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West Side Homes for Sale

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  • 276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    /38

    $2,350,000

    • 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
  • 17 Wagon Wheel Rd, Winchester, MA 01890
    17 Wagon Wheel Rd, Winchester, MA 01890
    17 Wagon Wheel Rd, Winchester, MA 01890
    /42

    $2,349,900 Open Sat 12PM - 1:30PM

    • 5 Beds
    • 5 Baths
    • 3,940 Sq Ft

    17 Wagon Wheel Rd, Winchester, MA 01890

    Experience breathtaking Boston skyline views from nearly every room in this exquisitely maintained dream home—your own private oasis of serenity and style. Thoughtfully expanded in 2020, it features a new en-suite with a private bath and a dramatically enlarged, open-concept kitchen ideal for entertaining. With 5 bedrooms and 5 beautifully appointed baths—including four en-suites—this home blends

    Yifei Wang Dreamega International Realty LLC

    17 Wagon Wheel Rd, Winchester, MA 01890
  • 5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    /40

    $2,299,000

    • 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
  • 10 Blossom Hill Rd, Winchester, MA 01890
    10 Blossom Hill Rd, Winchester, MA 01890
    10 Blossom Hill Rd, Winchester, MA 01890
    /42

    $1,688,888

    • 4 Beds
    • 2 Baths
    • 3,838 Sq Ft

    10 Blossom Hill Rd, Winchester, MA 01890

    Welcome to 10 Blossom Hill Road. Tucked away in a cozy and desirable West Side Winchester neighborhood, this enchanting storybook home is full of warmth, charm, and heart. Here you will find a lovingly cared-for 4-bedroom home with a guest or in-law suite offering wonderful flexibility to suit your needs. Inside, you’ll find light-filled spaces, thoughtful updates, and timeless character that

    Stephen DeConto Cameron Real Estate Group

    10 Blossom Hill Rd, Winchester, MA 01890
  • 5 Thornton Rd, Winchester, MA 01890
    5 Thornton Rd, Winchester, MA 01890
    5 Thornton Rd, Winchester, MA 01890
    /38

    $1,650,000

    • 4 Beds
    • 3.5 Baths
    • 2,755 Sq Ft

    5 Thornton Rd, Winchester, MA 01890

    This stately home near the Flats blends original character with modern-day living, 8' ceilings and awaits your personal touches. The living room features stunning woodwork, a fireplace, and French doors leading to a window-lined sunroom-ideal for a home office or playroom. The large circular floor plan connects the living room with a formal dining room, family room, half bath and newer kitchen.

    Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

    5 Thornton Rd, Winchester, MA 01890
  • 4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, Winchester, MA 01890
    4 Aricia Ln, Winchester, MA 01890
    /39

    $1,900,000

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

    4 Aricia Ln, Winchester, MA 01890

    Tucked into the tree-lined enclave of Aricia Lane, this striking contemporary residence delivers bold architectural design, abundant light, and the seamless indoor-outdoor living today’s buyers crave. Set on nearly half an acre in one of Winchester’s most peaceful pockets, this home is a rare fusion of modern comfort, space, and convenience offering the rarest of features: a five-car garage. From

    The McLaren D'Agostino Team Compass

    4 Aricia Ln, Winchester, MA 01890
  • 7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    /34

    $1,399,900

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

    7 Thornberry Rd, Winchester, MA 01890

    Renovated Contemporary Split-entry 3 Level home in the highly sought-after Vinson- Owen Elementary and West-side neighborhood. 15 minutes to Downtown Boston. 5 bedrooms, 2 full baths, Living, Dining PLUS family room & 2nd finished room ( play or office) ground level room heated & A/C walk access to outdoor deck & fire pit. Open concept kitchen area. Hardwood floors, 2 fireplace, 2 garage space,

    salim chowdhury TAJ Mahal Realty LLC

    7 Thornberry Rd, Winchester, MA 01890
  • 11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    11 Viking Rd, Winchester, MA 01890
    /4

    $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
  • 20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    20 Amberwood Dr, Winchester, MA 01890
    /34

    $3,598,000

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

    20 Amberwood Dr, Winchester, MA 01890

    Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The

    Dan Li Keller Williams Realty

    20 Amberwood Dr, 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

    • 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
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 $569,000. If you put a 20% down payment of $113,800 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $2,940 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $126K 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 Shakerhill, The Flats, Arlington Heights, Countryside and North Main.
Are home prices dropping in West Side?
Yes, home prices in West Side are down 8% in the last 12 months.

Home Trends in West Side, MA

On average, homes in West Side, Winchester sell after 63 days on the market compared to the national average of 70 days. The median sale price for homes in West Side, Winchester over the last 12 months is $537,000, up 17% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$537,000
Median Single Family Sale Price
$537,000
Median Townhouse Sale Price
$624,000
Median 2 Bedroom Sale Price
$409,950
Median 1 Bedroom Sale Price
$419,000
Average Price Per Sq Ft
$339
Number of Homes for Sale
4
Last 12 months Home Sales
41
Months of Supply
1.20
Median List Price
$569,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
17%
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