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Winchester Highlands Homes for Sale

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  • /42

    $2,599,000 Open Sat 11:30AM - 12:30PM

    • 4 Beds
    • 4.5 Baths
    • 5,501 Sq Ft

    15 Churchill Rd, Winchester, MA 01890

    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

    15 Churchill Rd, Winchester, MA 01890
  • /42

    $1,199,000 Open Fri 11:30AM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 1,906 Sq Ft

    44 Forest St, Winchester, MA 01890

    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

    44 Forest St, Winchester, MA 01890
  • /42

    $1,499,000 Open Fri 5:30PM - 6:30PM

    • 3 Beds
    • 4 Baths
    • 3,351 Sq Ft

    34 Fells Rd, Winchester, MA 01890

    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

    34 Fells Rd, Winchester, MA 01890

About Winchester Highlands

Winchester Highlands is a neighborhood known for its diverse and grand homes, ranging from late 19th-century builds to contemporary houses, featuring styles such as ranches, colonials, and two-family homes. The area is part of one of the best public school districts in the state, with highly rated institutions like Muraco Elementary, McCall Middle, and Winchester High School, all offering robust academic and extracurricular programs. The neighborhood is safer than the national average, providing a secure environment for residents. Outdoor enthusiasts will appreciate the proximity to the 2,200-acre Middlesex Fells Reservation, which features over 100 miles of trails, and the Tri-Community Greenway, a paved path for walking, jogging, and biking. Winchester Highlands also has local dining options like Eighty Eight Cafe and The Gingerbread Construction Co., with more restaurants and a Stop & Shop located in nearby Winchester Center. The neighborhood is well-connected, with the Massachusetts Bay Transportation Authority commuter rail at Winchester Center offering a roughly one-hour ride to Boston, and Interstate 93 providing a convenient 11-mile drive to the city. Additionally, Winchester Hospital, a 229-bed medical center, is located within the neighborhood. Residents can enjoy community events such as Winchester Town Day, which features a block party, street fair, and fireworks each June.

Frequently Asked Questions

Is Winchester Highlands a good place to live?
Winchester Highlands is a good place to live. Winchester Highlands is considered very car-dependent and somewhat bikeable. Winchester Highlands is a suburban neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. Winchester Highlands has 6 parks for recreational activities. It is fairly sparse in population with 5.2 people per acre and a median age of 43. The average household income is $187,882 which is above the national average. College graduates make up 70.1% of residents. A majority of residents in Winchester Highlands are home owners, with 23.9% of residents renting and 76.1% of residents owning their home. A local real estate agent serving Winchester Highlands can help you decide if this neighborhood is the right one for you. Learn more on our Winchester Highlands neighborhood guide.
Is Winchester Highlands, MA a safe neighborhood?
Winchester Highlands, MA is safer than the average neighborhood in the United States. It received a crime score of 2 out of 10.
How much do you need to make to afford a house in Winchester Highlands?
The median home price in Winchester Highlands is $1,249,000. If you put a 20% down payment of $249,800 and had a 30-year fixed mortgage with an interest rate of 6.83%, your estimated principal and interest payment would be $6,530 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $280K a year to afford the median home price in Winchester Highlands. The average household income in Winchester Highlands is $188K.
What are the best public schools in Winchester Highlands?
The best public schools that serve Winchester Highlands are:
What are the best private schools in Winchester Highlands?
The best private schools that serve Winchester Highlands are:
  • Greater Boston Academy has an A+ Niche grade, a student teacher ratio of 15:1 and an average review score of 4.9.
  • Acera School has an A- Niche grade, a student teacher ratio of 4:1 and an average review score of 4.4.
  • St. Patrick Elementary School has a student teacher ratio of 13:1 and an average review score of 5.0.
What are the most popular zip codes in Winchester Highlands, Winchester, MA?
The most popular zip codes in Winchester Highlands, Winchester, MA include 02127, 02128, 02116, 02118 and 02135.
What are the most popular neighborhoods near Winchester Highlands, Winchester, MA?
The most popular neighborhoods near Winchester Highlands, Winchester, MA are Walnut Hill, Nobility Hill, Haywardville, North Main and Downtown Woburn.

Home Trends in Winchester Highlands, MA

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%
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