Single Family Residence at 16 & 16A Glenwood Ave, Winchester MA 01890
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$2,099,000

16 & 16A Glenwood Ave, Winchester MA 01890
Winchester, MA 01890
Listed by Kim Covino & Co. Team
Bedrooms
6
Bathrooms
4.5
Living area
6,900 sqft
Year built
1966

About this home

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, dining room, 1st flr bedrm & full bath, plus a flexible suite w/ kitchenette, sitting room & full bath. Upstairs offers 3 add' bedrooms & a full bath. The finished lower level includes a family room, office, exercise space, bonus room w/ walkout, workshop, storage & cedar closet. Additional highlights include an oversized 2-car garage with EV charger, elevator lift, solar array, & direct access to the apartment featuring vaulted ceilings, gas fireplace, full kitchen, laundry & private deck. Set on an oversized level lot with mature landscaping, deck, patio & gazebo on a quiet cul-de-sac!

Highlights

Fireplace

Property details

MLS
MLS Property Information Network
MLS #
73507137
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
186
On market date
April 24, 2026
Stories
N/A
Total bathrooms
4.5
Garage spaces
2
Parking spaces
9
Lot size
0.44 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Lynch Elementary
0.26 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
506
Student:teacher ratio
11.8:1
District
Winchester
Middle
McCall Middle
1.08 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,059
Student:teacher ratio
11.8:1
District
Winchester
High
Winchester High School
0.74 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,349
Student:teacher ratio
13.8:1
District
Winchester

Walkability

Blended score for Winchester's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

91
Highly walkable
out of 100
EPA National Walkability Index
17.0 / 20 -- Most walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores4
Parks20
Schools20
Transit stops20
Pharmacies4

Market position

How this listing compares to current activity in Winchester, from live MLS data.

On the market 186 days -- 100 more days than Winchester's current average of 86 days.
For reference, the median list price across 178 active listings in Winchester right now is $870,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$12,790/mo
$419,800 down
$1,679,200 loan
Principal & interest$10,891
Property tax (est.)$1,749
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 10, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.