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Winchester, MA Houses for Sale

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  • 4 Chestnut St, Winchester, MA 01890
    4 Chestnut St, Winchester, MA 01890
    4 Chestnut St, Winchester, MA 01890
    /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

    Agent Photo

    Tyson Lynch

    The Proper Nest Real Estate

    (781) 633-6582

    4 Chestnut St, Winchester, MA 01890
  • 11 Fieldstone Dr, Winchester, MA 01890
    11 Fieldstone Dr, Winchester, MA 01890
    11 Fieldstone Dr, Winchester, MA 01890
    /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
  • 14 Grant Rd, Winchester, MA 01890
    14 Grant Rd, Winchester, MA 01890
    14 Grant Rd, Winchester, MA 01890
    /42

    $2,499,000

    • 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
  • 4 Norwood St, Winchester, MA 01890
    4 Norwood St, Winchester, MA 01890
    4 Norwood St, Winchester, MA 01890
    /40

    $3,399,000

    • 5 Beds
    • 4.5 Baths
    • 5,250 Sq Ft

    4 Norwood St, Winchester, MA 01890

    Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town center with easy access to Boston, this home features exquisite millwork, custom built-ins, and premium finishes throughout. The main home offers 4 bedrooms, 3.5 bathrooms, a living room, dining room, sitting room, pantry, and a bar alcove, along with an expansive second-floor

    Mark Donnellan Advisors Living - Winchester

    4 Norwood St, Winchester, MA 01890
  • 4 Fieldstone Dr, Winchester, MA 01890
    4 Fieldstone Dr, Winchester, MA 01890
    4 Fieldstone Dr, Winchester, MA 01890
    /41

    $2,190,000

    • 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
  • 58 Bacon St, Winchester, MA 01890
    58 Bacon St, Winchester, MA 01890
    58 Bacon St, Winchester, MA 01890
    /40

    $2,295,000

    • 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
  • 6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    6 Ivy Cir, Winchester, MA 01890
    /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
  • 9 Lakeview Terrace, Winchester, MA 01890
    9 Lakeview Terrace, Winchester, MA 01890
    9 Lakeview Terrace, Winchester, MA 01890
    /42

    $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
  • 1 Fox Hunt Ln, Winchester, MA 01890
    1 Fox Hunt Ln, Winchester, MA 01890
    1 Fox Hunt Ln, Winchester, MA 01890
    /41

    $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
  • 107 Cambridge St, Winchester, MA 01890
    107 Cambridge St, Winchester, MA 01890
    107 Cambridge St, Winchester, MA 01890
    /42

    $2,599,000

    • 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
  • 5 Stratford Rd, Winchester, MA 01890
    5 Stratford Rd, Winchester, MA 01890
    5 Stratford Rd, Winchester, MA 01890
    /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
  • 21 Fernway, Winchester, MA 01890
    21 Fernway, Winchester, MA 01890
    21 Fernway, Winchester, MA 01890
    /42

    $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
  • 10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    /42

    $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
  • 5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    /34

    $2,349,000

    • 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
  • 19 Laurel Hill Ln, Winchester, MA 01890
    19 Laurel Hill Ln, Winchester, MA 01890
    /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
  • 89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    /38

    $2,499,000 New Construction

    • 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
  • 4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, Winchester, MA 01890
    /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
  • 26 Olive St, Winchester, MA 01890
    26 Olive St, Winchester, MA 01890
    26 Olive St, Winchester, MA 01890
    /37

    $929,000

    • 3 Beds
    • 2 Baths
    • 1,977 Sq Ft

    26 Olive St, Winchester, MA 01890

    Don't miss this rare opportunity to own a charming home with an expansive yard on a quiet cul-de-sac street! This lovely 3-bedroom ranch is meticulously maintained and situated in the sought-after Muraco school district. The main floor features an eat-in kitchen, formal dining room, and a sun-filled living room with a fireplace, perfect for relaxing or entertaining. Gleaming hardwood floors run

    Andersen Group Realty Keller Williams Realty Boston Northwest

    26 Olive St, Winchester, MA 01890
  • 85 Loring Ave, Winchester, MA 01890
    85 Loring Ave, Winchester, MA 01890
    85 Loring Ave, Winchester, MA 01890
    /40

    $1,379,000

    • 3 Beds
    • 2.5 Baths
    • 2,340 Sq Ft

    85 Loring Ave, Winchester, MA 01890

    Beautifully updated Colonial in a prime Winchester location. This sun-filled 3-bed, 2.5-bath home features an open-concept layout with a spacious living room, dining area, modern kitchen, and bright sunroom—perfect for relaxing or entertaining. The finished lower level includes a cozy family room with a fireplace and a full bath. Set on a level corner lot with 4-car parking and a fenced-in yard

    Akiko Ghosh Oyama Investments, Ltd.

    85 Loring Ave, Winchester, MA 01890
  • 3 Socrates Way, Winchester, MA 01890
    3 Socrates Way, Winchester, MA 01890
    3 Socrates Way, Winchester, MA 01890
    /33

    $1,299,000

    • 4 Beds
    • 2.5 Baths
    • 2,570 Sq Ft

    3 Socrates Way, Winchester, MA 01890

    Unlock the potential of this tri-level home in one of Winchester’s sought-after neighborhoods! Set on a 20,000 sq ft lot, this 4 bed, 2.5 bath, 1966-built home offers 2,116 sf of living space, a 2 car garage, & endless possibilities for renovation or redevelopment. The main level features a formal living room, dining room, & kitchen leading to a deck overlooking the backyard. A cozy family room

    Pirani & Wile Group Advisors Living - Winchester

    3 Socrates Way, Winchester, MA 01890
  • 4 Worthen Rd, Winchester, MA 01890
    4 Worthen Rd, Winchester, MA 01890
    4 Worthen Rd, Winchester, MA 01890
    /40

    $1,999,000

    • 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
  • 9 Emerson Ct, Winchester, MA 01890
    9 Emerson Ct, Winchester, MA 01890
    9 Emerson Ct, Winchester, MA 01890
    /41

    $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
  • 35 Harvard St, Winchester, MA 01890
    35 Harvard St, Winchester, MA 01890
    35 Harvard St, Winchester, MA 01890
    /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
  • 10 Girard Rd, Winchester, MA 01890
    10 Girard Rd, Winchester, MA 01890
    10 Girard Rd, Winchester, MA 01890
    /41

    $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
  • 44 Amberwood Dr, Winchester, MA 01890
    44 Amberwood Dr, Winchester, MA 01890
    44 Amberwood Dr, Winchester, MA 01890
    /28

    $1,765,300

    • 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
  • 44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    /38

    $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
  • 571 Washington St, Winchester, MA 01890
    571 Washington St, Winchester, MA 01890
    571 Washington St, Winchester, MA 01890
    /34

    $959,000 Open Mon 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
  • 80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    /33

    $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
  • 54 Wedgemere Ave, Winchester, MA 01890
    54 Wedgemere Ave, Winchester, MA 01890
    54 Wedgemere Ave, Winchester, MA 01890
    /42

    $3,099,000

    • 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
  • 147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, Winchester, MA 01890
    /37

    $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
  • 3 Abby Rd, Winchester, MA 01890
    3 Abby Rd, Winchester, MA 01890
    3 Abby Rd, Winchester, MA 01890
    /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
  • 7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    /34

    $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
  • 14 Hillside Ave, Winchester, MA 01890
    14 Hillside Ave, Winchester, MA 01890
    14 Hillside Ave, Winchester, MA 01890
    /42

    $1,499,000

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

    14 Hillside Ave, Winchester, MA 01890

    Location, location, location! Rare opportunity to own this stunning Italianate home, in a desirable neighborhood, steps from Town Center! This property has been lovingly owned & maintained by the same family for 70+ years and is now ready for new owners. Prepare to fall in love with the charm and period details of this circa 1870 historic home, the first house built on Hillside Ave. The 1st floor

    Seeme Moreira Coldwell Banker Realty - Lexington

    14 Hillside Ave, Winchester, MA 01890
  • 14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    /42

    $2,850,000

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

    14 Nassau Dr, Winchester, MA 01890

    (Price Improved) 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

    Weidong Li WINN Real Estate & Consulting

    14 Nassau Dr, Winchester, MA 01890
  • 5 Squire Rd, Winchester, MA 01890
    5 Squire Rd, Winchester, MA 01890
    5 Squire Rd, Winchester, MA 01890
    /40

    $2,000,000

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

    5 Squire Rd, Winchester, MA 01890

    Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shiplap fireplace, opens to a spacious composite deck. The primary suite is a private retreat with a

    Alina Wang Coldwell Banker Realty - Lexington

    5 Squire Rd, Winchester, MA 01890
  • 11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    /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
  • 71 Woodside Rd, Winchester, MA 01890
    71 Woodside Rd, Winchester, MA 01890
    71 Woodside Rd, Winchester, MA 01890
    /22

    $1,295,000

    • 4 Beds
    • 1.5 Baths
    • 2,202 Sq Ft

    71 Woodside Rd, Winchester, MA 01890

    Nestled in the heart of Winchester, this charming 4-bedroom, 1.5-bathroom single-family home offers 2,202 square feet of living space on a 7,126-square-foot lot. Built in 1927, the home exudes timeless character with its spacious rooms, abundant natural light, and original architectural details. Perfect for homeowners and developers alike, the property offers endless potential for renovation,

    Jorge Rodriguez Carlton's Wharf & Co.

    71 Woodside Rd, Winchester, MA 01890
  • 8 Tanglewood Ln, Winchester, MA 01890
    8 Tanglewood Ln, Winchester, MA 01890
    8 Tanglewood Ln, Winchester, MA 01890
    /42

    $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
  • 20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    /34

    $3,698,000

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

    20 Amberwood Dr, Winchester, MA 01890

    Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The

    Dan Li Keller Williams Realty

    20 Amberwood Dr, Winchester, MA 01890
  • 26 Swan Rd, Winchester, MA 01890
    26 Swan Rd, Winchester, MA 01890
    26 Swan Rd, Winchester, MA 01890
    /42

    $3,989,000

    • 6 Beds
    • 6.5 Baths
    • 8,463 Sq Ft

    26 Swan Rd, Winchester, MA 01890

    Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with 2 primary suite options! This magnificent residence boasts expansive living spaces, elevator & indoor pool! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/custom cherry cabinetry & high end

    Kim Covino Compass

    26 Swan Rd, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 2

Massachusetts Winchester

Houses for Sale in Winchester, MA

Why Live in Winchester

Winchester, a peaceful suburban town located 8 miles north of Boston, offers a blend of residential charm and outdoor recreation. With a population of nearly 23,000, Winchester boasts a median household income of $218,176, double the state’s median. The town is known for its grand New England homes, ranging from historic Colonial Revivals to modern Cape Cods and ranch styles, particularly in neighborhoods like North Main and Winchester Highlands. Winchester Public Schools, rated as one of the best in Massachusetts, serve over 4,300 students with an impressive student-teacher ratio of 12-to-1. The Acera School, a private institution, also holds a high rating. Outdoor enthusiasts can enjoy Mystic Lakes State Park, Middlesex Fells Reservation, and the Tri-Community Greenway, which offers nearly 7 miles of trails connecting Winchester with neighboring towns. Downtown Winchester features a variety of markets, restaurants, taverns, and boutiques, primarily along Main Street and near Wedge and Mill Ponds. Community events such as Winchester Town Day, PRIDEFest, and summer concerts at Town Common foster a strong sense of local pride. Wright-Locke Farm, a historic conservancy, provides 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 11 miles away. The town's crime rate is below the national average, contributing to its appeal as a safe residential area.
Learn more about living in Winchester

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 $1,558,000, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,558,000
Median Single Family Sale Price
$1,910,000
Median Townhouse Sale Price
$1,330,000
Median 2 Bedroom Sale Price
$719,999
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$550
Number of Homes for Sale
50
Last 12 months Home Sales
225
Months of Supply
2.70
Median List Price
$1,599,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
11%
How to Buy a Home How to Finance a Home How to Sell a Home

In Winchester, there are currently 47 houses for sale, offering an array of options for potential buyers. With houses priced between $799,900 to $4,250,000, there's a range to accomodate every budget. As of June, 2025 the median home price in Winchester is $1,599,000, while the average sale price is $1,676,941, offering insights into the local housing market. On average, houses spend 23 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Winchester, MA and find the perfect place to call home.

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