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Winchester Highlands Homes 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
  • 6 Highland Ave, Winchester, MA 01890
    6 Highland Ave, Winchester, MA 01890
    6 Highland Ave, Winchester, MA 01890
    /31

    $1,500,000

    • 4 Beds
    • 2.5 Baths
    • 2,506 Sq Ft

    6 Highland Ave, Winchester, MA 01890

    4 BD, 2.5 BA home tucked away from the road for added privacy. Kitchen has spacious dining area for enjoying family meals & entertaining guests. Inviting family room, w/ FP brings warm ambiance & convenient access to the deck, enhancing your indoor-outdoor living experience. Large living/dining area w/ backyard views is a versatile space w/ an open layout make it a welcoming spot. Convenience is

    Peter Rooney Compass

    6 Highland Ave, 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
  • 60 Harvard St, Winchester, MA 01890
    60 Harvard St, Winchester, MA 01890
    60 Harvard St, Winchester, MA 01890
    /16

    $1,225,000

    • 4 Beds
    • 3 Baths
    • 1,860 Sq Ft

    60 Harvard St, Winchester, MA 01890

    Exceptional investment opportunity. Located in the heart of desirable Winchester, this multi family property offers a rare opportunity to own a ready to renovate vacant building with incredible potential. Two 1 bedroom, 1 bathroom units and 1 two bedroom unit. This property is primed for a full renovation. Perfect for investors, end users or travellers looking for their own pied-a'-terre, while

    Mark Krasnyansky eXp Realty

    60 Harvard 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

    • 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
  • 20 Grayson Rd, Winchester, MA 01890
    20 Grayson Rd, Winchester, MA 01890
    20 Grayson Rd, Winchester, MA 01890
    /36

    $1,899,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,825 Sq Ft

    20 Grayson Rd, Winchester, MA 01890

    Another Tree Top Group masterpiece—where natural light, luxury finishes, & thoughtful design come together in perfect harmony. This 5-bed, 4.5-bath new construction home boasts 9+ ft ceilings, exceptional light fixtures, and a stunning waterfall center island that anchors the designer kitchen w/ custom cabinetry that extends to the ceiling. Custom built-ins & storage throughout. A sleek linear

    Monte Marrocco Coldwell Banker Realty - Lexington

    20 Grayson Rd, Winchester, MA 01890
Massachusetts 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 very car-dependent and somewhat bikeable. Winchester Highlands is a suburban neighborhood with a crime score of 2, 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 2 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 $479,900. If you put a 20% down payment of $96,000 and had a 30-year fixed mortgage with an interest rate of 6.74%, your estimated principal and interest payment would be $2,490 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $107K a year to afford the median home price in Winchester Highlands. 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 4.4.
  • St. Patrick Elementary School has a student teacher ratio of 13:1 and an average review score of 5.0.
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, Walnut Hill, Haywardville, Downtown Woburn and The Flats.

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
$561
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%
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