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Winchester Highlands Homes for Sale

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  • 117 Highland Ave, Winchester, MA 01890
    117 Highland Ave, Winchester, MA 01890
    117 Highland Ave, Winchester, MA 01890
    /40

    $1,725,000

    • 5 Beds
    • 3.5 Baths
    • 3,722 Sq Ft

    117 Highland Ave, Winchester, MA 01890

    Classic curb appeal abounds at this expansive five-bedroom colonial in the desirable Winchester Highlands neighborhood. The sun-filled first floor features a gracious floor plan with a thoughtfully designed eat-in kitchen showcasing premium appliances including a Sub-Zero refrigerator and Fisher & Paykel DishDrawer. A dining room, living room with wood-burning fireplace, office, mudroom and

    Dara Singleton Better Homes and Gardens Real Estate - The Shanahan Group

    117 Highland Ave, Winchester, MA 01890
  • 423 Washington St, Winchester, MA 01890
    423 Washington St, Winchester, MA 01890
    423 Washington St, Winchester, MA 01890
    /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 inviting living room is enhanced by a large bay of windows and seamlessly connects with the dining room featuring classic wainscoting, and a decorative fireplace. The thoughtfully updated kitchen offers granite countertops, SS appliances, a breakfast

    Danielle Fleming MA Properties

    423 Washington St, Winchester, MA 01890
  • 63-65 Harvard St, Winchester, MA 01890
    63-65 Harvard St, Winchester, MA 01890
    63-65 Harvard St, 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
  • 9 Brookside Place, Winchester, MA 01890
    9 Brookside Place, Winchester, MA 01890
    9 Brookside Place, Winchester, MA 01890
    /41

    $1,899,000

    • 4 Beds
    • 2.5 Baths
    • 3,091 Sq Ft

    9 Brookside Place, Winchester, MA 01890

    This completely remodeled home is nestled on a dead end street off Brookside Road, offering a serene/ natural setting with unmatched privacy. This home offers 4 bedrooms, and 2.5 baths with three spacious finished levels. The completely reimagined open concept main floor features a stunning kitchen open to dining area and large family room, plus a separate living room, mudroom, half bath and

    Kim Covino Compass

    9 Brookside Place, Winchester, MA 01890
Massachusetts Middlesex County Winchester Winchester Highlands

Real Estate & Homes for Sale in Winchester Highlands, Winchester

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.
Learn more about living in Winchester Highlands

Winchester Highlands Home Prices vs. Nearby Winchester, MA Neighborhoods

Winchester Highlands North Main Arlington Heights Thompsonville
Median Home Price
$1,319,450
$1,269,900
$995,000
$1,049,900
Median Sale Price
$1,280,000
-2% YoY
$1,280,000
-19% YoY
$1,029,000
-2% YoY
$1,834,500
+5% YoY
Median Single Family Price
$1,340,000
$1,300,000
$1,205,000
$1,880,000
Median Townhouse Price
$1,350,000
$1,149,000
$990,000
$1,775,000
Median Condo Price
$919,000
$1,138,500
$765,000
$734,500
Total Active Listings
3
7
27
23
Market Conditions
1 Months of Supply
Seller's Market
5 Months of Supply
Balanced Market
1 Months of Supply
Seller's Market
4 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 $1,319,450. If you put a 20% down payment of $263,900 and had a 30-year fixed mortgage with an interest rate of 6.49%, your estimated principal and interest payment would be $6,660 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $285K 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 4.2.
  • 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 02148.
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 The Flats.
Are home prices dropping in Winchester Highlands?
Yes, home prices in Winchester Highlands are down 2% in the last 12 months.
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