Winchester, MA Homes for Sale

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  $2,899,000 Open Sat 2PM - 3PM

  • 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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  $2,890,000

  • 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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  $2,295,000 Open Fri 12PM - 1PM

  • 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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  $2,499,000 Open Fri 12PM - 1:30PM

  • 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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  $2,250,000

  • 5 Beds
  • 5 Baths
  • 5,000 Sq Ft

  1 Fox Hunt Ln, Winchester, MA 01890

  Expanded Colonial Ranch offering over 5,000 sq ft of versatile living space, set on a beautifully landscaped 1/2-acre lot on a quiet cul-de-sac near Winchester Country Club. The first floor features a welcoming formal living room just off the entry, a spacious primary suite with two walk-in closets and a private bath, a guest bedroom with en-suite bath, and a third bedroom or home office.

  Leigh Ventura Compass

  1 Fox Hunt Ln, Winchester, MA 01890
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  $2,599,000 Open Fri 11:30AM - 12:30PM

  • 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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  /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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  /40

  $2,299,000

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

  9 Prospect St, Winchester, MA 01890

  Step into timeless elegance with this Colonial Revival, a true celebration of classic architecture, refined style, and exceptional craftsmanship. From the moment you arrive, the home's rich character makes a striking first impression, setting the stage for everything that follows. Inside, you’ll discover a harmonious blend of historic charm and modern comfort. Gleaming hardwood floors, intricate

  Nancy Pallotta Advisors Living - Winchester

  9 Prospect St, Winchester, MA 01890
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  $3,175,000

  • 5 Beds
  • 4.5 Baths
  • 5,386 Sq Ft

  21 Fernway, Winchester, MA 01890

  Exceptional colonial on Myopia Hill showcasing an expansive rear family room addition, perfectly situated on an idyllic lot surrounded by lush gardens & mature landscape. This stately residence offers a true private oasis just minutes from all conveniences. Rich in finish, elegant in design w/ stunning living areas, large scale rooms & 4 fireplaces creating warm inviting spaces for every day

  Kim Covino Compass

  21 Fernway, Winchester, MA 01890
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  $2,899,000 Open Sat 12PM - 1PM

  • 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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  $3,249,000 Open Sat 11:30AM - 12:30PM

  • 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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  $2,249,900

  • 4 Beds
  • 3.5 Baths
  • 4,023 Sq Ft

  19 Sussex Rd, Winchester, MA 01890

  Ideally located in a very desirable neighborhood that abuts the town forest and surrounded by cul-de-sacs, this elegant well-designed 4-bedroom, 3.5-bathroom colonial home has been meticulously maintained by the original owners and features a spacious layout with ample room for comfortable living. The floorplan is thoughtfully designed, with a nice flow from one room to the next. The family room

  Ida Bianco Coldwell Banker Realty - Lexington

  19 Sussex Rd, Winchester, MA 01890
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  $3,475,000 Open Sat 12PM - 1:30PM

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

  80 Arlington St, Winchester, MA 01890

  This stunning Royal Barry Wills colonial estate, with 11 rooms, 5 bedrooms and 3.5 baths, is nestled alongside the 4th green of the exclusive Winchester Country Club. Take in views from the sun-splashed eat-in kitchen, complete w/ granite island, custom wood cabinetry, and a generous seating area. Unwind by the fireplace in the richly paneled study. Access the expansive wrap around patio from the

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

  80 Arlington St, Winchester, MA 01890
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  $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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  $2,349,000 Open Thu 5PM - 7PM

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

  5 Azalea Rd, Winchester, MA 01890

  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 and Mature Trees to Relax and Enjoy! Elegant Dining Room

  Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

  5 Azalea Rd, Winchester, MA 01890
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  $2,650,000

  • 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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  $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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  $2,499,000 Open Sat 11AM - 12PM

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

  89 Wildwood St, Winchester, MA 01890

  Brand-New Luxury Construction! This exquisite 7-bedroom, 5.5-bath home blends sophisticated design with functional elegance. Crafted w/ top-tier finishes throughout, the open-concept layout is ideal for modern living & effortless entertaining. The chef’s kitchen showcases an oversized quartz island, premium appliances, & a sunny breakfast nook w/ sliders opening to a private backyard oasis. A

  Monte Marrocco Coldwell Banker Realty - Lexington

  89 Wildwood St, Winchester, MA 01890
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  $799,900

  • 3 Beds
  • 2 Baths
  • 1,441 Sq Ft

  9 Emerson Ct, Winchester, MA 01890

  Looking for the ideal first home or a peaceful place to settle into your next chapter? This charming 3-bedroom, 2-bath home, nestled at the end of a quiet dead-end street, was completely remodeled in 2009. Step inside to a warm and welcoming space with a practical layout—everything you need without the fuss. Whether you're just getting started or looking to simplify, this move-in-ready home is a

  Rodrigo Serrano Leading Edge Real Estate

  9 Emerson Ct, Winchester, MA 01890
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  $1,699,000 Open Sat 12PM - 1:30PM

  • 5 Beds
  • 4 Baths
  • 2,853 Sq Ft

  32 Oneida Rd, Winchester, MA 01890

  Move right into this 5 b/r 4 bth colonial steps to Ambrose School! This picture perfect colonial features high ceilings,hdwd floors & an open first floor plan that creates an airy, welcoming atmosphere.The bright kitchen equipped with ss appliances & charming banquette seating is perfect for casual family meals; step outside to the deck overlooking the spacious yard or into the beautiful

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

  32 Oneida Rd, Winchester, MA 01890
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  $625,000 Open Fri 5:30PM - 6:30PM

  • 2 Beds
  • 1.5 Baths
  • 1,554 Sq Ft

  50 Lake St Unit B, Winchester, MA 01890

  A well-maintained 2-bed, 1.5-bath townhouse-style condo offering scenic views of Wedge Pond. The main level features hardwood floors, a spacious living area, half bath, and a kitchen with granite countertops and stainless steel appliances. Upstairs offers two bedrooms and a full bath. The finished lower level provides versatile space for a family room, home office, or gym. Additional highlights

  Andersen Group Realty Keller Williams Realty Boston Northwest

  50 Lake St Unit B, Winchester, MA 01890
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  $4,250,000

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

  9 Lakeview Terrace, Winchester, MA 01890

  LAKEFRONT! Nestled on the serene shore of Mystic Lake just 7 miles from Boston, this extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room! Located in one of Winchester’s most sought-after neighborhoods, the home blends high ceilings, rich original details, and a flowing floor plan ideal for both everyday living and

  Kim Covino Compass

  9 Lakeview Terrace, Winchester, MA 01890
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  $1,345,000 Open Fri 11AM - 12:30PM

  • 3 Beds
  • 2 Baths
  • 2,238 Sq Ft

  49 Lincoln St, Winchester, MA 01890

  Enter into the serene in this inviting Colonial, where timeless architecture meets thoughtful updates. High ceilings and sun-splashed, spacious rooms - accented by multiple bay windows and rich wood floors - create a light, airy feel. Featuring a cook’s kitchen with light cherry cabinets, gas cooktop with vented hood, generous storage, and a breakfast nook nestled in a five-window bay overlooking

  Vantage Point Team William Raveis R.E. & Home Services

  49 Lincoln St, Winchester, MA 01890
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  $1,099,000

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  8 Garfield Ave, Winchester, MA 01890

  Located in a beautiful neighborhood, this thoughtfully renovated 3-bed, 2-bath home with a brand new custom built cottage, blends timeless charm with modern comfort. Sunlight pours into the open living spaces, highlighting original details & gleaming refinished hardwood floors. The inviting living room features a cozy fireplace, while the formal dining room is perfect for gatherings. A bright

  Kim Covino Compass

  8 Garfield Ave, Winchester, MA 01890
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  $1,349,900 Open Sun 12PM - 1:30PM

  • 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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  $1,299,000 Open Sat 11AM - 12PM

  • 3 Beds
  • 3.5 Baths
  • 2,136 Sq Ft

  162 Swanton St Unit 162, Winchester, MA 01890

  Opportunity to own the last available end unit! Welcome to 162 Swanton Street, the final new construction townhome by Ron Roy in the heart of Winchester. This home blends modern design with exceptional craftsmanship. The open-concept first floor features hardwood floors, a cozy fireplace, and a chef-inspired kitchen with stainless steel appliances, a large island, and adjacent mudroom with half

  Monte Marrocco Coldwell Banker Realty - Lexington

  162 Swanton St Unit 162, Winchester, MA 01890
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  $1,349,000

  • 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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  $1,799,999

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

  44 Amberwood Dr, Winchester, MA 01890

  Incredibly well maintained, nicely updated 3-4 bedroom Colonial in a wonderful neighborhood in desirable VO School district! The first floor has an oversized kitchen w/cherry cabinets, all granite counters & breakfast bar that opens to a great room with FP and a recently added family room w/vaulted ceiling, computer cubby and 10' slider to a deck overlooking a beautiful landscaped yard & 2

  Hudson Santana Keller Williams Realty Boston Northwest

  44 Amberwood Dr, Winchester, MA 01890
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  $1,199,900

  • 4 Beds
  • 2.5 Baths
  • 2,302 Sq Ft

  518 Washington St, Winchester, MA 01890

  Set in the coveted Muraco School District, this classic 1915 Colonial offers the perfect blend of character and modern comfort. Featuring 4 bedrooms and 2.5 baths, the welcoming main level boasts an open-concept layout with an eat-in kitchen (granite countertops, stainless steel appliances), a dining room with charming built-ins, a spacious living room, and a convenient powder room with laundry.

  Rodrigo Serrano Leading Edge Real Estate

  518 Washington St, Winchester, MA 01890
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  $2,050,000

  • 5 Beds
  • 3.5 Baths
  • 3,874 Sq Ft

  4 Worthen Rd, Winchester, MA 01890

  Must see! Sprawling 5 bed 3.5 bath customized colonial situated on a gorgeous street with 1/2 acre lot! This sun-drenched home is filled w/ natural light & is perfectly designed for both everyday living & entertaining. The first floor features a spacious, updated kitchen w/ an oversized island, dining room w fplc & two beautiful great rooms on either side of the home w/ vaulted ceilings,

  Kim Covino Compass

  4 Worthen Rd, Winchester, MA 01890
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  $859,000

  • 2 Beds
  • 1 Bath
  • 1,123 Sq Ft

  22 Grove Place Unit 4, Winchester, MA 01890

  Looking to downsize or just live more modestly?Welcome to the sought-after White Horse Commons Condominiums, The perfect opportunity to enjoy the lovely town of Winchester and keep costs down. Near Symmes corner, downtown Winchester & Wedgemere train station, this wonderful 2 bedroom, 1 bathroom end unit lives and feels like a single home with windows on all three sides. The kitchen offers a

  Kim Covino Compass

  22 Grove Place Unit 4, Winchester, MA 01890
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  $959,000 Open Sat 11:30AM - 1PM

  • 3 Beds
  • 1 Bath
  • 1,425 Sq Ft

  571 Washington St, Winchester, MA 01890

  Welcome to this beautifully maintained 3-bedroom home just moments from vibrant Winchester Center. Ideal for commuters with quick access to I-95 and I-93, this home blends charm, comfort, and convenience. The updated kitchen features quartz countertops and generous cabinetry—perfect for cooking and gathering. Light-filled living spaces offer a warm, welcoming feel throughout. Unwind on the

  Ryan Wilson Keller Williams Realty

  571 Washington St, Winchester, MA 01890
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  $3,895,000 Open Sat 11:30AM - 12:30PM

  • 7 Beds
  • 8 Baths
  • 7,587 Sq Ft

  25 Wedgemere Ave, Winchester, MA 01890

  Stately elegance resides on one of the most desirable streets in the “Flats". This sprawling home details fine craftsmanship & modern finishes that a home of this caliber warrants. Sprawling open concept kitchen w/ impressive coffered ceilings, eat-in dining along w/ an adjoining family rm w/gas fireplace, dining room, and a formal living room make this the perfect space for entertaining. 7

  Prestige Homes Realty Team Prestige Homes Real Estate, LLC

  25 Wedgemere Ave, Winchester, MA 01890
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  $3,175,000

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

  54 Wedgemere Ave, Winchester, MA 01890

  SELLER WILL INCLUDE 50K of RESTORATION HARDWARE FURNISHINGS *w/ signed offer by 6/16* Exceptional living in this stunning Wedgemere Ave home w/ spectacular resort style back yard! Completely updated throughout w/ custom high end finishes, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive back yard featuring gorgeous patio

  Kim Covino Compass

  54 Wedgemere Ave, Winchester, MA 01890
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  $1,329,000

  • 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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  /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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  $1,449,900

  • 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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  $1,499,000 Open Sun 1PM - 2:30PM

  • 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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  $2,850,000

  • 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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  $2,000,000 Open Sat 12PM - 1:30PM

  • 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

Showing Results 1 - 40, Page 1 of 2

Why Live in 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 $1,804,013.

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

228 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, Grove Street and Winchester Highlands.

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

The median home price in Winchester is $1,624,000. If you put a 20% down payment of $324,800 and had a 30-year fixed mortgage with an interest rate of 6.84%, your estimated principal and interest payment would be $8,500 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $364K 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 50 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,539,250, up 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,539,250

Median Single Family Sale Price

$1,900,000

Median Townhouse Sale Price

$1,465,000

Median 2 Bedroom Sale Price

$732,500

Median 1 Bedroom Sale Price

$370,000

Average Price Per Sq Ft

$550

Number of Homes for Sale

48

Last 12 months Home Sales

228

Months of Supply

2.50

Median List Price

$1,624,000

Median Change From 1st List Price

0%

Median Home Sale Price YoY Change

10%