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

• 

  

  

  /17

  $375,000

  Open Wed 5:30PM - 6:30PM $24K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 606 Sq Ft

  200 Swanton St Unit 228, Winchester, MA 01890

  Welcome to Parkview Condos! 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 space, freshly

  

  Joan Powell

  REMAX Andrew Realty Services

  (781) 417-5122

  200 Swanton St Unit 228, Winchester, MA 01890
• 

  

  

  /19

  $505,000

  Open Sat 2PM - 3PM

  • 2 Beds
  • 1 Bath
  • 822 Sq Ft

  200 Swanton St Unit 303, Winchester, MA 01890

  Enjoy living in sought-after Winchester, just minutes from Winchester Center, local shops, dining, parks, and commuter access. This beautifully updated two-bedroom condo at Parkview features a modern kitchen with stainless steel appliances, perfect for entertaining, fresh paint throughout, and a bright open-concept layout. Both generously sized bedrooms offer excellent closet space and

  

  Joan Powell

  REMAX Andrew Realty Services

  (781) 562-4157

  200 Swanton St Unit 303, Winchester, MA 01890
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  /42

  $1,110,000

  $111K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 2,085 Sq Ft

  41 Cross St, Winchester, MA 01890

  Freshly painted side-entrance Colonial offering space, flexibility, and a prime Winchester location. The expansive eat-in kitchen flows seamlessly into the dining area and family room, creating an ideal layout for everyday living and entertaining. The main level includes a bedroom or office, full bath, mudroom with laundry, and is well-suited for one-level living. Upstairs features three

  Andersen Group Realty Keller Williams Realty Boston Northwest

  41 Cross St, Winchester, MA 01890
• 

  

  

  /40

  $1,799,000

  Open Sun 11:30AM - 1PM $100K PRICE DROP

  • 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
• 

  

  /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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  /37

  $749,000

  Open Sat 12:30PM - 2PM

  • 3 Beds
  • 4 Baths
  • 1,380 Sq Ft

  23 Shepard Ct Unit U23, Winchester, MA 01890

  Beautifully maintained townhouse-style condex offering 3 levels of living in a prime Winchester location. This sun-filled home features 3 bedrooms, 2 full baths, a convenient 3rd floor half bath, and an additional half bath in the basement. The third-floor bedroom offers flexibility as a primary suite, guest retreat, or home office. Recent updates include a 2019 high-efficiency gas boiler, 2019

  Nancy Zhang Zhenning Fairview Partners International LLC

  23 Shepard Ct Unit U23, Winchester, MA 01890
• 

  

  /42

  $1,799,000

  Open Sat 11AM - 12:30PM

  • 4 Beds
  • 3 Baths
  • 2,814 Sq Ft

  24 Hinds Rd, Winchester, MA 01890

  Welcome to the home that has it all! Where thoughtful upgrades meet effortless living. This tastefully updated open-concept home is designed for both quiet nights and grand entertaining. Enjoy one-level living with a stunning sun drenched family room, adjacent dining & renovated kitchen with direct outdoor access, ideal for hosting!The home features 4 generously sized bedrooms, and 3 full baths

  Kim Covino Compass

  24 Hinds Rd, Winchester, MA 01890
• 

  

  /39

  $1,999,000

  Open Sat 11AM - 12PM

  • 5 Beds
  • 4 Baths
  • 3,136 Sq Ft

  22 Hollywood Rd, Winchester, MA 01890

  Beautifully appointed 5BR, 2 full/2 half bath home with 3,136 sq ft of thoughtfully designed living space on a flat, fully fenced .34 acre lot. Renovated kitchen with quartz countertops and luxury appliances. Expansive and bright living room with custom built-ins, window seating, and gas fireplace. The main living level also offers 3 spacious bedrooms and a serene primary suite with a walk-in

  Andersen Group Realty Keller Williams Realty Boston Northwest

  22 Hollywood Rd, Winchester, MA 01890
• 

  

  /41

  $3,475,000

  $272K PRICE DROP

  • 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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  /26

  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 2,666 Sq Ft

  465 Washington St Unit 467, Winchester, MA 01890

  Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is

  Nancy Pallotta Gibson Sotheby's International Realty

  465 Washington St Unit 467, Winchester, MA 01890
• 

  

  /40

  $1,799,000

  Open Sat 1PM - 2:30PM

  • 4 Beds
  • 3 Baths
  • 3,366 Sq Ft

  94 Johnson Rd, Winchester, MA 01890

  Turnkey-ready 4BR, 3 full bath home set on a beautifully landscaped .82-acre lot directly across from the Swim & Tennis Club, where the new owner receives immediate membership! Extensively renovated & thoughtfully designed, this home offers exceptional style & comfort throughout.The stunning 2026 kitchen features custom cabinetry, quartz countertops, center island, designer backsplash, updated

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

  94 Johnson Rd, Winchester, MA 01890
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  /10

  $3,200,000

  $200K PRICE DROP

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

  9 Albamont Rd, Winchester, MA 01890

  Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases 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

  Kim Covino Compass

  9 Albamont Rd, Winchester, MA 01890
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  /41

  $1,350,000

  • 4 Beds
  • 3 Baths
  • 4,062 Sq Ft

  15 Thornberry Rd, Winchester, MA 01890

  Located on a level corner lot in the desirable Vinson Owen School district and nearby Winchester Swim & Tennis Club, this ranch-style home offers abundant space and a flexible floor plan. The main level features three bedrooms, a full bath, hardwood floors, and a fireplace living room that flows into the dining area and kitchen. A heated sunroom/mudroom with skylights and exposed beams connects

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

  15 Thornberry Rd, Winchester, MA 01890
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  /41

  $2,099,000

  Open Sat 1PM - 2:30PM $101K PRICE DROP

  • 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

  $2,549,000

  Open Sat 1PM - 2:30PM $46K PRICE DROP

  • 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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  /32

  $2,795,000

  Open Sat 11AM - 12:30PM

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

  18 Middlesex St, Winchester, MA 01890

  This European-inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the

  Tina Natale Luxury Living Real Estate

  18 Middlesex St, Winchester, MA 01890
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  /35

  $3,250,000

  Open Sun 12PM - 1PM

  • 5 Beds
  • 5.5 Baths
  • 6,500 Sq Ft

  8 Priscilla Ln, Winchester, MA 01890

  Truly one of a kind new construction blending timeless design with modern luxury, 8 Priscilla Ln offers 6,500± sq ft of thoughtfully designed living space. Elegant archways and a dramatic two-story living room create an immediate sense of scale and character. The chef’s kitchen features custom cabinetry, Thermador appliances, and an oversized island, flowing seamlessly into the main living and

  The Pezzano Group Rise Signature Homes

  8 Priscilla Ln, Winchester, MA 01890
• 

  

  /35

  $3,299,000

  Open Sat 11AM - 12:30PM $100K PRICE DROP

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

  1 Plymouth Rd, Winchester, MA 01890

  Ideally situated in one of Winchester's most desirable neighborhoods, 1 Plymouth offers the rare combination of exceptional living space and unmatched convenience just minutes to Winchester Center, top-rated schools, commuter rail access, country clubs, and local amenities.Thoughtfully expanded and rebuilt, this impressive residence features 7 bedrooms, 7 full baths, and 1 half bath, designed to

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  1 Plymouth Rd, Winchester, MA 01890
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  /36

  $2,799,000

  $51K PRICE DROP

  • 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
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  /12

  $2,599,000

  Open Sat 2PM - 3PM $200K PRICE DROP

  • 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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  /31

  $1,260,000

  $39K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,420 Sq Ft

  129 Washington St Unit 131, Winchester, MA 01890

  Prime Winchester location just moments from Winchester Center, within walking distance to elementary, middle, high school, downtown and commuter rail. Ideal for commuters and locals alike. This townhouse-style condo lives like a single-family, offering space, flow, and flexibility across four finished levels. The main living area is designed for how you actually live, with an open layout that

  The Mary Scimemi Team Leading Edge Real Estate

  129 Washington St Unit 131, 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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  /28

  $659,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,331 Sq Ft

  18 Bradford Rd, Winchester, MA 01890

  Welcome to this beautifully updated 3-bedroom,1.5-bath townhouse with a large flat Exclusive to use backyard (0.18 acres) located in Residences at Winchester, the highly desirable new Lynch School district with low condo fees. The spacious sun-filled living room offers large windows, abundant natural light, and gleaming hardwood floors throughout the home. The renovated kitchen features quartz

  Wei Wenny Fu Phoenix Real Estate

  18 Bradford Rd, Winchester, MA 01890
• 

  

  /41

  $4,449,000

  $250K PRICE DROP

  • 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

  $1,375,000

  Open Sat 1PM - 2:30PM

  • 6 Beds
  • 2 Baths
  • 5,047 Sq Ft

  303 Washington St, Winchester, MA 01890

  Pleased to present this meticulously maintained and nicely updated two family home in the heart of Winchester! Each spacious unit is one level & features seven rooms including 3 large bedrooms, living room w fplc, dining room w/wainscoting, sunroom, kitchen & updated baths. The generously sized flowing rooms are highlighted by high ceilings, oversized windows, beautiful original woodwork and

  Kim Covino Compass

  303 Washington St, Winchester, MA 01890
• 

  

  /13

  $414,500

  • 2 Beds
  • 1 Bath
  • 1,121 Sq Ft

  22 Arthur St, Winchester, MA 01890

  This property is available to and priced for Income Eligible families in 100% of the moderate-income range. See attached application for eligibility requirements. Throughout the tenure of the current homeowner many upgrades have been made to this property. Roof, new porch, updated Electrical, kitchen cabinets, Gas furnace, DE leading, new brick chimney. The exterior of the home is being prepped

  Karen Morand MCO Realty Service, LLC

  22 Arthur St, Winchester, MA 01890
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  /24

  $1,925,000

  Open Mon 6PM - 7PM

  • 5 Beds
  • 4 Baths
  • 3,315 Sq Ft

  8 Hawthorne Rd, Winchester, MA 01890

  Welcome to this spacious West Side home w/a versatile multi-level layout, offering ample room for comfortable living and entertaining. In the main level, you'll be greeted by a warm & inviting atmosphere, w/abundant natural light filtering through the windows. You enter a well-appointed kitchen, w/ample counter space, a breakfast nook and a french door access to the deck surrounded by tall trees.

  Elaine Song Coldwell Banker Realty - Lexington

  8 Hawthorne Rd, Winchester, MA 01890
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  /39

  $1,499,000

  Open Sat 11AM - 12:30PM

  • 4 Beds
  • 2.5 Baths
  • 2,233 Sq Ft

  10 Bonad Rd, Winchester, MA 01890

  Welcome home to this sun-filled, south-facing 4-bed Colonial in a beloved Winchester neighborhood. Hardwood floors guide you from the gracious foyer into a spacious, fireplaced living room ideal for gatherings. The airy formal dining room flows seamlessly onto a private back deck overlooking a professionally landscaped, fully fenced yard—perfect for al fresco dining & entertaining. The updated

  Kim Covino Compass

  10 Bonad Rd, Winchester, MA 01890
• 

  

  /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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  /35

  $1,899,000

  • 5 Beds
  • 2.5 Baths
  • 3,278 Sq Ft

  105 Thornberry Rd, Winchester, MA 01890

  Perfectly situated on Winchester’s sought-after Westside, this beautifully updated Colonial offers 5 bedrooms, 2.5 baths, and exceptional indoor-outdoor living. A recent renovation transformed and expanded the first floor, featuring an updated kitchen with oversized mahogany topped center island, family room, dining room, mudroom, and half bath. The kitchen opens seamlessly to a spacious family

  Monte Marrocco Coldwell Banker Realty - Lexington

  105 Thornberry Rd, Winchester, MA 01890
• 

  

  /40

  $1,495,000

  Open Sun 11AM - 12PM

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

  7 Sherman Place, Winchester, MA 01890

  Welcome to this sun-drenched newer construction & freshly updated 4 Bed 2.5 Bath luxury townhome, set on a quiet cul-de-sac with a private, professionally landscaped yard & secret garden. This spacious home lives like a free standing house with a thoughtful layout designed for both everyday living and entertaining. Highlights include soaring 9-foot ceilings, oversized windows & high efficiency

  Kim Covino Compass

  7 Sherman Place, Winchester, MA 01890
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  /38

  $3,600,000

  Open Sat 12:30PM - 1:30PM

  • 6 Beds
  • 6.5 Baths
  • 7,400 Sq Ft

  2 Atherton Rd, Winchester, MA 01890

  This extraordinary 6-bedroom, 6.5-bath luxury home offers approximately 7,400 square feet of impeccably crafted living space designed for sophisticated living and grand-scale entertaining. A dramatic open-concept floor plan is highlighted by soaring ceilings, a statement fireplace, and expansive walls of Pella windows that flood the interiors with natural light. The designer chef’s kitchen is

  Brooke Zarbano Regatta Realty

  2 Atherton Rd, Winchester, MA 01890
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  /39

  $1,550,000

  Open Sat 11:30AM - 1PM

  • 5 Beds
  • 5 Baths
  • 3,360 Sq Ft

  7 Ridge St, Winchester, MA 01890

  Beautiful 2 family-duplex nestled in Winchester's desirable West Side. It tells the story of a home that has been treasured and exceptionally maintained over the years. Rich in warmth offering the kind of enduring quality and care that is increasingly hard to find. It reflects years of thoughtful stewardship with inviting spaces, natural light & flow designed for everyday living. Unit 1 3 beds

  Paul Cirignano The Synergy Group

  7 Ridge St, Winchester, MA 01890
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  /9

  $379,900

  • 1 Bed
  • 1 Bath
  • 606 Sq Ft

  200 Swanton St Unit 318, Winchester, MA 01890

  Beautifully renovated oversized one-bedroom condo at Parkview Condominium featuring an open floor plan and private balcony overlooking a serene Japanese garden and duck pond. Spacious primary bedroom offers room for a king-size bed and includes a walk-in closet. Updated kitchen, bathroom, and flooring provide years of low-maintenance living. Amenities include swimming pool, cabana, picnic

  Mike Huang Lewis & Joyce Real Estate

  200 Swanton St Unit 318, Winchester, MA 01890
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  /42

  $2,599,000

  Open Sat 11AM - 12:30PM Pre-Foreclosure

  • 5 Beds
  • 3.5 Baths
  • 5,230 Sq Ft

  78 Bacon St, Winchester, MA 01890

  Must see this completely renovated & expanded stately brick home located just outside the town center offering the perfect blend of timeless charm & modern living. Thoughtfully re-designed with an open concept layout, the home features a custom high end kitchen that flows into a gorgeous oversized family room addition* w/ walls of windows overlooking a stunning private backyard. Formal LR and DR,

  Kim Covino Compass

  78 Bacon St, Winchester, MA 01890
• 

  

  /36

  $1,225,000

  Open Sun 11AM - 12PM

  • 3 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  53 Lake St, Winchester, MA 01890

  Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming

  Kim Covino Compass

  53 Lake St, Winchester, MA 01890
• 

  

  /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
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  /41

  $929,900

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,938 Sq Ft

  380 Cross St, Winchester, MA 01890

  This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The inviting 3 season porch with flagstone floor is a nice place for family to congregate and get to

  Rajive Dogra Coldwell Banker Realty - Lexington

  380 Cross St, Winchester, MA 01890
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  /35

  $2,675,000

  Open Sat 12PM - 1:30PM $75K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 4,540 Sq Ft

  47 Yale St, Winchester, MA 01890

  Timeless 1920 brick Tudor in the heart of the Flats neighborhood combines all of today’s modern amenities with classic architectural charm to create an exceptional home for modern living offering 6 bedrooms, 3 full and 2 half baths. A welcoming entry opens to a sun-filled living room with custom built-ins, fireplace, and French doors to a private office. The open dining room flows into a chef’s

  Molly Nolan Byrne Coldwell Banker Realty - Belmont

  47 Yale St, 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 $1,867,835.

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?

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

What is the average household income in Winchester, MA?

The average household income in Winchester, MA is $206K.

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, 02155, 02474 and 02420.

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 $1,612,500. If you put a 20% down payment of $322,500 and had a 30-year fixed mortgage with an interest rate of 6.48%, your estimated principal and interest payment would be $8,140 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $349K a year to afford the median home price in Winchester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winchester is $206K.

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 Prices in Winchester, MA

The median home sale price in Winchester, MA is $1,558,200, down 8% year-over-year. Homes in Winchester sell in 22 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price $1,558,200	Median Single Family Sale Price $1,737,500
Median Townhouse Sale Price $1,300,000	Median 2 Bedroom Sale Price $940,000
Average Price Per Sq Ft $559	Number of Homes for Sale 33
Last 12 months Home Sales 181	Months of Supply 2.20
Median List Price $1,612,500	Median Change From 1st List Price 1%
Median Home Sale Price YoY Change -8%