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Winchester Highlands Homes for Sale

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  • /42

    $1,350,000

    • 4 Beds
    • 3 Baths
    • 2,690 Sq Ft

    423 Washington St, Winchester, MA 01890

    Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The home offers exceptional curb appeal and privacy with mature evergreens, specialty trees, and an elevated setting. Inside, a central staircase creates a focal point while naturally defining the open concept living and dining rooms, perfect for everyday

    Danielle Fleming MA Properties

    423 Washington St, Winchester, MA 01890
  • /10

    $2,999,000

    • 5 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    5 Forest Cir, Winchester, MA 01890

    New construction currently underway. Estimated completion in approximately Spring/Summer 2027. Set on an impressive 22,629 sq. ft. lot, this beautifully crafted new construction offers exceptional space, thoughtful design, and a peaceful setting with easy access to the Middlesex Fells Reservation and I-93. Designed for today's lifestyle, the main level features a welcoming foyer, elegant living

    Pirani & Wile Group Gibson Sotheby's International Realty

    5 Forest Cir, Winchester, MA 01890
  • /33

    $1,110,000

    $40K PRICE DROP
    • 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.

Winchester Highlands, Winchester, MA Home Prices vs. Nearby Neighborhoods

Winchester Highlands North Main Arlington Heights East Lexington
Median Home Price
$1,399,000
$1,237,450
$1,024,000
$1,358,000
Median Sale Price
$1,425,000
+16% YoY
$1,325,000
-13% YoY
$1,048,411
0% YoY
$1,260,000
-9% YoY
Median Single Family Price
$1,510,000
$1,330,000
$1,221,777
$1,449,000
Median Townhouse Price
$1,350,000
$849,000
$1,025,000
$700,000
Median Condo Price
$919,000
$1,160,000
$757,500
$751,750
Total Active Listings
2 listings
7 listings
21 listings
5 listings
Market Conditions
1 Month of Supply
Seller's Market
5 Months of Supply
Balanced Market
1 Month of Supply
Seller's Market
3 Months of Supply
Seller's Market

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 somewhat dense in population with 6.0 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 24% of residents renting and 76% 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 $1,399,000. If you put a 20% down payment of $279,800 and had a 30-year fixed mortgage with an interest rate of 6.66%, your estimated principal and interest payment would be $7,190 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $308K 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 4.3.
  • St. Patrick Elementary School has an A- Niche grade, a student teacher ratio of 8:1 and an average review score of 4.6.
What are the most popular zip codes in Winchester Highlands, Winchester, MA?
The most popular zip codes in Winchester Highlands, Winchester, MA include 01890, 02180, 01801, 02155 and 02176.
What are the most popular neighborhoods near Winchester Highlands, Winchester, MA?
The most popular neighborhoods near Winchester Highlands, Winchester, MA are Nobility Hill, Haywardville, Walnut Hill, North Main and Downtown Woburn.
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