Winchester, MA Houses for Sale

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  /41

  $1,990,000

  • 4 Beds
  • 4.5 Baths
  • 4,474 Sq Ft

  4 Chestnut St, Winchester, MA 01890

  Space to grow, room to gather, and a location that feels like home. Just blocks from Winchester’s town center, commuter rail, and nearby schools, this warm and distinctive home offers four levels of flexible living. A vaulted-ceiling living room sets the tone, while the custom kitchen features blue cabinetry, copper accents, and bold designer touches. One bedroom opens to a composite deck

  

  Tyson Lynch

  The Proper Nest Real Estate

  (781) 633-6582

  4 Chestnut St, Winchester, MA 01890
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  /38

  $2,350,000

  • 5 Beds
  • 3.5 Baths
  • 5,006 Sq Ft

  276 High St, Winchester, MA 01890

  Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

  Kim Covino Compass

  276 High St, Winchester, MA 01890
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  /26

  $2,239,000

  • 5 Beds
  • 4.5 Baths
  • 4,798 Sq Ft

  61 Grove St, Winchester, MA 01890

  STUNNING CUSTOM-BUILT HOME, Welcome to this easy living, maintenance free sophisticated residence. Completely rebuilt and doubled in size with bright and sunny rooms and a flexible floor plan. FIRST FLOOR LUXURIOUS SUITE with a LARGE BEDROOM, marble bath w/double sink vanity, walk in shower & soaking tub. An exquisite kitchen with granite island, counters and back splash, All Bosch appliances,

  Dorothea Feffer Coldwell Banker Realty - Lexington

  61 Grove St, Winchester, MA 01890
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  /42

  $2,499,000 Open Sun 1PM - 2PM

  • 6 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  14 Grant Rd, Winchester, MA 01890

  Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester’s most desirable neighborhoods. Designed for modern lifestyles, this home features a chef’s kitchen that flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. A sun-drenched 3-season porch expands your living space

  Monte Marrocco Coldwell Banker Realty - Lexington

  14 Grant Rd, Winchester, MA 01890
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  /40

  $2,195,000

  • 6 Beds
  • 5.5 Baths
  • 5,791 Sq Ft

  58 Bacon St, Winchester, MA 01890

  Timeless elegance & contemporary comfort span four meticulously finished levels.This stately residence boasts 15 rooms, including six bedrooms and five-and-a-half bathrooms(2 en-suite). An inviting living room, anchored by a distinguished fireplace, flows seamlessly into an adjacent sunroom, offering a perfect retreat. The formal dining room opens to a covered porch, complete with a gas line for

  Real Estate Advisors Group Coldwell Banker Realty - Belmont

  58 Bacon St, Winchester, MA 01890
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  /35

  $2,399,000

  • 6 Beds
  • 5 Baths
  • 3,728 Sq Ft

  6 Ivy Cir, Winchester, MA 01890

  Stunning new construction Colonial tucked away at the end of a quiet cul-de-sac in "The Flats", offering the ideal combination of luxury, comfort, and convenience. Just minutes from Winchester Center, this beautifully crafted home places top-rated schools, boutique shopping, and vibrant dining right at your doorstep. Meticulously designed with high-end finishes throughout. Features include an

  Monte Marrocco Coldwell Banker Realty - Lexington

  6 Ivy Cir, Winchester, MA 01890
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  /42

  $2,499,000

  • 6 Beds
  • 4.5 Baths
  • 5,824 Sq Ft

  107 Cambridge St, Winchester, MA 01890

  Gracious and fully restored, this stunning 6-bedroom, 4.5-bath Victorian blends timeless elegance with luxurious modern updates. Rich with sumptuous period details and soaring 9' ceilings, the inviting first floor features a grand marble foyer with custom built-ins and a sweeping staircase. The formal living room offers a stately fireplace, while the chef’s kitchen—complete with expansive quartz

  Maija Sawyer Puleo William Raveis R.E. & Home Services

  107 Cambridge St, Winchester, MA 01890
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  /41

  $2,899,000

  • 7 Beds
  • 5.5 Baths
  • 5,864 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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  /42

  $2,349,900

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

  17 Wagon Wheel Rd, Winchester, MA 01890

  Experience breathtaking Boston skyline views from nearly every room in this exquisitely maintained dream home—your own private oasis of serenity and style. Thoughtfully expanded in 2020, it features a new en-suite with a private bath and a dramatically enlarged, open-concept kitchen ideal for entertaining. With 5 bedrooms and 5 beautifully appointed baths—including four en-suites—this home blends

  Yifei Wang Dreamega International Realty LLC

  17 Wagon Wheel Rd, Winchester, MA 01890
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  /39

  $3,249,000

  • 6 Beds
  • 6.5 Baths
  • 6,028 Sq Ft

  44 Cabot St, Winchester, MA 01890

  Welcome to 44 Cabot Street, a newly built home in one of Winchester’s most desirable neighborhoods. Offering over 6,000 square feet of beautifully crafted space, this residence features 6 bedrooms, 6.5 bathrooms, and a layout designed for modern living. Thoughtfully selected finishes, high ceilings, and an abundance of natural light create a warm and inviting atmosphere throughout. The

  Andersen Group Realty Keller Williams Realty Boston Northwest

  44 Cabot St, Winchester, MA 01890
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  /42

  $2,975,000

  • 6 Beds
  • 3.5 Baths
  • 5,238 Sq Ft

  54 Wedgemere Ave, Winchester, MA 01890

  Exceptional living in this stunning Wedgemere Ave home w/ spectacular resort style back yard surrounded by mature plants and trees encompassing the gorgeous yard/setting. Completely updated throughout w/ custom high end finishes, open floor plan, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive back yard featuring

  Kim Covino Compass

  54 Wedgemere Ave, Winchester, MA 01890
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  /40

  $2,299,000

  • 5 Beds
  • 3.5 Baths
  • 6,232 Sq Ft

  5 Azalea Rd, Winchester, MA 01890

  NEW PRICE! RENOVATIONS & UPDATES JUST COMPLETED THROUGHOUT! Pristine Home nestled in Winchester's Sought After West Side Neighborhood 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 New Composite Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials

  Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

  5 Azalea Rd, Winchester, MA 01890
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  /41

  $1,599,000

  • 3 Beds
  • 2.5 Baths
  • 2,283 Sq Ft

  17 Dennett Rd, Winchester, MA 01890

  Beautifully renovated multi-level home in top location abutting the town forest conservation/ walking trails & just minutes from downtown Winchester! This move-in ready property features many recent upgrades, 3+ bedrooms, hardwood floors w/an open concept spacious layout perfect for modern living. The large updated kitchen includes high-end appliances, gas stove, beverage fridge & an oversized

  Kim Covino Compass

  17 Dennett Rd, Winchester, MA 01890
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  /4

  $1,890,000

  • 5 Beds
  • 5 Baths
  • 3,301 Sq Ft

  166 Forest St, Winchester, MA 01890

  Tucked away on a picturesque street, this beautifully maintained Colonial offers 4 levels of thoughtfully designed living space. The open-concept main floor features a sun-filled living room with vaulted ceilings, skylights, gas fireplace, and an adjacent dining area. The gourmet kitchen boasts stainless steel appliances, breakfast bar, built-in desk, and sliders leading to a private deck. A

  Ning Sun United Real Estate, LLC

  166 Forest St, Winchester, MA 01890
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  /40

  $1,688,888

  • 4 Beds
  • 2 Baths
  • 3,838 Sq Ft

  10 Blossom Hill Rd, Winchester, MA 01890

  Welcome to 10 Blossom Hill Road. Tucked away in a cozy and desirable West Side Winchester neighborhood, this enchanting storybook home is full of warmth, charm, and heart. Here you will find a lovingly cared-for 4-bedroom home with a guest or in-law suite offering wonderful flexibility to suit your needs. Inside, you’ll find light-filled spaces, thoughtful updates, and timeless character that

  Stephen DeConto Cameron Real Estate Group

  10 Blossom Hill Rd, Winchester, MA 01890
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  /39

  $1,525,000

  • 3 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  178 Mystic Valley Pkwy, Winchester, MA 01890

  This carefully crafted Colonial, custom-built by Andrew Pywell, combines solid construction with a bounty of special touches and timeless charm. Delight in sun-splashed living spaces, gleaming hardwood floors, crown moldings, and a layout that balances an open flow, defined spaces and beautifully proportioned rooms across 2,850 square feet. The gracious formal living room, dining room, and

  Katherine Waters-Clark Compass

  178 Mystic Valley Pkwy, Winchester, MA 01890
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  /31

  $1,500,000

  • 4 Beds
  • 2.5 Baths
  • 2,506 Sq Ft

  6 Highland Ave, Winchester, MA 01890

  4 BD, 2.5 BA home tucked away from the road for added privacy. Kitchen has spacious dining area for enjoying family meals & entertaining guests. Inviting family room, w/ FP brings warm ambiance & convenient access to the deck, enhancing your indoor-outdoor living experience. Large living/dining area w/ backyard views is a versatile space w/ an open layout make it a welcoming spot. Convenience is

  Peter Rooney Compass

  6 Highland Ave, Winchester, MA 01890
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  /40

  $1,075,000

  • 3 Beds
  • 1.5 Baths
  • 1,414 Sq Ft

  5 Cutting St, Winchester, MA 01890

  OFFER DEADLINE TUE JULY 29th 5:00PM | Exceedingly charming + in-town location to be envied. Shops, schools + both MBTA stations at your fingertips. Step up onto your porch, pass the bench swing you’re yet to install; entering into the inviting foyer w/ original stairs preserved & tall ceilings. The main level is sophisticated & functional. A front facing dining room w/ plantation shutters +

  Oliver Koester Compass

  5 Cutting St, Winchester, MA 01890
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  /33

  $1,250,000

  • 4 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  162 Forest St, Winchester, MA 01890

  Located in the popular Winchester Highlands neighborhood with Elegance and Stature is this 4 bed, 1.5 bath Center Entrance Colonial with 2 car garage, minutes to I-93 and Winchester Center with boutique shops, cafes, restaurants, and newly renovated MBTA Station. Welcoming front vestibule opens to sprawling front-to-back living room with wood burning fireplace and attached sunroom. Formal dining

  Paul Cirignano The Synergy Group

  162 Forest St, Winchester, MA 01890
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  /42

  $3,599,000

  • 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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  /33

  $1,650,000 Open Fri 11AM - 12:30PM

  • 4 Beds
  • 3.5 Baths
  • 2,755 Sq Ft

  5 Thornton Rd, Winchester, MA 01890

  This stately home near the Flats blends original character with modern-day living, 8' ceilings and awaits your personal touches. The living room features stunning woodwork, a fireplace, and French doors leading to a window-lined sunroom-ideal for a home office or playroom. The large circular floor plan connects the living room with a formal dining room, family room, half bath and newer kitchen.

  Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

  5 Thornton Rd, Winchester, MA 01890
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  /42

  $1,899,000

  • 5 Beds
  • 3.5 Baths
  • 3,294 Sq Ft

  20 Grove Place, Winchester, MA 01890

  From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Cafe appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a

  Andersen Group Realty Keller Williams Realty Boston Northwest

  20 Grove Place, Winchester, MA 01890
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  /39

  $1,900,000

  • 4 Beds
  • 5 Baths
  • 5,361 Sq Ft

  4 Aricia Ln, Winchester, MA 01890

  Tucked into the tree-lined enclave of Aricia Lane, this striking contemporary residence delivers bold architectural design, abundant light, and the seamless indoor-outdoor living today’s buyers crave. Set on nearly half an acre in one of Winchester’s most peaceful pockets, this home is a rare fusion of modern comfort, space, and convenience offering the rarest of features: a five-car garage. From

  The McLaren D'Agostino Team Compass

  4 Aricia Ln, Winchester, MA 01890
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  /36

  $1,980,000

  • 5 Beds
  • 3.5 Baths
  • 4,378 Sq Ft

  4 Fieldstone Dr, Winchester, MA 01890

  Nestled in a desirable Westside neighborhood, this stunning California contemporary/colonial home sits on a quiet cul-de-sac and offers 5 bedrooms, 3.5 baths, and over 20,000 sq ft of beautifully landscaped grounds. The sun-drenched interior features an open-concept kitchen and dining room with five fully opening doors leading to a bright four-seasons sunroom—perfect for gatherings year-round.

  Wenli Zheng Fairview Partners International LLC

  4 Fieldstone Dr, Winchester, MA 01890
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  /42

  $3,895,000

  • 6 Beds
  • 3.5 Baths
  • 4,484 Sq Ft

  9 Lakeview Terrace, Winchester, MA 01890

  LAKEFRONT! Nestled on the serene shores of the Mystic Lakes just 7 miles from Boston, close to the center & steps to Wedgemere train station/ 2 stops to North Station! A truly one-of-a-kind opportunity to enjoy peaceful waterfront living so close to Boston! This extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room!

  Kim Covino Compass

  9 Lakeview Terrace, Winchester, MA 01890
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  /36

  $1,349,900

  • 5 Beds
  • 2 Baths
  • 1,706 Sq Ft

  35 Harvard St, Winchester, MA 01890

  Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well

  Joanne Mulkerin J. Mulkerin Realty

  35 Harvard St, Winchester, MA 01890
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  /39

  $3,599,000

  • 6 Beds
  • 4.5 Baths
  • 5,876 Sq Ft

  5 Stratford Rd, Winchester, MA 01890

  This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester’s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef’s kitchen includes a quartzite island, 8-burner Wolf

  Kim Covino Compass

  5 Stratford Rd, Winchester, MA 01890
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  /41

  $1,299,000

  • 3 Beds
  • 1.5 Baths
  • 3,335 Sq Ft

  10 Girard Rd, Winchester, MA 01890

  Unleash Your Vision in Winchester’s Coveted West Side! Don't miss this rare chance to transform this Mid-Century Modern ranch on a generous 15,024 square foot idyllic lot in one of Winchester’s most desirable neighborhoods. Whether you renovate, expand, or enjoy this home as it is, this 3-bed, 1.5-bath home offers endless potential. Nestled on a quiet, tree-lined street abutting conservation land

  Joanne Sexeny Coldwell Banker Realty - Lexington

  10 Girard Rd, Winchester, MA 01890
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  $1,765,300

  • 3 Beds
  • 2.5 Baths
  • 3,002 Sq Ft

  44 Amberwood Dr, Winchester, MA 01890

  Picture your family in this unique colonial, just one street over from the amazing Vinson-Owen school! 2 sizeable, private yards with lush grass, flagstone patios and even a dining room deck! Lots of upgrades include a new family room with brick wall, computer cubby, cathedral ceiling & mahogany deck. There's 3 bedrooms to start, including a spacious Primary Suite with walk-in closet, large

  Hudson Santana Keller Williams Realty Boston Northwest

  44 Amberwood Dr, Winchester, MA 01890
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  $3,475,000

  • 5 Beds
  • 3.5 Baths
  • 5,632 Sq Ft

  80 Arlington St, Winchester, MA 01890

  With its coveted setting, elegant bones, and enduring charm, this Royal Barry Wills home awaits your personal design statement, and the chance to build instant equity through strategic upgrades. Ideally located on the 4th green of Winchester Country Club’s storied Donald Ross-designed course, this beloved home offers 11 rooms, 5 bedrooms and 3.5 baths. Enjoy views from the sun-splashed eat-in

  Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group

  80 Arlington St, Winchester, MA 01890
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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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  /37

  $1,299,000

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

  147 Highland Ave, Winchester, MA 01890

  Call for a private showing anytime! 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 w/ a spacious living room w fplc that flows seamlessly into a sun-drenched updated

  Kim Covino Compass

  147 Highland Ave, Winchester, MA 01890
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  /34

  $1,399,900

  • 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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  /4

  $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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  /34

  $3,598,000

  • 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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  /42

  $3,699,000

  • 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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  /2

  $2,550,000

  • 5 Beds
  • 4.5 Baths
  • 3,800 Sq Ft

  19 Laurel Hill Ln, Winchester, MA 01890

  Nestled on a quiet street in one of Winchester’s most coveted neighborhoods, 19 Laurel Hill Lane will offer refined living just minutes from Boston and top-rated schools. This latest Mark Stephen Development project will feature 4 bedrooms and 4.5 bathrooms, including a flexible first-floor suite perfect for a guest room or study. The heart of the home will be a spacious kitchen flowing into a

  Mark Donnellan Advisors Living - Winchester

  19 Laurel Hill Ln, Winchester, MA 01890
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  /36

  $1,899,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,825 Sq Ft

  20 Grayson Rd, Winchester, MA 01890

  Another Tree Top Group masterpiece—where natural light, luxury finishes, & thoughtful design come together in perfect harmony. This 5-bed, 4.5-bath new construction home boasts 9+ ft ceilings, exceptional light fixtures, and a stunning waterfall center island that anchors the designer kitchen w/ custom cabinetry that extends to the ceiling. Custom built-ins & storage throughout. A sleek linear

  Monte Marrocco Coldwell Banker Realty - Lexington

  20 Grayson Rd, Winchester, MA 01890
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  /42

  $3,999,000 Open Thu 5PM - 7PM

  • 6 Beds
  • 4.5 Baths
  • 6,367 Sq Ft

  40 Foxcroft Rd, Winchester, MA 01890

  An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern luxury with timeless warmth in one of Winchester’s most coveted neighborhoods. Designed for elevated living, it features a chef’s kitchen with quartz counters, custom cabinetry, a large island, and built-in bar, opening to a sunlit dining area ideal for both casual meals and

  Monte Marrocco Coldwell Banker Realty - Lexington

  40 Foxcroft Rd, Winchester, MA 01890
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  /5

  $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

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

Home Trends in Winchester, MA

On average, homes in Winchester, MA sell after 28 days on the market compared to the national average of 70 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,300,000, down 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,300,000

Median Single Family Sale Price

$2,750,000

Median Townhouse Sale Price

$1,635,000

Median 2 Bedroom Sale Price

$630,000

Median 1 Bedroom Sale Price

$995,000

Average Price Per Sq Ft

$559

Number of Homes for Sale

0

Last 12 months Home Sales

53

Months of Supply

0.00

Median List Price

$1,458,000

Median Change From 1st List Price

0%

Median Home Sale Price YoY Change

-5%