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Winchester, MA Multifamily Homes & Duplexes for Sale

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  • 112 Church St, Winchester, MA 01890
    112 Church St, Winchester, MA 01890
    112 Church St, Winchester, MA 01890
    /40

    $1,650,000 Open Sat 12PM - 1:30PM

    • 8 Beds
    • 2.5 Baths
    • 3,591 Sq Ft

    112 Church St, Winchester, MA 01890

    Rare Opportunity: Spacious Side-by-Side Two-Family Home Less Than 1 Mile from Town Center. This charming two-family home offers classic period details, including fireplaced living rooms, formal dining rooms with built-in china cabinets located directly off the kitchen. Each unit features two large bedrooms with hardwood floors and a full bath on the second floor, plus two additional bedrooms and

    Catherine Albiani Better Homes and Gardens Real Estate - The Shanahan Group

    112 Church St, Winchester, MA 01890
  • 5 Bacon St, Winchester, MA 01890
    5 Bacon St, Winchester, MA 01890
    5 Bacon St, Winchester, MA 01890
    /42

    $2,245,000 Open Sat 1PM - 2:30PM

    • 6 Beds
    • 4 Baths
    • 4,385 Sq Ft

    5 Bacon St, Winchester, MA 01890

    This stunning Victorian home, in the style of Painted Ladies with soaring ceilings & hardwood floors, is in a prime neighborhood just moments from Winchester Center, the commuter rail, Shannon Beach, & a short ride to the Airport & downtown Boston. The house lives as a harmonious single family with an inlaw apartment on the 1st floor. It has 6 beds & 4 baths, over 4,385 SF of living area on 3

    Anne Spry Barrett Sotheby's International Realty

    5 Bacon St, Winchester, MA 01890
  • 60 Harvard St, Winchester, MA 01890
    60 Harvard St, Winchester, MA 01890
    60 Harvard St, Winchester, MA 01890
    /16

    $995,000

    • 4 Beds
    • 3 Baths
    • 1,860 Sq Ft

    60 Harvard St, Winchester, MA 01890

    Exceptional investment opportunity. Located in the heart of desirable Winchester, this multi family property offers a rare opportunity to own a ready to renovate, vacant building with incredible potential. Two 1 bedroom, 1 bathroom units and 1 two bedroom unit. This property is primed for a full renovation. Perfect for investors, end users or travellers looking for their own pied-a'-terre, while

    Mark Krasnyansky eXp Realty

    60 Harvard St, Winchester, MA 01890
Massachusetts Middlesex County Winchester

Multi-Family Homes & Duplexes for Sale in Winchester, MA

Why Live in Winchester

Winchester, MA, a peaceful Greater Boston suburb, has evolved from a rural farming community to a primarily residential town with a population of nearly 23,000. Located 8 miles north of Boston, Winchester is known for its grand New England homes, ranging from historic Colonial Revivals to modern Cape Cods and ranch styles. The town boasts one of the best school districts in the state, with Winchester Public Schools serving over 4,300 students and receiving high ratings. The private Acera School also offers quality education. Outdoor enthusiasts can enjoy Mystic Lakes State Park, Middlesex Fells Reservation, and the Tri-Community Greenway, which connects Winchester with Woburn and Stoneham. The town's downtown area, bordered by Wedge and Mill Ponds, features a variety of markets, restaurants, boutiques, and service shops. Community events such as Winchester Town Day, PRIDEFest, and summer concerts at Town Common foster a strong sense of community. Wright-Locke Farm, a 383-year-old sustainable conservancy, provides fresh 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 about 11 miles away. The town has a lower crime risk compared to the national average, with recent data indicating a decrease in violent crimes.

Learn more about living in Winchester

Home Trends in Winchester, MA

On average, homes in Winchester, MA sell after 22 days on the market compared to the national average of 52 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,670,000, up 14% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,670,000
Median Single Family Sale Price
$1,917,000
Median Townhouse Sale Price
$1,542,500
Median 2 Bedroom Sale Price
$940,000
Median 1 Bedroom Sale Price
$710,000
Average Price Per Sq Ft
$552
Number of Homes for Sale
29
Last 12 months Home Sales
163
Months of Supply
2.10
Median List Price
$1,750,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
14%
How to Buy a Home How to Finance a Home How to Sell a Home

In Winchester, there are currently 3 multi-family homes for sale, providing an appealing investment opportunity for buyers. With multi-family homes priced between $995,000 to $2,245,000, there's a range to accomodate every budget. As of September, 2025 the median home price in Winchester is $1,750,000, while the average sale price is $1,836,400, offering insights into the local housing market. On average, multi-family homes spend 22 days listed before being sold. Multi-family homes include a variety of property types, from duplexes, triplexes, and fourplexes, to apartment complexes, all within a single building divided to accommodate multiple families living separately. These multi-family properties for sale offer investors the chance to generate rental income. Whether you're considering a duplex for a beginner investment or an apartment complex for a more substantial venture, there are investment properties available to meet your requirements. Explore the range of multi-family homes for sale in Winchester, MA.

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