Winchester, MA Homes for Sale

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  $2,599,000 Open Sat 11:30AM - 12:30PM

  • 4 Beds
  • 4.5 Baths
  • 5,501 Sq Ft

  15 Churchill Rd, Winchester, MA 01890

  Indulge in modern luxury with this stunning home, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor

  Kim Covino Compass

  15 Churchill Rd, Winchester, MA 01890
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  $2,499,000 Open Fri 10:30AM - 11:30AM

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

  19 Yale St, Winchester, MA 01890

  Located in the TOP neighborhood that everyone wants! Welcome to the Flats, where elegance and charm abound. A gorgeous foyer welcomes you and flows easily into the living room and dining room, both impressively lit with natural light. A fireplace and custom built-ins add warmth and charm, beckoning for dinner parties and entertaining. A huge kitchen offers ample counter space, a sweet banquet,

  Nancy Pallotta Advisors Living - Winchester

  19 Yale St, Winchester, MA 01890
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  $2,950,000 Open Sat 12PM - 1:30PM

  • 6 Beds
  • 7 Baths
  • 6,968 Sq Ft

  14 Nassau Dr, Winchester, MA 01890

  Stunning Absolutely! Custom-built 6-bedroom house on a large and tranquil lot. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England

  Weidong Li WINN Real Estate & Consulting

  14 Nassau Dr, Winchester, MA 01890
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  $2,450,000

  • 5 Beds
  • 5 Baths
  • 3,940 Sq Ft

  17 Wagon Wheel Rd, Winchester, MA 01890

  Enjoy breathtaking Boston skyline views from nearly every room of this meticulously maintained home, offering the ultimate private retreat for peace and tranquility. The owners have thoughtfully upgraded the property, including a 2020 expansion that added an en-suite with a private bathroom and enlarged the open-concept kitchen. With 5 bedrooms and 5 bathrooms, including four en-suites, this home

  Dream Team Dreamega International Realty LLC

  17 Wagon Wheel Rd, Winchester, MA 01890
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  $2,199,000

  • 6 Beds
  • 3.5 Baths
  • 4,696 Sq Ft

  5 Squire Rd, Winchester, MA 01890

  Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shiplap fireplace, opens to a spacious composite deck. The primary suite is a private retreat with a walk-in closet, dual

  Alina Wang Coldwell Banker Realty - Lexington

  5 Squire Rd, Winchester, MA 01890
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  $3,599,000 Open Sat 1:30PM - 3PM

  • 6 Beds
  • 5.5 Baths
  • 7,431 Sq Ft

  27 Everett Ave, Winchester, MA 01890

  Completely renovated in 2023/2024! This is one of the most distinguished homes on Everett Avenue, with preeminent siting on more than half an acre. This residence combines the magnificence of early 1900s architecture with today's modern amenities., this home features hallmark architectural details including Tudor-style balusters and high ceilings. Large rooms, coffered ceilings, original crown

  Nancy Pallotta Advisors Living - Winchester

  27 Everett Ave, Winchester, MA 01890
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  $2,449,000 Open Sat 12:30PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 4,959 Sq Ft

  5 Azalea Rd, Winchester, MA 01890

  Exceptional Home nestled in one of Winchester's most desirable West Side Neighborhoods and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials and Mature Trees to Relax and Enjoy! Elegant Dining Room open

  Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

  5 Azalea Rd, Winchester, MA 01890
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  $3,799,900

  • 7 Beds
  • 7.5 Baths
  • 7,429 Sq Ft

  11 Viking Rd, Winchester, MA 01890

  Prepare to be captivated by the elegance of 11 Viking Rd. This magnificent home, boasting over 7,000 square feet of luxurious living space, offers an unparalleled opportunity for discerning buyers seeking the ultimate in comfort, style, and sophistication.Step inside and discover a world of meticulous details and thoughtful design. With 7 generously sized bedrooms and 7.5 exquisitely appointed

  The McLaren D'Agostino Team Compass

  11 Viking Rd, Winchester, MA 01890
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  $2,499,000 Open Fri 10:30AM - 11:30AM

  • 6 Beds
  • 3.5 Baths
  • 4,667 Sq Ft

  9 Prospect St, Winchester, MA 01890

  Step into a piece of history with this incredibly charming 1895 Colonial Revival, a home that exudes elegance, character, and masterful craftsmanship at every turn. From the moment you arrive, you’ll be captivated by its stately presence, classic architectural details, and warm, inviting ambiance. Inside, you’ll find an extraordinary blend of historic charm and modern livability.The craftsmanship

  Nancy Pallotta Advisors Living - Winchester

  9 Prospect St, Winchester, MA 01890
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  $3,350,000 Open Sun 11:30AM - 1PM

  • 6 Beds
  • 5 Baths
  • 5,198 Sq Ft

  21 Sheffield W, Winchester, MA 01890

  Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The stunning state of art chef’s kitchen was just completed & seamlessly connects to a butler’s pantry w/ wet bar & wine chiller, leading to an elegant dining room w/ fireplace. The oversized family room is bathed in natural light w/walls of

  Kim Covino Compass

  21 Sheffield W, Winchester, MA 01890
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  $2,399,000 Open Sat 12PM - 1PM

  • 5 Beds
  • 3.5 Baths
  • 5,077 Sq Ft

  276 High St, Winchester, MA 01890

  This stunning, freshly painted, home is located in a picturesque and unique setting, elevated on a small hill with a private half-acre lot in a tranquil cul-de-sac, near the Winchester/Lexington border. It’s far from road traffic, offering exceptional privacy. The residence spans four levels, featuring 5 bedrooms, 3.5 bathrooms, and two separate laundry areas. The expansive grounds showcase

  Andersen Group Realty Keller Williams Realty Boston Northwest

  276 High St, Winchester, MA 01890
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  $699,900 Open Sat 11AM - 12:30PM

  • 2 Beds
  • 1.5 Baths
  • 1,326 Sq Ft

  32 Clark St, Winchester, MA 01890

  A true diamond in the rough, Whether you're a first-time homebuyer, a savvy investor, or someone looking to customize a home to their liking, this residence presents the perfect blend of potential and location. This 2 bedroom single family home makes for a great condo alternative. Don't miss this rare chance to break into the Winchester market and enjoy all this town has to offer from it's great

  Rodrigo Serrano Leading Edge Real Estate

  32 Clark St, Winchester, MA 01890
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  $1,995,000 Open Sat 11AM - 12:30PM

  • 3 Beds
  • 2 Baths
  • 2,813 Sq Ft

  20 Seneca Rd, Winchester, MA 01890

  Welcome home to this picture-perfect Colonial, tucked away in a quiet, sought-after neighborhood just steps from Ambrose! Boasting gorgeous curb appeal & a warm, welcoming feel, this home offers the best of comfort & convenience.Step inside to a bright & open first floor designed for effortless entertaining, featuring oversized windows that flood the space with amazing natural light.The spacious

  Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

  20 Seneca Rd, Winchester, MA 01890
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  $1,199,000 Open Fri 11:30AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,906 Sq Ft

  44 Forest St, Winchester, MA 01890

  This charming home is move-in ready and situated on a beautiful fenced in level lot close to parks, the bike path, Muraco school & more! The interior of the home is flooded with sunlight & period details featuring open airy spaces and generously sized rooms that flow throughout the home, making each room easily accessible and enjoyable. The main floor has a lovely living room with gas fireplace,

  Kim Covino Compass

  44 Forest St, Winchester, MA 01890
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  $1,499,000 Open Sat 11:30AM - 1PM

  • 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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  $1,375,000 Open Sat 11:30AM - 1PM

  • 3 Beds
  • 2 Baths
  • 3,406 Sq Ft

  7 Hutchinson Rd, Winchester, MA 01890

  A great opportunity to reimagine this custom built spacious cape in a sought-after Winchester neighborhood! Set on a generous lot, this unique home has been lovingly maintained and is full of potential; ready for updates & your personal touch! The floor plan provides a flexible layout that’s ideal for easy living with a spacious first-floor bedroom, full bath, an oversized home office or add'l

  Kim Covino Compass

  7 Hutchinson Rd, Winchester, MA 01890
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  $1,949,000 Open Sat 12PM - 1:30PM

  • 5 Beds
  • 3.5 Baths
  • 3,478 Sq Ft

  10 Olde Lyme Rd, Winchester, MA 01890

  Beautifully updated 5 bed, 3.5 bath Colonial on Winchester's West Side with over 3400 sq ft of living space located on a quiet cul-de-sac in the coveted Vinson-Owen school district. Set on an 18,000 sq ft lot abutting Sucker Brook conservation area and walking trails. This home offers privacy, space and natural beauty. The main level features a spacious layout with an office/den, which could

  Darryl Brian RE/MAX Bentley's

  10 Olde Lyme Rd, Winchester, MA 01890
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  $1,499,900 Open Sat 12PM - 1:30PM

  • 5 Beds
  • 2 Baths
  • 3,033 Sq Ft

  7 Thornberry Rd, Winchester, MA 01890

  Renovated Contemporary Split-entry 3 Level home in the highly sought-after Vinson- Owen Elementary and West-side neighborhood. 15 minutes to Downtown Boston. 5 bedrooms, 2 full baths, Living, Dining PLUS family room & 2nd finished room ( play or office) ground level room heated & A/C walk access to outdoor deck & fire pit. Open concept kitchen area. Hardwood floors, 2 fireplace, 2 garage space,

  salim chowdhury TAJ Mahal Realty LLC

  7 Thornberry Rd, Winchester, MA 01890
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  $749,900 Open Fri 11AM - 12PM

  • 2 Beds
  • 2 Baths
  • 1,545 Sq Ft

  7 Conant Rd Unit 34, Winchester, MA 01890

  Rarely available at The Willows, you enter this unit with ease through your private, attached one car garage or the step-free front entrance—an ideal setup for everyday convenience. This beautifully maintained first-floor unit offers the perfect blend of comfort, style, and accessibility. Inside, you'll find two generously sized bedrooms, including a spacious en-suite with direct access to one of

  Melanie Lentini Leading Edge Real Estate

  7 Conant Rd Unit 34, Winchester, MA 01890
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  $1,650,000 Open Fri 11AM - 12PM

  • 3 Beds
  • 2.5 Baths
  • 2,605 Sq Ft

  14 Hillside Ave, Winchester, MA 01890

  Location, location, location! Rare opportunity to own this stunning Italianate home, in a desirable neighborhood, steps from Town Center! This property has been lovingly owned & maintained by the same family for 70+ years and is now ready for new owners. Prepare to fall in love with the charm and period details of this circa 1870 historic home, the first house built on Hillside Ave. The 1st floor

  Seeme Moreira Coldwell Banker Realty - Lexington

  14 Hillside Ave, Winchester, MA 01890
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  $1,149,000

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  83 Canal St Unit 85, Winchester, MA 01890

  This beautifully renovated, light-filled condo blends classic charm with modern updates in an ideal Winchester location. Completely gutted and converted in 2017, the home features an open-concept layout, highlighted by a spacious kitchen with granite countertops and a generous island—perfect for casual dining and entertaining. The finished basement adds versatile living space, while the primary

  Mary O'Hagan Barrett Sotheby's International Realty

  83 Canal St Unit 85, Winchester, MA 01890
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  $998,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 3 Baths
  • 2,333 Sq Ft

  48 Tremont St, Winchester, MA 01890

  Welcome to this well loved 4-bedroom expanded Cape, on quiet cul-de-sac, cared for by the original owners for nearly 65 years! Located in the brand new Lynch Elementary School district, just steps from Winchester HS, Skillings Field, less than a mile from the Commuter Rail and downtown Winchester. Great for commuters. First floor features mudroom with laundry, front-to-back fire-placed living

  Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

  48 Tremont St, Winchester, MA 01890
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  $1,299,000 Open Sun 12PM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,520 Sq Ft

  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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  $1,295,000 Open Sun 11AM - 12PM

  • 4 Beds
  • 1.5 Baths
  • 2,202 Sq Ft

  71 Woodside Rd, Winchester, MA 01890

  Nestled in the heart of Winchester, this charming 4-bedroom, 1.5-bathroom single-family home offers 2,202 square feet of living space on a 7,126-square-foot lot. Built in 1927, the home exudes timeless character with its spacious rooms, abundant natural light, and original architectural details. Perfect for homeowners and developers alike, the property offers endless potential for renovation,

  Jorge Rodriguez Carlton's Wharf & Co.

  71 Woodside Rd, Winchester, MA 01890
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  $1,199,000 Open Sat 12PM - 2PM

  • 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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  $1,499,000 Open Fri 5:30PM - 6:30PM

  • 3 Beds
  • 4 Baths
  • 3,351 Sq Ft

  34 Fells Rd, Winchester, MA 01890

  Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from the scenic Middlesex Fells Conservation Area, you'll have miles of trails for outdoor exploration right at your doorstep. With a commuter-friendly location, this home is ideal for those seeking both tranquility and convenience. A welcoming

  Andersen Group Realty Keller Williams Realty Boston Northwest

  34 Fells Rd, Winchester, MA 01890
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  $1,595,000

  • 3 Beds
  • 3.5 Baths
  • 3,763 Sq Ft

  7 Wainwright Rd Unit 8, Winchester, MA 01890

  Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first level makes this unit ready to move in.This is a perfect floor plan with living room, dining room and family room with fireplace and bookcases opening up to expansive kitchen with pantry. Enjoy the serenity of a private deck off family room. Primary suite on first floor.with large

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

  7 Wainwright Rd Unit 8, Winchester, MA 01890
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  $2,850,000

  • 4 Beds
  • 3 Baths
  • 4,276 Sq Ft

  8 Tanglewood Ln, Winchester, MA 01890

  This expansive contemporary residence exudes elegance & sophistication and offers the perfect layout for gatherings & everyday living. This gorgeous home, nestled into a cul-de-sac on the West side was custom designed with soaring ceilings & large scale rooms offering unparalleled views! Enjoy meals in the updated kitchen w/ high end appliances & direct access to deck overlooking private yard.

  Kim Covino Compass

  8 Tanglewood Ln, Winchester, MA 01890
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  $3,149,000 Open Sat 2PM - 3PM

  • 7 Beds
  • 5.5 Baths
  • 6,200 Sq Ft

  10 Sheffield Rd, Winchester, MA 01890

  This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master

  Andersen Group Realty Keller Williams Realty Boston Northwest

  10 Sheffield Rd, Winchester, MA 01890
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  $3,698,000 Open Sun 12:30PM - 2PM

  • 6 Beds
  • 7 Baths
  • 8,866 Sq Ft

  20 Amberwood Dr, Winchester, MA 01890

  Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The

  Dan Li Keller Williams Realty

  20 Amberwood Dr, Winchester, MA 01890
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  $2,695,000

  • 4 Beds
  • 4.5 Baths
  • 5,233 Sq Ft

  18 Middlesex St, Winchester, MA 01890

  This European-inspired estate is a masterpiece of design and craftsmanship. Every detail has been meticulously curated, blending timeless elegance with state-of-the-art amenities.Step into a grand foyer, where a striking curved staircase sets the stage for the home’s sophisticated ambiance. Expansive living and entertaining spaces flow seamlessly, featuring soaring ceilings, custom millwork, and

  Candice Macoul Luxury Living Real Estate

  18 Middlesex St, Winchester, MA 01890
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  $3,989,000 Open Sat 12PM - 1PM

  • 6 Beds
  • 6.5 Baths
  • 8,463 Sq Ft

  26 Swan Rd, Winchester, MA 01890

  Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with 2 primary suite options! This magnificent residence boasts expansive living spaces, elevator & indoor pool! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/custom cherry cabinetry & high end

  Kim Covino Compass

  26 Swan Rd, Winchester, MA 01890
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  $2,999,000

  • 5 Beds
  • 6 Baths
  • 5,354 Sq Ft

  8 Chestnut St, Winchester, MA 01890

  Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and 4 levels of living, discover thoughtful elegance at every turn . The designer kitchen offers high-end appliances including a gas stove, double oven, and wet-bar with beverage fridge. Featuring an open-concept, the kitchen effortlessly flows into the sun-drenched living and

  The McLaren D'Agostino Team Compass

  8 Chestnut St, Winchester, MA 01890
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  $699,900 Open Sat 12PM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,168 Sq Ft

  7 Conant Rd Unit 20, Winchester, MA 01890

  Beautifully renovated first-floor condo in the highly sought-after "Willows at Winchester" complex. This expansive, single-level unit features an open-concept living area with new hardwood flooring, a versatile space that can be used as a dining room, home office or home entertainment alcove and a cozy gas fireplace. The updated kitchen features fresh granite countertops and brand new appliances.

  Brian Woods Woods Properties Inc.

  7 Conant Rd Unit 20, Winchester, MA 01890
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  $3,699,000 Open Sat 12PM - 1PM

  • 7 Beds
  • 7.5 Baths
  • 7,982 Sq Ft

  54 Johnson Rd, Winchester, MA 01890

  This newly constructed home faces Old Village Dr. & redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master

  Kim Covino Compass

  54 Johnson Rd, Winchester, MA 01890
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  $3,499,000

  • 5 Beds
  • 4.5 Baths
  • 5,250 Sq Ft

  4 Norwood St, Winchester, MA 01890

  Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town center with easy access to Boston, this home features exquisite millwork, custom built-ins, and premium finishes throughout. The main home offers 4 bedrooms, 3.5 bathrooms, a living room, dining room, sitting room, pantry, and a bar alcove, along with an expansive second-floor

  Mark Donnellan Advisors Living - Winchester

  4 Norwood St, Winchester, MA 01890
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  $1,599,000 Open Sat 12:30PM - 2PM

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

  189 Mystic Valley Pkwy, Winchester, MA 01890

  Great price improvement - Ready to go at this price! Nestled in the heart of downtown Winchester, the stunning Barstow House boasts a unique Mansard roof & timeless colonial architecture. This historic gem features a versatile floorplan designed for modern living while preserving its classic charm. The first level beautifully blends form & function; the home office, mudroom, a dedicated laundry

  Anne Spry Barrett Sotheby's International Realty

  189 Mystic Valley Pkwy, Winchester, MA 01890
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  $2,899,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,627 Sq Ft

  11 Taft Dr, Winchester, MA 01890

  Luxury and location converge in this stunning 5-bedroom, 5.5-bathroom home nestled in one of Winchester’s most coveted Westside neighborhoods. Beautifully rehabbed and thoughtfully expanded, this turnkey residence offers over 4,600 sq. ft. of refined living space, just steps from Ambrose School, one block from the Alewife bus stop, & a short ½-mile stroll to the commuter rail. Every detail has

  Monte Marrocco Coldwell Banker Realty - Lexington

  11 Taft Dr, Winchester, MA 01890
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  $2,599,000 Open Sat 12PM - 1PM

  • 7 Beds
  • 5.5 Baths
  • 4,829 Sq Ft

  89 Wildwood St, Winchester, MA 01890

  NEW CONSTRUCTION! This stunning 7-bed, 5.5-bath luxury home boasts high-end finishes and a thoughtfully designed open floor plan, perfect for entertaining and modern living. The chef’s kitchen features an oversized quartz island, pro appliances, and a breakfast nook, with sliders leading to a private backyard. The spacious family room offers a gas fireplace, while the 1st floor includes a formal

  Monte Marrocco Coldwell Banker Realty - Lexington

  89 Wildwood St, Winchester, MA 01890
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  $1,099,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,290 Sq Ft

  160 Swanton St Unit 160, Winchester, MA 01890

  Welcome to 160 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel

  Monte Marrocco Coldwell Banker Realty - Lexington

  160 Swanton St Unit 160, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 2

About Winchester

Throughout the years, Winchester has grown from a rural farming community to a primarily residential town. Located in proximity to Broad Sound and 8 miles north of Boston, the peaceful suburb today is home to one of the best school districts in the state, grand New England homes and plenty of outdoor recreation space. Winchester has close to 23,000 people, and the median household income is $218,176, which is double the state’s median. Most people work in the science, technology and healthcare sectors, and many commute outside of town for work. ...

Learn more about living in Winchester

Frequently Asked Questions

What is the average home price in Winchester, MA?

Homes for sale in Winchester, MA have an average home price of $1,729,779.

How many homes have sold over the last 12 months in Winchester, MA?

244 homes have sold in Winchester, MA over the last 12 months.

Is Winchester, MA a safe city?

In general, the safest neighborhoods in Winchester, MA with lower crime scores are West Side, Grove Street, Winchester Highlands and Symmes Corner.

What are the most popular zip codes in Winchester, MA?

The most popular zip codes in Winchester, MA include 02127, 02128, 02116, 02118 and 02135.

What are the most popular neighborhoods in Winchester, MA?

The most popular neighborhoods in Winchester, MA with the most homes for sale are West Side, North Main, The Flats, Winchester Highlands and Symmes Corner.

How much do you need to make to afford a house in Winchester?

The median home price in Winchester is $1,599,000. If you put a 20% down payment of $319,800 and had a 30-year fixed mortgage with an interest rate of 6.83%, your estimated principal and interest payment would be $8,370 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $359K a year to afford the median home price in Winchester.

How are the schools in Winchester, MA?

Winchester, MA has highly rated public and private schools. Some of the best schools in Winchester based on Niche Grades are Lexington High School, Jonas Clarke Middle School and Vinson-Owen Elementary School. The neighborhoods in Winchester with the highest rated schools are West Side, North Main and The Flats. Browse all the schools in Winchester, MA to learn more.

Home Trends in Winchester, MA

On average, homes in Winchester, MA sell after 23 days on the market compared to the national average of 47 days. The average sale price for homes in Winchester, MA over the last 12 months is $1,622,206, up 11% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)

$1,546,250

Median Single Family Price

$1,875,000

Median Townhouse Price

$1,480,000

Median 2 Bedroom Price

$758,500

Median 1 Bedroom Price

$365,000

Average Price Per Sq Ft

$543

Number of Homes for Sale

40

Last 12 months Home Sales

244

Months of Supply

2.00

Median List Price

$1,599,000

Median Discount From 1st List Price

0%

Median Home Sale Price YoY Change

12%