Throughout the years, Winchester has grown from a rural farming community to a primarily residential town. Located in proximity to Broad Sound and 8 miles north of Boston, the peaceful suburb today is home to one of the best school districts in the state, grand New England homes and plenty of outdoor recreation space. Winchester has close to 23,000 people, and the median household income is $218,176, which is double the state’s median. Most people work in the science, technology and healthcare sectors, and many commute outside of town for work.
An overview of homes in the Winchester neighborhood.
Take a walk or bike ride on the Tri-Community Greenway that runs right through Winchester.
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Grand New England homes in Winchester
Built from the late 1800s to today, properties in Winchester uphold a quintessential New England look. Housing styles range from smaller Cape Cods and ranch styles to split-levels and larger Colonial Revivals. Older, more historic homes are usually in the North Main neighborhood. The West Side has more single-family residences, while communities such as Winchester Highlands and Symmes Corner offer a mix of real estate. The town’s median home price is $1,467,500, which is three times the national median. Single-family homes start around $700,000 and go over $4 million. Townhouses and duplexes are typically between $650,000 and $2 million. Depending on size and upkeep, condos, many of which are in The Flats community, may list between $300,000 and over $1 million. “Winchester has some high-end houses,” says Jack Lister, a Realtor at Berkshire Hathaway Verani Realty with 16 years of experience. “Most properties are $1 million or over with good-sized lots. Many older homes have been restored but still maintain a historic look.” Some subdivisions have monthly HOA fees, and houses situated in flood zones often need additional flood insurance.
A row of homes with a contempory and a Cape Cod styled homes in Winchester.
A large Farmhouse Colonial styled home Winchester, MA.
A traditional Cape Cod styled home in Winchester, MA.
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The reputable Winchester Public Schools
Rated by Niche as the No. 7 best public school district in Massachusetts, Winchester Public Schools serves over 4,300 students and has an A-plus Niche grade. The school system has one preschool, five elementary schools, one middle and one high school with an average student-teacher ratio of 12-to-1. “Many people come here for the schools,” Lister says. “Winchester has one of the best school systems in the state.” The town also has several private schools, including the A-minus Acera School. Higher institutions, such as Tufts University, Northeastern University’s Burlington campus and Bentley University in Waltham, are also close by.
Mccall Middle School's expansive sports fields are an asset to the whole Winchester community.
An aerial overview of Winchester High School and it's sports fields.
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Outdoor opportunities around Winchester and Medford
Some of Winchester’s outdoor destinations include Mystic Lakes State Park, which boasts the public Shannon Beach, and Middlesex Fells Reservation, featuring over 2,500 acres of woodlands, miles of trails and a pond. The Tri-Community Greenway connects Winchester with Woburn and Stoneham. It stretches close to 7 miles and is used for both commuting and recreational purposes. The town’s recreation department also offers many sports and enrichment programs, and community events often take place at Town Common.
A local Little Library in the Town Center in Winchester, MA.
The fields at Well Park in Winchester, MA.
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Shopping and dining around Winchester's downtown
Most of the town’s retailers are in the downtown area, which is bordered by Wedge and Mill Ponds. The town center has a range of markets, restaurants, taverns, boutiques and service shops. Additional stores are along Main Street.
Lucia Ristorante is a family style Italian restaurant in Winchester, MA.
The Black Horse Tavern is an established local restaurant in the downtown Winchester area.
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Community celebrations in Winchester
There are many events that celebrate the town and its community members, including Winchester Town Day, a tradition for over 40 years that features sports races and a fireworks show in late spring. Other celebrations include the annual PRIDEFest, a daddy-daughter dance, a garden tour and summer concerts at Town Common. Wright-Locke Farm, a 383-year-old sustainable conservancy dating back to the town’s founding era, offers a range of nature and farm-based enrichment experiences. Residents can get fresh, organic produce and seeds at the popular farm, or they can sign up for botanical courses or nature walks.
A cute car on dispaly at The Lighting Of The Trees Celebration in Winchester, MA.
Folks enjoy painting a masterpiece at Art in the Park.
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Easy access to the Boston metropolis
Winchester is accessible via U.S. Route 3 and Interstates 93 and 95. Public transit services include the MBTA bus and commuter rail, which connect to nearby towns and cities such as Boston and Cambridge. Logan International Airport is about 11 miles away, and Winchester Hospital is located right in town.
Crime data from 2023
According to Winchester’s police department, while violent crimes decreased, property crimes have slightly increased in 2023. The town's Cap Index Crime Score is 2 out of 10, which is below the national average of 4.
I have been involved in residential and commercial real estate for more than 15 years. My areas of expertise include selling, buying, rentals and property management. I come with decades of management experience in the hospitality and retail industries, prior to branching out into real estate. My strengths include quick turn around with Sales, buyer representation for primary residence purchases, as well as secondary, investment and vacation property purchases and rentals ., “I love the person-to-person relationships that are created in this industry, and I embrace bringing joy to anyone who is looking for that special place where they will build memories. I’ll go that extra mile for anyone to make a deal happen seamlessly.” Please call me at 617-590-6611 for all your Real Estate needs.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
