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Winchester, MA Open Houses

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  • /42

    $2,599,000 Open Sat 11:30AM - 12:30PM

    • 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
  • /40

    $1,995,000 Open Sat 11AM - 12:30PM

    • 3 Beds
    • 2 Baths
    • 2,813 Sq Ft

    20 Seneca Rd, Winchester, MA 01890

    Welcome home to this picture-perfect Colonial, tucked away in a quiet, sought-after neighborhood just steps from Ambrose! Boasting gorgeous curb appeal & a warm, welcoming feel, this home offers the best of comfort & convenience.Step inside to a bright & open first floor designed for effortless entertaining, featuring oversized windows that flood the space with amazing natural light.The spacious

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

    20 Seneca Rd, Winchester, MA 01890
  • /41

    $1,949,000 Open Sat 12PM - 1:30PM

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

    10 Olde Lyme Rd, Winchester, MA 01890

    Beautifully updated 5 bed, 3.5 bath Colonial on Winchester's West Side with over 3400 sq ft of living space located on a quiet cul-de-sac in the coveted Vinson-Owen school district. Set on an 18,000 sq ft lot abutting Sucker Brook conservation area and walking trails. This home offers privacy, space and natural beauty. The main level features a spacious layout with an office/den, which could

    Darryl Brian RE/MAX Bentley's

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

    $2,499,000 Open Sat 1:30PM - 3PM

    • 6 Beds
    • 3.5 Baths
    • 4,212 Sq Ft

    19 Yale St, Winchester, MA 01890

    Located in the TOP neighborhood that everyone wants! Welcome to the Flats, where elegance and charm abound. A gorgeous foyer welcomes you and flows easily into the living room and dining room, both impressively lit with natural light. A fireplace and custom built-ins add warmth and charm, beckoning for dinner parties and entertaining. A huge kitchen offers ample counter space, a sweet banquet,

    Nancy Pallotta Advisors Living - Winchester

    19 Yale St, Winchester, MA 01890
  • /42

    $2,950,000 Open Sat 12PM - 1:30PM

    • 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
  • /41

    $3,599,000 Open Sat 1:30PM - 3PM

    • 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
  • /19

    $2,449,000 Open Sat 12:30PM - 2PM

    • 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
  • /33

    $699,900 Open Sat 11AM - 12:30PM

    • 2 Beds
    • 1.5 Baths
    • 1,326 Sq Ft

    32 Clark St, Winchester, MA 01890

    A true diamond in the rough, Whether you're a first-time homebuyer, a savvy investor, or someone looking to customize a home to their liking, this residence presents the perfect blend of potential and location. This 2 bedroom single family home makes for a great condo alternative. Don't miss this rare chance to break into the Winchester market and enjoy all this town has to offer from it's great

    Rodrigo Serrano Leading Edge Real Estate

    32 Clark St, Winchester, MA 01890
  • /42

    $1,199,000 Open Sat 1:30PM - 3PM

    • 3 Beds
    • 1.5 Baths
    • 1,906 Sq Ft

    44 Forest St, Winchester, MA 01890

    This charming home is move-in ready and situated on a beautiful fenced in level lot close to parks, the bike path, Muraco school & more! The interior of the home is flooded with sunlight & period details featuring open airy spaces and generously sized rooms that flow throughout the home, making each room easily accessible and enjoyable. The main floor has a lovely living room with gas fireplace,

    Kim Covino Compass

    44 Forest St, Winchester, MA 01890
  • /40

    $1,499,000 Open Sat 11:30AM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 2,351 Sq Ft

    19 Cox Rd, Winchester, MA 01890

    Charming three-bedroom ranch on spectacular 20,000sf west side lot abutting conservation! The updated granite kitchen with newer appliances leads to the open concept dining room overlooking the beautiful, private yard. The spacious living room features a fplc & bay window; a sunroom, 3 spacious bedrooms, 1 bath & garage complete the main level; the lower level offers a large rec/ family room w

    Kim Covino Compass

    19 Cox Rd, Winchester, MA 01890
  • /40

    $1,375,000 Open Sat 11:30AM - 1PM

    • 3 Beds
    • 2 Baths
    • 3,406 Sq Ft

    7 Hutchinson Rd, Winchester, MA 01890

    A great opportunity to reimagine this custom built spacious cape in a sought-after Winchester neighborhood! Set on a generous lot, this unique home has been lovingly maintained and is full of potential; ready for updates & your personal touch! The floor plan provides a flexible layout that’s ideal for easy living with a spacious first-floor bedroom, full bath, an oversized home office or add'l

    Kim Covino Compass

    7 Hutchinson Rd, Winchester, MA 01890
  • /34

    $1,499,900 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
  • /36

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

    • 2 Beds
    • 2 Baths
    • 1,545 Sq Ft

    7 Conant Rd Unit 34, Winchester, MA 01890

    Rarely available at The Willows, you enter this unit with ease through your private, attached one car garage or the step-free front entrance—an ideal setup for everyday convenience. This beautifully maintained first-floor unit offers the perfect blend of comfort, style, and accessibility. Inside, you'll find two generously sized bedrooms, including a spacious en-suite with direct access to one of

    Melanie Lentini Leading Edge Real Estate

    7 Conant Rd Unit 34, Winchester, MA 01890
  • /42

    $1,650,000 Open Sat 12PM - 2PM

    • 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
  • /15

    $998,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 3 Baths
    • 2,333 Sq Ft

    48 Tremont St, Winchester, MA 01890

    Welcome to this well loved 4-bedroom expanded Cape, on quiet cul-de-sac, cared for by the original owners for nearly 65 years! Located in the brand new Lynch Elementary School district, just steps from Winchester HS, Skillings Field, less than a mile from the Commuter Rail and downtown Winchester. Great for commuters. First floor features mudroom with laundry, front-to-back fire-placed living

    Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

    48 Tremont St, Winchester, MA 01890
  • /23

    $1,299,000 Open Sun 12PM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 1,520 Sq Ft

    10 Allen Rd, Winchester, MA 01890

    Located in a very desirable East Hill neighborhood, this one owner Circa 1929 Dutch Colonial offers a wonderful opportunity for the next owners to bring their ideas and make this home their own. The interior features many generous sized rooms, hardwood floors, crown molding, built in China cabinet, French doors, a brick fireplace and many more original details. This home is traditional with the

    Sally Baldwin Coldwell Banker Realty - Lexington

    10 Allen Rd, Winchester, MA 01890
  • /22

    $1,295,000 Open Sun 11AM - 12PM

    • 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
  • /39

    $2,499,000 Open Sat 1:30PM - 3PM

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

    9 Prospect St, Winchester, MA 01890

    Step into a piece of history with this incredibly charming 1895 Colonial Revival, a 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. Inside, you’ll find an extraordinary blend of historic charm and modern livability.The craftsmanship

    Nancy Pallotta Advisors Living - Winchester

    9 Prospect St, Winchester, MA 01890
  • /16

    $1,199,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2 Baths
    • 2,621 Sq Ft

    61 Westland Ave, Winchester, MA 01890

    Welcome to this oversized Cape in a lovely west side neighborhood of Winchester. Opportunity for a little TLC or a significant renovation, the flexible layout of this 1952 gem offers many possibilities. Attention savvy buyers, contractors and builders! Sited on a 10,703sf lot within the Vinson-Owen school district. First floor offers living room, dining room, kitchen, sunroom/porch, 2 bedrooms

    Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

    61 Westland Ave, Winchester, MA 01890
  • /42

    $1,499,000 Open Fri 5:30PM - 6:30PM

    • 3 Beds
    • 4 Baths
    • 3,351 Sq Ft

    34 Fells Rd, Winchester, MA 01890

    Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from the scenic Middlesex Fells Conservation Area, you'll have miles of trails for outdoor exploration right at your doorstep. With a commuter-friendly location, this home is ideal for those seeking both tranquility and convenience. A welcoming

    Andersen Group Realty Keller Williams Realty Boston Northwest

    34 Fells Rd, Winchester, MA 01890
  • /42

    $3,350,000 Open Sun 11:30AM - 1PM

    • 6 Beds
    • 5 Baths
    • 5,198 Sq Ft

    21 Sheffield W, Winchester, MA 01890

    Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The stunning state of art chef’s kitchen was just completed & seamlessly connects to a butler’s pantry w/ wet bar & wine chiller, leading to an elegant dining room w/ fireplace. The oversized family room is bathed in natural light w/walls of

    Kim Covino Compass

    21 Sheffield W, 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
  • /40

    $3,149,000 Open Sat 2PM - 3PM

    • 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
  • /34

    $3,698,000 Open Sun 12:30PM - 2PM

    • 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
  • /42

    $3,989,000 Open Sat 12PM - 1PM

    • 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
  • /37

    $699,900 Open Sat 12PM - 1PM

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

    7 Conant Rd Unit 20, Winchester, MA 01890

    Beautifully renovated first-floor condo in the highly sought-after "Willows at Winchester" complex. This expansive, single-level unit features an open-concept living area with new hardwood flooring, a versatile space that can be used as a dining room, home office or home entertainment alcove and a cozy gas fireplace. The updated kitchen features fresh granite countertops and brand new appliances.

    Brian Woods Woods Properties Inc.

    7 Conant Rd Unit 20, Winchester, MA 01890
  • /42

    $3,699,000 Open Sat 12PM - 1PM

    • 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
  • /35

    $1,599,000 Open Sat 12:30PM - 2PM

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

    189 Mystic Valley Pkwy, Winchester, MA 01890

    Great price improvement - Ready to go at this price! Nestled in the heart of downtown Winchester, the stunning Barstow House boasts a unique Mansard roof & timeless colonial architecture. This historic gem features a versatile floorplan designed for modern living while preserving its classic charm. The first level beautifully blends form & function; the home office, mudroom, a dedicated laundry

    Anne Spry Barrett Sotheby's International Realty

    189 Mystic Valley Pkwy, Winchester, MA 01890
  • /9

    $2,599,000 Open Sat 12PM - 1PM

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

    89 Wildwood St, Winchester, MA 01890

    NEW CONSTRUCTION! This stunning 7-bed, 5.5-bath luxury home boasts high-end finishes and a thoughtfully designed open floor plan, perfect for entertaining and modern living. The chef’s kitchen features an oversized quartz island, pro appliances, and a breakfast nook, with sliders leading to a private backyard. The spacious family room offers a gas fireplace, while the 1st floor includes a formal

    Monte Marrocco Coldwell Banker Realty - Lexington

    89 Wildwood St, Winchester, MA 01890
  • /35

    $1,300,000 Open Sat 12:30PM - 1:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,668 Sq Ft

    23 Lantern Ln, Arlington, MA 02474

    Nestled in Arlington’s prestigious Morningside neighborhood, this impeccably maintained 3-bedroom, 2.5-bath home offers an ideal blend of elegance, functionality, and comfort. The main level boasts a spacious living room with a fireplace, a chef's kitchen with abundant counter space, and a dining room, perfect for entertaining. Three generously sized bedrooms, including a primary suite with

    Celina Doucette Herringbone Realty, LLC

    23 Lantern Ln, Arlington, MA 02474
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