10

West Side Homes for Sale

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  • 257 High St, Winchester, MA 01890
    257 High St, Winchester, MA 01890
    257 High St, Winchester, MA 01890
    /42

    $3,499,000

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

    $3,600,000 Open Sun 1PM - 3PM

    • 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

    Wei Wang WW Real Estate LLC

    20 Amberwood Dr, Winchester, MA 01890
  • 276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    /38

    $2,350,000 Open Sun 1PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 5,006 Sq Ft

    276 High St, Winchester, MA 01890

    Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

    Kim Covino Compass

    276 High St, Winchester, MA 01890
  • 11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    /42

    $3,799,900

    • 7 Beds
    • 7.5 Baths
    • 7,429 Sq Ft

    11 Viking Rd, Winchester, MA 01890

    Prepare to be captivated by the elegance of 11 Viking Rd. This magnificent home, boasting over 7,000 square feet of luxurious living space, offers an unparalleled opportunity for discerning buyers seeking the ultimate in comfort, style, and sophistication.Step inside and discover a world of meticulous details and thoughtful design. With 7 generously sized bedrooms and 7.5 exquisitely appointed

    The McLaren D'Agostino Team Compass

    11 Viking Rd, Winchester, MA 01890
  • 54 Johnson Rd, Winchester, MA 01890
    54 Johnson Rd, Winchester, MA 01890
    54 Johnson Rd, Winchester, MA 01890
    /42

    $3,699,000 Open Sun 1PM - 2PM

    • 7 Beds
    • 7.5 Baths
    • 7,982 Sq Ft

    54 Johnson Rd, Winchester, MA 01890

    This newly constructed home faces Old Village Dr. & redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master

    Kim Covino Compass

    54 Johnson Rd, Winchester, MA 01890
  • 5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    /40

    $2,199,000

    • 5 Beds
    • 3.5 Baths
    • 6,232 Sq Ft

    5 Azalea Rd, Winchester, MA 01890

    NEW PRICE! RENOVATIONS & UPDATES JUST COMPLETED THROUGHOUT! Pristine Home nestled in Winchester's Sought After West Side Neighborhood and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to New Composite Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials

    Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

    5 Azalea Rd, Winchester, MA 01890
  • 7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    /35

    $1,379,000 Open Sat 11:30AM - 12:30PM

    • 5 Beds
    • 2 Baths
    • 3,033 Sq Ft

    7 Thornberry Rd, Winchester, MA 01890

    Priced to SELL this newly renovated contemporary home, nestled in a highly sought-after West-side neighborhood with surprising space! This 3+ level home boasts 4-5 spacious bedrooms and 2 full stylish baths, this home offers versatile space for multiple home offices, in law/ au-pair space plus comfortable family spaces all great for entertaining. The main level features a beautiful open-concept

    Kim Covino Compass

    7 Thornberry Rd, Winchester, MA 01890
  • 59 Johnson Rd, Winchester, MA 01890
    59 Johnson Rd, Winchester, MA 01890
    59 Johnson Rd, Winchester, MA 01890
    /24

    $1,249,900

    • 3 Beds
    • 2.5 Baths
    • 2,458 Sq Ft

    59 Johnson Rd, Winchester, MA 01890

    Welcome to this stunning updt’d 3-bed, 2.5-bath multi-level home in one of Winchester’s most desirable neighborhoods, just two blocks to Vinson-Owen Elementary! Freshly painted inside&out for a modern, crisp feel, the home offers a perfect blend of style, comfort, convenience. Open layout with a beautiful fireplace, living room, bay windows, and formal dining room lead to a spacious deck and

    Angela Zhang Greatland Real Estate LLC

    59 Johnson Rd, Winchester, MA 01890
  • 4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, Winchester, MA 01890
    /42

    $1,729,000

    • 4 Beds
    • 5 Baths
    • 5,361 Sq Ft

    4 Aricia Ln, Winchester, MA 01890

    Rare 5-car garage on a quiet, tree-lined cul-de-sac in one of Winchester’s most exclusive enclaves! Offering both serene privacy and seamless connectivity, 4 Aricia is perfectly positioned within walking distance to a coveted elementary school and Wright-Locke Farm, and minutes from the commuter rail and Routes 128 & 93. Set on nearly .5 acres of manicured grounds, the home’s exterior is framed

    The McLaren D'Agostino Team Compass

    4 Aricia Ln, Winchester, MA 01890
  • 5 Squire Rd, Winchester, MA 01890
    5 Squire Rd, Winchester, MA 01890
    5 Squire Rd, Winchester, MA 01890
    /40

    $2,000,000 Open Sat 1:30PM - 2:30PM

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

    5 Squire Rd, Winchester, MA 01890

    Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shiplap fireplace, opens to a spacious composite deck. The primary suite is a private retreat with a

    Alina Wang Coldwell Banker Realty - Lexington

    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. 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.
How much do you need to make to afford a house in West Side?
The median home price in West Side is $1,697,000. If you put a 20% down payment of $339,400 and had a 30-year fixed mortgage with an interest rate of 6.26%, your estimated principal and interest payment would be $8,370 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $359K a year to afford the median home price in West Side. 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, 02474, 02420 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, Arlington Heights, Countryside and North Main.

Home Trends in West Side, MA

On average, homes in West Side, Winchester sell after 26 days on the market compared to the national average of 52 days. The median sale price for homes in West Side, Winchester over the last 12 months is $1,589,000, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,589,000
Median Single Family Sale Price
$1,771,049
Median 2 Bedroom Sale Price
$1,070,000
Average Price Per Sq Ft
$500
Number of Homes for Sale
10
Last 12 months Home Sales
52
Months of Supply
2.30
Median List Price
$1,697,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
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