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West Side Homes for Sale

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  • 20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    /36

    $3,600,000 Open Sun 12PM - 1:30PM

    • 6 Beds
    • 7 Baths
    • 8,866 Sq Ft

    20 Amberwood Dr, Winchester, MA 01890

    Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador

    Agent Photo

    Wei Wang

    WW Real Estate LLC

    (781) 678-8050

    20 Amberwood Dr, Winchester, MA 01890
  • 7 Trinity Rd, Winchester, MA 01890
    7 Trinity Rd, Winchester, MA 01890
    7 Trinity Rd, Winchester, MA 01890
    /42

    $1,188,888 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 2,130 Sq Ft

    7 Trinity Rd, Winchester, MA 01890

    Welcome to 7 Trinity Road, a warm & inviting split level home tucked away on a quiet side street in sought after Winchester. From the moment you step inside, the home feels welcoming & comfortable, offering 3 bed & 2.5 baths with a layout that easily supports both everyday living & entertaining. Your foyer provides a convenient place to arrive home, with direct access to the attached garage. The

    Gayle Winters Compass

    7 Trinity Rd, Winchester, MA 01890
  • 16 Ridge St, Winchester, MA 01890
    16 Ridge St, Winchester, MA 01890
    16 Ridge St, Winchester, MA 01890
    /42

    $1,149,000 Open Sat 11:30AM - 12:30PM

    • 3 Beds
    • 2.5 Baths
    • 1,844 Sq Ft

    16 Ridge St, Winchester, MA 01890

    27,000 SF lot!!! Set far back from the street~ Don't miss this opportunity! Whether looking to lightly update/ expand or completely renovate; this well maintained 3 bedroom split entry home with a stunning oversized private yard offers tremendous potential! The first floor is spacious with large sunny rooms incl. a generously sized living room with picture window & wood burning fireplace, a

    Kim Covino Compass

    16 Ridge St, Winchester, MA 01890
  • 26 Berkshire Dr, Winchester, MA 01890
    26 Berkshire Dr, Winchester, MA 01890
    26 Berkshire Dr, Winchester, MA 01890
    /41

    $1,460,000

    • 3 Beds
    • 2.5 Baths
    • 2,316 Sq Ft

    26 Berkshire Dr, Winchester, MA 01890

    Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is

    DANIEL BEIRNE OpenDoor Brokerage LLC

    26 Berkshire Dr, Winchester, MA 01890
  • 257 High St, Winchester, MA 01890
    257 High St, Winchester, MA 01890
    257 High St, Winchester, MA 01890
    /42

    $3,299,000

    • 5 Beds
    • 7 Baths
    • 7,101 Sq Ft

    257 High St, Winchester, MA 01890

    Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck,

    Kim Covino Compass

    257 High St, Winchester, MA 01890
  • 139 High St, Winchester, MA 01890
    139 High St, Winchester, MA 01890
    139 High St, Winchester, MA 01890
    /24

    $969,000 Open Sat 12PM - 1:30PM

    • 3 Beds
    • 1.5 Baths
    • 1,302 Sq Ft

    139 High St, Winchester, MA 01890

    This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to

    Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

    139 High St, Winchester, MA 01890
Massachusetts Middlesex County Winchester West Side

Real Estate & Homes for Sale in West Side, Winchester

Why Live in West Side
The West Side neighborhood in Winchester offers a blend of early- to mid-20th-century architecture, with homes ranging from 1920s and 1930s Colonials to midcentury Cape Cods, ranch-styles, split-levels, and more recent Modern Traditional builds from 2015 to 2024. Two-unit townhouses are also present on the south side. The area is characterized by large front and back lawns, wooded lots, and winding suburban streets without sidewalks. Residents enjoy proximity to natural features like Mount Pisgah and Whipple Hill, which offer hiking trails and off-leash areas for dogs. The Winchester Country Club provides an 18-hole golf course, while Upper Mystic Lake is a spot for fishing. The Minuteman Commuter Bikeway offers a flat, 9-mile trail for cyclists. Essential shopping is accessible with Whole Foods 3 miles away, and Market Basket and H-Mart 4 miles north in Burlington. The Burlington Mall, less than 5 miles away, features over 185 retailers and restaurants. Downtown Winchester is known for its boutiques and dining options. Community events, such as Spirit Weekend and activities at the Arthur Griffin Photography Museum, foster a strong local spirit. Route 3 and Interstate 95 provide connectivity, with Wedgemere train station offering a 20-minute ride to Boston's North Station. Logan International Airport is about 14 miles southeast. The neighborhood is served by highly rated schools, including Vinson-Owen Elementary, McCall Middle, Winchester High, and Lexington Christian Academy. The crime rate in the area is lower than the national average, contributing to a sense of security for residents.
Learn more about living in West Side

Frequently Asked Questions

Is West Side a good place to live?
West Side is a good place to live. West Side is considered very car-dependent and somewhat bikeable. West Side is a suburban neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. West Side has 7 parks for recreational activities. It is somewhat dense in population with 9.4 people per acre and a median age of 46. The average household income is $235,217 which is above the national average. College graduates make up 83.1% of residents. A majority of residents in West Side are home owners, with 4.4% of residents renting and 95.6% of residents owning their home. A local real estate agent serving West Side can help you decide if this neighborhood is the right one for you. Learn more on our West Side neighborhood guide.
Is West Side, MA a safe neighborhood?
West Side, 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 West Side?
The median home price in West Side is $1,712,000. If you put a 20% down payment of $342,400 and had a 30-year fixed mortgage with an interest rate of 6.21%, your estimated principal and interest payment would be $8,400 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $360K a year to afford the median home price in West Side. Learn how much home you can afford with our Home Affordability Calculator. The average household income in West Side is $235K.
What are the best public schools in West Side?
The best public schools that serve West Side are:
What are the best private schools in West Side?
The best private schools that serve West Side are:
What are the most popular zip codes in West Side, Winchester, MA?
The most popular zip codes in West Side, Winchester, MA include 01890, 01801, 02420, 02474 and 02476.
What are the most popular neighborhoods near West Side, Winchester, MA?
The most popular neighborhoods near West Side, Winchester, MA are The Flats, Shakerhill, Countryside, Arlington Heights and North Main.

Home Trends in West Side, MA

On average, homes in West Side, Winchester sell after 23 days on the market compared to the national average of 53 days. The median sale price for homes in West Side, Winchester over the last 12 months is $1,665,500, up 11% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,665,500
Median Single Family Sale Price
$1,667,250
Median 2 Bedroom Sale Price
$1,070,000
Average Price Per Sq Ft
$521
Number of Homes for Sale
6
Last 12 months Home Sales
50
Months of Supply
1.40
Median List Price
$1,712,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
11%
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