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Winchester, MA Condos for Sale

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  • 29 Vine St Unit 8, Winchester, MA 01890
    29 Vine St Unit 8, Winchester, MA 01890
    29 Vine St Unit 8, Winchester, MA 01890
    /31

    $625,000

    • 2 Beds
    • 1.5 Baths
    • 1,157 Sq Ft

    29 Vine St Unit 8, Winchester, MA 01890

    Ideally located for commuters, this stylish 2-bed, 1.5-bath condo sits in the heart of vibrant downtown Winchester—just steps from the Commuter Rail for a quick ride into Boston. Enjoy easy access to major routes and nearby Sheepfold Park for weekend recreation. The main level boasts a sunlit living room with vaulted ceilings and a dedicated dining area, and a sleek kitchen with stainless steel

    Martha Sotiropoulos Lamacchia Realty, Inc.

    29 Vine St Unit 8, Winchester, MA 01890
  • 666 Main St Unit 206, Winchester, MA 01890
    666 Main St Unit 206, Winchester, MA 01890
    666 Main St Unit 206, Winchester, MA 01890
    /28

    $724,999

    • 2 Beds
    • 2 Baths
    • 1,170 Sq Ft

    666 Main St Unit 206, Winchester, MA 01890

    Back on Market - buyer got cold feet. Welcome to Wedgewood Place at 666 Main Street in Winchester Center - a perfect blend of small-town charm and urban convenience. This desirable and well-maintained 2 bed/2 bath home comes with 1 covered parking. Enjoy a spacious open-concept layout with a wood-burning fireplace, screened-in balcony overlooking courtyard & pool, and updated kitchen and guest

    Sveta Vakhitova Berkshire Hathaway HomeServices Warren Residential

    666 Main St Unit 206, 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

    $679,900 Open Sun 1PM - 2PM

    • 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
Massachusetts Winchester

Condos 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 $1,575,000, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,575,000
Median Single Family Sale Price
$1,915,000
Median Townhouse Sale Price
$1,330,000
Median 2 Bedroom Sale Price
$724,999
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$550
Number of Homes for Sale
51
Last 12 months Home Sales
224
Months of Supply
2.70
Median List Price
$1,649,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
13%
How to Buy a Home How to Finance a Home How to Sell a Home

In Winchester, there are currently 3 condos for sale, providing a variety of options for potential buyers. With condos priced between $625,000 to $724,999, there's a range to accomodate every budget. As of June, 2025 the median home price in Winchester is $1,649,000, while the average sale price is $1,682,572, offering insights into the local housing market. On average, condos spend 23 days listed before being sold. Whether you're considering condominiums, apartments for sale, or modern condos, there are options to cater to different lifestyles. Browse the range of condos for sale in Winchester, MA, and discover your ideal residence.

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