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Winchester, MA Open Houses

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  • /40

    $1,899,000 Open Sun 11:30AM - 1PM

    • 3 Beds
    • 3.5 Baths
    • 3,010 Sq Ft

    1 Town Way, Winchester, MA 01890

    Welcome home to this completely renovated gem, ideally situated on a corner lot in the highly sought-after Lincoln Elementary School district. Warm, inviting, and truly move-in ready, this home offers the open-concept first floor buyers dream of—featuring a beautiful kitchen flowing seamlessly into the dining and living areas, plus a sunken family room perfect for relaxing or entertaining. Enjoy

    Philip Vita Compass

    1 Town Way, Winchester, MA 01890
  • /41

    $815,000 Open Fri 5:30PM - 6:30PM

    • 3 Beds
    • 1.5 Baths
    • 1,710 Sq Ft

    49 Spruce St, Winchester, MA 01890

    Fantastic opportunity to own in Winchester! This inviting home is move-in ready and offers a flexible layout. The bright living room with picture window opens to the dining area, with a kitchen and a convenient half bath with laundry just beyond. Upstairs features a comfortable primary bedroom, sunny home office, additional bedroom, and a full bath. The third-floor bedroom spans the length of the

    Andersen Group Realty Keller Williams Realty Boston Northwest

    49 Spruce St, Winchester, MA 01890
  • /42

    $2,899,000 Open Sun 11:30AM - 1PM

    • 5 Beds
    • 5.5 Baths
    • 5,257 Sq Ft

    19 Town Way, Winchester, MA 01890

    Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artful lighting to the seamless flow of the open yet intentionally defined floor plan. The impressive

    Philip Vita Compass

    19 Town Way, Winchester, MA 01890
  • /42

    $2,595,000 Open Sat 11AM - 12:30PM

    • 4 Beds
    • 4 Baths
    • 5,674 Sq Ft

    10 Viking Rd, Winchester, MA 01890

    Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas—ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4

    Anne Spry Barrett Sotheby's International Realty

    10 Viking Rd, Winchester, MA 01890
  • /42

    $1,425,000 Open Fri 5:30PM - 6:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,112 Sq Ft

    10 Trinity Rd, Winchester, MA 01890

    Welcome to 10 Trinity Road, an inviting split-level home located on a low-traffic cul-de-sac in a desirable Winchester neighborhood. The main level features an open-concept kitchen that flows into the family and dining areas, ideal for everyday living and entertaining. Three bedrooms and two full baths complete this level, including a primary bedroom with an ensuite bath. The lower level provides

    Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Trinity Rd, Winchester, MA 01890
  • /39

    $3,599,000 Open Sat 1PM - 2:30PM

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

    27 Everett Ave, Winchester, MA 01890

    This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are

    Nancy Pallotta Gibson Sotheby's International Realty

    27 Everett Ave, Winchester, MA 01890
  • /32

    $1,299,000 Open Sat 11:30AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 2,803 Sq Ft

    36 Middlesex St Unit 38, Winchester, MA 01890

    Thoughtfully designed newer construction townhome offering the feel and privacy of a single family home. This 4 bed, 3.5 bath home features a sought-after 1st floor primary suite, sun-filled interiors, and dramatic ceiling height that enhances the home’s bright, airy feel. Hardwood floors and a gas fireplaced family room flow to sliders leading to a private deck, patio, and fenced yard. The

    Pirani & Wile Group Gibson Sotheby's International Realty

    36 Middlesex St Unit 38, Winchester, MA 01890
  • /30

    $1,025,000 Open Sat 10AM - 11:30AM

    • 6 Beds
    • 2 Baths
    • 2,605 Sq Ft

    353-355 Washington St, Winchester, MA 01890

    Investor alert! About one mile from an array of shops, restaurants, & the commuter rail to Boston, this Winchester multi-family is a rare opportunity waiting to be redesigned! Held by the same family for many years, the property offers substantial square footage & endless potential for those ready to roll up their sleeves. While it requires significant renovation, the reward will be well worth

    Julie Gibson Gibson Sotheby's International Realty

    353-355 Washington St, Winchester, MA 01890
  • /42

    $1,649,000 Open Sat 12PM - 1:30PM

    • 4 Beds
    • 4 Baths
    • 3,343 Sq Ft

    263 Highland Ave, Winchester, MA 01890

    Exceptional Victorian era gem, steps from Town Center, schools, commuter rail, and the Fells! This spacious period home seamlessly blends modern elegance with timeless charm. It’s special features include: an inviting farmer’s porch, generous living and dining rooms well-suited for entertaining, first floor family room, covered porch for al fresco dining, primary suite with ensuite bath, home

    Seeme Moreira Coldwell Banker Realty - Lexington

    263 Highland Ave, Winchester, MA 01890
  • /33

    $699,000 Open Fri 5PM - 6PM

    • 2 Beds
    • 2 Baths
    • 1,532 Sq Ft

    7 Conant Rd Unit 33, Winchester, MA 01890

    Rarely available ground-floor townhouse at The Willows with easy access to a private garage. This bright and sunny 2-bedroom, 2-bath condo offers the convenience and comfort today’s buyers are seeking. Open concept kitchen with a breakfast bar, and an adjacent dining area—perfect for everyday living or entertaining. The expansive living room is highlighted by a gas fireplace and slider that opens

    Pirani & Wile Group Gibson Sotheby's International Realty

    7 Conant Rd Unit 33, Winchester, MA 01890
  • /40

    $2,250,000 Open Sun 12PM - 1:30PM

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

    6 Ivy Cir, Winchester, MA 01890

    Spacious newly gut renovated colonial set back on a cul-de-sac! Unbeatable location in quiet neighborhood less than a mile from all Winchester's amazing public schools and Wedge Pond. Hardwood floors throughout with gorgeous kitchen featuring huge island, large living and dining rooms. A vaulted family room with authentic barn board detailing sits adjacent to the kitchen, opening to a large

    Rose Hall Blue Ocean Realty, LLC

    6 Ivy Cir, Winchester, MA 01890
  • /42

    $2,199,000 Open Sat 1PM - 3PM

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

    61 Grove St, Winchester, MA 01890

    Experience the perfect blend of luxury and effortless living in this stunning custom-built residence, thoughtfully rebuilt and expanded to offer a sophisticated, maintenance-free lifestyle. Bathed in natural light, the flexible floor plan begins with a magnificent first-floor primary suite featuring a marble-clad bath, soaking tub, and walk-in shower. The heart of the home is a chef’s kitchen

    Dorothea Feffer Churchill Properties

    61 Grove St, Winchester, MA 01890
  • /31

    $1,325,999 Open Sat 11AM - 1PM

    • 3 Beds
    • 3.5 Baths
    • 2,909 Sq Ft

    2 Mason Way Unit 6524, Woburn, MA 01801

    This stunning new construction end-unit townhome offers 3 bedrooms, 3.5 bathrooms, and a finished basement with full bath—perfect for flexible living or guest space. The chef’s kitchen boasts stainless steel appliances, a large center island, and abundant cabinetry, opening seamlessly to the spacious living room and private deck. A formal dining room with a charming bay window adds warmth and

    Erin Sullivan Pulte Homes of New England

    2 Mason Way Unit 6524, Woburn, MA 01801
  • /31

    $1,224,999 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 2,143 Sq Ft

    6 Mason Way Unit 6324, Woburn, MA 01801

    New Construction Move- In Ready Townhome at Highland at Vale in Woburn! The Jackson floor plan offers over 2,100 sq. ft. of thoughtfully designed living space with 3 spacious bedrooms and 2.5 baths. The main level features a bright kitchen with stainless steel appliances, abundant cabinetry, and a large center island, flowing into an oversized gathering room and an octagon-shaped dining room with

    Erin Sullivan Pulte Homes of New England

    6 Mason Way Unit 6324, Woburn, MA 01801

Home Trends in Winchester, MA

Housing Trends

Median Sale Price
$1,650,000
Median Single Family Sale Price
$1,800,000
Median Townhouse Sale Price
$1,399,000
Median 2 Bedroom Sale Price
$940,000
Average Price Per Sq Ft
$562
Number of Homes for Sale
10
Last 12 months Home Sales
171
Months of Supply
0.70
Median List Price
$1,693,944
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
7%
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