$1,455,302Average Value$588Average Price per Sq Ft5Homes For Sale
A Boston suburb high on appeal
Explore Winchester Highland’s carefully organized residential blocks and one will find an eclectic mix of homes that share a certain grandeur no matter what era they were built. But that’s just one line on a long list of appeals here. This neighborhood opens the door to one of the best public school districts in the state, offers access to a variety of expansive outdoor recreation opportunities, is conveniently situated in relation to Winchester’s downtown and posts CAP Index Crime Scores much better than the national average. “Winchester is a beautiful town,” says Winchester Highlands resident Christina Larson, owner and principal of Larson Financial Planning. “And the Winchester Highlands area is very close to beautiful walking trails and forests. Winchester’s also strategically located so it’s easy to get to the highway, and the schools are superb.”
You can find many trails and ponds in the town of Winchester Highlands.
Winchester Highlands makes up the city of Winchester and offers a cultural and art district.
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Variety characterizes housing inventory
The houses in Winchester Highlands include ones built in the late 19th century, others built over the course of the 20th century and even some built in recent years. Yet the homes here seem to include style elements that lend to a level of harmonious uniformity, like vibrant vinyl siding and shutters. “There’s a very diverse stock here. There are ranches, there are colonials, there are two-families. Houses here are 100 years old and there are a lot of new houses,” says Larson. Winchester Highlands features straight-line blocks accented by mature trees on spacious lots. Many of the neighborhood’s lots stretch at least .10 acres, enough for both a front and back lawn. There are some townhome-style options that sell for $600,000 to $1.2 million, but the area has mostly single-family homes priced from $800,000 to $2.4 million based on size and condition.
Rows of front yards stretch out to the Winchester Highlands' street.
You can find traditional colonial homes in Winchester Highlands.
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Schools are a major draw
Some come to the area just for the schools, Larson says. And it makes sense — the Winchester Public Schools system boasts an A-plus overall rating on Niche and is No. 10 on the site’s list of the best school districts across Massachusetts. Many of the neighborhood’s homes are within reasonable walking distance of the A-rated Muraco Elementary, which offers before- and afterschool programming through the area organization Kidsborough. Students in town can then advance to the A-plus-rated McCall Middle, whose extracurricular opportunities include everything from a Coding Club to Model UN. Winchester High School also carries an A-plus grade and features a dedicated technology department with classes on topics such as web design, robotics and engineering design.
Winchester High School maintains an A+ rating on Niche.
McCall Middle School In Winchester has an A+ rating on Niche.
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Outdoor fun is conveniently close
Streets around Winchester Highlands are lined with sidewalks, and it’s common to see people out and about, taking a walk on a nice day. And that’s just the tip of the iceberg when it comes to outdoor opportunities here. For one, part of the 2,200-acre Middlesex Fells Reservation spills into the neighborhood. “I would say the Middlesex Fells is probably the most important outdoor feature,” says local Realtor Naomi DeLairre, of Barrett Sotheby's International Realty. “It’s a nature preserve shared by Winchester, Medford and Stoneham. It’s acres and acres of natural reserves.” Middlesex Fells features more than 100 miles of trails to peruse. The almost 7-mile Tri-Community Greenway runs through Winchester Highlands as well, a paved path locals use for walking, jogging and biking.
Residents of Winchester Highlands enjoy the changing color leaves at Middlesex Fells Trails.
The Tri-Community Greenway runs through Davidson Park in Winchester, MA.
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Retail amenities come easy
Winchester Highlands is primarily residential, but it does have a couple of options for locals looking to grab a bite to eat. Eighty Eight Cafe is a well-liked Chinese takeout spot in the neighborhood. And those with a sweet tooth can enjoy The Gingerbread Construction Co. “That’s a favorite spot for wonderful cakes and muffins,” Larson says.
Winchester Highlands residents can also hop in the car for a quick ride to the Winchester Center area to choose from an assortment of more restaurants, like Italian institution Lucia Ristorante or First Horse Pub, popular in part for its burgers. There’s also a Stop & Shop in the Winchester Center area, which is convenient for picking up groceries and other essentials.
Among Winchester Highland’s other perks is a medical center right in the neighborhood, Winchester Hospital, which has 229 beds.
Pick up all your daily needs from Winchester Drug near Winchester Highlands.
Pick out your favorite pastry at the Gingerbread Construction Co. in Winchester Highlands.
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Take a trip on the train
Neighborhood residents can take advantage of their proximity to the Winchester Center area to quickly hop on the Massachusetts Bay Transportation Authority commuter rail. The Winchester Center station is part of the Lowell Line and can take riders down to Boston in roughly an hour. The station is currently being renovated and is scheduled for a partial reopening in late September 2024. Drivers in Winchester Highlands can also hop on nearby Interstate 93 for commutes to Boston, just about 11 miles away.
Commuters have the accessibility of MBTA in Winchester Highlands.
The town of Winchester Highlands offers a slow and peaceful lifestyle.
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Celebrate summer with Town Day
Winchester Highlands locals can jump down to the center of town for an annual tradition each June: Winchester Town Day. Town Day celebrates the start of summer with a Friday block party, a Saturday street fair and fireworks in the evening.
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 Highlands, Winchester sell after 17 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester Highlands, Winchester over the last 12 months is $1,238,000, up 3% from the median home sale price over the previous 12 months.
Nestled directly across from the breathtaking Middlesex Fells Reservation, this home offers the perfect blend of charm, space, and potential. This classic 3-bedroom, 2.5 bath Cape is beautifully situated on over half an acre in one of Winchester’s most desirable locations. The home features mostly hardwood floors throughout, a brand-new roof, and a newer heating and AC system. The second floor
Paula SughrueBetter Homes and Gardens Real Estate - The Shanahan Group
Attention renovators and investors! This Cape-style home in need of significant renovation offers 7 rooms, 4 bedrooms, and 2 full baths. Features include a fireplace living room, dining room, and hardwood flooring throughout. Enjoy a private yard for outdoor enjoyment. Prime location directly across from the Middlesex Fells Reservation and minutes to Winchester Center, schools, shops, and
This beautiful Victorian home, featuring an inviting front porch, stunning period detail including wainscoting, original tin ceilings, custom built-ins, and three fireplaces is not to be missed! Maple hardwood floors flow through an open-concept layout to a spacious eat-in kitchen with a lovely exposed brick wall. The second floor has three bedrooms and a full bath plus a sweet window seat and an
Lynne RussoBetter Homes and Gardens Real Estate - The Shanahan Group
Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester’s most desirable neighborhoods. Designed for modern lifestyles, this home features a chef’s kitchen that flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. A sun-drenched 3-season porch expands your living space
Here, smart design imbues modern comforts with alfresco joys. Quartz countertops, glass-enclosed showers, and quality stainless steel appliances add to your quality of life. Energy-efficient windows stream in sunlight while wood-style flooring inspires your next jaunt outside. But with thoughtful features like our enhanced fitness center and cyber studio, you won't have to wander far to activate
A rare find! Newer construction rental home/ attached single family/ featuring 5 bedrooms & 4 baths over 4 finished levels, close to Winchester center and Muraco Elementary School. This great home features large spacious rooms, a sunny granite kitchen w/ maple cabinets, hardwood floors/ open concept w/ family room & a gas fireplace w/ sliders that lead to a spacious deck overlooking a fenced in
Sunny 2-Bedroom in Winchester! Beautifully maintained 5-room apartment featuring 2 bedrooms, 1 bath, and parking for 2 cars. This first-floor unit offers gleaming hardwood floors throughout, a bright kitchen with dishwasher and spacious pantry, and a dining room with built-in cabinet and charming chandelier. Two generously sized bedrooms with closets, a full bath, and both front (enclosed) and
Danielle StorellaBerkshire Hathaway HomeServices Commonwealth Real Estate
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