5

North Main Homes for Sale

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  • /41

    $2,099,000

    $101K 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

    $2,099,000

    $101K 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
  • /40

    $1,495,000

    • 4 Beds
    • 2.5 Baths
    • 2,605 Sq Ft

    7 Sherman Place, Winchester, MA 01890

    Welcome to this sun-drenched newer construction & freshly updated 4 Bed 2.5 Bath luxury townhome, set on a quiet cul-de-sac with a private, professionally landscaped yard & secret garden. This spacious home lives like a free standing house with a thoughtful layout designed for both everyday living and entertaining. Highlights include soaring 9-foot ceilings, oversized windows & high efficiency

    Kim Covino Compass

    7 Sherman Place, Winchester, MA 01890
  • /36

    $1,225,000

    • 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 ...

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 $1,329,450. If you put a 20% down payment of $265,900 and had a 30-year fixed mortgage with an interest rate of 6.48%, your estimated principal and interest payment would be $6,710 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $288K 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, 02155, 02474 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, Winchester Highlands, West Side and Shakerhill.
Are home prices dropping in North Main?
Yes, home prices in North Main are down 3% in the last 12 months.

North Main Home Prices vs. Nearby Winchester, MA Neighborhoods

North Main Winchester Highlands Newton Highlands West Newton
Median Home Price
$1,329,450
$1,250,000
$1,537,000
$1,400,000
Median Sale Price
$1,280,000
-12% YoY
$1,250,000
-3% YoY
$1,460,000
-17% YoY
$1,325,000
-65% YoY
Median Single Family Price
$1,305,000
$1,280,000
$1,668,000
$1,910,000
Median Townhouse Price
$1,610,000
$1,350,000
$2,200,000
$1,985,000
Median Condo Price
$1,495,000
$919,000
$1,397,500
$1,101,250
Total Active Listings
5
4
34
34
Market Conditions
3 Months
Seller's Market
1 Months
Seller's Market
3 Months
Seller's Market
4 Months
Seller's Market
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