Nestled just eight miles north of Boston, Winchester, Massachusetts, is a town that beautifully marries history with contemporary living. Steeped in rich historical significance dating back to the 17th century, Winchester is a town that values its past while embracing the latest trends in real estate.
Today, you'll find a range of housing options, from meticulously preserved colonial-era homes to stunning modern properties equipped with all the amenities demanded by today's homeowners. The town's strong sense of community, excellent schools, and easy access to Boston make it a highly desirable place to live for families and professionals alike.
Historic charm meets modern convenience
Tree-lined streets with historic homes near the Mystic Lakes. Features Winchester Country Club and numerous parks.
View PropertiesHeart of the town with the iconic Town Common, library, and easy access to dining and MBTA station.
Explore AreaMore affordable options with great community feel. Home to Skillings Field and multiple playgrounds.
Neighborhood InfoTrendy area with modern condos and proximity to Arlington line. Popular with young professionals.
Discover South EndWinchester's history is a testament to its enduring charm. Incorporated in 1850, the town is home to numerous historical landmarks, including the picturesque Winchester Town Common, which has been a gathering place for residents for centuries.
The town's commitment to preserving its heritage is evident in the many well-maintained historic buildings that grace its streets. While walking through Winchester, you can't help but feel a deep connection to the past.
Explore HistoryWinchester offers excellent schools, picturesque neighborhoods, and a strong sense of community. It provides a suburban lifestyle with easy access to Boston's amenities and cultural attractions.
Winchester features single-family homes, townhouses, condos, and apartments. Many properties showcase classic New England architecture in well-established neighborhoods.
The market is competitive with strong demand. Property values remain high due to excellent schools and desirability. Local agent guidance is recommended.
Some areas have guidelines to protect historic architecture. Significant changes to historic properties may require approval.
Winchester offers parks, recreation facilities, shopping districts, and dining. Proximity to Boston provides additional cultural and entertainment options.
The commuter rail takes about 25 minutes to North Station. By car, it's approximately 30 minutes to downtown depending on traffic.
22,875 people live in Winchester, where the median age is 42.4 and the average individual income is $90,356. Data provided by the U.S. Census Bureau.
Total Population
Median Age
Population Density Population Density This is the number of people per square mile in a neighborhood.
Average individual Income
Winchester has 8,149 households, with an average household size of 2.77. Data provided by the U.S. Census Bureau. Here’s what the people living in Winchester do for work — and how long it takes them to get there. Data provided by the U.S. Census Bureau. 22,875 people call Winchester home. The population density is 3,792.47 and the largest age group is Data provided by the U.S. Census Bureau.
Total Population
Population Density Population Density This is the number of people per square mile in a neighborhood.
Median Age
Men vs Women
Population by Age Group
0-9 Years
10-17 Years
18-24 Years
25-64 Years
65-74 Years
75+ Years
Education Level
Total Households
Average Household Size
Average individual Income
Households with Children
With Children:
Without Children:
Marital Status
Blue vs White Collar Workers
Blue Collar:
White Collar:
Get a clear path to closing — start with a pre-listing inspection.
06/20/25   |   Kim Covino & CoKey Considerations for a Successful Home Purchase.
06/20/25   |   Kim Covino & CoDiscover the Best Outdoor Activities for All Ages in One of Massachusetts’ Most Scenic Towns.
06/10/25   |   Kim Covino & CoMy team and I have a proven track record when it comes to negotiating skills and sourcing buyers from many different markets thanks to our premiere listings and strong referral base spanning Winchester and beyond. Referrals from past and present clients have become the base of our business, further proving our unmatched service!