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West Side Homes for Sale

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  • 12 Cox Rd, Winchester, MA 01890
    12 Cox Rd, Winchester, MA 01890
    12 Cox Rd, Winchester, MA 01890
    /41

    $1,799,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 2,818 Sq Ft

    12 Cox Rd, Winchester, MA 01890

    SHOWINGS BEGIN AT OPEN HOUSE THURSDAY MAY 7th 5:00-6:30pm. Fabulous 11 room, 4 bedroom Colonial set on a beautiful lot on Winchester’s west side. The first floor offers a bright and sunny, open concept kitchen and family room which creates the perfect space for everyday living and entertaining which leads to a mud room, laundry, and home offic . Completing the first floor is half bath off

    Darryl Brian RE/MAX Bentley's

    12 Cox Rd, Winchester, MA 01890
  • 37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    37 Mayflower Rd, Winchester, MA 01890
    /40

    $3,379,000

    • 7 Beds
    • 7.5 Baths
    • 8,540 Sq Ft

    37 Mayflower Rd, Winchester, MA 01890

    Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz

    Kim Covino Compass

    37 Mayflower Rd, Winchester, MA 01890
  • 14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    /36

    $2,799,000

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

    14 Nassau Dr, Winchester, MA 01890

    Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. 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 England

    Weidong Li WINN Real Estate & Consulting

    14 Nassau Dr, Winchester, MA 01890
  • 1 Plymouth Rd, Winchester, MA 01890
    1 Plymouth Rd, Winchester, MA 01890
    1 Plymouth Rd, Winchester, MA 01890
    /35

    $3,399,000

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

    1 Plymouth Rd, Winchester, MA 01890

    Discover a beautifully reimagined home in one of Winchester’s most sought-after neighborhoods, offering exceptional space, comfort, and convenience in a truly prime location. With 7 bedrooms, 7 full baths, and 1 half bath, 1 Plymouth has been thoughtfully expanded and rebuilt with high-end finishes throughout to suit today’s lifestyle. At the heart of the home is a stunning fireplaced family room

    George Sarkis Douglas Elliman Real Estate - The Sarkis Team

    1 Plymouth Rd, Winchester, MA 01890
  • 94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    94 Johnson Rd, Winchester, MA 01890
    /42

    $1,849,999 Open Thu 5PM - 6:30PM

    • 4 Beds
    • 3 Baths
    • 3,512 Sq Ft

    94 Johnson Rd, Winchester, MA 01890

    This quintessential Colonial blends timeless charm with modern updates, offering a truly move-in ready home in a unique location! Directly across the street, the Winchester Swim and Tennis Club presents a rare opportunity for immediate membership—enjoy your own private club lifestyle just in time for summer! Just a few doors from Vinson-Owen Elementary, morning drop-offs couldn’t be easier.

    Philip Vita Compass

    94 Johnson Rd, Winchester, MA 01890
  • 276 High St, Winchester, MA 01890
    276 High St, Winchester, MA 01890
    276 High St, 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
  • 9 Albamont Rd, Winchester, MA 01890
    9 Albamont Rd, Winchester, MA 01890
    9 Albamont Rd, Winchester, MA 01890
    /10

    $3,400,000

    • 6 Beds
    • 5.5 Baths
    • 6,100 Sq Ft

    9 Albamont Rd, Winchester, MA 01890

    Brand new high end construction in prime Winchester location! Currently under construction w/ completion expected late spring 2026. A thoughtfully designed home with immense curb appeal showcasing stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer

    Kim Covino Compass

    9 Albamont Rd, 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

    • 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
Massachusetts Middlesex County Winchester West Side

Real Estate & Homes for Sale in West Side, Winchester

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 car-dependent and very bikeable with minimal transit options. 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 $1,725,000. If you put a 20% down payment of $345,000 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $8,540 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $366K 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, 02420, 02474, 01801 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, Countryside, Arlington Heights, East Lexington and Cummingsville.
Are home prices dropping in West Side?
Yes, home prices in West Side are down 3% in the last 12 months.

Home Trends in West Side, MA

On average, homes in West Side, Winchester sell after 21 days on the market compared to the national average of 57 days. The median sale price for homes in West Side, Winchester over the last 12 months is $1,613,500, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,613,500
Median Single Family Sale Price
$1,695,750
Average Price Per Sq Ft
$529
Number of Homes for Sale
9
Last 12 months Home Sales
60
Months of Supply
1.80
Median List Price
$1,725,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
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