Winchester Highlands
Suburban Neighborhood in Winchester, Massachusetts
Middlesex County 01890, 02155, 02180
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.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.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.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.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.



Agents Specializing in this Area
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Darcy Bento
Bento Real Estate Group, Inc.
(857) 837-6383
65 Total Sales
1 in Winchester Highlands
$880,000 Price
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Kelly Dimbat
Responds QuicklyLamacchia Realty, Inc.
(781) 557-4147
136 Total Sales
1 in Winchester Highlands
$769,000 Price
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Karen R. Brown
Responds QuicklyRE/MAX Innovative Properties
(351) 208-1975
116 Total Sales
1 in Winchester Highlands
$980,000 Price
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Alexander Koziakov
Responds QuicklyCompass
(781) 417-5576
79 Total Sales
1 in Winchester Highlands
$774,000 Price
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Warren Cormier
Responds QuicklyLamacchia Realty, Inc.
(781) 805-3022
52 Total Sales
1 in Winchester Highlands
$810,000 Price
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Nannette Shanahan
Responds QuicklyBetter Homes and Gardens Real Estate - The Shanahan Group
(351) 666-6458
39 Total Sales
1 in Winchester Highlands
$1,252,000 Price
Schools
Interested in learning more about homes in this area? Reach out to
, an experienced agent in this neighborhood.Parks in this Area
Transit
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 $1,350,000, up 13% from the median home sale price over the previous 12 months.
Housing Trends
Neighborhood Facts
Open Houses
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Saturday, Jun 1411am - 12:30pm
Distribution of Home Values
Homes for Sale
Homes for Rent
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Property Mix - Square Feet
This Neighborhood Has More Owners
Demographics
Finances
Education and Workforce
Weather
Area Factors
Somewhat Bikeable
Bike Score®
Car-Dependent
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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