Winchester, MA Homes for Sale

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  /41

  $2,899,000

  • 5 Beds
  • 4.5 Baths
  • 6,904 Sq Ft

  11 Fieldstone Dr, Winchester, MA 01890

  Stunning 5BD/4.5BA contemporary estate on a private cul-de-sac in Winchester’s most coveted neighborhood. Modern design with soaring two-story ceilings, skylights, wide-plank hardwoods, and a dramatic stone fireplace. Gourmet chef’s kitchen with all-white waterfall island, Sub-Zero appliances, and butler’s pantry. Luxe primary suite with dual walk-in closet, spa bath, and private terrace. Fully

  Andersen Group Realty Keller Williams Realty Boston Northwest

  11 Fieldstone Dr, Winchester, MA 01890
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  /42

  $2,250,000

  • 5 Beds
  • 3.5 Baths
  • 3,719 Sq Ft

  17 Harrison St, Winchester, MA 01890

  Classic architecture meets modern luxury in this Royal Barry Wills Colonial on an oversized lot in Winchester’s beautiful Flats neighborhood. This meticulously renovated 5-bedroom home features a chef's kitchen with custom cabinetry, granite surfaces, center island, beverage cooler & built-in china cabinet. Natural light floods the expansive family room, featuring custom built-ins & oversized

  Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

  17 Harrison St, Winchester, MA 01890
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  /13

  $2,999,999

  • 5 Beds
  • 4.5 Baths
  • 5,716 Sq Ft

  3 Abby Rd, Winchester, MA 01890

  Welcome to your dream home! This brand-new, meticulously crafted residence offers the perfect blend of luxury & comfort in Winchester’s newest neighborhood. Boasting 4 beds & 4.5 designer baths, every detail has been thoughtfully curated. The chef’s kitchen boasts custom cabinetry, professional-grade appliances & island — ideal for both everyday living & elegant entertaining. The adjoining dining

  Philip Vita Compass

  3 Abby Rd, Winchester, MA 01890
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  /41

  $2,599,000

  • 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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  /40

  $1,995,000

  • 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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  /42

  $2,950,000

  • 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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  /41

  $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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  /40

  $2,099,000

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

  5 Squire Rd, Winchester, MA 01890

  Great value in Town! 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

  Alina Wang Coldwell Banker Realty - Lexington

  5 Squire Rd, Winchester, MA 01890
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  /41

  $3,599,000

  • 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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  /13

  $2,449,000

  • 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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  /42

  $2,399,000

  • 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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  /39

  $1,449,000

  • 3 Beds
  • 2.5 Baths
  • 2,282 Sq Ft

  20 Fletcher St Unit 20, Winchester, MA 01890

  Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! W its breathtaking design, this residence boasts a thoughtful layout; the open-concept first floor has high ceilings and an abundance of natural light. The thoughtfully selected finishes, tiles, and fixtures add a touch of elegance and sophistication throughout.

  Kim Covino Compass

  20 Fletcher St Unit 20, Winchester, MA 01890
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  /39

  $1,449,000

  • 3 Beds
  • 2.5 Baths
  • 2,282 Sq Ft

  20 Fletcher St Unit 20, Winchester, MA 01890

  Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! With its breathtaking design, this residence boasts a thoughtful layout; the open-concept first floor has high ceilings and an abundance of natural light. The thoughtfully selected finishes, tiles, and fixtures add a touch of elegance and sophistication

  Kim Covino Compass

  20 Fletcher St Unit 20, Winchester, MA 01890
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  /42

  $1,849,000

  • 4 Beds
  • 5 Baths
  • 3,148 Sq Ft

  15 Kendall St, Winchester, MA 01890

  Explore this pristine newer construction, freshly updated home just outside the center!! Situated on a gorgeous level lot with slider to patio & expansive rear yard, this captivating home has an absolutely beautiful setting w/natural stone walls, raised planting beds w/flowering trees, perennials & a spectacular rose garden! Enjoy the lovely farmers porch & desirable layout w/sun-drenched kitchen

  Kim Covino Compass

  15 Kendall St, Winchester, MA 01890
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  /33

  $1,599,000

  • 4 Beds
  • 3.5 Baths
  • 3,338 Sq Ft

  34 Coolidge Rd, Winchester, MA 01890

  A chance to update and create your personal design that is located in Winchester's sought after Vinson Owen School district. Set on a impressive massive manicured corner lot that has been maintained since it has been custom built by its original owners. Scenic backyard with a patio off the kitchen that spills on a large private backyard that has an inground pool. Set the stage with a large foyer

  Pauline Marino Coldwell Banker Realty - Lexington

  34 Coolidge Rd, Winchester, MA 01890
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  /19

  $734,900

  • 2 Beds
  • 2.5 Baths
  • 1,634 Sq Ft

  7 Conant Rd Unit 60, Winchester, MA 01890

  Welcome to the highly coveted condominium living in Winchester: the Willows. This unit has over 1,600 sq. ft., with two stories/duplex style condo, 2 beds, and 2.5 baths, making it one of the larger units in the complex. It features many modern amenities such as hardwood floors in the living area, three balconies, in-unit washer/dryer, gas fireplace, and Central A/C & heating with Nest

  Irene Novia Loka Matahari Real Estate LLC

  7 Conant Rd Unit 60, Winchester, MA 01890
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  $1,379,000

  • 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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  /42

  $1,399,000

  • 3 Beds
  • 2.5 Baths
  • 2,141 Sq Ft

  117 Mount Vernon St, Winchester, MA 01890

  Available for the first time in over four decades and nestled just footsteps from Winchester Center, welcome to 117 Mount Vernon Street! As you enter, you are greeted by tall ceilings adorned with beautiful molding and a flood of natural light that fills the space with warmth and tranquility. The home offers three spacious bedrooms, including a flexible primary suite that boasts an adjoining

  Philip Vita Compass

  117 Mount Vernon St, Winchester, MA 01890
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  /38

  $1,500,000

  • 4 Beds
  • 3 Baths
  • 2,897 Sq Ft

  195 Mystic Valley Pkwy, Winchester, MA 01890

  Lovely brick home just up the road from EVERYTHING!!! Commuter Rail, Library, Schools, Shopping, Restaurants, Town Hall. Less than 9 miles to Boston! So close to the Middlesex Fells and the Tri-Community Greenway. Location, location, location - CHECK! Now the structure...classic brick home built to stand the test of time with BIG IMPROVEMENTS. Grand front to back living room with fireplace leads

  Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  195 Mystic Valley Pkwy, Winchester, MA 01890
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  /31

  $385,000

  • 1 Bed
  • 1 Bath
  • 613 Sq Ft

  200 Swanton St Unit 722, Winchester, MA 01890

  Top-Floor Penthouse Condo with Scenic Views at Parkview Condominiums Move right into this beautifully updated 1-bedroom, 1-bath top-floor unit at the highly desirable Parkview Condominiums in Winchester. Centrally located on the 7th floor, this penthouse offers stunning treetop and pond views from your private balcony—perfect for enjoying peaceful moments all year round. Inside, you'll find a

  Yang Liu Weston Realty LLC

  200 Swanton St Unit 722, Winchester, MA 01890
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  /37

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 1,884 Sq Ft

  147 Highland Ave, Winchester, MA 01890

  Discover this charming renovated 3 bed 2 bath home with close proximity to the Fells trails & Winchester town center including schools, train to Boston, restaurants, shops & all the town has to offer!! Beautifully renovated & lovingly maintained, this great home welcomes you with a spacious living room w fplc that flows seamlessly into a sun-drenched updated kitchen featuring stainless steel

  Kim Covino Compass

  147 Highland Ave, Winchester, MA 01890
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  $749,900

  • 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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  $1,199,000

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

  44 Forest St, Winchester, MA 01890

  This charming home is move-in ready with many updates throughout, situated on a large 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

  Kim Covino Compass

  44 Forest St, Winchester, MA 01890
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  /37

  $1,899,000

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

  10 Olde Lyme Rd, Winchester, MA 01890

  PRICE IMPROVEMENT.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

  Darryl Brian RE/MAX Bentley's

  10 Olde Lyme Rd, Winchester, MA 01890
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  /34

  $1,499,900

  • 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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  /42

  $1,650,000

  • 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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  /15

  $965,000

  • 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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  /3

  $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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  /22

  $1,295,000

  • 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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  /39

  $2,499,000

  • 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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  /16

  $1,199,000

  • 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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  /42

  $1,389,000

  • 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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  /41

  $3,199,000

  • 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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  /42

  $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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  /40

  $3,149,000

  • 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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  /34

  $3,698,000

  • 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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  /38

  $2,695,000

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

  18 Middlesex St, Winchester, MA 01890

  Open House Sunday Noon-1:00. 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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  /42

  $3,989,000

  • 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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  /42

  $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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  /37

  $699,900

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

  7 Conant Rd Unit 20, Winchester, MA 01890

  Rarely available and beautifully renovated first-floor unit at The Willows designed with everyday functionality in mind. This one-story unit offers stair-free access and living, along with easy accessibility from the adjacent one-car garage with an attic and a tandem parking spot. Upon entry, you’ll find an inviting open concept living and dining area with freshly installed hardwood flooring, a

  Brian Woods Woods Properties Inc.

  7 Conant Rd Unit 20, 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 $1,748,523.

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

239 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 6.76%, your estimated principal and interest payment would be $8,310 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $356K 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 48 days. The average sale price for homes in Winchester, MA over the last 12 months is $1,647,852, up 14% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)

$1,570,000

Median Single Family Price

$1,890,000

Median Townhouse Price

$1,480,000

Median 2 Bedroom Price

$756,000

Median 1 Bedroom Price

$370,000

Average Price Per Sq Ft

$542

Number of Homes for Sale

43

Last 12 months Home Sales

239

Months of Supply

2.20

Median List Price

$1,599,000

Median Discount From 1st List Price

0%

Median Home Sale Price YoY Change

14%