Middlesex, MA Homes

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  /41

  $2,299,900

  • 6 Beds
  • 4 Baths
  • 4,385 Sq Ft

  5 Bacon St, Winchester, MA 01890

  This meticulously updated home blends timeless character with modern comfort, offering flexibility as a two-family or multi-generational single-family residence. Prior owners embraced multi-generational living, appreciating the spacious layout and exquisite built-ins that grace both living and dining rooms with elegance and timeless appeal. A grand central staircase links all 3 levels, while

  Anne Spry Barrett Sotheby's International Realty

  5 Bacon St, Winchester, MA 01890
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  Explore Symmes Corner

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  /32

  $1,115,000 Sold Jul 15, 2025

  • 1,978 Sq Ft
  • $564/SF
  • 9 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1951

  48 Winford Way, Winchester, MA 01890

  Welcome to 48 Winford Way, a three bed, two bath Cape on a lovely level lot with a family room addition and a garage. A perfect starter home or downsizer with a full bath on each floor. Living room with large windows and a fireplace, dining room with an impressive chandelier and built-in china cabinet, eat-in kitchen with quartz countertops, tiled backsplash, and pantry closet. First floor family

  Rebecca Brennan Better Homes and Gardens Real Estate - The Shanahan Group

  48 Winford Way, Winchester, MA 01890
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  /42

  Est $1,286,294 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,341 Sq Ft

  30 Symmes Rd, Winchester, MA 01890

  30 Symmes Rd, Winchester, MA 01890
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  /41

  $1,599,000

  • 3 Beds
  • 2.5 Baths
  • 2,283 Sq Ft

  17 Dennett Rd, Winchester, MA 01890

  Beautifully renovated multi-level home in top location abutting the town forest conservation/ walking trails & just minutes from downtown Winchester! This move-in ready property features many recent upgrades, 3+ bedrooms, hardwood floors w/an open concept spacious layout perfect for modern living. The large updated kitchen includes high-end appliances, gas stove, beverage fridge & an oversized

  Kim Covino Compass

  17 Dennett Rd, Winchester, MA 01890
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  /9

  $2,899,000 Sold Jun 27, 2025

  • 5,658 Sq Ft
  • $512/SF
  • 25 Days On Market

  • 6 Beds
  • 7.5 Baths
  • Built 2025

  5 Clearwater Rd, Winchester, MA 01890

  Welcome to a rare opportunity to select the final finishes in your dream home right within Winchester’s most coveted neighborhoods. 5 Clearwater presents a luxurious canvas for your vision, offering 6 bedrooms, 7.5 baths, and 5,658 sq. ft. of meticulously planned living space. The spectacular floor plan seamlessly combines modern sophistication with timeless elegance, offering the perfect

  Monte Marrocco Coldwell Banker Realty - Lexington

  5 Clearwater Rd, Winchester, MA 01890
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  /30

  Est $1,346,053 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  350 S Border Rd, Winchester, MA 01890

  350 S Border Rd, Winchester, MA 01890
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  /42

  $1,999,900 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,607 Sq Ft

  4 Winslow Rd, Winchester, MA 01890

  Situated in a coveted Winchester neighborhood, this classical five-bedroom home unfolds across 3 levels above grade—boasting sunlit living & dining spaces framed by walls of windows overlooking lush greenery, a chef’s kitchen appointed with an expansive butcher-block island & dual fuel oven & a serene primary suite featuring a private bath & walk-in closet. 2 additional bedrooms occupy the second

  Anne Spry Barrett Sotheby's International Realty

  4 Winslow Rd, Winchester, MA 01890
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  /23

  $1,182,000 Sold Jun 09, 2025

  • 1,520 Sq Ft
  • $778/SF
  • 24 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1929

  10 Allen Rd, Winchester, MA 01890

  Located in a very desirable East Hill neighborhood, this one owner Circa 1929 Dutch Colonial offers a wonderful opportunity for the next owners to bring their ideas and make this home their own. The interior features many generous sized rooms, hardwood floors, crown molding, built in China cabinet, French doors, a brick fireplace and many more original details. This home is traditional with the

  Sally Baldwin Coldwell Banker Realty - Lexington

  10 Allen Rd, Winchester, MA 01890
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  /35

  Est $1,448,763 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,441 Sq Ft

  155 Main St, Winchester, MA 01890

  155 Main St, Winchester, MA 01890
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  /36

  $999,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,335 Sq Ft

  163 Main St, Winchester, MA 01890

  Charming multi-level home in close proximity to Winchester Center, public transit, Lincoln Elementary, and McCall. The main level offers an open floor plan with beautiful hardwood floors, bay windows, a skylit eat-in kitchen, and abundant natural light. Perfect for entertaining, the living and dining rooms flow seamlessly to a spacious yard, relaxing patio, and mature gardens. The top floor

  Andersen Group Realty Keller Williams Realty Boston Northwest

  163 Main St, Winchester, MA 01890
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  /42

  $1,475,000 Sold May 29, 2025

  • 3,067 Sq Ft
  • $481/SF
  • 9 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1961

  36 Winford Way, Medford, MA 02155

  Move right into this charming home in the heart of West Medford! Nestled in a prime location near Middlesex Fells and Playstead Park, this beautifully renovated home offers a perfect blend of modern upgrades & classic charm. Thoughtfully updated in 2018, with an additional renovation in 2020 that includes a spacious basement office suite, playroom, and ample storage space, this home is designed

  Andersen Group Realty Keller Williams Realty Boston Northwest

  36 Winford Way, Medford, MA 02155
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  /39

  Est $1,794,171 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,705 Sq Ft

  17 Stowell Rd, Winchester, MA 01890

  17 Stowell Rd, Winchester, MA 01890
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  /2

  $999,999 Pending

  • 2 Beds
  • 1 Bath
  • 1,666 Sq Ft

  26 North Gateway, Winchester, MA 01890

  LOCATION, LOCATION, LOCATION This has it.....Current building is a 2 bedroom ranch with lr,dr,k.needing TLC..Great potential for a Complete rebuild and/or restoration All offers must be on attached OFFER TO PURCHASE form and prior to entering property the attached " Hold Harmless" agreement must be signed. All offers must include the OTP, Proof of funds and/or preapproval and copy of

  Robert Dell Homes Unlimited

  26 North Gateway, Winchester, MA 01890
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  /42

  $2,499,000 Sold May 19, 2025

  • 4,270 Sq Ft
  • $585/SF
  • 0 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2024

  50 Winford Way, Winchester, MA 01890

  Just completed!! New construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the living room, complete w/ a cozy fireplace, open dining leads to sitting room & out to a deck

  Kim Covino Compass

  50 Winford Way, Winchester, MA 01890
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  /34

  Est $1,636,172 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,251 Sq Ft

  9 Everell Rd, Winchester, MA 01890

  9 Everell Rd, Winchester, MA 01890
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  /38

  $2,850,000 Sold May 07, 2025

  • 5,044 Sq Ft
  • $565/SF
  • 5 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2025

  22 Standish Ln, Winchester, MA 01890

  This distinguished residence, built by premier local developer, represents the pinnacle of elegant living! Soaring ~9' ceilings & pristine hardwood floors set an impressive tone in this meticulously crafted new construction offering 4 levels of refined living space. The eye-catching foyer ushers guests into a realm of sophisticated design, where premium finishes & high-end appliances elevate

  Michaela Mahtani Leading Edge Real Estate

  22 Standish Ln, Winchester, MA 01890
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  /34

  Est $1,657,823 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,314 Sq Ft

  20 Stowell Rd, Winchester, MA 01890

  20 Stowell Rd, Winchester, MA 01890
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  /42

  $1,815,000 Sold Apr 15, 2025

  • 2,810 Sq Ft
  • $646/SF
  • 8 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1935

  29 Allen Rd, Winchester, MA 01890

  This expanded 4-bedroom, 2.5-bath colonial is a true gem in the heart of a serene Lincoln School neighborhood. Impeccably maintained by the same family for over 40 years, this home has been thoughtfully updated w/ modern comforts, incl. AC throughout. The 1st floor features a remodeled kitchen w/ stainless steel appliances, granite countertops & breakfast bar, flowing into a spacious family room

  Carolyn Walsh Better Homes and Gardens Real Estate - The Shanahan Group

  29 Allen Rd, Winchester, MA 01890
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  /42

  Est $2,007,000 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,816 Sq Ft

  26 Stowell Rd, Winchester, MA 01890

  26 Stowell Rd, Winchester, MA 01890
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  /38

  $2,199,000 Sold Jan 27, 2025

  • 3,431 Sq Ft
  • $641/SF
  • 21 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  11 Alden Ln, Winchester, MA 01890

  This stunning new 4 Bed 3.5 BA home in Winchester’s sought-after East Side is a must see! The first floor boasts a dramatic contemporary design with high ceilings and designer finishes with oversized windows drawing attention to the setting w/ large rear yard & oversized deck, great for entertaining and family enjoyment.The open airy layout features a great entry w/ mud room, high-end kitchen

  Kim Covino Compass

  11 Alden Ln, Winchester, MA 01890
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  /39

  Est $2,194,178 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,588 Sq Ft

  445 Highland Ave, Winchester, MA 01890

  445 Highland Ave, Winchester, MA 01890
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  /30

  $2,050,000 Sold Jan 24, 2025

  • 3,450 Sq Ft
  • $594/SF
  • 89 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1953

  9 South Gateway, Winchester, MA 01890

  Completely renovated colonial style home on a quiet cul-de-sac within walking distance to downtown Winchester! This home features 5 bedrooms, 3.5 bathrooms and an attached 2 car garage. The first floor offers kitchen, dining, living room and den/study. The flexible first floor also has a bedroom with en suite bath and an office/additional bedroom. Completing the first floor are a half bath

  Mark Donnellan Advisors Living - Winchester

  9 South Gateway, Winchester, MA 01890
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  /40

  Est $1,122,382 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,589 Sq Ft

  437 Highland Ave, Winchester, MA 01890

  437 Highland Ave, Winchester, MA 01890
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  /36

  $1,875,000 Sold Dec 23, 2024

  • 3,376 Sq Ft
  • $555/SF
  • 28 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1925

  10 Marshall Rd, Winchester, MA 01890

  Fully renovated in 2012,this charming colonial is nestled on a side street near Winchester Center, both train stations and local schools.Step into a welcoming ,traditional foyer that leads to the living room, complete with custom built-ins, a cozy fireplace and French doors opening to a sunroom bathed in natural light. The chefs kitchen boasts high end appliances and flows seamlessly into a

  Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

  10 Marshall Rd, Winchester, MA 01890
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  /31

  Est $2,175,858 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,380 Sq Ft

  1 Marshall Rd, Winchester, MA 01890

  1 Marshall Rd, Winchester, MA 01890
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  /40

  $1,115,000 Sold Dec 05, 2024

  • 3,364 Sq Ft
  • $331/SF
  • 82 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1935

  708 Winthrop St, Medford, MA 02155

  On A Lovely Corner Lot In West Medford And Right On The Winchester Line Sits This Stunning Four Bedroom Home. As You Step Into This Stately Residence You Are Captured By The Elegant Staircase And Abounding Natural Sunlight This Exquisite Space Has To Offer. You Are Met With Charm & Character At Every Turn. The Attached Garage Offers Parking And Additional Living Space. You Have A Rare Opportunity

  Corey Mastrocola Welcome Home Properties, Inc.

  708 Winthrop St, Medford, MA 02155
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  /28

  Est $1,565,749 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,912 Sq Ft

  11 Marshall Rd, Winchester, MA 01890

  11 Marshall Rd, Winchester, MA 01890
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  /42

  $2,250,000 Sold Nov 20, 2024

  • 4,026 Sq Ft
  • $559/SF
  • 10 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2006

  18 Town Way, Winchester, MA 01890

  Stunning 2006 Colonial, meticulously maintained & decorator-perfect. A grand entry with high ceilings and elegant archways welcomes you into this sun-filled home. The charming living & dining rooms showcase custom details throughout. The gourmet granite kitchen features an oversized island with seating for four, dining area & high-end amenities. A mudroom with ample storage is conveniently

  Nannette Shanahan Better Homes and Gardens Real Estate - The Shanahan Group

  18 Town Way, Winchester, MA 01890
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  /42

  Est $1,884,686 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,866 Sq Ft

  16 Marshall Rd, Winchester, MA 01890

  16 Marshall Rd, Winchester, MA 01890
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  /38

  $1,485,000 Sold Oct 25, 2024

  • 3,028 Sq Ft
  • $490/SF
  • 6 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1953

  10 Robinson Rd, Medford, MA 02155

  A beautifully done, full renovation on the Winchester/Medford line. An open concept first floor with a tremendous Great Room that features high ceilings, gas fireplace and sliding doors leading to a composite deck. The kitchen features a waterfall island with seating for three to four. Brand new cabinets, countertops and stainless steel appliances make this kitchen stand out. A sizable mud

  Dave Beeching Advisors Living - Arlington

  10 Robinson Rd, Medford, MA 02155
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  /38

  Est $1,229,116 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,072 Sq Ft

  428 Highland Ave, Winchester, MA 01890

  428 Highland Ave, Winchester, MA 01890
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  /28

  $2,357,000 Sold Oct 18, 2024

  • 3,679 Sq Ft
  • $641/SF
  • 3 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2017

  57 Winford Way, Winchester, MA 01890

  Offer accepted,Open House cancel!Stunning custom-built colonial home from 2017! This property boasts an open floor plan with soaring ceilings, abundant natural light, and hardwood floors paired with recessed lighting throughout. The first floor features a spacious layout centered around a show-stopping kitchen, crafted by Bespoke of Winchester, equipped with BlueStar/Sub-Zero stainless steel

  Dan Li Keller Williams Realty

  57 Winford Way, Winchester, MA 01890
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  /33

  Est $1,694,931 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,835 Sq Ft

  4 Sargent Rd, Winchester, MA 01890

  4 Sargent Rd, Winchester, MA 01890
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  /24

  $1,070,000 Sold Sep 27, 2024

  • 3,417 Sq Ft
  • $313/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  21 Winford Way, Medford, MA 02155

  REMARKABLE SERENITY is found in renovated Custom Built Ranch with over 3400sf of finished living space on two levels in desirable Colonial Village neighborhood on the Winchester line. Luxury upgrades include a NEW custom chef's kitchen, NEW custom tile bathroom, central air, new windows & new heating system. Mid-century home seekers will love the open, flowing space of this wide home. Large

  Kelly Catallo Realty ONE Group Cosmopolitan

  21 Winford Way, Medford, MA 02155
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  /34

  Est $1,702,706 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,810 Sq Ft

  26 Sargent Rd, Winchester, MA 01890

  26 Sargent Rd, Winchester, MA 01890
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  /38

  $1,380,000 Sold Sep 04, 2024

  • 2,364 Sq Ft
  • $584/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1940

  27 Ledyard Rd, Winchester, MA 01890

  Discover the endless potential of this charming 3-bedroom, 1.5-bathroom home, perfectly positioned on a sought-after Winchester lot with excellent frontage and a generously sized yard. The finished lower level features a convenient walkout to a private backyard, creating additional living space and ample opportunities for outdoor enjoyment. This property presents a fantastic opportunity for a

  Andersen Group Realty Keller Williams Realty Boston Northwest

  27 Ledyard Rd, Winchester, MA 01890
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  /29

  Est $1,562,382 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,769 Sq Ft

  50 Allen Rd, Winchester, MA 01890

  50 Allen Rd, Winchester, MA 01890
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  /3

  $1,610,000 Sold Aug 15, 2024

  • 2,212 Sq Ft
  • $728/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1920

  12 Everell Rd, Winchester, MA 01890

  Nestled in sought-after Symmes neighborhood this timeless home was renovated in 2019-2020 providing a refreshed layout and modern amenities while keeping the home's original charm. The gracious foyer leads to a front to back living room with fireplace, window seat and French doors opening to a new family room with a walkout to the patio and backyard. The dining room with bow window flows into the

  Quinn Simpson Compass

  12 Everell Rd, Winchester, MA 01890
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  /38

  Est $1,467,557 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,664 Sq Ft

  7 Perkins Rd, Winchester, MA 01890

  7 Perkins Rd, Winchester, MA 01890
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  /35

  $1,199,000 Sold Aug 06, 2024

  • 2,332 Sq Ft
  • $514/SF
  • 11 Days On Market

  • 5 Beds
  • 1.5 Baths
  • Built 1880

  9 Bacon St, Winchester, MA 01890

  Introducing this updated townhouse condo, with a single-family feel, in a top location. It has all the amenities that buyers desire, plus energy-efficient features such as solar panels, 2023 high-efficiency heating & A/C system, EV charger, and newer windows. Enjoy morning coffee on the spacious front porch, and gardening or hosting friends in the private backyard. Large sunlit rooms welcome you

  Elena Langlois Compass

  9 Bacon St, Winchester, MA 01890

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