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North Main Homes for Sale

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  • /36

    $1,064,000

    Open Sat 11AM - 12PM $35K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,777 Sq Ft

    46 Clark St, Winchester, MA 01890

    Welcome to this meticulously renovated four-bedroom Colonial, ideally situated on a quiet dead-end street just steps from downtown Winchester, the commuter rail, and the newly built Lynch Elementary School. The sun-filled first floor features gorgeous floors, a charming living room, a dining room that opens to a spacious deck, a stunning updated kitchen with new countertops and appliances, as

    Andersen Group Realty Keller Williams Realty Boston Northwest

    46 Clark St, Winchester, MA 01890
  • /41

    $1,899,000

    $301K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 6,900 Sq Ft

    16 Glenwood Ave, Winchester, MA 01890

    Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr

    Kim Covino Compass

    16 Glenwood Ave, Winchester, MA 01890
  • /32

    $2,795,000

    • 4 Beds
    • 4.5 Baths
    • 5,233 Sq Ft

    18 Middlesex St, Winchester, MA 01890

    This European-inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the

    Tina Natale Luxury Living Real Estate

    18 Middlesex St, Winchester, MA 01890
  • /41

    $1,899,000

    $301K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 6,900 Sq Ft

    16 & 16A Glenwood Ave, Winchester, MA 01890

    Must see! sprawling 2-3 family beautifully renovated & expanded home offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace,

    Kim Covino Compass

    16 & 16A Glenwood Ave, Winchester, MA 01890
  • /21

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft

    50 Middlesex St Unit 52, Winchester, MA 01890

    Completely renovated from top to bottom, this brand-new 2-bedroom, 2-bath condo offers the privacy and feel of a single-family home in one of Winchester's most desirable neighborhoods. Tucked away on a quiet, tree-lined street just moments from vibrant downtown, this home features its own private entrance, driveway, and backyard. Inside, enjoy white oak hardwood floors, a stunning chef's kitchen

    The North Star Group Keller Williams Realty Evolution

    50 Middlesex St Unit 52, Winchester, MA 01890
  • /30

    $950,000

    Open Sat 11AM - 12:30PM
    • 3 Beds
    • 1 Bath
    • 1,356 Sq Ft

    47 Water St, Winchester, MA 01890

    Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds

    The Mary Scimemi Team Leading Edge Real Estate

    47 Water St, Winchester, MA 01890
  • /24

    $849,000

    Open Sat 11AM - 12:30PM
    • 3 Beds
    • 1.5 Baths
    • 1,340 Sq Ft

    15 Clark St Unit 15, Winchester, MA 01890

    Walkable to nearly everything, 15 Clark St presents an exceptional opportunity to enjoy refined living in one of Winchester's most sought-after neighborhoods. This sun-drenched townhome offers 3 bedrooms, 1.5 bathrooms, and approximately 1,336 sq ft of thoughtfully curated living space. Rich hardwood floors, soaring natural light, and an effortless open layout create a warm yet sophisticated

    Jeffrey Hsu Coldwell Banker Realty - Milton

    15 Clark St Unit 15, Winchester, MA 01890
  • /42

    $1,199,000

    Open Sat 12:30PM - 2PM $26K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,235 Sq Ft

    53 Lake St, Winchester, MA 01890

    Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming

    Kim Covino Compass

    53 Lake St, Winchester, MA 01890

Why Live in North Main

With well-kept single-family homes, tranquil waterfront recreation areas and highly rated public schools, North Main has all the trappings of a classic Boston commuter suburb. Bordered by a section of Main Street that Winchester’s planners have ...

North Main Home Prices vs. Nearby Winchester, MA Neighborhoods

North Main Horace Mann Winchester Highlands Melrose East Side
Median Home Price
$1,212,000
$899,000
$1,319,450
$975,000
Median Sale Price
$1,200,000
-21% YoY
$949,000
+10% YoY
$1,290,000
+5% YoY
$1,051,000
+23% YoY
Median Single Family Price
$1,200,000
$982,500
$1,340,000
$1,051,000
Median Townhouse Price
$999,000
--
$1,350,000
$879,000
Median Condo Price
$1,082,000
$550,000
$919,000
$607,500
Total Active Listings
7
8
2
8
Market Conditions
6 Months of Supply
Balanced Market
3 Months of Supply
Seller's Market
1 Months of Supply
Seller's Market
1 Months of Supply
Seller's Market

Frequently Asked Questions

Is North Main a good place to live?
North Main is a good place to live. North Main is considered somewhat walkable and very bikeable with some transit options. North Main is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. North Main has 2 parks for recreational activities. It has a median age of 42. The average household income is $195,583 which is above the national average. College graduates make up 74.7% of residents. A majority of residents in North Main are home owners, with 20% of residents renting and 80% of residents owning their home. A local real estate agent serving North Main can help you decide if this neighborhood is the right one for you. Learn more on our North Main neighborhood guide.
Is North Main, MA a safe neighborhood?
North Main, 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 North Main?
The median home price in North Main is $1,212,000. If you put a 20% down payment of $242,400 and had a 30-year fixed mortgage with an interest rate of 6.58%, your estimated principal and interest payment would be $6,180 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $265K a year to afford the median home price in North Main. Learn how much home you can afford with our Home Affordability Calculator. The average household income in North Main is $196K.
What are the best public schools in North Main?
The best public schools that serve North Main are:
What are the best private schools in North Main?
The best private schools that serve North Main are:
What are the most popular zip codes in North Main, Winchester, MA?
The most popular zip codes in North Main, Winchester, MA include 01890, 01801, 02474, 02155 and 02180.
What are the most popular neighborhoods near North Main, Winchester, MA?
The most popular neighborhoods near North Main, Winchester, MA are The Flats, Downtown Woburn, West Side, Shakerhill and Arlington Heights.
Are home prices dropping in North Main?
Yes, home prices in North Main are down 6% in the last 12 months.
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