$1,454,077Average Value$575Average Price per Sq Ft10Homes 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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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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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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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.
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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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.
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
Interested in learning more about homes in this area?
Reach out to
Darcy Bento,
an experienced agent in this neighborhood.
Parks in this Area
Ginn Field
Manchester Field
Middlesex Fells Reservation
Leland Park
Elliot Park
Davidson Park
Transit
Airport
General Edward Lawrence Logan International
21 min drive
Crime and Safety
1 - Low Crime, 10 - High Crime
Winchester Highlands
US
Homicide
2
4
Sexual Assault
2
4
Assault with Weapon
2
4
Robbery
3
4
Burglary
3
4
Motor Vehicle Theft
3
4
Larceny
3
4
Crime Score
2
4
Source: WhatIsMyCrimeRisk.com
Winchester Highlands Demographics and Home Trends
On average, homes in Winchester Highlands, Winchester sell after 19 days on the market compared to the national average of 49 days. The median sale price for homes in Winchester Highlands, Winchester over the last 12 months is $1,280,000, up 7% from the median home sale price over the previous 12 months.
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
Located in a beautiful neighborhood, this thoughtfully renovated 3-bed, 2-bath home with a brand new custom built cottage, blends timeless charm with modern comfort. Sunlight pours into the open living spaces, highlighting original details & gleaming refinished hardwood floors. The inviting living room features a cozy fireplace, while the formal dining room is perfect for gatherings. A bright
Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well
Set in the coveted Muraco School District, this classic 1915 Colonial offers the perfect blend of character and modern comfort. Featuring 4 bedrooms and 2.5 baths, the welcoming main level boasts an open-concept layout with an eat-in kitchen (granite countertops, stainless steel appliances), a dining room with charming built-ins, a spacious living room, and a convenient powder room with laundry.
Charming, fully renovated colonial in a prime Winchester neighborhood! The sunny front porch welcomes you in, leading to a bright bow front living room w/ high ceilings, that flows into the dining room & beautifully updated kitchen w/ stainless appliances & custom cabinetry w/ generous counter space. Off the kitchen, there’s a half bath and a bonus room—great as an office, playroom, or casual
Welcome to this beautifully maintained 3-bedroom home just moments from vibrant Winchester Center. Ideal for commuters with quick access to I-95 and I-93, this home blends charm, comfort, and convenience. The updated kitchen features quartz countertops and generous cabinetry—perfect for cooking and gathering. Light-filled living spaces offer a warm, welcoming feel throughout. Unwind on the
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
This top-floor beautiful home features a spacious living room and dining room with hardwood floors throughout. The kitchen features stainless steel appliances, gas stove, and an abundance of cabinet space. The two bedrooms provide ample closet space and an adjacent full bath. A bonus room can be an office or a guest room. Two baconies, one open, one closed. Access to the shared garage from the
2-Bedroom apartment in a desirable Winchester neighborhood for rent. Situated at a quiet street, this two-bedroom and one-bathroom in a two-family house setting has a nice floor plan and decent flow. Hardwood floor throughout. It has a spacious eat-in kitchen with a pantry and with stainless appliances, granite counter tops and a side door that leads to the big and bright backyard. Two bright
Interested in learning more about homes in this area?
Reach out to
Darcy Bento,
an experienced agent in this neighborhood.
Average Home Value
Source: Public Records
Property Mix - Square Feet
This Neighborhood Has More Owners
Demographics
Total Population
4,196
Median Age
43
Population Density
6 ppl/acre
Population under 18
25.8%
On par with the national average
23.8%
Population over 65
17.1%
On par with the national average
19.1%
Finances
Median Household Income
$168,497
Significantly above the national average
$71,702
Average Household Income
$187,882
Education and Workforce
High School Graduates
97.7%
College Graduates
70.1%
Significantly above the national average
34.1%
Advanced Degrees
44%
Significantly above the national average
13.3%
% Population in Labor Force
75.8%
Weather
Annual Precipitation
49''
Average Winter Low Temperature
18°F
Average Summer High Temperature
83°F
Annual Snowfall
20''
Area Factors
Somewhat Bikeable
Bike Score®
32/ 100
Car-Dependent
Walk Score®
12/ 100
Source: Walk Score
Source: Walk Score
Sound Score® measures the noise level of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.
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.
