5

West Side Homes for Sale

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

    $3,600,000

    • 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
  • 10 Viking Rd, Winchester, MA 01890
    10 Viking Rd, Winchester, MA 01890
    10 Viking Rd, Winchester, MA 01890
    /42

    $2,595,000

    • 4 Beds
    • 4 Baths
    • 5,674 Sq Ft

    10 Viking Rd, Winchester, MA 01890

    Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas—ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4

    Anne Spry Barrett Sotheby's International Realty

    10 Viking Rd, Winchester, MA 01890
  • 15 Mayflower Rd, Winchester, MA 01890
    15 Mayflower Rd, Winchester, MA 01890
    15 Mayflower Rd, Winchester, MA 01890
    /39

    $3,425,000 Open Sat 11AM - 12:30PM

    • 7 Beds
    • 7.5 Baths
    • 7,226 Sq Ft

    15 Mayflower Rd, Winchester, MA 01890

    Discover a stunningly reimagined home nestled in one of Winchester’s most sought after neighborhoods—an exceptional opportunity to own a beautifully crafted, completely transformed residence. Expanded and rebuilt with intention, 15 Mayflower delivers the space, layout, and flexibility today’s lifestyle demands, with a thoughtful floor plan that balances open concept living and well defined

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    15 Mayflower Rd, Winchester, MA 01890
  • 10 Hawthorne Rd, Winchester, MA 01890
    10 Hawthorne Rd, Winchester, MA 01890
    10 Hawthorne Rd, Winchester, MA 01890
    /34

    $1,998,000 Open Wed 4:30PM - 6PM

    • 5 Beds
    • 6 Baths
    • 3,191 Sq Ft

    10 Hawthorne Rd, Winchester, MA 01890

    Spectacular 5 bedroom home set on an impressive fenced lot in a picturesque neighborhood setting! The interior underwent a major renovation in 2016, including a new dormer, updated systems, + upgraded finishes throughout. The bright, updated kitchen features honed countertops, a tiered island, separate refrigerator + freezer units, recessed lighting, and an open flow to the dining area.

    Susan Kadilak Fiv Realty Co.

    10 Hawthorne Rd, Winchester, MA 01890
  • 5 Squire Rd, Winchester, MA 01890
    5 Squire Rd, Winchester, MA 01890
    5 Squire Rd, Winchester, MA 01890
    /42

    $1,899,000 Open Thu 5:30PM - 6:30PM

    • 6 Beds
    • 3.5 Baths
    • 4,696 Sq Ft

    5 Squire Rd, Winchester, MA 01890

    Designed for modern living and effortless entertaining, this home’s exceptional open-concept main level sets it apart from the moment you enter. Anchored by a chef’s kitchen with stone countertops, an oversized island, and premium Viking appliances, the space flows seamlessly into the family room with a striking shiplap fireplace and direct access to a spacious composite deck. Set in a desirable

    Andersen Group Realty Keller Williams Realty Boston Northwest

    5 Squire Rd, 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 $1,749,900. If you put a 20% down payment of $350,000 and had a 30-year fixed mortgage with an interest rate of 6.31%, your estimated principal and interest payment would be $8,670 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $372K 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 24 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 $1,656,000, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,656,000
Median Single Family Sale Price
$1,725,000
Median 2 Bedroom Sale Price
$1,070,000
Average Price Per Sq Ft
$504
Number of Homes for Sale
4
Last 12 months Home Sales
51
Months of Supply
0.90
Median List Price
$1,749,900
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
0%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group