Winchester, MA Homes

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  /42

  $2,400,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,215 Sq Ft

  12 Olde Lyme Rd, Winchester, MA 01890

  *** OPEN HOUSE CANCELLED**** OFFER ACCEPTED Presenting 12 Olde Lyme Rd, where classic Colonial charm meets modern style + convenience. Nestled at the end of a private cul-de-sac, and just a short walk to the coveted Vinson-Owen school, this 5-bedroom, 4.5-bath home has been expanded with purpose and thoughtfully renovated in 2017. The redesign includes high-end finishes and exquisite updates

  Mary Beth McGillicuddy Engel & Völkers , South Shore

  12 Olde Lyme Rd, Winchester, MA 01890
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  /25

  $1,000,000 Sold Dec 23, 2024

  • 2,355 Sq Ft
  • $425/SF
  • 11 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 1900

  37-39 Middlesex St, Winchester, MA 01890

  Motivated Sellers! Wonderful 2 Family on a quiet side street area just off Wedge Pond. Welcome to 37 - 39 Middlesex Street, Winchester. Lack of inside pictures is to protect privacy of the tenants and NOT an indication of poor condition. This is a very solid Two-Family Large Backyard with tremendous privacy behind property abutting Town owned land. Reciprocal side by side duplex with separate

  Craig Celli Century 21 North East

  37-39 Middlesex St, Winchester, MA 01890
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  /42

  Est $2,167,278 Not Listed For Sale

  • 7 Beds
  • 3 Baths
  • 4,090 Sq Ft

  5 Swan Rd, Winchester, MA 01890

  5 Swan Rd, Winchester, MA 01890
• 

  

  

  /38

  $1,550,000 Pending

  • 6 Beds
  • 2.5 Baths
  • 3,543 Sq Ft

  189 Mystic Valley Pkwy, Winchester, MA 01890

  Perfectly situated just moments from the vibrant heart of Winchester, this Mansard-roofed beauty offers a harmonious blend of refined style and comfort. A spacious front porch overlooking a sizable side yard invites you to relax and enjoy the energy of the nearby town center. Inside, the main level blends form and function; expansive living spaces are complemented by a mudroom, home office, and

  Anne Spry Barrett Sotheby's International Realty

  189 Mystic Valley Pkwy, 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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  /41

  Est $1,364,243 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,092 Sq Ft

  32 Cambridge St, Winchester, MA 01890

  32 Cambridge St, Winchester, MA 01890
• 

  

  /40

  $1,449,000 Pending

  • 3 Beds
  • 4.5 Baths
  • 3,186 Sq Ft

  7 Wainwright Rd Unit 13, Winchester, MA 01890

  Welcome to The Ledges, Winchester’s premier townhouse community! This extraordinary F Style corner unit is truly one of a kind with soaring ceilings, sun-filled spaces, and rare flat backyard space with two decks. A landscaped courtyard leads to a gracious foyer and transitions into an expansive open layout. The chef’s kitchen opens to the dining rm and features ss appliances, granite countertops

  Nancy Pallotta Advisors Living - Winchester

  7 Wainwright Rd Unit 13, Winchester, MA 01890
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  /25

  $1,000,000 Sold Dec 19, 2024

  • 1,840 Sq Ft
  • $543/SF
  • 8 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1937

  15 Westland Ave, Winchester, MA 01890

  A dIamond in the rough!!! Are you a contractor or handy end user looking for a project in sought after WInchester? Look no further than this 1937, 4 bedroom Colonial brimming with potential. The charm of yesteryear shows through with custom built-ins, crown moldings, hardwood flooring and so much more. Full walk out unfinished basement with double soapstone sink and a full walk up attic lends

  Libby Rankin Hamill Berkshire Hathaway HomeServices Stephan Real Estate

  15 Westland Ave, Winchester, MA 01890
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  /39

  Est $1,255,159 Not Listed For Sale

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

  10 Chesterford Rd E, Winchester, MA 01890

  10 Chesterford Rd E, Winchester, MA 01890
• 

  

  /39

  $1,325,000 Pending

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

  9 Thornberry Rd, Winchester, MA 01890

  Nestled on a picturesque lot with lush landscaping and mature trees, 9 Thornberry Road offers a perfect blend of natural beauty and refined living. Sunlight pours into this thoughtfully designed home, featuring an open-concept layout ideal for comfortable living and entertaining. The main level includes a welcoming fireplace, hardwood floors, large living room, dining area, and an updated kitchen

  Louise Coakley Better Homes and Gardens Real Estate - The Shanahan Group

  9 Thornberry Rd, Winchester, MA 01890
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  /27

  $2,120,000 Sold Dec 19, 2024

  • 4,255 Sq Ft
  • $498/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  2 Loring Ct, Winchester, MA 01890

  UNDER CONSTRUCTION to be completed by 11/24! Desirable 4+ bedroom home w/ thoughtful design & high end finishes! This home is spacious & inviting, offering a grand open floor plan ideal for entertaining & modern day family living. The kitchen features an oversized island w/ seating, quartz countertops, high-end appliances and walk in pantry. Off the kitchen is a spacious family room w/gas

  Kim Covino Compass

  2 Loring Ct, Winchester, MA 01890
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  /42

  Est $1,189,231 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,657 Sq Ft

  8 Chesterford Rd E, Winchester, MA 01890

  8 Chesterford Rd E, Winchester, MA 01890
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  /16

  $499,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,007 Sq Ft

  27 Elm St, Winchester, MA 01890

  Attention investors, contractors, and handy owner occupants looking to build sweat equity! This single family home is in need of major renovation and is the perfect opportunity for a contractor to make a profitable investment or an owner occupant to unlock instant sweat equity. Dream location just around the corner to Winchester Center's shops and restaurants, less than 0.3 miles to the top rated

  Shao Realty Group RE/MAX Executive Realty

  27 Elm St, Winchester, MA 01890
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  /37

  $2,150,000 Sold Dec 18, 2024

  • 3,048 Sq Ft
  • $705/SF
  • 12 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1963

  18 Dix St, Winchester, MA 01890

  Elegant and timeless, this beautifully renovated colonial in the heart of Winchester Center offers the perfect blend of classic design and modern luxury. With a high-end chef’s kitchen featuring an oversized island, the home’s open floor plan seamlessly connects to a spacious family room and dining area, ideal for gatherings. The first floor also boasts a formal front-to-back living room with a

  Karen Garrett Better Homes and Gardens Real Estate - The Shanahan Group

  18 Dix St, Winchester, MA 01890
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  /35

  Est $1,954,196 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,846 Sq Ft

  12 Ardley Place, Winchester, MA 01890

  12 Ardley Place, Winchester, MA 01890
• 

  

  /16

  $1,150,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,621 Sq Ft

  61 Westland Ave, Winchester, MA 01890

  Welcome to this oversized Cape in a lovely west side neighborhood of Winchester. Opportunity for a little TLC or a significant renovation, the flexible layout of this 1952 gem offers many possibilities. Attention savvy buyers, contractors and builders! Sited on a 10,703sf lot within the Vinson-Owen school district. First floor offers living room, dining room, kitchen, sunroom/porch, 2 bedrooms

  Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  61 Westland Ave, Winchester, MA 01890
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  /24

  $962,000 Sold Dec 18, 2024

  • 1,890 Sq Ft
  • $509/SF
  • 21 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1969

  25 Hemingway St, Winchester, MA 01890

  Discover the potential of this charming and well-maintained 2-story Cape-style home, offering both comfort and privacy in a highly desirable Winchester location. Conveniently situated near a public elementary school, public transportation, healthcare services, and a variety of dining options, this home ensures easy access to everything you need. Featuring 3 spacious bedrooms and 2 full baths, the

  Andersen Group Realty Keller Williams Realty Boston Northwest

  25 Hemingway St, Winchester, MA 01890
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  /37

  Est $1,451,860 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,350 Sq Ft

  8 Parker Rd, Winchester, MA 01890

  8 Parker Rd, Winchester, MA 01890
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  /39

  $849,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,528 Sq Ft

  703 Washington St, Winchester, MA 01890

  Delightful ranch, well maintained and located conveniently near the major routes. The kitchen is spacious and opens to the comfortable dining area with large built in hutch. It has been updated and features a tile backsplash, stainless steel appliances and recessed lighting. The living room is fireplaced and is nicely appointed with hardwood floors. Easy one level living with two first floor

  Michael Barrett Barrett, Chris. J., REALTORS®

  703 Washington St, Winchester, MA 01890
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  /26

  $1,725,000 Sold Dec 18, 2024

  • 3,143 Sq Ft
  • $549/SF
  • 75 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1939

  7 Ardley Rd, Winchester, MA 01890

  Spacious 4-bedroom colonial home w/a Nantucket vibe, sited on manicured lawns in a cul-de-sac neighborhood! Just a block from the newly being built elementary school, close to the bike path, Horn Pond & hiking trails, this property is sure to please! 7 Ardley Road features a flowing & welcoming floor plan w/lots of natural light. Beautiful gleaming hardwood flooring is found in the living room

  Vantage Point Team William Raveis R.E. & Home Services

  7 Ardley Rd, Winchester, MA 01890
• 

  

  /39

  Est $1,680,734 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,592 Sq Ft

  59 Woodside Rd, Winchester, MA 01890

  59 Woodside Rd, Winchester, MA 01890
• 

  

  /30

  $1,300,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,629 Sq Ft

  17 Mason St, Winchester, MA 01890

  Nestled on a quiet, tree-lined street near Winchester’s vibrant town center, this delightful storybook colonial offers charm, character, and exceptional potential. Beautifully sited on a 10,000+ sq ft wooded lot, this three-bedroom, two-bath home invites your vision to blend timeless architectural details with thoughtful updates. A fireplaced front-to-back living room flows seamlessly into a

  Karen Garrett Better Homes and Gardens Real Estate - The Shanahan Group

  17 Mason St, Winchester, MA 01890
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  /37

  $773,000 Sold Dec 16, 2024

  • 1,430 Sq Ft
  • $541/SF
  • 13 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1984

  171 Swanton St Unit 16, Winchester, MA 01890

  Welcome to this fabulous sought after end unit townhouse located at The Village,close to town,schools, and conservation.This home has been meticulously maintained and updated including new windows. Inviting living room has gas fireplace and private seating area with skylight looking over a private wooded setting and patio. Kitchen has cherry custom cabinets with granite and stainless

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

  171 Swanton St Unit 16, Winchester, MA 01890
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  /29

  Est $1,090,825 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,630 Sq Ft

  7 Brantwood Rd, Winchester, MA 01890

  7 Brantwood Rd, Winchester, MA 01890
• 

  

  /17

  $299,000 Pending

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft

  200 Swanton St Unit T4, Winchester, MA 01890

  Immaculate, recently renovated Jumbo Studio Condominium with a private/direct-entry terrace level. This unit is spacious and bright, featuring a slider that leads to a private patio overlooking scenic duck ponds and lush landscaping. The large eat-in kitchen features white cabinets, with a white tiled backsplash and granite countertops. The bathroom was recently updated with new fixtures,

  Michael Masci North Atlantic Realty Group

  200 Swanton St Unit T4, Winchester, MA 01890
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  /34

  $2,960,000 Sold Dec 12, 2024

  • 4,860 Sq Ft
  • $609/SF
  • 72 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2024

  39 Everett Ave, Winchester, MA 01890

  Welcome to this stunning, brand-new construction in Winchester's most desired neighborhood. This home offers modern luxury and timeless elegance. The custom kitchen features two-toned countertops with a Pegasus marble island and Jet Mist granite perimeter, along with brass accents. The pantry provides for ample additional storage with floor to ceiling cabinets, jet mist counters and a wine

  Mark Donnellan Advisors Living - Winchester

  39 Everett Ave, Winchester, MA 01890
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  /40

  Est $1,764,104 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,395 Sq Ft

  4 Ardley Rd, Winchester, MA 01890

  4 Ardley Rd, Winchester, MA 01890
• 

  

  /42

  $2,600,000 Pending

  • 4 Beds
  • 4 Baths
  • 4,704 Sq Ft

  34 Swan Rd, Winchester, MA 01890

  Situated in the prestigious Myopia Hill neighborhood, this exceptional sprawling ranch offers a rare combination of timeless elegance & modern comfort. Set on a lush, private acre, offering nearly 4,500 sq ft of beautifully maintained living space designed for both everyday living & grand-scale entertaining. Exquisite custom woodwork, built-ins & moldings lend sophistication throughout.

  Laurie Cappuccio Classified Realty Group

  34 Swan Rd, Winchester, MA 01890
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  /37

  $2,750,000 Sold Dec 12, 2024

  • 4,212 Sq Ft
  • $653/SF
  • 21 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1935

  56 Salisbury St, Winchester, MA 01890

  Beautifully renovated 4 bedroom home in sought after Winchester Flats! Featuring a picturesque combination of stylish comfort and modern design. The 1st floor welcomes with an oversized custom mudroom leading to a spacious chef's kitchen featuring upgraded Wolf appliances including gas range, steam oven, and 2 built-in beverage fridges. The family room invites with custom built-in window seats,

  The McLaren D'Agostino Team Compass

  56 Salisbury St, Winchester, MA 01890
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  /22

  Est $1,456,576 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,495 Sq Ft

  166 Pond St, Winchester, MA 01890

  166 Pond St, Winchester, MA 01890
• 

  

  /37

  $1,379,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft

  26 Ridge St, Winchester, MA 01890

  Set on a generous, beautifully landscaped lot, this meticulously maintained home showcases numerous recent upgrades, and offers both comfort and style. The newly renovated kitchen features upscale appliances and custom quartz countertops, perfect for everyday living and entertaining alike.Hardwood floors, two fireplaces, a sunlit living room, and a separate family room create inviting spaces

  Dream Team Dreamega International Realty LLC

  26 Ridge St, Winchester, MA 01890
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  /38

  $1,650,000 Sold Dec 11, 2024

  • 3,158 Sq Ft
  • $522/SF
  • 6 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  31 Girard Rd, Winchester, MA 01890

  Welcome to 31 Girard Road, a lovely colonial gracefully positioned on a prominent corner lot in the Vinson Owen School district! As you step inside, you’ll pass an exquisite curved staircase on your way to the front-to-back living room with custom built-ins. The heart of the home is the open kitchen, seamlessly connected to a bright and airy dining area. This space is perfect for hosting

  Philip Vita Compass

  31 Girard Rd, Winchester, MA 01890
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  /42

  Est $2,498,533 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,659 Sq Ft

  10 Norfolk Rd, Winchester, MA 01890

  10 Norfolk Rd, Winchester, MA 01890
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  /32

  $749,900 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,931 Sq Ft

  235 Cross St, Winchester, MA 01890

  Lovingly cared for by its original owners for nearly 70 years, this charming ranch-style home rests proudly on a desirable corner lot in a welcoming, established neighborhood. Offering 3 comfortable bedrooms, 1.5 bathrooms, and two fireplaces, the home is filled with warmth, character, and exciting potential for new owners to make it their own. The yard comes alive each spring with vibrant

  Melanie Lentini Leading Edge Real Estate

  235 Cross St, Winchester, MA 01890
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  /42

  $1,755,000 Sold Dec 10, 2024

  • 2,886 Sq Ft
  • $608/SF
  • 7 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1911

  19 Warren St, Winchester, MA 01890

  Step into this beautifully designed 3-bedroom, 3-bathroom single-family home located in the sought-after Flats of Winchester. Nestled in a wonderful neighborhood, this home offers a perfect blend of charm and modern living. The spacious living room with a cozy fireplace flows seamlessly into a bright sunroom, filling the space with natural light. The eat-in kitchen is equipped with stainless

  Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

  19 Warren St, Winchester, MA 01890
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  /42

  Est $1,760,814 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,180 Sq Ft

  85 Pond St, Winchester, MA 01890

  85 Pond St, Winchester, MA 01890
• 

  

  /40

  $1,499,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 2,351 Sq Ft

  19 Cox Rd, Winchester, MA 01890

  Charming three-bedroom ranch on spectacular 20,000sf west side lot abutting conservation! The updated granite kitchen with newer appliances leads to the open concept dining room overlooking the beautiful, private yard. The spacious living room features a fplc & bay window; a sunroom, 3 spacious bedrooms, 1 bath & garage complete the main level; the lower level offers a large rec/ family room w

  Kim Covino Compass

  19 Cox Rd, Winchester, MA 01890
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  /40

  $1,225,000 Sold Dec 09, 2024

  • 3,350 Sq Ft
  • $366/SF
  • 27 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1988

  7 Wainwright Rd Unit 29, Winchester, MA 01890

  Imagine arriving home to peace & serenity at The Ledges, a hilltop oasis on Winchester's West side. This tranquil retreat offers carefree living & your private sanctuary. Relax in the fireplace living room, sliders to your private deck & expansive views. The main bedroom en suite, is conveniently located on the first floor. Second level finds a loft, skylit bonus room perfect for a home office,

  Joanne Sexeny Coldwell Banker Realty - Lexington

  7 Wainwright Rd Unit 29, Winchester, MA 01890
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  /41

  Est $2,073,231 Not Listed For Sale

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

  73 Pond St, Winchester, MA 01890

  73 Pond St, Winchester, MA 01890
• 

  

  /28

  $1,299,000 Pending

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

  261 Cambridge St Unit 261 G, Winchester, MA 01890

  Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms,

  Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

  261 Cambridge St Unit 261 G, Winchester, MA 01890

Showing Results 281 - 320, Page 8 of 18