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Winchester Highlands Homes for Sale

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  • /26

    $1,300,000

    Open Fri 11:30AM - 12:30PM
    • 4 Beds
    • 2.5 Baths
    • 2,666 Sq Ft

    465 Washington St Unit 467, Winchester, MA 01890

    Refined, sophisticated, and designed for effortless modern living, this exceptional 4 bedroom, 3 bath townhouse blends expansive open-concept spaces with thoughtfully curated luxury finishes throughout. Sunlight pours into the main living area where a designer chef’s kitchen anchors the home with oversized island seating, premium appliances, and seamless flow for entertaining and everyday life

    Nancy Pallotta Gibson Sotheby's International Realty

    465 Washington St Unit 467, Winchester, MA 01890
  • /42

    $2,495,000

    Open Thu 4:30PM - 5:30PM
    • 6 Beds
    • 3.5 Baths
    • 5,121 Sq Ft

    112 Highland Ave, Winchester, MA 01890

    Timeless Victorian grandeur meets modern living in this iconic Winchester home situated on the corner of Wilson Street w/ easy access to Fells trails! This recently renovated sun-filled 6 BR 4 BA home offers nearly 5000 ft.2 of beautifully scaled living spaces filled w/ extraordinary architectural charm & elegant details featuring a brand new state of the art gorgeous kitchen w/ Wolf & Sub Zero

    Kim Covino Compass

    112 Highland Ave, Winchester, MA 01890
  • /33

    $1,150,000

    • 5 Beds
    • 3 Baths
    • 2,186 Sq Ft

    63-65 Harvard St, Winchester, MA 01890

    Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home.

    Beth Sager Group Keller Williams Realty Boston Northwest

    63-65 Harvard St, Winchester, MA 01890

Why Live in 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 somewhat walkable and a biker's paradise with minimal transit options. Winchester Highlands is a suburban neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Winchester Highlands has 7 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 1 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 $1,299,950. If you put a 20% down payment of $260,000 and had a 30-year fixed mortgage with an interest rate of 6.37%, your estimated principal and interest payment would be $6,480 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $278K a year to afford the median home price in Winchester Highlands. Learn how much home you can afford with our Home Affordability Calculator. 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 4.1.
  • St. Patrick Elementary School has an A- Niche grade, a student teacher ratio of 13:1 and an average review score of 4.2.
What are the most popular zip codes in Winchester Highlands, Winchester, MA?
The most popular zip codes in Winchester Highlands, Winchester, MA include 01890, 01801, 02180, 02155 and 02176.
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 The Flats.
Are home prices dropping in Winchester Highlands?
Yes, home prices in Winchester Highlands are down 4% in the last 12 months.

Home Trends in Winchester Highlands, MA

Housing Trends

Median Sale Price
$1,250,000
Median Single Family Sale Price
$1,290,000
Median Townhouse Sale Price
$1,300,000
Average Price Per Sq Ft
$592
Number of Homes for Sale
2
Last 12 months Home Sales
37
Months of Supply
0.60
Median List Price
$1,299,950
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
3%
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