Winchester, MA Homes for Sale

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  /36

  $3,600,000

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

  20 Amberwood Dr, Winchester, MA 01890

  Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador

  

  Wei Wang

  WW Real Estate LLC

  (781) 678-8050

  20 Amberwood Dr, Winchester, MA 01890
• Explore Winchester

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  /26

  $375,000

  • 1 Bed
  • 1 Bath
  • 606 Sq Ft

  200 Swanton St Unit 228, Winchester, MA 01890

  Welcome to Parkview Condominiums in Winchester. This one bed one bath, bright unit features an open layout with peaceful views overlooking the pond. The low HOA fee includes heat, hot water, electricity, and air conditioning—an exceptional value. Highlights include a spacious living area, updated kitchen with new stainless steel appliances, a large bedroom with new flooring and excellent closet

  

  Joan Powell

  RE/MAX Andrew Realty Services

  (781) 417-5122

  200 Swanton St Unit 228, Winchester, MA 01890
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  /37

  $1,899,999

  • 4 Beds
  • 3 Baths
  • 3,512 Sq Ft

  94 Johnson Rd, Winchester, MA 01890

  This quintessential Colonial blends timeless charm with modern updates, offering a truly move-in ready home in a unique location! Directly across the street, the Winchester Swim and Tennis Club presents a rare opportunity for immediate membership—enjoy your own private club lifestyle just in time for summer! Just a few doors from Vinson-Owen Elementary, morning drop-offs couldn’t be easier.

  Philip Vita Compass

  94 Johnson Rd, Winchester, MA 01890
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  /40

  $1,874,000

  • 3 Beds
  • 3.5 Baths
  • 3,010 Sq Ft

  1 Town Way, Winchester, MA 01890

  Welcome home to this completely renovated gem, ideally situated on a corner lot in the highly sought-after Lincoln Elementary School district. Warm, inviting, and truly move-in ready, this home offers the open-concept first floor buyers dream of—featuring a beautiful kitchen flowing seamlessly into the dining and living areas, plus a sunken family room perfect for relaxing or entertaining. Enjoy

  Philip Vita Compass

  1 Town Way, Winchester, MA 01890
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  /40

  $3,379,000

  • 7 Beds
  • 7.5 Baths
  • 8,540 Sq Ft

  37 Mayflower Rd, Winchester, MA 01890

  Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz

  Kim Covino Compass

  37 Mayflower Rd, Winchester, MA 01890
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  /32

  $2,800,000

  • 4 Beds
  • 4.5 Baths
  • 3,945 Sq Ft

  2 Edgewater Place, Winchester, MA 01890

  A quiet cul-de-sac near the Mystic Lakes sets the stage for this exceptional Royal Barry Wills residence, masterfully reimagined. Every inch reflects elevated craftsmanship and a refined sense of luxury, with bespoke finishes and thoughtfully curated amenities throughout. The main level unfolds with effortless elegance, anchored by a state-of-the-art chef’s kitchen featuring custom cabinetry,

  Nancy Pallotta Gibson Sotheby's International Realty

  2 Edgewater Place, Winchester, MA 01890
• 

  

  /41

  $3,747,000

  • 7 Beds
  • 6 Baths
  • 7,043 Sq Ft

  2 Everett Ave, Winchester, MA 01890

  Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end

  Joan Francis Sullivan Better Homes and Gardens Real Estate - The Shanahan Group

  2 Everett Ave, Winchester, MA 01890
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  /10

  $3,400,000

  • 6 Beds
  • 5.5 Baths
  • 6,100 Sq Ft

  9 Albamont Rd, Winchester, MA 01890

  Brand new high end construction in prime Winchester location! Currently under construction w/ completion expected late spring 2026. A thoughtfully designed home with immense curb appeal showcasing stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer

  Kim Covino Compass

  9 Albamont Rd, Winchester, MA 01890
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  /24

  $727,000

  • 2 Beds
  • 1 Bath
  • 1,029 Sq Ft

  115 Washington St Unit 2A, Winchester, MA 01890

  Newly Renovated! 2 Bd at Church Place in Winchester Center! This stunning corner unit renovation was just completed & is ideally located in the heart of the center. Perfect for down-sizers or anyone seeking easy living w/ access to the train, restaurants, shops & top-rated schools - all the conveniences right outside your door! This bright & airy unit offers an open floor plan w/ beautiful arched

  Kim Covino Compass

  115 Washington St Unit 2A, Winchester, MA 01890
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  /37

  $899,000

  • 3 Beds
  • 1.5 Baths
  • 1,799 Sq Ft

  9 Governors Ave Unit 2, Winchester, MA 01890

  Perfectly positioned just moments from the charm and vibrancy of the town center, this inviting 3-bedroom, 1.5-bath condo offers a lifestyle as appealing as its location. Step inside to discover a bright, thoughtfully designed layout filled with generous living spaces and abundant natural light. Three bedrooms provide the versatility you need—whether for family, guests, or a home office. Enjoy

  Philip Vita Compass

  9 Governors Ave Unit 2, Winchester, MA 01890
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  /42

  $2,595,000

  • 4 Beds
  • 3.5 Baths
  • 4,403 Sq Ft

  50 Brooks St, Winchester, MA 01890

  Discover this picture perfect 4 BD 3.5 BA colonial in coveted Brooks neighborhood! This distinguished property offers a gourmet kitchen featuring sleek SS appliances, AGA dual fuel range w/ gas burners, center island & tall wine cooler w/sunny brkfst area. The family rm is an architectural focal point, boasting cathedral ceilings, skylights & a cozy fireplace. Natural light floods the home &

  Kim Covino Compass

  50 Brooks St, Winchester, MA 01890
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  /38

  $2,500,000

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

  15 York Rd, Winchester, MA 01890

  This 5-bed colonial was built in 2017 and offers a bright open floor plan ideal for today’s lifestyle. The kitchen features a large quartz island, breakfast nook, and flows into dining and living areas with gas fireplace. Sliders open to a private lot with stone patio and fire pit. First floor includes half bath, pantry, and an enormous mudroom with cubbies for everyone. The oversized primary

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

  15 York Rd, Winchester, MA 01890
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  /36

  $2,799,000

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

  14 Nassau Dr, Winchester, MA 01890

  Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. 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
• 

  

  /35

  $2,975,000 Open Thu 5PM - 6:30PM

  • 7 Beds
  • 6 Baths
  • 5,888 Sq Ft

  115 Church St, Winchester, MA 01890

  Distinguished Colonial Revival located in the desirable “Flats" neighborhood offering 5,888 SF with 7 bedrooms and 6 baths across three finished levels. Period details include a quartered oak foyer and staircase, bay windows, pocket doors, and decorative millwork. Chef's kitchen features a Viking gas range, Thermador refrigerator, and granite countertops. Family room has a wood-burning fireplace

  Jennifer Ryer Better Homes and Gardens Real Estate - The Shanahan Group

  115 Church St, Winchester, MA 01890
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  /42

  $2,490,000

  • 6 Beds
  • 3.5 Baths
  • 4,573 Sq Ft

  7 Cliff St, Winchester, MA 01890

  Gracious 1890 colonial on .3 acre lot on dead end overlooking Middlesex Fells. Close to I-93, town center, train, and top Winchester schools (Lincoln Elementary). Welcoming front porch leads to a beautiful foyer. First floor features a living room with wood FP and bookshelves, and a large family room with gas FP accessing a side porch, a back deck and the kitchen. Renovated kitchen has large

  Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Cliff St, Winchester, MA 01890
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  /39

  $2,750,000

  • 7 Beds
  • 3.5 Baths
  • 3,676 Sq Ft

  15 Yale St, Winchester, MA 01890

  Beautifully renovated 5 bedroom, 11 room home w 2 home offices located in the desirable FLATS area of town. An inviting front porch welcomes you into this special home showcasing the charm & character of historic Winchester, with amenities and layout desired today. Magazine worthy kitchen/dining/ family room! Open concept first floor with 3 rooms directly overlooking gorgeous and private rear

  Kim Covino Compass

  15 Yale St, Winchester, MA 01890
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  /16

  $2,799,000

  • 5 Beds
  • 4 Baths
  • 5,083 Sq Ft

  53 Winford Way, Winchester, MA 01890

  Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient

  Andersen Group Realty Keller Williams Realty Boston Northwest

  53 Winford Way, Winchester, MA 01890
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  /21

  $625,000

  • 1 Bed
  • 1 Bath
  • 985 Sq Ft

  2 Stratton Dr Unit 307, Woburn, MA 01801

  2024-built 1 bedroom condo at Highland at Vale offering easy single-level living! This bright, open-concept home features an airy, contemporary layout ideal for both everyday living and entertaining. The stylish white kitchen showcases stainless steel appliances, ample storage, and a center island, seamlessly flowing into the dining and living areas. Sliders from the living room lead to a private

  Kim Covino Compass

  2 Stratton Dr Unit 307, Woburn, MA 01801
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  /28

  $1,199,000

  • 4 Beds
  • 2 Baths
  • 2,129 Sq Ft

  31 Mystic Ave Unit 33, Winchester, MA 01890

  Charming, beautifully updated town home in prime downtown Winchester neighborhood! This 4 bed 2 bath home offers living space across 3 levels, blending classic character w/ everyday functionality. The layout features a welcoming main level with high ceilings, oversized windows & a nice open flow between the living room, dining room, family room & kitchen, creating an ideal setup for both daily

  Kim Covino Compass

  31 Mystic Ave Unit 33, Winchester, MA 01890
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  /42

  $1,700,000

  • 5 Beds
  • 5 Baths
  • 3,500 Sq Ft

  307 Cross St, Winchester, MA 01890

  Thoughtfully reimagined & expanded in 2019, this sophisticated colonial offers 5-6 bedrooms & 5 baths with a beautiful open floor plan - perfect for a growing family or multi-generational living. A striking granite kitchen with crisp white cabinetry, premium stainless appliances & oversized island flows seamlessly into the dining area - ideal for everyday living & refined entertaining. A

  Dara Singleton Better Homes and Gardens Real Estate - The Shanahan Group

  307 Cross St, Winchester, MA 01890
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  /39

  $3,290,000

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

  27 Everett Ave, Winchester, MA 01890

  This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are

  Nancy Pallotta Gibson Sotheby's International Realty

  27 Everett Ave, Winchester, MA 01890
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  /35

  $3,399,000

  • 7 Beds
  • 7.5 Baths
  • 7,226 Sq Ft

  1 Plymouth Rd, Winchester, MA 01890

  Discover a beautifully reimagined home in one of Winchester’s most sought-after neighborhoods, offering exceptional space, comfort, and convenience in a truly prime location. With 7 bedrooms, 7 full baths, and 1 half bath, 1 Plymouth has been thoughtfully expanded and rebuilt with high-end finishes throughout to suit today’s lifestyle. At the heart of the home is a stunning fireplaced family room

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  1 Plymouth Rd, Winchester, MA 01890
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  /39

  $1,299,000

  • 3 Beds
  • 1.5 Baths
  • 2,030 Sq Ft

  12 Hancock St, Winchester, MA 01890

  This beautifully maintained home blends timeless craftsmanship with thoughtful modern updates. Architectural details, including stunning stained-glass windows, add warmth and personality throughout, and pair beautifully with the updated kitchen and baths. Spacious rooms, oversized windows, 9-foot ceilings, and a desirable layout create an airy, expansive feeling that lives larger than the square

  Elena Langlois Compass

  12 Hancock St, Winchester, MA 01890
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  /31

  $1,250,000

  • 5 Beds
  • 1.5 Baths
  • 2,688 Sq Ft

  6 Hancock St, Winchester, MA 01890

  Classic turn-of-the-century Victorian filled with charm and character, ready for its next owner. 5 total bedrooms; 4 on the second floor and 1 on the 3rd floor, plus 3rd floor office. 1.5 baths, this well-maintained home awaits your finishing touches and features hardwood floors throughout, showcasing its timeless architectural details. Enjoy warm summer evenings on the inviting screened front

  Pirani & Wile Group Gibson Sotheby's International Realty

  6 Hancock St, Winchester, MA 01890
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  /41

  $2,200,000

  • 6 Beds
  • 4.5 Baths
  • 6,900 Sq Ft

  16 Glenwood Ave, Winchester, MA 01890

  Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr

  Kim Covino Compass

  16 Glenwood Ave, Winchester, MA 01890
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  /42

  $3,299,000

  • 5 Beds
  • 4.5 Baths
  • 5,202 Sq Ft

  74 Wedgemere Ave, Winchester, MA 01890

  The most idyllic setting in town! This beautifully renovated and expanded Colonial blends timeless charm with modern sophistication. Perfectly sited on an 18,000 sq ft lot abutting conservation land, it offers exceptional privacy in one of the town’s most coveted neighborhoods. This stunning home features 5+ bedrooms and 4.5 baths, with new windows, updated systems, an expanded kitchen, and

  Kim Covino Compass

  74 Wedgemere Ave, Winchester, MA 01890
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  /42

  $3,650,000

  • 6 Beds
  • 4.5 Baths
  • 6,460 Sq Ft

  40 Foxcroft Rd, Winchester, MA 01890

  40 Foxcroft Road presents exceptional new construction in the highly desirable Flats of Winchester. This 6BR, 4.5BA residence spans 6,460 sqft and showcases thoughtfully curated design with an open concept floor plan ideal for modern living and entertaining. The sun-filled living room features soaring vaulted ceilings with exposed wood beams and a gas fireplace, framed by expansive Pella windows.

  The Boston ONE Team Serhant

  40 Foxcroft Rd, Winchester, MA 01890
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  /34

  $1,100,000

  • 2 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  83 Church St Unit 15, Winchester, MA 01890

  Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal

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

  83 Church St Unit 15, Winchester, MA 01890
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  /31

  $3,390,000

  • 4 Beds
  • 3.5 Baths
  • 4,847 Sq Ft

  25 Myopia Rd, Winchester, MA 01890

  A timeless home of exceptional craftsmanship on the coveted slope of Myopia Hill, offering tranquil views of lush gardens and rolling hills. Thoughtful architectural details enrich every space, while multiple patios and wrap-around porch create an effortless flow between indoor& outdoor. The gracious main level unfolds into beautifully connected living spaces, featuring an office, elegant dining

  Wenjun Cao Engel & Volkers Boston

  25 Myopia Rd, Winchester, MA 01890
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  /42

  $4,449,000

  • 5 Beds
  • 5.5 Baths
  • 6,526 Sq Ft

  4 Dartmouth St, Winchester, MA 01890

  Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully maintained and updated, blending classic architecture with modern comfort. This 5 bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and

  Nancy Pallotta Gibson Sotheby's International Realty

  4 Dartmouth St, Winchester, MA 01890
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  /42

  $2,999,000

  • 5 Beds
  • 4 Baths
  • 4,028 Sq Ft

  10 Dartmouth St, Winchester, MA 01890

  Winchester's premiere location! This stunning waterfront gem is perfectly situated on Winter Pond, offering over 80 feet of direct water frontage with expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this property presents a rare opportunity to enjoy water activities such as kayaking, paddleboarding, fishing, ice skating and hockey all

  Kim Covino Compass

  10 Dartmouth St, Winchester, MA 01890
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  /42

  $3,099,000

  • 5 Beds
  • 4.5 Baths
  • 5,406 Sq Ft

  10 Rangeley Rd, Winchester, MA 01890

  Exceptionally rare 1911 property, fully renovated on prestigious Rangeley Road, steps to town. Set on what is widely regarded as the most iconic street in Winchester, this 5 bedroom, 4.5 bath home captures the essence of the coveted Rangeley Estates lifestyle. Over 7,300 sq ft of total space & architectural character, blending classic design with modern luxury. Grand, sun drenched interiors & a

  Karima Alami Compass

  10 Rangeley Rd, Winchester, MA 01890
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  /23

  $688,000

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  666 Main St Unit 315, Winchester, MA 01890

  Beautiful 2BR/2BA waterfront condo at Wedgewood Place located at 666 Main Street. This open-concept corner unit features a bright living/dining area with private balcony, granite counter-tops in the kitchen, and hardwood floors. The primary bedroom is bright with lots of windows and offers a walk-in closet and en-suite bath. Additional highlights include in-unit laundry, assigned parking,

  Jing Chen Peace of Mind Realty

  666 Main St Unit 315, Winchester, MA 01890
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  /36

  $2,000,000

  • 6 Beds
  • 5 Baths
  • 3,403 Sq Ft

  6 Ivy Cir, Winchester, MA 01890

  Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves

  Valerie Post Engel & Volkers Boston

  6 Ivy Cir, Winchester, MA 01890
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  /13

  $279,000

  • 1 Bath
  • 394 Sq Ft

  200 Swanton St Unit 538, Winchester, MA 01890

  Michael Masci North Atlantic Realty Group

  200 Swanton St Unit 538, Winchester, MA 01890
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  /42

  $3,499,000

  • 5 Beds
  • 7.5 Baths
  • 6,899 Sq Ft

  54 Johnson Rd, Winchester, MA 01890

  This STUNNING newly constructed home facing Old Village Drive 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

  Kim Covino Compass

  54 Johnson Rd, Winchester, MA 01890
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  /41

  $1,799,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,818 Sq Ft

  12 Cox Rd, Winchester, MA 01890

  SHOWINGS BEGIN AT OPEN HOUSE THURSDAY MAY 7th 5:00-6:30pm. Fabulous 11 room, 4 bedroom Colonial set on a beautiful lot on Winchester’s west side. The first floor offers a bright and sunny, open concept kitchen and family room which creates the perfect space for everyday living and entertaining which leads to a mud room, laundry, and home offic . Completing the first floor is half bath off

  Darryl Brian RE/MAX Bentley's

  12 Cox Rd, Winchester, MA 01890
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  /39

  $1,099,000

  • 3 Beds
  • 1.5 Baths
  • 1,973 Sq Ft

  15 East St, Winchester, MA 01890

  Move in ready & nicely remodeled ranch on a fabulous 10K fenced lot! This 3-4bedroom, 2 full bath home w/full lower level including office, family room/bedroom & full bath offers a sunny, functional layout w/ tasteful updates throughout.The main living spaces flow seamlessly, highlighted by a newer eat-in kitchen w/ access to deck & great yard; perfect for indoor/outdoor living & entertaining.

  Kim Covino Compass

  15 East St, Winchester, MA 01890
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  /26

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  2 George Rd Unit 2, Winchester, MA 01890

  Inviting 3 Bed 2 bath townhouse situated on one of the largest lots in the neighborhood offering a perfect blend of space and natural light. This home is in great condition with hardwood floors and an updated kitchen with direct access to the yard. The living room with picture window flows into an open concept dining area. Upstairs find three bedrooms and a full updated bath. The finished lower

  Kim Covino Compass

  2 George Rd Unit 2, Winchester, MA 01890
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  /30

  $364,900

  • 1 Bed
  • 1 Bath
  • 613 Sq Ft

  200 Swanton St Unit 717, Winchester, MA 01890

  Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for

  Cameron Moniz Coldwell Banker Realty - Lexington

  200 Swanton St Unit 717, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 2

Why Live in Winchester

Winchester, MA, a peaceful Greater Boston suburb, has evolved from a rural farming community to a primarily residential town with a population of nearly 23,000. Located 8 miles north of Boston, Winchester is known for its grand New England homes, ranging from historic Colonial Revivals to modern Cape Cods and ranch styles. The town boasts one of the best school districts in the state, with Winchester Public Schools serving over 4,300 students and receiving high ratings. The private Acera School also offers quality education. Outdoor enthusiasts can enjoy Mystic Lakes State Park, Middlesex Fells Reservation, and the Tri-Community Greenway, which connects Winchester with Woburn and Stoneham. The town's downtown area, bordered by Wedge and Mill Ponds, features a variety of markets, restaurants, boutiques, and service shops. Community events such as Winchester Town Day, PRIDEFest, and summer concerts at Town Common foster a strong sense of community. Wright-Locke Farm, a 383-year-old sustainable conservancy, provides fresh organic produce and nature-based activities. Winchester is accessible via U.S. Route 3 and Interstates 93 and 95, with public transit options including the MBTA bus and commuter rail. Logan International Airport is about 11 miles away. The town has a lower crime risk compared to the national average, with recent data indicating a decrease in violent crimes.

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 $1,908,131.

Are home prices dropping in Winchester?

Yes, home prices in Winchester are down 2% in the last 12 months.

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

172 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 The Flats, 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 01890, 01801, 02474, 02420 and 02155.

What are the most popular neighborhoods in Winchester, MA?

The most popular neighborhoods in Winchester, MA with the most homes for sale are North Main, The Flats, West Side, 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 $1,688,888. If you put a 20% down payment of $337,800 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $8,360 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $358K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator.

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 Greater Boston Academy, Lexington Christian Academy and Lexington High School. The neighborhoods in Winchester with the highest rated schools are North Main, The Flats and West Side. 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 57 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,554,500, down 7% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,554,500

Median Single Family Sale Price

$1,775,000

Median Townhouse Sale Price

$1,350,000

Median 2 Bedroom Sale Price

$1,100,000

Average Price Per Sq Ft

$562

Number of Homes for Sale

28

Last 12 months Home Sales

172

Months of Supply

2.00

Median List Price

$1,688,888

Median Change From 1st List Price

1%

Median Home Sale Price YoY Change

-7%