves S.C.E. Real Estate

  11 Harmony Ln, Framingham, MA 01702
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  /28

  $6,998,000

  • 6 Beds
  • 6 Baths
  • 7,409 Sq Ft

  35 Metacomet Rd, Newton, MA 02468

  A rare masterpiece in Waban Village by Excelsior Development Partners, this luxury estate blends modern design with exceptional craftsmanship, nestled on a quiet street next to Braeburn Country Club. This six-bedroom sanctuary offers unparalleled luxury with a commanding floating staircase, natural oak floors, soaring ceilings, and custom built-ins. The bespoke kitchen is a chef’s dream with

  O & C Homes Team William Raveis R.E. & Home Services

  35 Metacomet Rd, Newton, MA 02468
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  /39

  $1,200,000

  • 5 Beds
  • 3.5 Baths
  • 4,336 Sq Ft

  51 Tamarack Rd, Dracut, MA 01826

  Stunning young Colonial in desirable Meadow Creek community features beautiful finishes throughout. This home features 9’ ceilings, hardwood floors and high-end finishes with sought after open floor plan. Large Kitchen w/ center island, recessed lights, granite counters, Bosh appliances, double oven. Kitchen/eat-in area opens to gas fireplace Family Room. 1st floor half bath. Second floor

  Sam Zhu Keller Williams Realty

  51 Tamarack Rd, Dracut, MA 01826
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  /38

  $2,500,000

  Open Sat 11AM - 1PM

  • 5 Beds
  • 2.5 Baths
  • 3,550 Sq Ft

  70 Oxford St, Somerville, MA 02143

  Set on a quiet tree-lined street in Somerville’s sought-after Spring Hill neighborhood, this grand Victorian blends timeless character with exceptional scale, charm, and flexibility. Situated on a nearly 6,500 sq ft lot, the home features soaring ceilings, oversized windows, beautiful original detail, and multiple levels of living. A welcoming covered front porch overlooks one of the

  The Moving Great Boston Team Berkshire Hathaway HomeServices Warren Residential

  70 Oxford St, Somerville, MA 02143
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  /40

  $1,999,900

  Open Sun 12PM - 1PM

  • 7 Beds
  • 4.5 Baths
  • 3,718 Sq Ft

  7 2nd St, Medford, MA 02155

  A truly unique opportunity for savvy investors in Medford—this fully renovated two-family property showcases Medford’s first detached ADU, delivering exceptional flexibility and income potential. Unit 1 features a flexible bi-level layout with 2 bedrooms and 1 bath on the main level, plus a finished lower level offering an additional bedroom, full bath, and versatile media rooms. Unit 2 occupies

  Jacqui Webb Gibson Sotheby's International Realty

  7 2nd St, Medford, MA 02155
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  /28

  $1,225,000

  • 5 Beds
  • 3 Baths
  • 2,583 Sq Ft

  1465 Sudbury Rd, Concord, MA 01742

  Offered for the first time in over half a century, this expansive 5-bedroom Cape is gracefully set on a breathtaking 1.5-acre pastoral parcel, surrounded by sweeping farmland and protected conservation land—an extraordinary backdrop of open skies and serene natural beauty.The home offers generous living space and a flexible layout, providing a strong foundation for its next chapter. With

  Sharon Mendosa Compass

  1465 Sudbury Rd, Concord, MA 01742
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  /9

  $1,045,000

  $95K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,246 Sq Ft

  248 Powder House Blvd, Somerville, MA 02144

  You cannot beat the location,close to Tufts University,within short walk to Stop&Shop ,Teele Square,only 1 mile from the Davis Square Red Line stop and 0.7 miles to green line College Ave T Stop.Off street parking for 3 cars. 100 amp breakers

  mark medeiros Cambridge Realty

  248 Powder House Blvd, Somerville, MA 02144
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  /39

  $3,916,000

  • 5 Beds
  • 8 Baths
  • 3,927 Sq Ft

  25 High St, Newton, MA 02461

  New Construction(2) Luxury Townhomes coming to Newton. Completion Spring 2027! Rare opportunity to Customize with Edge Builders Newest Luxury Build. Hidden on a quiet street with minimal activity gives you privacy and solitude. Soaring 10ft ceilings, open floor plan and refined details throughout set a tone of modern sophistication and comfort. Each Unit features A custom Chef's kitchen with

  Maureen Kelly-Fromm RE/MAX Preferred Properties

  25 High St, Newton, MA 02461
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  /32

  $1,750,000

  • 5 Beds
  • 5 Baths
  • 3,528 Sq Ft

  255 Worthen Rd E, Lexington, MA 02421

  Magnificent 5 Bed, 5 Bath home with picturesque half acre lot totally redesigned, renovated, and expanded in 2016! Perfectly located for Bowman Grade School, Clarke Middle School, and LHS, top ed institutions in the US. 2025 gas furnace. Modern, sunny, and spacious open layout offers bright and versatile spaces for comfortable living. Integrated gourmet kitchen features a central island and gas

  Xinyi Zhao Hestia

  255 Worthen Rd E, Lexington, MA 02421
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  /39

  $2,399,000

  $251K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 6,130 Sq Ft

  76 Hollis St, Sherborn, MA 01770

  This extensively renovated home is a masterpiece of design and functionality, offering a stunning fusion of modern sophistication and elegance. Set well back from the road in an idyllic setting, it provides a sense of peace and privacy that's hard to find. At its heart is the light-filled gourmet kitchen, family room and breakfast nook/sunroom. Combined with five spacious bedrooms, four and a

  Stephanie Sugden Compass

  76 Hollis St, Sherborn, MA 01770
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  /25

  $1,299,000

  $200K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,480 Sq Ft

  105-107 Warwick Rd, Newton, MA 02465

  Two family located in great West Newton location. 3-bedroom and a 2-bedroom unit with room to grow in the basement. Great rental location or condo conversion. Nice private back yard. Close to schools, shopping, parks and public transportation. Units are vacant...

  Joe Denucci DeNucci Realty Group, Inc.

  105-107 Warwick Rd, Newton, MA 02465
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  /41

  $4,899,000

  • 6 Beds
  • 6.5 Baths
  • 6,556 Sq Ft

  1640 Commonwealth Ave, West Newton, MA 02465

  JUST COMPLETED. FINAL LANDSCAPING UNDERWAY. Timeless home by a premier local developer in iconic West Newton Hill. A sun-drenched foyer with custom millwork, soaring ceilings, & expansive windows creates a striking first impression, opening to elegant living & dining spaces. The kitchen is the heart of the home, outfitted with high-end appliances, inset cabinetry, an oversized waterfall island,

  Lena Voloshin LV Group Real Estate

  1640 Commonwealth Ave, West Newton, MA 02465
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  /42

  $1,388,000

  • 5 Beds
  • 3.5 Baths
  • 4,812 Sq Ft

  16 Shipley Cir, Westford, MA 01886

  Presenting 16 Shipley Cir at the desirable Lakeside Meadows subdivision. This magnificent residence, sitting on a 37,026 Sq. Ft. lot, has been meticulously remodeled with high-quality craftsmanship & attention to detail. Spanning 4 beautifully finished levels, it offers the perfect blend of luxury & functionality. The main level features a formal living room with a cozy fireplace, dining room, a

  Yessenia Alvarado Coldwell Banker Realty - Marblehead

  16 Shipley Cir, Westford, MA 01886
• 

  

  /23

  $2,695,000

  $100K PRICE DROP

  • 8 Beds
  • 6 Baths
  • 4,517 Sq Ft

  252-254 Crescent St, Waltham, MA 02453

  HIGHLY DESIRABLE SOUTH SIDE LOCALE NEAR THE CHARLES! IMMACULATE FULLY UPDATED TURN KEY SIX FAMILY HOME featuring newer kitchens w/stone tops and stainless appliances, newer tiled bathrooms, hardwood flooring throughout, laundry, lots of off street parking, garage and much more! Walk to Charles River, Moody Street shops, restaurants and public transportation! Perfectly located for quick access to

  Dave DiGregorio Jr. Coldwell Banker Realty - Waltham

  252-254 Crescent St, Waltham, MA 02453
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  /32

  $1,099,999

  • 5 Beds
  • 2 Baths
  • 2,054 Sq Ft

  75 Orchard St, Medford, MA 02155

  Calling all investors and developers! Charming two-family just 0.5 miles from Tufts University with excellent buy/update/hold or condo conversion potential. The first-floor unit offers 2 bedrooms plus a den (previously used as a 3rd bedroom), living room, full bath, and an eat-in kitchen with pantry, gas stove, and dishwasher, plus a bonus room with potential to be an excellent office or sun

  Michael Wilson-P mwilsonpierce@cambridgere Cambridge Realty Group, Inc.

  75 Orchard St, Medford, MA 02155

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