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Winchester Highlands

Winchester Highlands

Suburban Neighborhood in Winchester, Massachusetts

Middlesex County 01890, 02155, 02180

$1,439,855 Average Value
$553 Average Price per Sq Ft
3 Homes 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.
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.
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.
Rows of front yards stretch out to the Winchester Highlands' street.
You can find traditional colonial homes in Winchester Highlands.
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.
Winchester High School maintains an A+ rating on Niche.
McCall Middle School In Winchester has 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.
Residents of Winchester Highlands enjoy the changing color leaves at Middlesex Fells Trails.
The Tri-Community Greenway runs through Davidson Park in Winchester, MA.
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 up all your daily needs from Winchester Drug near Winchester Highlands.
Pick out your favorite pastry at the Gingerbread Construction Co. in 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.
Commuters have the accessibility of MBTA in Winchester Highlands.
The town of Winchester Highlands offers a slow and peaceful lifestyle.
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.

Wayne Epps Jr.
Written By
Wayne Epps Jr.
Anhella Sanchez
Photography Contributed By
Anhella Sanchez
Edward Pokoj
Video By
Edward Pokoj

Agents Specializing in this Area

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Schools

Source:
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 Kelly Dimbat, an experienced agent in this neighborhood.

Parks in this Area

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

Demographics and Home Trends

Home Trends

Median Price (12 Mo)
$1,205,000
Median Single Family Price
$1,437,500
Median Townhouse Price
$1,210,000
Median 1 Bedroom Price
$455,000
Average Price Per Sq Ft
$553
Number of Homes for Sale
3
Last 12 months Home Sales
28
Months of Supply
1.30
Median List Price
$1,249,000
Median Discount From 1st List Price
0%
Median Home Sale Price YoY Change
2%

Home Facts

Number of Homes in Neighborhood
1,065
Median Year Built
1940
Avg. Single Family Home Size Sq Ft
2,429
Above the national average
1,935
Average Townhouse Size Sq Ft
2,489
Average 2 Bedroom Size Sq Ft
1,148
Average 1 Bedroom Size Sq Ft
778
Median Lot Size Sq Ft
10,018

Open Houses

  • Saturday, Apr 26
    11:30am - 12:30pm

    15 Churchill Rd, Winchester, MA 01890

    $2,599,000

    • 4 Beds
    • 4.5 Baths
    • 5,501 Sq Ft
    • 15 Churchill Rd
    • New 1 day ago

    Indulge in modern luxury with this stunning home, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor

    Kim Covino Compass

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  • Friday, Apr 25
    11:30am - 1pm

    44 Forest St, Winchester, MA 01890

    $1,199,000

    • 3 Beds
    • 1.5 Baths
    • 1,906 Sq Ft
    • 44 Forest St
    • New 2 days ago

    This charming home is move-in ready and situated on a beautiful fenced in level lot close to parks, the bike path, Muraco school & more! The interior of the home is flooded with sunlight & period details featuring open airy spaces and generously sized rooms that flow throughout the home, making each room easily accessible and enjoyable. The main floor has a lovely living room with gas fireplace,

    Kim Covino Compass

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  • Friday, Apr 25
    5:30 - 6:30pm

    34 Fells Rd, Winchester, MA 01890

    $1,499,000

    • 3 Beds
    • 4 Baths
    • 3,351 Sq Ft
    • 34 Fells Rd
    • New 24 days ago

    Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from the scenic Middlesex Fells Conservation Area, you'll have miles of trails for outdoor exploration right at your doorstep. With a commuter-friendly location, this home is ideal for those seeking both tranquility and convenience. A welcoming

    Andersen Group Realty Keller Williams Realty Boston Northwest

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Distribution of Home Values

Source: Public Records

Homes for Rent

Interested in learning more about homes in this area? Reach out to Kelly Dimbat, 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®

28 / 100

Car-Dependent

Walk Score®

6 / 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.

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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.
NEIGHBORHOOD
Winchester Highlands