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Winchester Highlands Homes for Sale

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  • 465 Washington St Unit 467, Winchester, MA 01890
    465 Washington St Unit 467, Winchester, MA 01890
    465 Washington St Unit 467, Winchester, MA 01890
    /26

    $1,300,000

    Open Sat 1PM - 2:30PM
    • 4 Beds
    • 2.5 Baths
    • 2,666 Sq Ft

    465 Washington St Unit 467, Winchester, MA 01890

    Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is

    Nancy Pallotta Gibson Sotheby's International Realty

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

    $1,375,000

    Open Sat 12:30PM - 2PM
    • 6 Beds
    • 2 Baths
    • 5,047 Sq Ft

    303 Washington St, Winchester, MA 01890

    Pleased to present this meticulously maintained and nicely updated two family home in the heart of Winchester! Each spacious unit is one level & features seven rooms including 3 large bedrooms, living room w fplc, dining room w/wainscoting, sunroom, kitchen & updated baths. The generously sized flowing rooms are highlighted by high ceilings, oversized windows, beautiful original woodwork and

    Kim Covino Compass

    303 Washington St, Winchester, MA 01890
  • 18 Grayson Rd, Winchester, MA 01890
    18 Grayson Rd, Winchester, MA 01890
    18 Grayson Rd, Winchester, MA 01890
    /37

    $1,699,000

    Open Sat 11:30AM - 12:30PM
    • 3 Beds
    • 2.5 Baths
    • 2,992 Sq Ft

    18 Grayson Rd, Winchester, MA 01890

    OPEN HOUSES ONLY Discover this meticulously maintained 3 bed colonial just steps from Muraco Elementary and the Middlesex Fells. Rich hardwood floors flow through the formal dining room into the oversized, fireplaced living room ideal for entertaining. The beautifully appointed kitchen features a sunny breakfast area with access to a private deck. Upstairs, you'll find 2 spacious bedrooms and a

    Andersen Group Realty Keller Williams Realty Boston Northwest

    18 Grayson Rd, 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
  • 55 Brookside Ave, Winchester, MA 01890
    55 Brookside Ave, Winchester, MA 01890
    55 Brookside Ave, Winchester, MA 01890
    /14

    $799,000

    • 3 Beds
    • 1 Bath
    • 1,245 Sq Ft

    55 Brookside Ave, Winchester, MA 01890

    This affordable Colonial in the highly sought-after Muraco School district is brimming with potential and ready for your personal vision. An ideal starter home, it features a spacious backyard overlooking Davidson Park, creating a private and peaceful setting. Conveniently located near parks, bike trails, and public transportation, this home offers an exceptional combination of value, location,

    Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

    55 Brookside Ave, 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

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 $1,299,000. If you put a 20% down payment of $259,800 and had a 30-year fixed mortgage with an interest rate of 6.53%, your estimated principal and interest payment would be $6,590 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $282K 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, 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.
Are home prices dropping in Winchester Highlands?
Yes, home prices in Winchester Highlands are down 2% in the last 12 months.

Home Trends in Winchester Highlands, MA

On average, homes in Winchester Highlands, Winchester sell after 19 days on the market compared to the national average of 58 days. The median sale price for homes in Winchester Highlands, Winchester over the last 12 months is $1,250,000, down 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,250,000
Median Single Family Sale Price
$1,265,000
Median Townhouse Sale Price
$1,300,000
Average Price Per Sq Ft
$597
Number of Homes for Sale
3
Last 12 months Home Sales
39
Months of Supply
0.90
Median List Price
$1,299,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-3%
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