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Winchester Highlands Houses for Sale

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  • 166 Forest St, Winchester, MA 01890
    166 Forest St, Winchester, MA 01890
    166 Forest St, Winchester, MA 01890
    /4

    $1,890,000

    • 5 Beds
    • 5 Baths
    • 3,301 Sq Ft

    166 Forest St, Winchester, MA 01890

    Tucked away on a picturesque street, this beautifully maintained Colonial offers 4 levels of thoughtfully designed living space. The open-concept main floor features a sun-filled living room with vaulted ceilings, skylights, gas fireplace, and an adjacent dining area. The gourmet kitchen boasts stainless steel appliances, breakfast bar, built-in desk, and sliders leading to a private deck. A

    Ning Sun United Real Estate, LLC

    166 Forest St, Winchester, MA 01890
  • 162 Forest St, Winchester, MA 01890
    162 Forest St, Winchester, MA 01890
    162 Forest St, Winchester, MA 01890
    /33

    $1,250,000

    • 4 Beds
    • 1.5 Baths
    • 1,900 Sq Ft

    162 Forest St, Winchester, MA 01890

    Located in the popular Winchester Highlands neighborhood with Elegance and Stature is this 4 bed, 1.5 bath Center Entrance Colonial with 2 car garage, minutes to I-93 and Winchester Center with boutique shops, cafes, restaurants, and newly renovated MBTA Station. Welcoming front vestibule opens to sprawling front-to-back living room with wood burning fireplace and attached sunroom. Formal dining

    Paul Cirignano The Synergy Group

    162 Forest St, Winchester, MA 01890
  • 14 Grant Rd, Winchester, MA 01890
    14 Grant Rd, Winchester, MA 01890
    14 Grant Rd, Winchester, MA 01890
    /42

    $2,499,000 Open Sun 1PM - 2PM

    • 6 Beds
    • 4.5 Baths
    • 4,200 Sq Ft

    14 Grant Rd, Winchester, MA 01890

    Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester’s most desirable neighborhoods. Designed for modern lifestyles, this home features a chef’s kitchen that flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. A sun-drenched 3-season porch expands your living space

    Monte Marrocco Coldwell Banker Realty - Lexington

    14 Grant Rd, Winchester, MA 01890
  • 35 Harvard St, Winchester, MA 01890
    35 Harvard St, Winchester, MA 01890
    35 Harvard St, Winchester, MA 01890
    /36

    $1,349,900 Open Sun 11:30AM - 1PM

    • 5 Beds
    • 2 Baths
    • 1,706 Sq Ft

    35 Harvard St, Winchester, MA 01890

    Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well

    Joanne Mulkerin J. Mulkerin Realty

    35 Harvard St, Winchester, MA 01890
  • 147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, Winchester, MA 01890
    /37

    $1,299,000

    • 3 Beds
    • 2 Baths
    • 1,884 Sq Ft

    147 Highland Ave, Winchester, MA 01890

    Call for a private showing anytime! Discover this charming renovated 3 bed 2 bath home with close proximity to the Fells trails & Winchester town center including schools, train to Boston, restaurants, shops & all the town has to offer!! Beautifully renovated & lovingly maintained, this great home welcomes you w/ a spacious living room w fplc that flows seamlessly into a sun-drenched updated

    Kim Covino Compass

    147 Highland Ave, Winchester, MA 01890
  • 19 Laurel Hill Ln, Winchester, MA 01890
    19 Laurel Hill Ln, Winchester, MA 01890
    /2

    $2,550,000

    • 5 Beds
    • 4.5 Baths
    • 3,800 Sq Ft

    19 Laurel Hill Ln, Winchester, MA 01890

    Nestled on a quiet street in one of Winchester’s most coveted neighborhoods, 19 Laurel Hill Lane will offer refined living just minutes from Boston and top-rated schools. This latest Mark Stephen Development project will feature 4 bedrooms and 4.5 bathrooms, including a flexible first-floor suite perfect for a guest room or study. The heart of the home will be a spacious kitchen flowing into a

    Mark Donnellan Advisors Living - Winchester

    19 Laurel Hill Ln, Winchester, MA 01890
Massachusetts Middlesex County Winchester Winchester Highlands

Houses 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

Home Trends in Winchester Highlands, MA

On average, homes in Winchester Highlands, Winchester sell after 174 days on the market compared to the national average of 70 days. The median sale price for homes in Winchester Highlands, Winchester over the last 12 months is $775,000, up 94% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$775,000
Median Single Family Sale Price
$429,900
Median Townhouse Sale Price
$330,000
Average Price Per Sq Ft
$559
Number of Homes for Sale
6
Last 12 months Home Sales
28
Months of Supply
2.60
Median List Price
$479,900
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
94%
How to Buy a Home How to Finance a Home How to Sell a Home

In Winchester Highlands, there are currently 6 houses for sale, offering a variety of options for prospective buyers. With houses ranging from $1,250,000 to $2,550,000, there's something for every budget. As of July, 2025 the median home price in Winchester Highlands, Winchester is $479,900, while the average sale price is $1,686,807, providing insight into local market trends. On average, houses spend 174 days on the market before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options available to suit every lifestyle. Browse properties and houses for sale in Winchester Highlands, Winchester and find the perfect place to call home.

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