$1,767,688Average Value$550Average Price per Sq Ft51Homes For Sale
Peaceful living in a Greater Boston suburban town
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.
Written By
Christina Xu
Photography Contributed By
Sam Adams
Video By
Barry Ridgeway
Interested in learning more about homes in this area?
Reach out to
Alexander Koziakov,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Winchester, MA sell after 23 days on the market compared to the national average of 49 days. The median sale price for homes in Winchester, MA over the last 12 months is $1,539,250, up 10% from the median home sale price over the previous 12 months.
LAKEFRONT! Nestled on the serene shore of Mystic Lake just 7 miles from Boston, this extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room! Located in one of Winchester’s most sought-after neighborhoods, the home blends high ceilings, rich original details, and a flowing floor plan ideal for both everyday living and
Enter into the serene in this inviting Colonial, where timeless architecture meets thoughtful updates. High ceilings and sun-splashed, spacious rooms - accented by multiple bay windows and rich wood floors - create a light, airy feel. Featuring a cook’s kitchen with light cherry cabinets, gas cooktop with vented hood, generous storage, and a breakfast nook nestled in a five-window bay overlooking
Vantage Point TeamWilliam Raveis R.E. & Home Services
Your very own private oasis tucked away in a cul-de-sac-like neighborhood just mins. to Winchester Center! Set on a deep, tree-lined lot, this stunning home offers 5 beds, 3.5 baths, & over 3,000 sq. ft. The versatile floor plan offers ground-level entry w/ a 2 car garage, 2 bedrooms (which can also function as work/play space,) & full bath/laundry area. The upper level is the heart of the home –
HEAT, HOT WATER, AC and ELECTRIC included. Enjoy scenic pond views from this beautifully updated second-floor condo, perfectly situated overlooking the pond. This two-bedroom unit features an inviting open-concept layout that flows seamlessly onto a spacious private balcony—ideal for relaxing or entertaining outdoors. Generous closet space is found throughout the home, with additional storage
The Sanctuary at Winchester North is designed for the way you live - casual fireside gatherings in the Den, a game of billiards in the Hive, a meal with friends prepared in the Nest's Chef's Kitchen. Maybe you prefer to make a splash in the pool, or stay on track with personal health goals in the fitness and health facility. With meticulously appointed common spaces designed for work, play, and
No equal. Stunning, newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage parking completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2-1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim
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.
