10

West Side Homes for Sale

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  • /25

    $949,000

    • 4 Beds
    • 1.5 Baths
    • 2,162 Sq Ft

    41 Squire Rd, Winchester, MA 01890

    Mid Century Side Hall Colonial w Attached Garage on an Attractive Corner Lot in Winchester. Available for the first time in more than fifty years, this inviting home awaits its next owners' vision and personal touch. Exceptional opportunity to add immediate value with the right repairs and upgrades. Main floor features an open living room with fireplace, adjoining dining room with southwest

    William Cordts Charlesgate Realty Group, llc

    41 Squire Rd, Winchester, MA 01890
  • /24

    $969,000 Open Sun 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
  • /41

    $1,475,000

    • 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
  • /41

    $2,600,000 Open Sun 1PM - 2:30PM

    • 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
  • /42

    $1,149,000

    • 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
  • /42

    $1,999,000

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

    5 Azalea Rd, Winchester, MA 01890

    NEW PRICE & UPDATES BEAUTIFULLY REIMAGINED!Welcome home to this stunning brick ranch tucked on a quiet cul-de-sac in Winchester’s coveted West Side. Every space has been thoughtfully designed, blending classic craftsmanship with distinct elegance. The bright open layout invites you in with a chef’s granite and stainless kitchen, sun-filled family room framed by floor-to-ceiling windows, and

    Anthony Marino The Marino Group Collection

    5 Azalea Rd, Winchester, MA 01890
  • /30

    $2,850,000

    • 6 Beds
    • 7 Baths
    • 6,968 Sq Ft

    14 Nassau Dr, Winchester, MA 01890

    Amazing custom-built 6-bedroom / 5+ bathroom house on a quiet neighborhood in Winchester. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New

    Weidong Li WINN Real Estate & Consulting

    14 Nassau Dr, 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
  • /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

    Wei Wang WW Real Estate LLC

    20 Amberwood Dr, Winchester, MA 01890
  • /38

    $2,299,000

    • 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

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 6.23%, your estimated principal and interest payment would be $8,420 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $361K 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

Housing Trends

Median Sale Price
$1,650,000
Median Single Family Sale Price
$1,713,000
Median 2 Bedroom Sale Price
$1,070,000
Average Price Per Sq Ft
$514
Number of Homes for Sale
10
Last 12 months Home Sales
52
Months of Supply
2.30
Median List Price
$1,712,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
10%
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