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Winchester, MA Homes for Sale

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  • 12 Olde Lyme Rd, Winchester, MA 01890
    12 Olde Lyme Rd, Winchester, MA 01890
    12 Olde Lyme Rd, Winchester, MA 01890
    /42

    $2,400,000 Open Thu 4PM - 6PM

    • 5 Beds
    • 4.5 Baths
    • 4,215 Sq Ft

    12 Olde Lyme Rd, Winchester, MA 01890

    Welcome to 12 Olde Lyme Rd, where classic Colonial charm meets modern style + convenience. Nestled at the end of a private cul-de-sac, and just a short walk to the coveted Vinson-Owen school, this 5-bedroom, 4.5-bath home has been expanded with purpose and thoughtfully renovated in 2017. The redesign includes high-end finishes and exquisite updates throughout, with no area left untouched.

    Mary Beth McGillicuddy Engel & Völkers , South Shore

    12 Olde Lyme Rd, Winchester, MA 01890
  • 44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    /40

    $3,399,000 Open Sat 12PM - 1PM

    • 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
  • 21 Fernway, Winchester, MA 01890
    21 Fernway, Winchester, MA 01890
    21 Fernway, Winchester, MA 01890
    /42

    $3,349,000

    • 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
  • 9 Prospect St, Winchester, MA 01890
    9 Prospect St, Winchester, MA 01890
    9 Prospect St, Winchester, MA 01890
    /41

    $2,379,000

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

    9 Prospect St, Winchester, MA 01890

    Intensely beautiful Colonial Revival! This home that exudes elegance, character, and masterful craftsmanship at every turn. From the moment you arrive, you’ll be captivated by its stately presence, classic architectural details, and warm, inviting ambiance. There's a blend of historic charm and modern livability. The craftsmanship is remarkable—gleaming hardwood floors, intricate leaded glass

    Nancy Pallotta Advisors Living - Winchester

    9 Prospect St, Winchester, MA 01890
  • 80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    /42

    $3,675,000

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

    $2,749,000 Open Sat 11AM - 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
  • 25 Wedgemere Ave, Winchester, MA 01890
    25 Wedgemere Ave, Winchester, MA 01890
    25 Wedgemere Ave, Winchester, MA 01890
    /42

    $3,895,000 Open Sat 12PM - 1PM

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

    $3,199,000

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

    54 Wedgemere Ave, Winchester, MA 01890

    Experience exceptional living in this stunning Wedgemere Ave home w/ spectacular resort style back yard! Thoughtfully updated throughout with 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 & maintenance free heated POOL with in- floor cleaning system & auto

    Kim Covino Compass

    54 Wedgemere Ave, Winchester, MA 01890
  • 15 Churchill Rd, Winchester, MA 01890
    15 Churchill Rd, Winchester, MA 01890
    15 Churchill Rd, Winchester, MA 01890
    /41

    $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
  • 5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    /13

    $2,449,000

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

    5 Azalea Rd, Winchester, MA 01890

    Exceptional Home nestled in one of Winchester's most desirable West Side Neighborhoods 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 Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials and Mature Trees to Relax and Enjoy! Elegant Dining Room open

    Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

    5 Azalea 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
  • 276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    /42

    $2,399,000 Open Sat 12PM - 1PM

    • 5 Beds
    • 3.5 Baths
    • 5,077 Sq Ft

    276 High St, Winchester, MA 01890

    This stunning, freshly painted, home is located in a picturesque and unique setting, elevated on a small hill with a private half-acre lot in a tranquil cul-de-sac, near the Winchester/Lexington border. It’s far from road traffic, offering exceptional privacy. The residence spans four levels, featuring 5 bedrooms, 3.5 bathrooms, and two separate laundry areas. The expansive grounds showcase

    Andersen Group Realty Keller Williams Realty Boston Northwest

    276 High St, Winchester, MA 01890
  • 63 Church St, Winchester, MA 01890
    63 Church St, Winchester, MA 01890
    63 Church St, Winchester, MA 01890
    /27

    $1,389,900 Open Thu 4PM - 5:30PM

    • 4 Beds
    • 2.5 Baths
    • 3,157 Sq Ft

    63 Church St, Winchester, MA 01890

    Back Bay meets Winchester in this victorian style attached residence in a premier Flats/ downtown location. This lovingly modernized home offers central air, first floor laundry, gas heating & cooking & tremendous closet space. The kitchen seamlessly transitions to the deck & huge manicured fenced in yard perfect for kids, pets & all outdoor fun. First floor is adorned with a dining room with

    Nancy McLaughlin Redfin Corp.

    63 Church St, Winchester, MA 01890
  • 22 Grove Place Unit 4, Winchester, MA 01890
    22 Grove Place Unit 4, Winchester, MA 01890
    22 Grove Place Unit 4, Winchester, MA 01890
    /37

    $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
  • 18 Hemingway St, Winchester, MA 01890
    18 Hemingway St, Winchester, MA 01890
    18 Hemingway St, Winchester, MA 01890
    /32

    $1,359,900 Open Sat 11:30AM - 1PM

    • 5 Beds
    • 3.5 Baths
    • 2,137 Sq Ft

    18 Hemingway St, Winchester, MA 01890

    This COMPLETEDLY GUTTED AND REBUILT IN 2015 5B3.5B colonia-preserving a portion of original foundation, is located in a quiet neighborhood yet just minutes to Town Center, Elementary & High School, Town beach, Horn Pond, Fells Reservation, commuter rail station/Bus 134 to Wellington T. The architect-designed home features hardwood flooring throughout, high ceiling & abundant natural light. 1st

    Julia Xie Keller Williams Realty-Merrimack

    18 Hemingway St, Winchester, MA 01890
  • 19 Sussex Rd, Winchester, MA 01890
    19 Sussex Rd, Winchester, MA 01890
    19 Sussex Rd, Winchester, MA 01890
    /26

    $2,249,900 Open Sat 12PM - 2PM

    • 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
  • 50 Johnson Rd, Winchester, MA 01890
    50 Johnson Rd, Winchester, MA 01890
    50 Johnson Rd, Winchester, MA 01890
    /42

    $1,699,000

    • 3 Beds
    • 4 Baths
    • 2,646 Sq Ft

    50 Johnson Rd, Winchester, MA 01890

    One of the most picturesque homes in Winchester is now available! An iconic Mid-Century Modern originally designed by renowned architect Don Davis. Thoughtfully updated for today’s lifestyle, this architectural gem blends timeless design with modern functionality. The bold exterior opens into a dramatic living room featuring soaring cathedral ceilings, a statement fireplace, and custom built-ins.

    Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

    50 Johnson Rd, Winchester, MA 01890
  • 571 Washington St, Winchester, MA 01890
    571 Washington St, Winchester, MA 01890
    571 Washington St, Winchester, MA 01890
    /34

    $1,100,000 Open Fri 1:30PM - 3PM

    • 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
  • 63 Church St, Winchester, MA 01890
    63 Church St, Winchester, MA 01890
    63 Church St, Winchester, MA 01890
    /35

    $1,389,900 Open Thu 4PM - 5:30PM

    • 4 Beds
    • 2.5 Baths
    • 3,157 Sq Ft

    63 Church St, Winchester, MA 01890

    Back Bay meets Winchester in this victorian style attached residence in a premier Flats/ downtown location. This lovingly modernized home offers central air, first floor laundry, gas heating & cooking & tremendous closet space. The kitchen seamlessly transitions to the deck & huge manicured fenced in yard perfect for kids, pets & all outdoor fun. First floor is adorned with a dining room with

    Nancy McLaughlin Redfin Corp.

    63 Church St, Winchester, MA 01890
  • 7 Conant Rd Unit 37, Winchester, MA 01890
    7 Conant Rd Unit 37, Winchester, MA 01890
    7 Conant Rd Unit 37, Winchester, MA 01890
    /25

    $749,900 Open Sat 11AM - 12:30PM

    • 2 Beds
    • 2.5 Baths
    • 1,539 Sq Ft

    7 Conant Rd Unit 37, Winchester, MA 01890

    Welcome to this beautifully updated corner unit townhouse-style condo, offering ample-sized rooms, abundant natural light, & hardwood floors throughout! The layout includes 5 well proportioned rooms. Kitchen, living room w/gas fireplace with marble surround, dining room & 2.5 bathrooms, creating a comfortable & functional living space. Both bedrooms are en-suite, providing privacy & convenience,

    McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

    7 Conant Rd Unit 37, Winchester, MA 01890
  • 20 Fletcher St Unit 20, Winchester, MA 01890
    20 Fletcher St Unit 20, Winchester, MA 01890
    20 Fletcher St Unit 20, Winchester, MA 01890
    /39

    $1,449,000

    • 3 Beds
    • 2.5 Baths
    • 2,282 Sq Ft

    20 Fletcher St Unit 20, Winchester, MA 01890

    Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! W its breathtaking design, this residence boasts a thoughtful layout; the open-concept first floor has high ceilings and an abundance of natural light. The thoughtfully selected finishes, tiles, and fixtures add a touch of elegance and sophistication throughout.

    Kim Covino Compass

    20 Fletcher St Unit 20, Winchester, MA 01890
  • 20 Fletcher St Unit 20, Winchester, MA 01890
    20 Fletcher St Unit 20, Winchester, MA 01890
    20 Fletcher St Unit 20, Winchester, MA 01890
    /39

    $1,449,000

    • 3 Beds
    • 2.5 Baths
    • 2,282 Sq Ft

    20 Fletcher St Unit 20, Winchester, MA 01890

    Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! With its breathtaking design, this residence boasts a thoughtful layout; the open-concept first floor has high ceilings and an abundance of natural light. The thoughtfully selected finishes, tiles, and fixtures add a touch of elegance and sophistication

    Kim Covino Compass

    20 Fletcher St Unit 20, 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 Open Sat 12PM - 1PM

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

    $1,399,000

    • 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
  • 10 Olde Lyme Rd, Winchester, MA 01890
    10 Olde Lyme Rd, Winchester, MA 01890
    10 Olde Lyme Rd, Winchester, MA 01890
    /31

    $1,825,000

    • 5 Beds
    • 3.5 Baths
    • 3,478 Sq Ft

    10 Olde Lyme Rd, Winchester, MA 01890

    Come see this spacious 5-bedroom home offered at a NEW PRICE of $1,825,000! Located near the end of a quiet cul-de-sac in a wonderful neighborhood, this home offers privacy, space and natural beauty, just a short distance to Winchester Center and surrounding towns. Walking distance to the Vinson-Owen school, which has consistently been rated as one of the best elementary schools in the state.

    Darryl Brian RE/MAX Bentley's

    10 Olde Lyme 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 Open Sat 12PM - 1:30PM

    • 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 Open Sat 11AM - 12:30PM

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

    $2,950,000

    • 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
  • 5 Squire Rd, Winchester, MA 01890
    5 Squire Rd, Winchester, MA 01890
    5 Squire Rd, Winchester, MA 01890
    /40

    $2,099,000 Open Sat 1PM - 2:30PM

    • 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
  • 27 Everett Ave, Winchester, MA 01890
    27 Everett Ave, Winchester, MA 01890
    27 Everett Ave, Winchester, MA 01890
    /41

    $3,599,000

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

    27 Everett Ave, Winchester, MA 01890

    Completely renovated in 2023/2024! This is one of the most distinguished homes on Everett Avenue, with preeminent siting on more than half an acre. This residence combines the magnificence of early 1900s architecture with today's modern amenities., this home features hallmark architectural details including Tudor-style balusters and high ceilings. Large rooms, coffered ceilings, original crown

    Nancy Pallotta Advisors Living - Winchester

    27 Everett Ave, 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
  • 10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    /40

    $3,149,000 Open Sat 12PM - 1PM

    • 7 Beds
    • 5.5 Baths
    • 6,200 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
  • 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
  • 8 Chestnut St, Winchester, MA 01890
    8 Chestnut St, Winchester, MA 01890
    8 Chestnut St, Winchester, MA 01890
    /42

    $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
  • 7 Conant Rd Unit 20, Winchester, MA 01890
    7 Conant Rd Unit 20, Winchester, MA 01890
    7 Conant Rd Unit 20, Winchester, MA 01890
    /37

    $699,900

    • 2 Beds
    • 2 Baths
    • 1,168 Sq Ft

    7 Conant Rd Unit 20, Winchester, MA 01890

    Rarely available and beautifully renovated first-floor unit at The Willows designed with everyday functionality in mind. This one-story unit offers stair-free access and living, along with easy accessibility from the adjacent one-car garage with an attic and a tandem parking spot. Upon entry, you’ll find an inviting open concept living and dining area with freshly installed hardwood flooring, a

    Brian Woods Woods Properties Inc.

    7 Conant Rd Unit 20, Winchester, MA 01890
  • 54 Johnson Rd, Winchester, MA 01890
    54 Johnson Rd, Winchester, MA 01890
    54 Johnson Rd, Winchester, MA 01890
    /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
  • 189 Mystic Valley Pkwy, Winchester, MA 01890
    189 Mystic Valley Pkwy, Winchester, MA 01890
    189 Mystic Valley Pkwy, Winchester, MA 01890
    /38

    $1,550,000

    • 6 Beds
    • 2.5 Baths
    • 3,543 Sq Ft

    189 Mystic Valley Pkwy, Winchester, MA 01890

    Perfectly situated just moments from the vibrant heart of Winchester, this Mansard-roofed beauty offers a harmonious blend of refined style and comfort. A spacious front porch overlooking a sizable side yard invites you to relax and enjoy the energy of the nearby town center. Inside, the main level blends form and function; expansive living spaces are complemented by a mudroom, home office, and

    Anne Spry Barrett Sotheby's International Realty

    189 Mystic Valley Pkwy, Winchester, MA 01890

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